gamma cyclodextrins


Summary: Cyclic GLUCANS consisting of eight (8) glucopyranose units linked by 1,4-glycosidic bonds.

Top Publications

  1. Wong J, Yuen K. Inclusion complexation of artemisinin with alpha-, beta-, and gamma-cyclodextrins. Drug Dev Ind Pharm. 2003;29:1035-44 pubmed
    ..The respective estimated percentage of ART complexed by the CyDs were 85%, 40%, and 12%. ..
  2. Fenyvesi E, Gruiz K, Verstichel S, De Wilde B, Leitgib L, Csabai K, et al. Biodegradation of cyclodextrins in soil. Chemosphere. 2005;60:1001-8 pubmed
    ..In the field experiments, the depletion of RAMEB to about 40% of its initial level was observed for a period of 2 years in hydrocarbon-contaminated soils of high organic matter and cell concentration. ..
  3. Liao W, Lin C, Chen C, Kuo C, Liu Y, Wu J, et al. Enantioseparation of phenothiazines in CD-modified CZE using single isomer sulfated CD as a chiral selector. Electrophoresis. 2007;28:3922-9 pubmed
    ..Comparative studies on the enantioseparations of phenothiazines with single CD and dual CD systems containing SI-S-beta-CD and randomly sulfate-substituted beta-CD (MI-S-beta-CD) were made. ..
  4. Naguib M. Sugammadex: another milestone in clinical neuromuscular pharmacology. Anesth Analg. 2007;104:575-81 pubmed
    ..The clinical use of sugammadex promises to eliminate many of the shortcomings in our current practice with regard to the antagonism of rocuronium and possibly other steroidal neuromuscular blockers. ..
  5. Higashi T, Hirayama F, Yamashita S, Misumi S, Arima H, Uekama K. Slow-release system of pegylated lysozyme utilizing formation of polypseudorotaxanes with cyclodextrins. Int J Pharm. 2009;374:26-32 pubmed publisher
  6. Cameron K, Fielding L, Palin R, Uhrin D. NMR spectra and dynamics of the sodium salt of per(6-thiobenzoic acid)-gamma-cyclodextrin. Magn Reson Chem. 2005;43:647-53 pubmed
    ..On the NMR time-scale, the cyclodextrin is highly dynamic; the lower temperature minimum energy conformation has one of the aromatic rings self-complexed and a distorted cyclodextrin torus. ..
  7. Sridharan G, Gaudreau S, Dalstein L, Huiban C, Lejeune A, Fragata M. Effect of alpha-, beta- and gamma-cyclodextrins on oxygen evolution by the thylakoid membrane. influence of pH and temperature. Z Naturforsch C. 2001;56:792-802 pubmed
  8. Groudine S, Soto R, Lien C, Drover D, Roberts K. A randomized, dose-finding, phase II study of the selective relaxant binding drug, Sugammadex, capable of safely reversing profound rocuronium-induced neuromuscular block. Anesth Analg. 2007;104:555-62 pubmed
    ..The mean time to recovery decreased with increasing doses. Profound rocuronium-induced neuromuscular block can be reversed successfully with sugammadex at doses >/=2 mg/kg. ..
  9. Beaufour M, Morin P, Ribet J. Chiral separation of the four stereoisomers of a novel antianginal agent using a dual cyclodextrin system in capillary electrophoresis. J Sep Sci. 2005;28:529-33 pubmed
    ..The resulting run time and resolutions were respectively about 17 min and between 1.95 and 2.84. Linearity curves (0.993 < r2 < 0.998) are also shown. ..

More Information


  1. Klang V, Matsko N, Zimmermann A, Vojnikovic E, Valenta C. Enhancement of stability and skin permeation by sucrose stearate and cyclodextrins in progesterone nanoemulsions. Int J Pharm. 2010;393:152-60 pubmed publisher
  2. Bordello J, Reija B, Al Soufi W, Novo M. Host-assisted guest self-assembly: enhancement of the dimerization of pyronines Y and B by gamma-cyclodextrin. Chemphyschem. 2009;10:931-9 pubmed publisher
    ..The gamma-cyclodextrin host acts like a belt to assist the guest self-assembly. The differences in the stability of pyronine B and pyronine Y dimers are explained on the basis of their structure and geometry. ..
  3. Mondal S, Sahu K, Ghosh S, Sen P, Bhattacharyya K. Excited-state proton transfer from pyranine to acetate in gamma-cyclodextrin and hydroxypropyl gamma-cyclodextrin. J Phys Chem A. 2006;110:13646-52 pubmed
    ..ESPT of HPTS in substituted gamma-CD is found to be slower than that in the unsubstituted one. This is attributed to the hydroxypropyl groups, which prevent close approach of acetate to HPTS. ..
  4. Takeda J. [Muscle relaxants in ambulatory anesthesia]. Masui. 2008;57:845-52 pubmed
    ..Sugammadex will resolve many issues in using nondepolarizing neuromuscular agents in ambulatory anesthesia. ..
  5. Nishimura K, Higashi T, Yoshimatsu A, Hirayama F, Uekama K, Arima H. Pseudorotaxane-like supramolecular complex of coenzyme Q10 with gamma-cyclodextrin formed by solubility method. Chem Pharm Bull (Tokyo). 2008;56:701-6 pubmed
    ..Consequently, the present study showed that CoQ10 forms the pseudorotaxane-like supramolecular complex with gamma-CyD in water. ..
  6. Trichard L, Fattal E, Le Bas G, Duchene D, Grossiord J, Bochot A. Formulation and characterisation of beads prepared from natural cyclodextrins and vegetable, mineral or synthetic oils. Int J Pharm. 2008;354:88-94 pubmed
    ..Manufacturing process of paraffin- and silicon-based beads need further optimisation to increase fabrication yield and later on, to take advantages from the high stability of both oils for the formulation of drugs with beads. ..
  7. Cammu G, de Kam P, De Graeve K, van den Heuvel M, Suy K, Morias K, et al. Repeat dosing of rocuronium 1.2 mg kg-1 after reversal of neuromuscular block by sugammadex 4.0 mg kg-1 in anaesthetized healthy volunteers: a modelling-based pilot study. Br J Anaesth. 2010;105:487-92 pubmed publisher
    ..Re-onset of block took longer if second rocuronium dose was <25 min after sugammadex. The duration of action of second rocuronium dose increased with later repeat dose time points. ..
  8. Nehmé R, Perrin C, Guerlavais V, Fehrentz J, Cottet H, Martinez J, et al. Use of coated capillaries for the electrophoretic separation of stereoisomers of a growth hormone secretagogue. Electrophoresis. 2009;30:3772-9 pubmed publisher
    ..Very good repeatability of analysis was obtained (RSD(migration time)<1%). ..
  9. Booij L, Van Egmond J, Driessen J, de Boer H. In vivo animal studies with sugammadex. Anaesthesia. 2009;64 Suppl 1:38-44 pubmed publisher
    ..These results offer support for the further development of sugammadex for clinical use in humans. ..
  10. Lin Z, Kong D, Zhong P, Yin K, Dong L. Influence of hydroxypropylcyclodextrins on the toxicity of mixtures. Chemosphere. 2005;58:1301-6 pubmed
    ..This provides information to assist the application of HPCDs in remediation of environmental pollution. ..
  11. Zhu W, Wu F, Raushel F, Vigh G. Capillary electrophoretic separation of the enantiomers of organophosphates with a phosphorus stereogenic center using the sodium salt of octakis(2,3-diacetyl-6-sulfo)-gamma-cyclodextrin as resolving agent. J Chromatogr A. 2000;895:247-54 pubmed
    ..This work extends the utility of ODAS-gammaCD to a hitherto unexplored field, the capillary electrophoretic separation of the enantiomers of organophosphorus compounds. ..
  12. Dzikovski B, Tipikin D, Livshits V, Earle K, Freed J. Multifrequency ESR study of spin-labeled molecules in inclusion compounds with cyclodextrins. Phys Chem Chem Phys. 2009;11:6676-88 pubmed publisher
    ..The visual clarity and the simplicity of analysis of the ESR spectra shown in this work should provide a benchmark for future studies of molecular motion by HFHF ESR. ..
  13. Marziali E, Raggi M, Komarova N, Kenndler E. Octakis-6-sulfato-gamma-cyclodextrin as additive for capillary electrokinetic chromatography of dibenzoazepines: carbamazepine, oxcarbamazepine and their metabolites. Electrophoresis. 2002;23:3020-6 pubmed
    ..5). Compared to heptakis-6-sulfato-beta-cyclodextrin, selectivity differs and stereoselectivity is more pronounced. ..
  14. Unterbuchner C, Fink H, Blobner M. The use of sugammadex in a patient with myasthenia gravis. Anaesthesia. 2010;65:302-5 pubmed publisher
  15. Song J, Guo Y, Zhao Q, Shuang S, Dong C, Choi M. Assemblies of brilliant cresyl violet to DNA in the presence of gamma-cyclodextrin. Talanta. 2010;82:681-6 pubmed publisher
    ..Our work postulates the importance of the initial concentration of dye and host molecule on the interaction of dye with DNA in living bodies. ..
  16. Chambers D, Paulden M, Paton F, Heirs M, Duffy S, Hunter J, et al. Sugammadex for reversal of neuromuscular block after rapid sequence intubation: a systematic review and economic assessment. Br J Anaesth. 2010;105:568-75 pubmed publisher
    ..The use of sugammadex in combination with high-dose rocuronium is efficacious. Further research is needed to clarify key parameters in the analysis and to allow a fuller economic assessment. ..
  17. Vanacker B, Vermeyen K, Struys M, Rietbergen H, Vandermeersch E, Saldien V, et al. Reversal of rocuronium-induced neuromuscular block with the novel drug sugammadex is equally effective under maintenance anesthesia with propofol or sevoflurane. Anesth Analg. 2007;104:563-8 pubmed
    ..There were no treatment-related serious adverse events and no discontinuations or deaths. No residual paralysis occurred. The safety profile of sugammadex was somewhat more favorable under propofol than under sevoflurane anesthesia. ..
  18. Caldwell J, Miller R. Clinical implications of sugammadex. Anaesthesia. 2009;64 Suppl 1:66-72 pubmed publisher
    ..The ultimate clinical utility of sugammadex will be clear only after large-scale clinical use. ..
  19. Munro I, Newberne P, Young V, Bar A. Safety assessment of gamma-cyclodextrin. Regul Toxicol Pharmacol. 2004;39 Suppl 1:S3-13 pubmed
    ..On basis of these studies it is concluded that gamma-CD is generally recognized as safe (GRAS) for its intended uses in food. ..
  20. Cserhati T. Charge-transfer chromatographic study of the complex formation of some anticancer drugs with gamma-cyclodextrin. Anal Biochem. 1995;225:328-32 pubmed
  21. Kurzawski P, Bogdanski A, Schurig V, Wimmer R, Hierlemann A. Direct determination of the enantiomeric purity or enantiomeric composition of methylpropionates using a single capacitive microsensor. Anal Chem. 2009;81:1969-75 pubmed publisher
    ..Moreover, the results disclosed here show that sensor techniques can be used to reveal details of enantioselective analyte-receptor and analyte-matrix interactions. ..
  22. Horakova H, Vespalec R. Chiral separability of hydrophobic boron cluster anions with native cyclodextrins in water-methanol background electrolytes. Electrophoresis. 2007;28:3639-49 pubmed
  23. Gurnev P, Harries D, Parsegian V, Bezrukov S. The dynamic side of the Hofmeister effect: a single-molecule nanopore study of specific complex formation. Chemphyschem. 2009;10:1445-9 pubmed publisher
    ..The kinetics underlying the dynamic equilibrium are studied to reveal qualitatively different dynamic actions of various cosolute salts. ..
  24. Groenning M, Olsen L, van de Weert M, Flink J, Frokjaer S, Jørgensen F. Study on the binding of Thioflavin T to beta-sheet-rich and non-beta-sheet cavities. J Struct Biol. 2007;158:358-69 pubmed
    ..We propose a similar ThT binding mode in amyloid fibrils, where cavities of an appropriate size running parallel to the fibril axis have previously been proposed in several amyloid fibril models. ..
  25. Kaewprasert S, Okada M, Aoyama Y. Nutritional effects of cyclodextrins on liver and serum lipids and cecal organic acids in rats. J Nutr Sci Vitaminol (Tokyo). 2001;47:335-9 pubmed
    ..It seems likely that the suppression of serum cholesterol levels by alpha- and beta-cyclodextrins might be due to the increasing acetate and propionate productions in the cecum. cecal organic acid, cyclodextrin, serum cholesterol, rats ..
  26. Rojas M, Castral T, Giordano R, Tardioli P. Development and validation of a simple high performance liquid chromatography - evaporative light scattering detector method for direct quantification of native cyclodextrins in a cyclization medium. J Chromatogr A. 2015;1410:140-6 pubmed publisher
    ..05g/L for alpha- and 0.06g/L for beta- and gamma-cyclodextrins. The new HPLC-ELSD method could accurately quantify the three cyclodextrins directly in a cyclization medium, without pretreatment of the samples. ..
  27. Bom A, Bradley M, Cameron K, Clark J, Van Egmond J, Feilden H, et al. A novel concept of reversing neuromuscular block: chemical encapsulation of rocuronium bromide by a cyclodextrin-based synthetic host. Angew Chem Int Ed Engl. 2002;41:266-70 pubmed
  28. Dong T, He Y, Shin K, Inoue Y. Formation and characterization of inclusion complexes of poly(butylene succinate) with alpha- and gamma-cyclodextrins. Macromol Biosci. 2004;4:1084-91 pubmed
    ..Through the formation of ICs, the PBS chain possibly adopts the kink conformation in the included state, as indicated by NMR analysis. ..
  29. Becket G, Schep L, Tan M. Improvement of the in vitro dissolution of praziquantel by complexation with alpha-, beta- and gamma-cyclodextrins. Int J Pharm. 1999;179:65-71 pubmed
    ..However, only the beta-complex had a stability constant in the optimum range for pharmaceutical use, suggesting that the preferred complex for further development would be a water-soluble beta-CD derivative. ..
  30. Geczy J, Bruhwyler J, Scuvee Moreau J, Seutin V, Masset H, Van Heugen J, et al. The inclusion of fluoxetine into gamma-cyclodextrin increases its bioavailability: behavioral, electrophysiological and pharmacokinetic studies. Psychopharmacology (Berl). 2000;151:328-34 pubmed
  31. Berzas Nevado J, Villaseñor Llerena M, Guiberteau Cabanillas C, Rodríguez Robledo V. Enantiomeric screening of racemic citalopram and metabolites in human urine by entangled polymer solution capillary electrophoresis: an innovatory robustness/ruggedness study. Electrophoresis. 2006;27:905-17 pubmed
    ..Both of the proposed methods proved to be very useful in the chiral pharmacokinetic screening of CIT and related metabolites in clinical human urine samples. ..
  32. Flood K, Reynolds E, Snow N. Determination of apparent association constants of steroid-cyclodextrin inclusion complexes using a modification of the Hummel-Dreyer method. J Chromatogr A. 2001;913:261-8 pubmed
    ..Limitations of the modified Hummel-Dreyer method are discussed. In particular, the accuracy of the method is poor when measuring small apparent association constants. ..
  33. Monnaert V, Tilloy S, Bricout H, Fenart L, Cecchelli R, Monflier E. Behavior of alpha-, beta-, and gamma-cyclodextrins and their derivatives on an in vitro model of blood-brain barrier. J Pharmacol Exp Ther. 2004;310:745-51 pubmed
    ..Finally, the endothelial permeability of each CD has been determined. Surprisingly, no structure/permeability relationship has been observed according to the nature and chemical modifications of CDs. ..
  34. Hunt M, Rusa C, Tonelli A, Maurice Balik C. Structure and stability of columnar cyclomaltooctaose (gamma-cyclodextrin) hydrate. Carbohydr Res. 2005;340:1631-7 pubmed
    ..0. Sorption equilibrium is reached long before the crystal structure transformation is complete, indicating that a significant amount of molecular mobility exists in the various hydrated gamma-CD crystal structures. ..
  35. Toropainen T, Heikkilä T, Leppänen J, Matilainen L, Velaga S, Jarho P, et al. Crystal structure changes of gamma-cyclodextrin after the SEDS process in supercritical carbon dioxide affect the dissolution rate of complexed budesonide. Pharm Res. 2007;24:1058-66 pubmed
    ..The crystal structure of gamma-CD and subsequently, the dissolution rate of complexed budesonide, can be modified with the processing conditions. ..
  36. Park C, Kim S, Park S, Kim J, Kim J, Park G, et al. Inclusion complex of conjugated linoleic acid (CLA) with cyclodextrins. J Agric Food Chem. 2002;50:2977-83 pubmed
    ..The oxidation of CLA induced at 35 degrees C for 80 h was completely prevented by the formation of CLA/CDs inclusion complexes. ..
  37. Huang H, Yu H, Tang G, Wang Q, Li J. Low molecular weight polyethylenimine cross-linked by 2-hydroxypropyl-gamma-cyclodextrin coupled to peptide targeting HER2 as a gene delivery vector. Biomaterials. 2010;31:1830-8 pubmed publisher
  38. Cserhati T, Forgacs E. Effect of pH and sodium chloride on the strength and selectivity of the interaction of gamma [correction for tau] -cyclodextrin with some antisense nucleosides. Int J Pharm. 2003;254:189-96 pubmed
    ..The length of hydrophobic alkyl substituents in antisense molecules influenced both the strength and selectivity of the interaction. The character of the base structure affected only the selectivity. ..
  39. Schappler J, Guillarme D, Prat J, Veuthey J, Rudaz S. Enhanced method performances for conventional and chiral CE-ESI/MS analyses in plasma. Electrophoresis. 2006;27:1537-46 pubmed
    ..With PP, signal suppression was observed out of the analyses migration window, while for LLE no relevant matrix effect occurred in all experiments. ..
  40. Wen X, Liu Z, Zhu T, Zhu M, Jiang K, Huang Q. Evidence for the 2:1 molecular recognition and inclusion behaviour between beta- and gamma-cyclodextrins and cinchonine. Bioorg Chem. 2004;32:223-33 pubmed
    ..Molecular modeling calculations have been carried out to rationalize the experimental findings and predict the lowest energy molecular structure of inclusion complex. ..
  41. Takada M, Nakagawa Y, Yamamoto M. Biochemical and genetic analyses of a novel gamma-cyclodextrin glucanotransferase from an alkalophilic Bacillus clarkii 7364. J Biochem. 2003;133:317-24 pubmed
    ..Comparison of the deduced amino acid sequence of gamma-CGTase with those of other known CGTases that have different product specificities revealed the importance of subsites -3 and -7 for the preferential gamma-cyclization activity. ..
  42. Saito Y, Hashizaki K, Taguchi H, Ogawa N. Complexation of butylbenzenes with 2-hydroxypropyl-cyclodextrins in aqueous solution. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2003;38:771-7 pubmed
    ..In addition, the binding effects are discussed in relation to the different alkyl groups of BBs. ..
  43. Donati F. Sugammadex: a cyclodextrin to reverse neuromuscular blockade in anaesthesia. Expert Opin Pharmacother. 2008;9:1375-86 pubmed
    ..To date, there appear to be few side effects. Inadequate dosage may lead to reparalysis. More data are needed, especially in patients with renal failure and those who require neuromuscular blockade again soon after receiving sugammadex. ..
  44. Terada Y, Yanase M, Takata H, Takaha T, Okada S. Cyclodextrins are not the major cyclic alpha-1,4-glucans produced by the initial action of cyclodextrin glucanotransferase on amylose. J Biol Chem. 1997;272:15729-33 pubmed
    ..Based on these results, a new model for the action of CGTase on amylose was proposed, which may contradict the widely held view of the cyclization reaction of CGTase. ..
  45. Ramshini H, Rezaei Ghaleh N, Ebrahim Habibi A, Saboury A, Nemat Gorgani M. Thermally induced changes in the structure and activity of yeast hexokinase B. Biophys Chem. 2008;137:88-94 pubmed publisher
    ..Deamidation of a critical Asn or Gln residue(s) may also play an important role. ..
  46. Hirano K, Ishihara T, Ogasawara S, Maeda H, Abe K, Nakajima T, et al. Molecular cloning and characterization of a novel gamma-CGTase from alkalophilic Bacillus sp. Appl Microbiol Biotechnol. 2006;70:193-201 pubmed
    ..CGTase825-6 should be a useful tool to produce gamma-CD and to study the differences of producing mechanisms between gamma-CD and beta-CD. ..
  47. Gijsenbergh F, Ramael S, Houwing N, van Iersel T. First human exposure of Org 25969, a novel agent to reverse the action of rocuronium bromide. Anesthesiology. 2005;103:695-703 pubmed
    ..9 within 2 min after its administration. No signs of recurarization were observed. Org 25969 was both well tolerated and effective in reversing neuromuscular block induced by rocuronium in 29 human volunteers. ..
  48. de Boer H, Driessen J, Van Egmond J, Booij L. Non-steroidal neuromuscular blocking agents to re-establish paralysis after reversal of rocuronium-induced neuromuscular block with sugammadex. Can J Anaesth. 2008;55:124-5; author reply 125-6 pubmed
  49. Busby M, Maldonado O, Vigh G. Nonaqueous capillary electrophoretic separation of basic enantiomers using octakis(2,3-O-dimethyl-6-O-sulfo)-gamma-cyclodextrin, a new, single-isomer chiral resolving agent. Electrophoresis. 2002;23:456-61 pubmed
    ..Fast, efficient separations were achieved for both comparatively small and large enantiomers. ..
  50. Tongiani S, Velde D, Ozeki T, Stella V. Sulfoalkyl ether-alkyl ether cyclodextrin derivatives, their synthesis, NMR characterization, and binding of 6alpha-methylprednisolone. J Pharm Sci. 2005;94:2380-92 pubmed
    ..The improved binding capacity of these new modified CDs with the model drug 6alpha-methylprednisolone is reported. ..
  51. Jones R, Caldwell J, Brull S, Soto R. Reversal of profound rocuronium-induced blockade with sugammadex: a randomized comparison with neostigmine. Anesthesiology. 2008;109:816-24 pubmed publisher
    ..Sugammadex is a novel reversal agent, reversing the effects of rocuronium by encapsulation. This study assessed the efficacy and safety of sugammadex versus neostigmine for reversal of profound rocuronium-induced neuromuscular blockade...
  52. Saavedra L, Nickerson B, Borjas R, Lynen F, Sandra P. Enantioseparation of pharmaceutical compounds by multiplexed capillary electrophoresis using highly sulphated alpha-, beta- and gamma-cyclodextrins. J Chromatogr B Analyt Technol Biomed Life Sci. 2008;875:248-53 pubmed publisher
    ..Intra-day precision (n=6) ranged from 2.0 to 16.5% and from 2.2 to 15.5% for migration time and resolution, respectively. These values increased with ca. 10% for intermediate precision. ..
  53. Kopman A. Sugammadex: a revolutionary approach to neuromuscular antagonism. Anesthesiology. 2006;104:631-3 pubmed