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Structural characterization and cytotoxicity studies of ruthenium(II)–dmso–chloro complexes of chalcone and flavone derivatives
VOLUME 30. No. 10.
OCTOBER 2016
ISSN 0951-256X
2016 Nobel Prize in Chemistry for
Molecular Machines
The Royal Swedish Academy of Sciences has decided to award Jean-Pierre Sauvage, Sir
James Fraser Stoddart and Bernard (Ben) L. Feringa the Nobel Prize in Chemistry 2016
“for the design and synthesis of molecular machines”. This is a high recognition for
supramolecular chemistry utilizing building blocks of host-guest complexes including also
cyclodextrin complexes.
The molecular machines mimic the movements of machines in a highly miniaturized scale.
They need external fueling which is usually light or other energy. The first approach was
topological entanglement (interlocked molecular assemblies). The building blocks are not
covalently bound together but are entangled through loops and stoppers. Catenanes consisting
of two interlocked rings and rotaxanes based on a ring threaded over an axle with stoppers are
the main groups (Fig. 1).
Fig. 1. Examples of molecules with topological entanglement: a) [3]catenane, b) trefoil knot,
c) Solomon link (redrawn after [1]) synthesized by Jean-Pierre Sauvage et al. (CNRS, Louis
Pasteur University, Strasbourg, France) in the eighties [2] and d) scheme of rotaxane
Dramatic, reversible changes in the catenanes’ molecular shape were observed upon
decomplexation and recomplexation of the metal coordination entities with Cu(I) as first
examples of translational isomerism [3].
The group of Sir James Fraser Stoddart (University of Sheffield, UK) synthesized paraquat
cyclophane structure threaded around an axle containing two hydroquinol units [4] (Fig. 2).
The resulting rotaxane cyclophane ring could be shown to act as a molecular shuttle, able to
move between the two hydroquinol stations on the axle. The trigger of the motion is
electrochemical oxidation-reduction or pH change.
VOLUME 30. No 10.
Fig. 2. Translational isomerism, molecular shuttle: the macrocycle can move between two
positions
In parallel with the development of interlocked structures, systems based on isomerizable
unsaturated bonds able to rotate unidirectionally in a controlled manner were synthesized.
One of the
first
approaches
published
by
Feringa’s
group
(University
of Groningen,
the Netherlands) is illustrated in Fig. 3 [5]. Taking together 4 such motors into one structure
resembling to a 4-wheeled car, this group constructed the prototype of a ‘nanocar’ (fourwheeled molecule) [6].
Fig. 3. Unidirectional molecular rotary motor (the cis–trans isomerization of the double bond on
the effect of UV-light is the driving force) and the ‘nanocar’ equipped with 4 such rotors [6, 7]
Both linear and rotary motion was achieved on molecular scale providing artificial molecular
machines built up from shuttles and switches (motors and pumps) where supplies of energy
in the form of chemical fuel, electrochemical potential and light activation become a minimum
requirement for them to function away from equilibrium [8].
Activity of Nobel laureates with cyclodextrins
According to Scopus all the three Nobel-Prize laureates have abundantly published their
findings (Table 1). Although all of them mentioned CDs in their reviews or introduction of their
research papers, only Stoddart was active in the development of novel structures including CD
as building block.
Edited and produced by: CYCLOLAB – page: 2
VOLUME 30. No 10.
Table 1 Publications statistics (Scopus, accessed on 24 November 2016)
No. of papers
No. of papers
mentioning CDs
CDs in the title,
abstract or keywords
Stoddart, J.F.
904
279
59
Sauvage, J.P.
533
73
0
Feringa, B.J.
739
26
0
Stoddart was born in 1942 and studied at Edinburgh University. Later on he made research at
various universities in the US, UK and Canada. He was made a Knight Bachelor by Her Majesty
Queen Elizabeth II. in 2007 for his services in chemistry and molecular nanotechnology.
Sir J.F. Stoddart was identified as one of the most-cited chemists in 1995–2005 period with
over 11000 citations [9]. In October 2016 he had 83941 citations, 35439 since 2011 (Google
Scholar, accessed on 20 November, 2016) with 7 papers of over 1000 citations. The three
most cited papers are:
●
Artificial molecular machines (Angew. Chemie [10], No. of citations: 2102)
●
Self‐assembly in natural and unnatural systems (Angew. Chemie [11], No. of citations:
1919)
●
Electronically configurable molecular-based logic gates (Science [4], No. of citations:
1823)
Stoddart started to use the following expressions in his papers: switchable molecular devices
[12], artificial molecular pumps [13], supramolecular devices, mechanically linked polymers,
molecular elevators [14], molecular computers, molecular electronics [15], molecular logic
gates [16], etc.
His CD-related activity covered also other topics, such as gold recovery, catalysis, metalorganic frameworks, sensors, etc.
Molecular machines with CDs
Preparation of interlocked systems
The very first attempt to thread CD on an axle molecule was a catenane prepared by the group
of Friedrich Cramer (Fig. 4) preceding the works of the present Nobel laureates.
Fig. 4. Scheme of the very first catenane using αCD prepared by Cramer’s group published in
1958 [17]
Edited and produced by: CYCLOLAB – page: 3
VOLUME 30. No 10.
The very first rotaxane containing CD was prepared by Hiroshi Ogino (Tohoku University,
Japan) utilizing the non-covalent interaction between α,ω-diaminoalkenes and CD using
CoCl(ethylenediamine)2 bulky groups as stoppers [18].
The first polyrotaxanes containing several CDs threaded on an axle molecule was published in
the same year (in 1992) by Harada et al. and Wenz et al. (Fig. 5) [19, 20]. Harada used
diamine-terminated polyethylene glycol and aCD to get a molecular necklace attaching
dinitrofluorobenzene
groups
as
stoppers,
while
Wenz
stringed
αCD
rings
on
polyiminooligomethylene chains and terminated the chains with nicotinoyl groups. However,
these systems did not show controllable motion.
Fig. 5. Scheme of polyrotaxanes
Stimuli-responsive molecular devices and molecular machines with CDs
Typical
photoswitchable
molecular
devices
based
on
cis–trans
photoisomerization
of
azobenzene moiety (Fig. 6) were prepared by several groups [21, 22]. Light-driven rotaxane
molecular shuttles and nanovalves containing αCD and azobenzene unit were constructed. The
cis–trans photoisomerization of azobenzene moiety induces reversible motion of the CD ring on
the effect of UV (hν) and visible (hν1) irradiation (Fig. 6 and 7) [23].
Fig. 6. Photoisomerization of azobenzene
CD selectively binds to trans-azobenzene, which is less hydrophilic than the cis isomer. Upon
irradiation the trans-azobenzene is transformed into the cis form causing αCD to unthread.
Thermal relaxation allows cis-azobenzene to transform back to trans isomer and αCD to rebind.
Edited and produced by: CYCLOLAB – page: 4
VOLUME 30. No 10.
Fig. 7. Nanovalves based on cis–trans photoisomerization of azobenzene attached to
mesopores of silica nanoparticles [23]
Various other stimuli-responsive systems have been published. For instance, pH-responsive
materials (Fig. 8) [24], redox-switchable molecular machines [25], etc. Some recent reviews
give detailed overview on such systems [26–30].
Fig. 8. Molecular pistons used for controlled drug delivery [redrawn after 24]. This invention of
Stoddart’s team is based on phosphonate-coated silica nanoparticles with a BCD monolayer.
Rhodamine B-benzidine conjugate as nanopiston moving in and out of the CD cavity controls
the release of the drug from the nanopores of silica. The trigger is the increase or decrease of
the pH.
It is a great honor to the entire cyclodextrin society of the world that molecular machines were
selected for 2016 Nobel Prize, a field of supramolecular chemistry including advances in
cyclodextrin chemistry.
Edited and produced by: CYCLOLAB – page: 5
VOLUME 30. No 10.
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Pharmaceutics,
2016,
513,
518-527;
Desai, S.; Poddar, A.; Sawant, K.
Formulation of cyclodextrin inclusion complex-based orally disintegrating tablet of
eslicarbazepine acetate for improved oral bioavailability
Fast onset of anti-epileptic action, Super disintegrants, β-Cyclodextrin, Solid dispersion
Materials Science and Engineering: C, 2016, 58, 826-834; DOI:10.1016/j.msec.2015.09.019
Deshmukh, K.; Tanwar, Y. S.; Sharma, S.; Shende, P.; Cavalli, R.
Functionalized nanosponges for controlled antibacterial and antihypocalcemic actions
Lysozyme impregnated surface-active nanosponges, Peptidoglycan, Controlled release, βCyclodextrin
Biomedicine & Pharmacotherapy, 2016, 84, 485-494; DOI:10.1016/j.biopha.2016.09.017
Dora, C. P.; Trotta, F.; Kushwah, V.; Devasari, N.; Singh, C.; Suresh, S.; Jain, S.
Potential of erlotinib cyclodextrin nanosponge complex to enhance solubility,
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VOLUME 30. No 10.
dissolution rate, in vitro cytotoxicity and oral bioavailability
Optimized stoichiometry concentration, Tyrosine kinase inhibitor
Carbohydrate Polymers, 2016, 137, 339-349; DOI:10.1016/j.carbpol.2015.10.080
Galus, A.; Mallet, J.-M.; Lembo, D.; Cagno, V.; Djabourov, M.; Lortat-Jacob, H.; Bouchemal, K.
Hexagonal-shaped chondroitin sulfate self-assemblies have exalted anti-HSV-2
activity
Mixing hydrophobically-modified chondroitin sulfate with α-cyclodextrin, Biomimetic
formulation, Nanoassembly
Carbohydrate Polymers, 2016, 136, 113-120; DOI:10.1016/j.carbpol.2015.08.054
García-González, L.; Yépez-Mulía, L.; Ganem, A.
Effect of β-cyclodextrin on the internalization of nanoparticles into intestine epithelial
cells
PLGA nanoparticles, Interaction with mucin, Caco-2 cells
European
Journal
of
Pharmaceutical
DOI:10.1016/j.ejps.2015.10.012
Sciences,
2016,
81,
113-118;
Gharib, R.; Auezova, L.; Charcosset, C.; Greige-Gerges, H.
Drug-in-cyclodextrin-in-liposomes as a carrier system for volatile essential oil
components: Application to anethole
Phospholipids, Photoprotection, HP-β-CD, Double loading
Food Chemistry, 2017, 218, 365-371; DOI:10.1016/j.foodchem.2016.09.110
Hu, X.; Tan, H.; Wang, X.; Chen, P.
Surface functionalization of hydrogel by thiol-yne click chemistry for drug delivery
β-CD functionalized hydrogel, Orfloxacin, Thiol-yne photopolymerization
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2016, 489, 297-304;
DOI:10.1016/j.colsurfa.2015.11.007
Joseph, L. M.; Chibale, K.; Caira, M. R.
Preparation and physicochemical characterization of an inclusion complex between
dimethylated β-cyclodextrin and a drug lead from a new class of orally active
antimalarial 3,5-diaryl-2-aminopyridines
Phase-solubility studies, Hydrogen bonds, Oral drug delivery, β-CD, HP-β-CD, DIMEB,
Crystal structure, Thermal analysis, X-ray diffractometry
Journal of Pharmaceutical Sciences, 2016, 105, 3344-3350; DOI:10.1016/j.xphs.2016.07.030
Leclercq, L.; Nardello-Rataj, V.
Pickering emulsions based on cyclodextrins: A smart solution for antifungal azole
derivatives topical delivery
Pathogen
European
Journal
of
Pharmaceutical
DOI:10.1016/j.ejps.2015.11.017
Edited and produced by: CYCLOLAB – page: 13
Sciences,
2016,
82,
126-137;
VOLUME 30. No 10.
Lenik, J.; Wesoły, M.; Ciosek, P.; Wróblewski, W.
Evaluation of taste masking effect of diclofenac using sweeteners and cyclodextrin by
a potentiometric electronic tongue
Sucrose, Lactose, Acesulfame K, Sodium saccharin, 2-Hydroxypropyl-β-cyclodextrin, Ionselective electrodes
Journal
of
Electroanalytical
DOI:10.1016/j.jelechem.2016.09.017
Chemistry,
2016,
780,
153-159;
Li, G.; Yu, N.; Gao, Y.; Tao, Q.; Liu, X.
Polymeric hollow spheres assembled from ALG-g-PNIPAM and β-cyclodextrin for
controlled drug release
Sodium
alginate-graft-poly(N-isopropylacrylamide),
complexation
International
Journal
of
Biological
DOI:10.1016/j.ijbiomac.2015.11.010
5-Fluorouracil,
Macromolecules,
2016,
Inclusion
82,
381-386;
Mahmood, A.; Ahmad, M.; Sarfraz, R. M.; Minhas, M. U.
β-CD based hydrogel microparticulate system to improve the solubility of acyclovir:
Optimization through in-vitro, in-vivo and toxicological evaluation
N,N'-methylene bisacrylamide, Ammonium persulfate, pH independent swelling and
release,
β-Cyclodextrin-g-poly(AMPS)
hydrogel
microparticles,
Free
radical
polymerization
Journal
of
Drug
Delivery
DOI:10.1016/j.jddst.2016.09.005
Science
and
Technology,
2016,
36,
75-88;
Masood, F.
Polymeric nanoparticles for targeted drug delivery system for cancer therapy
Biodegradability, Biocompatibility, Non-toxicity, Prolonged circulation, Poly(lactic-coglycolic acid) and cyclodextrin based nanoparticles, Site specific target
Materials Science and Engineering: C, 2016, 60, 569-578; DOI:10.1016/j.msec.2015.11.067
Masood, F.; Yasin, T.; Bukhari, H.; Mujahid, M.
Characterization and application of roxithromycin loaded
nanoparticles for treatment of multidrug resistant bacteria
β-Cyclodextrin, Hydroxypropyl-β-cyclodextrin,
Inclusion complex
cyclodextrin
Poly-(lactic-co-glycolic
acid)
based
(PLGA),
Materials Science and Engineering: C, 2016, 61, 1-7; DOI:10.1016/j.msec.2015.11.076
Messiad, H.; Yousfi, T.; Djemil, R.; Amira-Guebailia, H.
Modeling of the inclusive complexation
tetrahydroxystilbene with β-cyclodextrin
of
natural
drug
trans
3,5,3′,4′-
Piceatannol, PM3, HOMO, LUMO, Molecular modeling
Comptes Rendus Chimie, 2016, In Press; DOI:10.1016/j.crci.2016.08.008
Michalska, P.; Wojnicz, A.; Ruiz-Nuño, A.; Abril, S.; Buendia, I.; León, R.
Inclusion complex of ITH12674 with 2-hydroxypropyl-β-cyclodextrin: Preparation,
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VOLUME 30. No 10.
physical characterization and pharmacological effect
Treatment of brain ischemia, Phase II antioxidant response, Stability
Carbohydrate Polymers, 2017, 157, 94-104; DOI:10.1016/j.carbpol.2016.09.072
Misiuk, W.
Investigation of inclusion complex of HP-γ-cyclodextrin with ceftazidime
Bioavailability, UV/vis, FT-IR, NMR, Molecular docking
Journal of Molecular Liquids, 2016, 224, Part A, 387-392; DOI:10.1016/j.molliq.2016.10.009
Monteil, M.; Lecouvey, M.; Landy, D.; Ruellan, S.; Mallard, I.
Cyclodextrins: A promising drug delivery vehicle for bisphosphonate
Aqueous solubility, Bioavalibity, Host-guest complex, Formation constant
Carbohydrate Polymers, 2017, 156, 285-293; DOI:10.1016/j.carbpol.2016.09.030
Monteiro, A. P.; Rocha, C. M.; Oliveira, M. F.; Gontijo, S. M.; Agudelo, R. R.; Sinisterra, R. D.;
Cortés, M. E.
Nanofibers containing tetracycline/β-cyclodextrin: Physico-chemical characterization
and antimicrobial evaluation
Electrospun process, Polycaprolactone, Biological absorption, Inclusion compound
Carbohydrate Polymers, 2017, 156, 417-426; DOI:10.1016/j.carbpol.2016.09.059
Nakao, Y.; Horiguchi, M.; Nakamura, R.; Sasaki-Hamada, S.; Ozawa, C.; Funane, T.; Ozawa,
R.; Oka, J.-I.; Yamashita, C.
LAURETH-25 and β-CD improve central transitivity and central pharmacological effect
of the GLP-2 peptide
Glucagon-like peptide-2, Nasal
Polyoxyethylene (25) lauryl ether
formulation,
International
Journal
of
DOI:10.1016/j.ijpharm.2016.09.054
Brain
Pharmaceutics,
drug
delivery
2016,
and
515,
targeting,
37-45;
Nobusawa, K.; Naito, M.
Chapter 11 - Nanoarchitectonics for
nanoassembly of therapeutic agents
Nanomedicine, Stimuli responsibility,
interaction, Supramolecular manipulation
cyclodextrin-mediated
Phototherapeutic
solubilization
applications,
and
Host–guest
Supra-Materials Nanoarchitectonics, Ariga, K.; Aono, M. Eds., William Andrew Publishing,
2017, 247-262; DOI:10.1016/B978-0-323-37829-1.00011-0
de Oliveira, C.; Ferreira, N.; Mota, G.
A DFT study of infrared spectra and Monte Carlo predictions of the solvation shell of
Praziquantel and β-cyclodextrin inclusion complex in liquid water
Molecular mechanics simulations
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2016, 153, 102-107;
DOI:10.1016/j.saa.2015.08.011
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VOLUME 30. No 10.
Oprean, C.; Mioc, M.; Csányi, E.; Ambrus, R.; Bojin, F.; Tatu, C.; Cristea, M.; Ivan, A.; Danciu,
C.; Dehelean, C.; Paunescu, V.; Soica, C.
Improvement of ursolic and oleanolic acids’ antitumor activity by complexation with
hydrophilic cyclodextrins
2-Hydroxypropyl-β-cyclodextrin, 2-Hydroxypropil-γ-cyclodextrin, Pentacyclic triterpenes,
Anti-proliferative, Melanoma
Biomedicine & Pharmacotherapy, 2016, 83, 1095-1104; DOI:10.1016/j.biopha.2016.08.030
Ouerghemmi, S.; Degoutin, S.; Tabary, N.; Cazaux, F.; Maton, M.; Gaucher, V.; Janus, L.;
Neut, C.; Chai, F.; Blanchemain, N.; Martel, B.
Triclosan loaded electrospun nanofibers based on a cyclodextrin polymer and
chitosan polyelectrolyte complex
Positively charged chitosan, Anionic hydroxypropyl-β-cyclodextrin-citric acid polymer,
Prolonged release, Antibacterial activity, Controlled release
International
Journal
of
DOI:10.1016/j.ijpharm.2016.09.060
Pharmaceutics,
2016,
513,
483-495;
Paczkowska, M.; Mizera, M.; Szymanowska-Powałowska, D.; Lewandowska, K.; Błaszczak, W.;
Gościańska, J.; Pietrzak, R.; Cielecka-Piontek, J.
β-Cyclodextrin complexation as an effective drug delivery system for meropenem
Inclusion complex, Solubility, Stability, Microbiological activity
European
Journal
of
Pharmaceutics
DOI:10.1016/j.ejpb.2015.10.013
and
Biopharmaceutics,
2016,
99,
24-34;
Palanisamy, M.; James, A.; Khanam, J.
Atorvastatin–cyclodextrin systems: Physiochemical and biopharmaceutical evaluation
HP-β-CD, Freeze drying method, Bioavailability, Dissolution rate, Solid state analysis
Journal
of
Drug
Delivery
DOI:10.1016/j.jddst.2015.11.003
Science
and
Technology,
2016,
31,
41-52;
Pápay, Z. E.; Sebestyén, Z.; Ludányi, K.; Kállai, N.; Balogh, E.; Kósa, A.; Somavarapu, S.;
Böddi, B.; Antal, I.
Comparative evaluation of the effect of cyclodextrins and pH on aqueous solubility of
apigenin
α-CD, β-CD, γ-CD, SBE-β-CD, HP-β-CD, RM-β-CD, Drug delivery, Solubility improvement,
Phase solubility studies, Antioxidant activity
Journal
of
Pharmaceutical
and
DOI:10.1016/j.jpba.2015.08.019
Biomedical
Analysis,
2016,
117,
210-216;
Paulsen, Z.; Onani, M. O.; Allard, G. R.; Kiplagat, A.; Okil, J. O.; Dejene, F. B.; Mahanga, G.
M.
The effect of varying the capping agent of magnetic/luminescent Fe 3O4–InP/ZnSe
core–shell nanocomposite
Multifunctional
drug
carrier
system,
3-Mercaptopropionic
acid,
β-Cyclodextrin, Multifunctional, Superparamagnetic, Photoluminescence
Oleylamine,
Physica B: Condensed Matter, 2016, 480, 156-162; DOI:10.1016/j.physb.2015.09.005
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VOLUME 30. No 10.
Sebaaly, C.; Charcosset, C.; Stainmesse, S.; Fessi, H.; Greige-Gerges, H.
Clove essential oil-in-cyclodextrin-in-liposomes in the aqueous and lyophilized states:
From laboratory to large scale using a membrane contactor
Hydroxypropyl-β-cyclodextrin,
Scale- up
Double
loading
technique,
Eugenol,
Freeze-drying,
Carbohydrate Polymers, 2016, 138, 75-85; DOI:10.1016/j.carbpol.2015.11.053
Shen, J.; Song, L.; Xin, X.; Wu, D.; Wang, S.; Chen, R.; Xu, G.
Self-assembled supramolecular hydrogel induced by β-cyclodextrin and ionic liquidtype imidazolium gemini surfactant
Temperature, External stimuli, Hydrogen bonding, Mechanical properties
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2016, 509, 512-520;
DOI:10.1016/j.colsurfa.2016.09.064
Silva, J. C.; Almeida, J. R.; Quintans, J. S.; Gopalsamy, R. G.; Shanmugam, S.; Serafini, M.
R.; Oliveira, M. R.; Silva, B. A.; Martins, A. O.; Castro, F. F.; Menezes, I. R.; Coutinho, H. D.;
Oliveira, R. C.; Thangaraj, P.; Araújo, A. A.; Quintans-Júnior, L. J.
Enhancement of orofacial antinociceptive effect of carvacrol, a monoterpene present
in oregano and thyme oils, by β-cyclodextrin inclusion complex in mice
Morphine, Capsaicin, Glutamate, Orofacial pain, Opioid
Biomedicine & Pharmacotherapy, 2016, 84, 454-461; DOI:10.1016/j.biopha.2016.09.065
Singh, B.; Dhiman, A.; Rajneesh; Kumar, A.
Slow release of ciprofloxacin from β-cyclodextrin containing drug delivery system
through network formation and supramolecular interactions
Hydrogels, Sterculia gum comprising of glucuronic acid and galacturonic acid and
carbopol, Non-Fickian diffusion mechanism, Korsmeyer-Peppas model
International
Journal
of
Biological
DOI:10.1016/j.ijbiomac.2016.07.060
Macromolecules,
2016,
92,
390-400;
Soo, E.; Thakur, S.; Qu, Z.; Jambhrunkar, S.; Parekh, H. S.; Popat, A.
Enhancing delivery and cytotoxicity of resveratrol through a dual nanoencapsulation
approach
Cyclodextrin–resveratrol inclusion complexes, Liposome, Anticancer, Colorectal cancer
Journal of Colloid and Interface Science, 2016, 462, 368-374; DOI:10.1016/j.jcis.2015.10.022
Tan, S.; Ang, C.; Zhao, Y.
Smart therapeutics achieved via host–guest assemblies
Stimuli-triggered drug release, Targeting, Biomedical applications, Calixarenes, Crown
ethers, Cucurbiturils, Cyclodextrins, Drug delivery, Pillararenes
Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier, 2016;
DOI:10.1016/B978-0-12-409547-2.12575-2
Tang, P.; Yang, H.; Tang, B.; Wu, D.; Du, Q.; Xu, K.; Li, H.
Dimethyl-β-cyclodextrin/salazosulfapyridine
nanoparticles for sustained release
Edited and produced by: CYCLOLAB – page: 17
inclusion
complex-loaded
chitosan
VOLUME 30. No 10.
Job’s plot, Toxicity, 2,6-Dimethyl-β-cyclodextrin
Carbohydrate Polymers, 2017, 156, 215-222; DOI:10.1016/j.carbpol.2016.09.038
Thiry, J.; Krier, F.; Ratwatte, S.; Thomassin, J.-M.; Jerome, C.; Evrard, B.
Hot-melt extrusion as a continuous
cyclodextrin inclusion complexes
manufacturing
process
to
form
ternary
HP-β-CD, RAMEB, Sulfobutylether-β-cyclodextrin (Captisol®), Crysmeb®, Itraconazole,
Solubility enhancement, Solid dispersion
European Journal of Pharmaceutical Sciences, 2016, In Press; DOI:10.1016/j.ejps.2016.09.032
Trapani, A.; Laurentis, N. D.; Armenise, D.; Carrieri, A.; Defrenza, I.; Rosato, A.; Mandracchia,
D.; Tripodo, G.; Salomone, A.; Capriati, V.; Franchini, C.; Corbo, F.
Enhanced solubility and antibacterial activity of lipophilic fluoro-substituted
N- benzoyl-2-aminobenzothiazoles by complexation with β-cyclodextrins
β-CD, HP-β-CD, Microbial resistance, Nuclear magnetic resonance, Molecular modelling
International
Journal
of
DOI:10.1016/j.ijpharm.2015.11.024
Pharmaceutics,
2016,
497,
18-22;
Vestland, T. L.; Jacobsen, Ø.; Sande, S. A.; Myrset, A. H.; Klaveness, J.
Characterization of omega-3 tablets
β-Cyclodextrin as encapsulating agent
Food Chemistry, 2016, 197, Part A, 496-502; DOI:10.1016/j.foodchem.2015.10.142
Wang, L.; Yan, J.; Li, Y.; Xu, K.; Li, S.; Tang, P.; Li, H.
The influence of hydroxypropyl-β-cyclodextrin on the solubility,
cytotoxicity, and binding of riluzole with human serum albumin
dissolution,
Toxicity, Fluorescence quenching, Inclusion complex
Journal
of
Pharmaceutical
and
DOI:10.1016/j.jpba.2015.09.033
Biomedical
Analysis,
2016,
117,
453-463;
Wang, L.-L.; Zheng, W.-S.; Chen, S.-H.; Han, Y.-X.; Jiang, J.-D.
Development of rectal delivered thermo-reversible gelling film encapsulating a
5-fluorouracil hydroxypropyl-β-cyclodextrin complex
Transport efficiency, Cellular uptake, Colorectal cancer
Carbohydrate Polymers, 2016, 137, 9-18; DOI:10.1016/j.carbpol.2015.10.042
Wang, W.-X.; Feng, S.-S.; Zheng, C.-H.
A comparison between conventional liposome and drug-cyclodextrin complex in
liposome system
Initial burst release, Risperidone
International
Journal
of
DOI:10.1016/j.ijpharm.2016.09.043
Pharmaceutics,
2016,
513,
387-392;
Wathoni, N.; Motoyama, K.; Higashi, T.; Okajima, M.; Kaneko, T.; Arima, H.
Enhancing effect of γ-cyclodextrin on wound dressing properties of sacran hydrogel
film
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VOLUME 30. No 10.
Cross-linked hydrogel film, Swelling ratio, Porosity, α-CD, β-CD, γ-CD
International Journal of Biological
DOI:10.1016/j.ijbiomac.2016.09.093
Macromolecules,
2017,
94,
Part
A,
181-186;
Wu, L.; Liao, Z.; Liu, M.; Yin, X.; Li, X.; Wang, M.; Lu, X.; Lv, N.; Singh, V.; He, Z.; Li, H.;
Zhang, J.
Fabrication of non-spherical Pickering emulsion droplets by cyclodextrins mediated
molecular self-assembly
Average roundness, Castor oil, Drug delivery system
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2016, 490, 163-172;
DOI:10.1016/j.colsurfa.2015.11.036
Xiao, S.; Si, L.; Tian, Z.; Jiao, P.; Fan, Z.; Meng, K.; Zhou, X.; Wang, H.; Xu, R.; Han, X.; Fu,
G.; Zhang, Y.; Zhang, L.; Zhou, D.
Pentacyclic triterpenes grafted on CD cores to interfere with influenza virus entry:
A dramatic multivalent effect
Copper-catalyzed azide-alkyl cycloaddition reaction, Microwave activation, Oseltamivir,
Oleanolic acid, Hemagglutinin
Biomaterials, 2016, 78, 74-85; DOI:10.1016/j.biomaterials.2015.11.034
Yang, D. H.; Kim, H. J.; Kim, J. K.; Chun, H. J.; Park, K.
Preparation of redox-sensitive β-CD-based nanoparticles with controlled release of
curcumin for improved therapeutic effect on liver cancer in vitro
1-Dodecanethiol, Per-6-thiol-β-CD, Rhodamine B, Anticancer effect on mouse hepatoma
Hepa 1-6 cells, Disulfide bond formation
Journal
of
Industrial
and
DOI:10.1016/j.jiec.2016.09.018
Engineering
Chemistry,
2016,
In
Press;
Yang, K.; Wan, S.; Chen, B.; Gao, W.; Chen, J.; Liu, M.; He, B.; Wu, H.
Dual pH and temperature responsive hydrogels based on β-cyclodextrin derivatives
for atorvastatin delivery
2-Methylacrylic acid modified β-cyclodextrin, 2-Methylacrylic acid, N,N′-methylene
diacrylamide, Swelling rate, Drug release
Carbohydrate Polymers, 2016, 136, 300-306; DOI:10.1016/j.carbpol.2015.08.096
Yang, L.-J.; Xia, S.; Ma, S.-X.; Zhou, S.-Y.; Zhao, X.-Q.; Wang, S.-H.; Li, M.-Y.; Yang, X.-D.
Host–guest system of hesperetin and β-cyclodextrin or its derivatives: Preparation,
characterization, inclusion mode, solubilization and stability
Herbal medicines, Binding behaviors
Materials Science and Engineering: C, 2016, 59, 1016-1024; DOI:10.1016/j.msec.2015.10.037
Yang, Y.; Gao, J.; Ma, X.; Huang, G.
Inclusion complex of tamibarotene with hydroxypropyl-β-cyclodextrin: Preparation,
characterization, in-vitro and in-vivo evaluation
Freeze-drying method, In vivo studies, Solubility, Bioavailability
Asian Journal of Pharmaceutical Sciences, 2016, In Press; DOI:10.1016/j.ajps.2016.08.009
Edited and produced by: CYCLOLAB – page: 19
VOLUME 30. No 10.
Yu, N.; Li, G.; Gao, Y.; Liu, X.; Ma, S.
Stimuli-sensitive hollow spheres from chitosan-graft-β-cyclodextrin for controlled
drug release
Sodium tripolyphosphate, Doxorubicin, Cytotoxicity tests, Polymeric hollow spheres
International
Journal
of
Biological
DOI:10.1016/j.ijbiomac.2016.09.068
Macromolecules,
2016,
In
Press;
Zhang, D.; Zhang, J.; Jiang, K.; Li, K.; Cong, Y.; Pu, S.; Jin, Y.; Lin, J.
Preparation, characterisation and antitumour activity of β-, γ- and HP-β-cyclodextrin
inclusion complexes of oxaliplatin
Job plot, Cytotoxicity
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2016, 152, 501-508;
DOI:10.1016/j.saa.2015.07.088
Zhang, L.; Man, S.; Qiu, H.; Liu, Z.; Zhang, M.; Ma, L.; Gao, W.
Curcumin-cyclodextrin complexes enhanced the anti-cancer effects of curcumin
Saturated aqueous solution method, Cell cycle arrest, Apoptosis
Environmental
Toxicology
DOI:10.1016/j.etap.2016.09.021
and
Pharmacology,
2016,
48,
31-38;
Nagy, N.; Fenyvesi, É.; Kiss, É.
Comparision of polymeric nanosystems containing of highly dispersed curcumin
HPBCD, Soluble β-CD polymer crosslinked with epichlorohydrin, Curcumin-loaded
Pluronic 105 + 123 mixed micelles with β-CD
2nd International Symposium on Scientific and Regulatory Advances in Complex Drugs, October
10-11, 2016, Budapest; Final Program & Book of Abstracts, Klebovich. I.; Crommelin, D. J. A.;
Mühlebach, S.; Shah, V. P. Eds., OOK-Press Ltd., Veszprém, pp. 58., P-2.
4. CDs in Cell Biology
Alawin, O. A.; Ahmed, R. A.; Ibrahim, B. A.; Briski, K. P.; Sylvester, P. W.
Antiproliferative effects of γ-tocotrienol are associated with lipid raft disruption in
HER2-positive human breast cancer cells
Hydroxypropyl-β-cyclodextrin, Accumulation in the lipid raft microdomain, Cytotoxicity,
Caveolin-1
The
Journal
of
Nutritional
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Biochemistry,
2016,
27,
266-277;
Contreras, P. S.; Gonzalez-Zuñiga, M.; González-Hódar, L.; Yáñez, M. J.; Dulcey, A.; Marugan,
J.; Seto, E.; Alvarez, A. R.; Zanlungo, S.
Neuronal gene repression in Niemann–Pick type C models is mediated by the
c-Abl/HDAC2 signaling pathway
Edited and produced by: CYCLOLAB – page: 20
VOLUME 30. No 10.
Treatment with methyl-β-cyclodextrin and vitamin E, Histone deacetylase 2, Tyrosine
kinase c-Abl, Imatinib
Biochimica et Biophysica Acta
- Gene Regulatory Mechanisms, 2016, 1859, 269-279;
DOI:10.1016/j.bbagrm.2015.11.006
Fan, G.; Fan, M.; Wang, Q.; Jiang, J.; Wan, Y.; Gong, T.; Zhang, Z.; Sun, X.
Bio-inspired polymer envelopes around adenoviral vectors to reduce immunogenicity
and improve in vivo kinetics
Cleavable PEGylated β-cyclodextrin-polyethyleneimine conjugate, Innate and adaptive
immunogenicity of adenovirus particles, Cancer gene therapy
Acta Biomaterialia, 2016, 30, 94-105; DOI:10.1016/j.actbio.2015.11.005
Horák, D.; Beneš, M.; Procházková, Z.; Trchová, M.; Borysov, A.; Pastukhov, A.; Paliienko, K.;
Borisova, T.
Effect of O-methyl-β-cyclodextrin-modified magnetic nanoparticles on the uptake and
extracellular level of L-glutamate in brain nerve terminals
Extraction
of
cholesterol
from
the
plasma
membrane,
Triethoxy(3- isocyanatopropyl)silane, Magnetic manipulation, Maghemite nanoparticles
Colloids and Surfaces B: Biointerfaces, 2017, 149, 64-71; DOI:10.1016/j.colsurfb.2016.10.007
Longobardi, V.; Albero, G.; Canditiis, C. D.; Salzano, A.; Natale, A.; Balestrieri, A.; Neglia, G.;
Campanile, G.; Gasparrini, B.
Cholesterol-loaded cyclodextrins prevent
(Bubalus bubalis) cryopreserved sperm
cryocapacitation
damages
in
buffalo
Viability/capacitation status, Fertilizing ability
Theriogenology, 2016, In Press; DOI:10.1016/j.theriogenology.2016.09.048
Niyonzima, N.; Halvorsen, B.; Sporsheim, B.; Garred, P.; Aukrust, P.; Mollnes, T. E.;
Espevik, T.
Complement activation by cholesterol crystals triggers a subsequent cytokine
response
2-Hydroxypropyl-β-cyclodextrin, Atherosclerosis, Inflammasome, Interleukin-1β
Molecular Immunology, 2016, In Press; DOI:10.1016/j.molimm.2016.09.019
Pratelli, A.; Colao, V.
Critical role of the lipid rafts in caprine herpesvirus type 1 infection in vitro
Cholesterol depletion by methyl-β-cyclodextrin, Plasma membrane, Infectivity
Virus Research, 2016, 211, 186-193; DOI:10.1016/j.virusres.2015.10.013
Rajoriya, J.; Prasad, J.; Ramteke, S.; Perumal, P.; Ghosh, S.; Singh, M.; Pande, M.;
Srivastava, N.
Enriching membrane cholesterol improves stability and cryosurvival of buffalo
spermatozoa
Cholesterol-loaded-cyclodextrins, Phospholipids, Induced acrosome reaction, Membrane
fluidity, Membrane integrity
Animal Reproduction Science, 2016, 164, 72-81; DOI:10.1016/j.anireprosci.2015.11.014
Edited and produced by: CYCLOLAB – page: 21
VOLUME 30. No 10.
Reis, A. H.; Moreno, M. M.; Maia, L. A.; Oliveira, F. P.; Santos, A. S.; Abreu, J. G.
Cholesterol-rich membrane microdomains
gradient during Xenopus development
modulate
Wnt/β-catenin
morphogen
Disruption by methyl-beta-cyclodextrin, Head development, Embryo
Mechanisms of Development, 2016, 142, 30-39; DOI:10.1016/j.mod.2016.09.001
Takashima, A.; Fukuda, D.; Tanaka, K.; Higashikuni, Y.; Hirata, Y.; Nishimoto, S.; Yagi, S.;
Yamada, H.; Soeki, T.; Wakatsuki, T.; Taketani, Y.; Shimabukuro, M.; Sata, M.
Combination of n-3 polyunsaturated fatty acids reduces atherogenesis
apolipoprotein E-deficient mice by inhibiting macrophage activation
in
Lipid raft disruption by methyl-β-cyclodextrin, Inflammation, Toll-like receptor 4
Atherosclerosis, 2016, 254, 142-150; DOI:10.1016/j.atherosclerosis.2016.10.002
Zeuner, M.-T.; Krüger, C. L.; Volk, K.; Bieback, K.; Cottrell, G. S.; Heilemann, M.; Widera, D.
Biased signalling is an essential feature of TLR4 in glioma cells
Treatment with
Biased agonism
methyl-β-cyclodextrin,
Biochimica
et
Biophysica
Acta
DOI:10.1016/j.bbamcr.2016.09.016
-
Lipopolysaccharides,
Molecular
Cell
Inflammatory
Research,
2016,
In
balance,
Press;
5. CDs in Food, Cosmetics and Agrochemicals
Abarca, R. L.; Rodríguez, F. J.; Guarda, A.; Galotto, M. J.; Bruna, J. E.
Characterization of beta-cyclodextrin inclusion complexes containing an essential oil
component
Active packaging, Co-precipitation method, 2-Nonanone, Antimicrobial
Food Chemistry, 2016, 196, 968-975; DOI:10.1016/j.foodchem.2015.10.023
Abdelmalek, L.; Fatiha, M.; Leila, N.; Mouna, C.; Nora, M.; Djameleddine, K.
Computational study of inclusion complex formation between carvacrol and βcyclodextrin in vacuum and in water: Charge transfer, electronic transitions and NBO
analysis
Hydrophobic interaction, Hydrogen bonding, PM3, ONIOM2, DFT, TD-DFT
Journal of Molecular Liquids, 2016, 224, Part A, 62-71; DOI:10.1016/j.molliq.2016.09.053
Balto, A. S.; Lapis, T. J.; Silver, R. K.; Ferreira, A. J.; Beaudry, C. M.; Lim, J.; Penner, M. H.
On the use of differential solubility in aqueous ethanol solutions to narrow the DP
range of food-grade starch hydrolysis products
Corn syrup solids, Maltooligosaccharides, Maltopolysaccharides, Ethanol-fractionation,
Dispersity
Food Chemistry, 2016, 197, Part A, 872-880; DOI:10.1016/j.foodchem.2015.10.120
Edited and produced by: CYCLOLAB – page: 22
VOLUME 30. No 10.
Budryn, G.; Zaczyńska, D.; Pałecz, B.; Rachwał-Rosiak, D.; Belica, S.; den Haan, H.;
Peña-García, J.; Pérez-Sánchez, H.
Interactions of free and encapsulated hydroxycinnamic acids from green coffee with
egg ovalbumin, whey and soy protein hydrolysates
Proteolytic digestion, Availability from processed food, β-Cyclodextrin
LWT - Food Science and Technology, 2016, 65, 823-831; DOI:10.1016/j.lwt.2015.09.001
Ceborska, M.
Structural investigation of the β-cyclodextrin complexes with linalool and
isopinocampheol – Influence of monoterpenes cyclicity on the host–guest
stoichiometry
Chiral terpene alcohols, 2:2 stoichiometry
Chemical Physics Letters, 2016, 651, 192-197; DOI:10.1016/j.cplett.2016.03.051
Chen, G.; Liu, B.
Cellulose sulfate based film with slow-release antimicrobial properties prepared by
incorporation of mustard essential oil and β-cyclodextrin
Edible film, Coating for packaging
Food Hydrocolloids, 2016, 55, 100-107; DOI:10.1016/j.foodhyd.2015.11.009
Cheong, A. M.; Tan, K. W.; Tan, C. P.; Nyam, K. L.
Kenaf (Hibiscus cannabinus L.) seed oil-in-water Pickering nanoemulsions stabilised
by mixture of sodium caseinate, Tween 20 and β-cyclodextrin
Emulsifier mixtures, Synergistic effect
Food Hydrocolloids, 2016, 52, 934-941; DOI:10.1016/j.foodhyd.2015.09.005
Gong, L.; Li, T.; Chen, F.; Duan, X.; Yuan, Y.; Zhang, D.; Jiang, Y.
An inclusion complex of eugenol into β-cyclodextrin:
physicochemical and antifungal characterization
Preparation,
and
Postharvest fresh litchi fruits, In vivo assays, Damage to hyphal and/or sporangiophore
cell walls and membrane structures
Food Chemistry, 2016, 196, 324-330; DOI:10.1016/j.foodchem.2015.09.052
Ho, B. T.; Hofman, P. J.; Joyce, D. C.; Bhandari, B. R.
Uses of an innovative ethylene-α-cyclodextrin inclusion complex powder for ripening
of mango fruit
Fruit colour and firmness, In-transit ripening
Postharvest
Biology
and
DOI:10.1016/j.postharvbio.2015.11.005
Technology,
2016,
113,
77-86;
Hodyna, D.; Bardeau, J.-F.; Metelytsia, L.; Riabov, S.; Kobrina, L.; Laptiy, S.; Kalashnikova,
L.; Parkhomenko, V.; Tarasyuk, O.; Rogalsky, S.
Efficient antimicrobial activity and reduced toxicity of 1-dodecyl-3-methylimidazolium
tetrafluoroborate ionic liquid/β-cyclodextrin complex
Imidazolium ionic liquid, Acute toxicity studies
Chemical Engineering Journal, 2016, 284, 1136-1145; DOI:10.1016/j.cej.2015.09.041
Edited and produced by: CYCLOLAB – page: 23
VOLUME 30. No 10.
Kfoury, M.; Sahraoui, A. L.-H.; Bourdon, N.; Laruelle, F.; Fontaine, J.; Auezova, L.;
Greige-Gerges, H.; Fourmentin, S.
Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in
cyclodextrins
Freeze-dried inclusion complexes, Phytopathogenic fungi, Encapsulation efficiency
Food Chemistry, 2016, 196, 518-525; DOI:10.1016/j.foodchem.2015.09.078
Laokuldilok, N.; Thakeow, P.; Kopermsub, P.; Utama-ang, N.
Optimisation of microencapsulation of turmeric extract for masking flavour
Binary blend of wall materials, Brown rice flour, β-CD, HPLC, Headspace GC–MS
Food Chemistry, 2016, 194, 695-704; DOI:10.1016/j.foodchem.2015.07.150
Li, J. F.; Zhang, J. X.; Wang, Z. G.; Yao, Y. J.; Han, X.; Zhao, Y. L.; Liu, J. P.; Zhang, S. Q.
Identification of a cyclodextrin inclusion complex of antimicrobial peptide CM4 and its
antimicrobial activity
Novel food preservative, Susceptibility to proteinases, β-Cyclodextrin, Antibacterial assay,
Stability
Food Chemistry, 2016, In Press; DOI:10.1016/j.foodchem.2016.10.040
Liu, M.; Zheng, Y.; Wang, C.; Xie, J.; Wang, B.; Wang, Z.; Han, J.; Sun, D.; Niu, M.
Improved stability of (+)-catechin and (−)-epicatechin by complexing
hydroxypropyl-β-cyclodextrin: Effect of pH, temperature and configuration
with
HP-β-CD, Protection effect, Isothermal titration calorimetry, Fluorescence spectroscopy,
Stability
Food Chemistry, 2016, 196, 148-154; DOI:10.1016/j.foodchem.2015.09.016
Mendes, A. C.; Stephansen, K.; Chronakis, I. S.
Electrospinning of food proteins and polysaccharides
Biopolymers, Nanofibers, Microfibers
Food Hydrocolloids, 2016, In Press; DOI:10.1016/j.foodhyd.2016.10.022
Navarro, R.; Arancibia, C.; Herrera, M. L.; Matiacevich, S.
Effect of type of encapsulating agent on physical properties of edible films based on
alginate and thyme oil
Organoleptic characteristics, Trehalose, β-Cyclodextrin, Tween 20, Emulsions
Food and Bioproducts Processing, 2016, 97, 63-75; DOI:10.1016/j.fbp.2015.11.001
Poór, M.; Matisz, G.; Kunsági-Máté, S.; Derdák, D.; Szente, L.; Lemli, B.
Fluorescence spectroscopic investigation of the interaction of citrinin with native and
chemically modified cyclodextrins
Nephrotoxic mycotoxin, Contaminant of different foods
β-cyclodextrins, Fluorescence enhancement, Toxin binder
and
drinks,
Journal of Luminescence, 2016, 172, 23-28; DOI:10.1016/j.jlumin.2015.11.011
Edited and produced by: CYCLOLAB – page: 24
Methylated
VOLUME 30. No 10.
Rutenberg, R.; Bernstein, S.; Paster, N.; Fallik, E.; Poverenov, E.
Antimicrobial films based on cellulose-derived hydrocolloids. A synergetic effect of
host–guest interactions on quality and functionality
Fresh harvested wheat grains,
β-Cyclodextrin, Propionic acid
Colloids
and
Surfaces
B:
DOI:10.1016/j.colsurfb.2015.06.022
Bio-active
hydrocolloids,
Biointerfaces,
2016,
Controlled
137,
release,
138-145;
Sukhtezari, S.; Almasi, H.; Pirsa, S.; Zandi, M.; Pirouzifard, M.
Development of bacterial cellulose based slow-release active films by incorporation of
Scrophularia striata Boiss. extract
Intrinsic compactness, Food active packaging, β-Cyclodextrin, Physical properties,
Antioxidant activity, Controlled release
Carbohydrate Polymers, 2017, 156, 340-350; DOI:10.1016/j.carbpol.2016.09.058
Wen, P.; Zhu, D.-H.; Feng, K.; Liu, F.-J.; Lou, W.-Y.; Li, N.; Zong, M.-H.; Wu, H.
Fabrication of electrospun polylactic acid nanofilm incorporating cinnamon essential
oil/β-cyclodextrin inclusion complex for antimicrobial packaging
Co-precipitation
concentration
method,
Minimum
inhibitory
concentration,
Minimum
bactericidal
Food Chemistry, 2016, 196, 996-1004; DOI:10.1016/j.foodchem.2015.10.043
Wen, P.; Zhu, D.-H.; Wu, H.; Zong, M.-H.; Jing, Y.-R.; Han, S.-Y.
Encapsulation of cinnamon essential oil in electrospun nanofibrous film for active
food packaging
Prolong the shelf-life of strawberry, Polyvinyl alcohol, Antimicrobial activity
Food Control, 2016, 59, 366-376; DOI:10.1016/j.foodcont.2015.06.005
Zhang, S.; Zhang, H.; Xu, Z.; Wu, M.; Xia, W.; Zhang, W.
Chimonanthus praecox extract/cyclodextrin inclusion complexes: Selective inclusion,
enhancement of antioxidant activity and thermal stability
Flavonoids, Food additive, Natural antioxidants
Industrial Crops and Products, 2017, 95, 60-65; DOI:10.1016/j.indcrop.2016.09.033
Zolfaghari, G.
β-Cyclodextrin incorporated nanoporous carbon: Host–guest inclusion for removal of
p-nitrophenol and pesticides from aqueous solutions
1,4-Phenylene diisocyanate linker, DDT, DDD, DDE, Adsorption
Chemical Engineering Journal, 2016, 283, 1424-1434; DOI:10.1016/j.cej.2015.08.110
Edited and produced by: CYCLOLAB – page: 25
VOLUME 30. No 10.
6. CDs for other Industrial Applications
Abdolmaleki, A.; Mallakpour, S.; Mahmoudian, M.; Sabzalian, M. R.
A new polyamide adjusted triazinyl-β-cyclodextrin side group embedded magnetic
nanoparticles for bacterial capture
One-pot co-precipitation, Triphenyl phosphite, Monochlorotriazinyl-β-cyclodextrin,
Nano-adsorbent, Poly(isophthalamide), Direct polycondensation
Chemical Engineering Journal, 2016, In Press; DOI:10.1016/j.cej.2016.10.063
Cao, H.; Jiang, Y.; Zhang, H.; Nie, K.; Lei, M.; Deng, L.; Wang, F.; Tan, T.
Enhancement of methanol resistance of Yarrowia lipolytica lipase 2 using βcyclodextrin as an additive: Insights from experiments and molecular dynamics
simulation
Enzymatic biodiesel production, Surface modification
Enzyme and Microbial Technology, 2016, In Press; DOI:10.1016/j.enzmictec.2016.10.007
Celebioglu, A.; Sen, H. S.; Durgun, E.; Uyar, T.
Molecular entrapment of
cyclodextrin nanofibers
volatile
organic
compounds
(VOCs)
by
electrospun
HP-βCD, HP-γCD, Aniline, Benzene, Electrospinning, Air filtration
Chemosphere, 2016, 144, 736-744; DOI:10.1016/j.chemosphere.2015.09.029
Goulas, A.; Haudin, C.-S.; Bergheaud,
Bourdat-Deschamps, M.; Benoit, P.
V.;
Dumény,
V.;
Ferhi,
S.;
Nélieu,
S.;
A new extraction method to assess the environmental availability of ciprofloxacin in
agricultural soils amended with exogenous organic matter
Borax, Na2EDTA,
fraction level
2-Hydroxypropyl-β-cyclodextrin,
Soil/compost
mixtures,
Available
Chemosphere, 2016, 165, 460-469; DOI:10.1016/j.chemosphere.2016.09.040
Jiang, L.; Liu, Y.; Liu, S.; Hu, X.; Zeng, G.; Hu, X.; Liu, S.; Liu, S.; Huang, B.; Li, M.
Fabrication of β-cyclodextrin/poly(l-glutamic acid) supported magnetic graphene
oxide and its adsorption behavior for 17β-estradiol
Film diffusion, Intraparticle diffusion, Regeneration experiments
Chemical Engineering Journal, 2017, 308, 597-605; DOI:10.1016/j.cej.2016.09.067
Kubli, M. R.; Yatsimirsky, A. K.
Phosphodiester
cyclodextrins
cleavage
by
trivalent
lanthanides
in
the
presence
of
native
Binuclear polyhydroxocomplexes, Metal–β-CD and phosphodiester–β-CD interactions,
Kinetics, Hydrolysis, Catalysis
Inorganica Chimica Acta, 2016, 440, 9-15; DOI:10.1016/j.ica.2015.10.039
Edited and produced by: CYCLOLAB – page: 26
VOLUME 30. No 10.
Kuklin, S.; Maximov, A.; Zolotukhina, A.; Karakhanov, E.
New approach for highly selective hydrogenation of phenol to cyclohexanone:
Combination of rhodium nanoparticles and cyclodextrins
Ionic liquid
Catalysis Communications, 2016, 73, 63-68; DOI:10.1016/j.catcom.2015.10.005
Lannoy, A.; Kania, N.; Bleta, R.; Fourmentin, S.; Machut-Binkowski, C.; Monflier, E.;
Ponchel, A.
Photocatalysis of volatile organic compounds in water: Towards a deeper
understanding of the role of cyclodextrins in the photodegradation of toluene over
titanium dioxide
α-CD, β-CD, γ-CD, RAME-β-CD, Delay in the photodegradation process, Adsorption,
Inclusion complex
Journal of Colloid and Interface Science, 2016, 461, 317-325; DOI:10.1016/j.jcis.2015.09.022
Li, X.; Shi, J.; Wu, K.; Luo, F.; Zhang, S.; Guan, X.; Lu, M.
A novel pH-sensitive aqueous supramolecular structured photoinitiator comprising of
6-modified per-methylated β-cyclodextrin and 1-hydroxycyclohexyl phenyl ketone
6I-Acryloyl ethylenediamine-6I-deoxy-2I,3I-di-O-methyl-hexakis (2II−VII, 3II−VII, 6II−VII-tri-Omethyl)-β-cyclodextrin, Water-souble
Journal of Photochemistry and Photobiology
DOI:10.1016/j.jphotochem.2016.10.001
A:
Chemistry,
2017,
333,
18-25;
Liu, J.; Xiao, Y.; Liao, K.-S.; Chung, T.-S.
Highly permeable and aging resistant 3D architecture from polymers of intrinsic
microporosity incorporated with beta-cyclodextrin
Gas separation performance, CO2 permeability, Physical aging
Journal of Membrane Science, 2017, 523, 92-102; DOI:10.1016/j.memsci.2016.10.001
Liu, Y.; Zou, C.; Li, C.; Lin, L.; Chen, W.
Evaluation of β-cyclodextrin–polyethylene glycol as green scale inhibitors for
produced-water in shale gas well
Aggregation of calcium carbonate crystals, Environmentally friendly, Water treatment
Desalination, 2016, 377, 28-33; DOI:10.1016/j.desal.2015.09.007
Okamoto, Y.; Ward, T.
Supramolecular enzyme mimics
Review, Artificial metalloenzyme, Cyclodextrin-based artificial enzymes, Supramolecular
cages, Proteins, DNA, Molecular recognition, Dative and supramolecular anchoring
Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier, 2016;
DOI:10.1016/B978-0-12-409547-2.12551-X
Peng, K.; Chen, C.; Pan, W.; Liu, W.; Wang, Z.; Zhu, L.
Preparation
and
properties
of
β-cyclodextrin/4,4′-diphenylmethane
diisocyanate/polyethylene glycol (β-CD/MDI/PEG) crosslinking copolymers as
polymeric solid–solid phase change materials
Edited and produced by: CYCLOLAB – page: 27
VOLUME 30. No 10.
Crosslinking density, Thermal energy storage
Solar
Energy
Materials
and
DOI:10.1016/j.solmat.2015.10.031
Solar
Cells,
2016,
145,
Part
3,
238-247;
Takeshita, T.; Umeda, T.; Hara, M.
Fabrication of a dye-sensitized solar cell containing a noncarboxylated spiropyranderived photomerocyanine with cyclodextrin
Carboxymethyl-β-cyclodextrin sodium
Photoresponsivity, Inclusion complex
salt
Journal of Photochemistry and Photobiology
DOI:10.1016/j.jphotochem.2016.10.017
(CM-β-CD),
A:
Photovoltaic
Chemistry,
2017,
conversion,
333,
87-91;
Optimization study on continuous separation of equol enantiomers
enantioselective liquid–liquid extraction in centrifugal contactor separators
using
Tang, K.; Wang, Y.; Zhang, P.; Huang, Y.; Hua, J.
Multistage enantioselective liquid–liquid extraction, HP-β-CD, Countercurrent cascade of
centrifugal contactor separators, Simulation, Chiral separation
Process Biochemistry, 2016, 51, 113-123; DOI:10.1016/j.procbio.2015.11.021
Vasconcelos, D. A.; Kubota, T.; Santos, D. C.; Araujo, M. V.; Teixeira, Z.; Gimenez, I. F.
Preparation of Aun quantum clusters with catalytic activity in β-cyclodextrin
polyurethane nanosponges
1,6-Hexamethylene diisocyanate, Core-etching of glutathione-capped Au nanoparticles,
Reduction of 4-nitrophenol
Carbohydrate Polymers, 2016, 136, 54-62; DOI:10.1016/j.carbpol.2015.09.010
Wang, L.; Chen, B.; Meng, Z.; Luo, B.; Wang, X.; Zhao, Y.
High performance carbon-coated lithium zinc titanate as an anode material for
lithium-ion batteries
β-CD as the carbon source
Electrochimica Acta, 2016, 188, 135-144; DOI:10.1016/j.electacta.2015.11.124
Xing, W.; Li, C.; Chen, G.; Han, Z.; Zhou, Y.; Hu, Y.; Meng, Q.
Incorporating a novel metal-free interlayer into g-C3N4 framework for efficiency
enhanced photocatalytic H2 evolution activity
Thermal polymerization of the β-cyclodextrin and melamine, Charge transfer
Applied Catalysis B: Environmental, 2017, 203, 65-71; DOI:10.1016/j.apcatb.2016.09.075
Yu, L.; Vazquez-Cuevas, G.; Duan, L.; Semple, K. T.
Buffered cyclodextrin extraction of 14C-phenanthrene from black carbon amended soil
Soil organic matter, Hydroxylpropyl-β-cyclodextrin extraction, Mineralization, pH
Environmental Technology & Innovation, 2016, 6, 177-184; DOI:10.1016/j.eti.2016.09.002
Zhao, F.; Repo, E.; Meng, Y.; Wang, X.; Yin, D.; Sillanpää, M.
An EDTA-β-cyclodextrin material for the adsorption of rare earth elements and its
Edited and produced by: CYCLOLAB – page: 28
VOLUME 30. No 10.
application in preconcentration of rare earth elements in seawater
La(III), Ce(III), and Eu(III), Multi-component adsorption
Journal of Colloid and Interface Science, 2016, 465, 215-224; DOI:10.1016/j.jcis.2015.11.069
7. CDs in Sensing and Analysis
Cârcu-Dobrin, M.; Budău, M.; Hancu, G.; Gagyi, L.; Rusu, A.; Kelemen, H.
Enantioselective analysis of fluoxetine in pharmaceutical formulations by capillary
zone electrophoresis
Cyclodextrin modified capillary electrophoresis, TRIMEB, Selective serotonin reuptake
inhibitor, Chiral separation
Saudi Pharmaceutical Journal, 2016, In Press; DOI:10.1016/j.jsps.2016.09.007
Fanali, S.
Nano-liquid chromatography applied to enantiomers separation
Chiral selectors, Cyclodextrins, Glycopeptide antibiotics, Polysaccharides
Journal of Chromatography A, 2016, In Press; DOI:10.1016/j.chroma.2016.10.028
Gao, J.; Zhang, S.; Liu, M.; Tai, Y.; Song, X.; Qian, Y.; Song, H.
Synergistic combination of cyclodextrin edge-functionalized graphene and multiwall
carbon nanotubes as conductive bridges toward enhanced sensing response of
supramolecular recognition
Dopamine, Uric acid, Tryptophan, Oxidation peak currents, β-Cyclodextrin, Conductive
network
Electrochimica Acta, 2016, 187, 364-374; DOI:10.1016/j.electacta.2015.11.073
Gao, Y.-q.; Li, T.; Wang, X.-t.; Qi, Y.-c.; Wen, Q.; Shen, J.-w.; Qiu, L.-y.; Wan-zhi, M.
Optical sensing composites for cysteine detection: Combining rhodamine-based
chemosensors with up-conversion nanocrystals
Nanocrystals, α-Cyclodextrin, Emission decay lifetime
Sensors and Actuators B: Chemical, 2016, In Press; DOI:10.1016/j.snb.2016.09.106
Garrido, J.; Rahemi, V.; Borges, F.; Brett, C.; Garrido, E.
Carbon nanotube β-cyclodextrin modified electrode as enhanced sensing platform for
the determination of fungicide pyrimethanil
Pome fruit, Electrocatalytic oxidation, Voltammetric sensor
Food Control, 2016, 60, 7-11; DOI:10.1016/j.foodcont.2015.07.001
Izumi, K.; Utiyama, M.; Maruo, Y. Y.
A porous glass-based ozone sensing chip impregnated with potassium iodide and
α-cyclodextrin
Supressing volatilization of iodine
Sensors and Actuators B: Chemical, 2017, 241, 116-122; DOI:10.1016/j.snb.2016.10.026
Edited and produced by: CYCLOLAB – page: 29
VOLUME 30. No 10.
Kai, S.; Cheng-Wen, L.; Yi-Nan, D.; Tian, L.; Guang-Ye, W.; Jing-Mei, L.; Li-Quan, G.
An optical sensing composite for cysteine detection using up-conversion
nanoparticles and a rhodamine-derived chemosensor: Construction, characterization,
photophysical feature and sensing performance
α-Cyclodextrin, Excitation host
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2016, 155, 81-87;
DOI:10.1016/j.saa.2015.11.009
Kan, X.; Zhang, T.; Zhong, M.; Lu, X.
CD/AuNPs/MWCNTs based electrochemical sensor for quercetin dual-signal detection
Mercapto-β-cyclodextrin,
Gold
nanoparticles,
Hydroquinone, Electrochemical marker, Sensitivity
Multi-walled
carbon
nanotubes,
Biosensors and Bioelectronics, 2016, 77, 638-643; DOI:10.1016/j.bios.2015.10.033
Khodaveisi, J.; Dadfarnia, S.; Shabani, A. M. H.; Saberi, D.
Colorimetric determination of nabumetone based on localized surface plasmon
resonance of functionalized gold nanoparticles as a chemical sensor
Aggregation of the thiolated β-cyclodextrin functionalized gold nanoparticles
Sensors and Actuators B: Chemical, 2016, In Press; DOI:10.1016/j.snb.2016.09.110
Li, J.; Wang, X.; Duan, H.; Wang, Y.; Bu, Y.; Luo, C.
Based on magnetic graphene oxide highly sensitive and selective imprinted sensor for
determination of sunset yellow
Ionic liquid, Gold nanoparticles, Imprinted electrochemical sensor
Talanta, 2016, 147, 169-176; DOI:10.1016/j.talanta.2015.09.056
Luo, C.; Dong, Q.; Qian, M.; Zhang, H.
Thermosensitive polymer-modified gold nanoparticles with sensitive fluorescent
properties
Low critical solution temperature, Solvent, β-CD
Chemical Physics Letters, 2016, 664, 89-95; DOI:10.1016/j.cplett.2016.10.019
Maniyazagan, M.; Rameshwaran, C.; Mariadasse, R.; Jeyakanthan, J.; Premkumar, K.;
Stalin, T.
Fluorescence sensor for Hg2+ and Fe3+ ions using 3,3′–dihydroxybenzidine:
α-cyclodextrin supramolecular complex: Characterization, in-silico and cell imaging
study
3,3′–Dihydroxybenzidine:α–cyclodextrin,
Fluorescence enhancement, Bio-imaging
Co-precipitation,
Kneading
method,
Sensors and Actuators B: Chemical, 2016, In Press; DOI:10.1016/j.snb.2016.09.093
Miękus, N.; Olędzka, I.; Plenis, A.; Kowalski, P.; Bień, E.; Miękus, A.; Krawczyk, M. A.;
Adamkiewicz-Drożyńska, E.; Bączek, T.
Determination of urinary biogenic amines’ biomarker profile in neuroblastoma and
pheochromocytoma patients by MEKC method with preceding dispersive liquid–liquid
microextraction
Edited and produced by: CYCLOLAB – page: 30
VOLUME 30. No 10.
α-Cyclodextrin-modified micellar electrokinetic chromatography, Cancer biomarkers
Journal
of
Chromatography
DOI:10.1016/j.jchromb.2016.10.007
B,
2016,
1036–1037,
114-123;
Moreira, F. T.; Sales, M. G. F.
Smart naturally plastic antibody based
β-amyloid-42 soluble oligomer detection
on
poly(α-cyclodextrin)
polymer
for
Protein imprinting, Peptide biomarker, Alzheimer disease, α-CD, Natural building blocks,
Screen-printed electrodes, Biosensor
Sensors and Actuators B: Chemical, 2017, 240, 229-238; DOI:10.1016/j.snb.2016.08.150
Palanisamy, S.; Sakthinathan, S.; Chen, S.-M.; Thirumalraj, B.; Wu, T.-H.; Lou, B.-S.; Liu, X.
Preparation of β-cyclodextrin entrapped graphite composite for sensitive detection of
dopamine
Electrochemical sensor, Screen-printed carbon electrode, Differential pulse voltammetry
Carbohydrate Polymers, 2016, 135, 267-273; DOI:10.1016/j.carbpol.2015.09.008
Palanisamy, S.; Thirumalraj, B.; Chen, S.-M.
A novel amperometric nitrite sensor based on screen printed carbon electrode
modified with graphite/β-cyclodextrin composite
Catalytic activity,
Amperometry
Oxidation
overpotential,
Journal
of
Electroanalytical
DOI:10.1016/j.jelechem.2015.11.017
Sensitivity,
Chemistry,
Electrochemical
sensor,
760,
97-104;
2016,
Qin, Q.; Bai, X.; Hua, Z.
Electropolymerization of a conductive β-cyclodextrin polymer on reduced graphene
oxide modified screen-printed electrode for simultaneous determination of ascorbic
acid, dopamine and uric acid
Cyclic voltammetry, Differential pulse voltammetry, Sensor
Journal
of
Electroanalytical
DOI:10.1016/j.jelechem.2016.10.004
Chemistry,
2016,
782,
50-58;
Song, C.; Yang, X.; Wang, K.; Wang, Q.; Liu, J.; Huang, J.; Zhou, M.; Guo, X.
Steric hindrance regulated supramolecular assembly between β-cyclodextrin polymer
and pyrene for alkaline phosphatase fluorescent sensing
Pyrene attached on mononucleotides
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2016, 156, 131-137;
DOI:10.1016/j.saa.2015.12.001
Szabó, Z.-I.; Tóth, G.; Völgyi, G.; Komjáti, B.; Hancu, G.; Szente, L.; Sohajda, T.; Béni, S.;
Muntean, D.-L.; Noszál, B.
Chiral separation of asenapine enantiomers by capillary electrophoresis and
characterization of cyclodextrin complexes by NMR spectroscopy, mass spectrometry
and molecular modeling
β-CD, Antipsychotic, Experimental design
Journal
of
Pharmaceutical
and
DOI:10.1016/j.jpba.2015.09.022
Edited and produced by: CYCLOLAB – page: 31
Biomedical
Analysis,
2016,
117,
398-404;
VOLUME 30. No 10.
Tang, J.; Pang, L.; Zhou, J.; Zhang, S.; Tang, W.
Per(3-chloro-4-methyl)phenylcarbamate cyclodextrin clicked stationary phase for
chiral separation in multiple modes high-performance liquid chromatography
Aromatic alcohols, Flavonoids,
stationary phase
β-Blockers, Amino
acids,
Enantioselectivity,
Chiral
Analytica Chimica Acta, 2016, In Press; DOI:10.1016/j.aca.2016.10.015
Teka, S.; Gaied, A.; Jaballah, N.; Xiaonan, S.; Majdoub, M.
Thin sensing layer based on semi-conducting β-cyclodextrin rotaxane for toxic metals
detection
Hg2+, Cu2+ and Pb2+ cations, Impedance spectroscopy, Electrochemical properties
Materials Research Bulletin, 2016, 74, 248-257; DOI:10.1016/j.materresbull.2015.10.040
Toot, J.; Donegan, M.; Orens, P.; Gibbs, A.; Neely, A.; Bennett, M.; Boggs, J.; Atterson, P.
Bioanalytical analysis of plasma cocaine exposure in a preliminary self-administration
study utilizing different concentrations of cyclodextrin
Journal
of
Pharmacological
DOI:10.1016/j.vascn.2016.02.003
and
Toxicological
Methods,
2016,
81,
335;
Wang, S.; Han, C.; Wang, S.; Bai, L.; Li, S.; Luo, J.; Kong, L.
Development of a high speed counter-current chromatography system with Cu(II)chiral ionic liquid complexes and hydroxypropyl-β-cyclodextrin as dual chiral
selectors for enantioseparation of naringenin
[1-Butyl-3-methylimidazolium][L-Pro]
Journal of Chromatography A, 2016, In Press; DOI:10.1016/j.chroma.2016.10.036
Xu, Q.; Tan, S.; Petrova, K.
Development and validation of a hydrophilic interaction chromatography method
coupled with a charged aerosol detector for quantitative analysis of nonchromophoric
α–hydroxyamines, organic impurities of metoprolol
Comprehensive column screening, HILIC stationary phases, Metoprolol succinate
Journal
of
Pharmaceutical
and
DOI:10.1016/j.jpba.2015.11.002
Biomedical
Analysis,
2016,
118,
242-250;
Yang, L.; Zhao, H.; Li, Y.; Zhang, Y.; Ye, H.; Zhao, G.; Ran, X.; Liu, F.; Li, C.-P.
Insights into the recognition of dimethomorph by disulfide bridged β–cyclodextrin
and its high selective fluorescence sensing based on indicator displacement assay
Safranine T, SS–β–CD functionalized reduced graphene oxide, “Switch–on” fluorescence
response, Graphene
Biosensors and Bioelectronics, 2017, 87, 737-744; DOI:10.1016/j.bios.2016.09.044
Yang, M.; Wu, X.; Xi, X.; Zhang, P.; Yang, X.; Lu, R.; Zhou, W.; Zhang, S.; Gao, H.; Li, J.
Using β-cyclodextrin/attapulgite-immobilized ionic liquid as sorbent in dispersive
solid-phase microextraction to detect the benzoylurea insecticide contents of honey
and tea beverages
Enrichment factors, High-performance liquid chromatography, Plackett–Burman design
Food Chemistry, 2016, 197, Part B, 1064-1072; DOI:10.1016/j.foodchem.2015.11.107
Edited and produced by: CYCLOLAB – page: 32
VOLUME 30. No 10.
Yi, Y.; Zhu, G.; Wu, X.; Wang, K.
Highly sensitive and simultaneous electrochemical determination of 2-aminophenol
and
4-aminophenol
based
on
poly(l-arginine)-β-cyclodextrin/carbon
nanotubes@graphene nanoribbons modified electrode
Core-shell heterostructure
Biosensors and Bioelectronics, 2016, 77, 353-358; DOI:10.1016/j.bios.2015.09.052
Edited and produced by: CYCLOLAB – page: 33
Edited and produced by: CYCLOLAB
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