N.A. Nikitin - Ph.D. (Med.), Senior Research Scientist, Ufa Eye Research Institute E-mail: nna-12@yandex.ru

Cyclodextrins, discovered in 1891, actively attract attention of scientists till now. Cyclodextrines are formed from glucopyranose units and have a form of conical cylinder with cavity insight. The last gives opportunity to form an inclusion complex with hydrophobic molecules or their fragments. It results in increasing of their stability, solubility, bioavailability and other properties. But some factors promoting the complex formation are needed. Among them are kneading, co-evaporation, spray-drying, freeze-drying, sealed-heating etc. For confirmation of complex formation such methods like X-ray diffractometry, mass spectrophotometry, ultraviolet and infrared spectroscopies are used. Electrospray mass photometry and proton nuclear magnetic resonance are the most important methods. The gotten results form the basis for subsequent works followed on evaluation of the biochemical, pharmacological, toxicological and properties of inclusion complex.

 

1. VilliersM.A.Surlatransformationdelaféculeendextrineparlefermentbutyrique // ComptesRendusdel-AcadémiedesSciences. 1891. V. 112. P. 435-438.
2. Schardinger F. Über thermophile bakterien aus verschiedenen Speisen und milch. sowie über einige Umsetzungsprodukte derselben in kohlenhydrathaltigen Nährlösungen, darunter krystallisierte polysaccharide (dextrine) aus stärke // Zeitschrift für Untersuchung der nahrungs- und genußmittel. 1903. V. 6. P. 865-880.
3. Freudenberg K., Blomquist G., Ewald L., Soff K. Hydrolysis and acetolysis of stärch and of the Schardinger dextrins // Berichte der Deutschen chemischen Gesellschaft zu Berlin. 1936. V. 69. P. 1258-1266.
4. Freudenberg K., Cramer F. Die konstitution der Schardinger-dextrine α, β und γ // Zeitschrift für Naturforschung. 1948. V. B 3. P. 464-468.
5. Freudenberg K., Cramer F., Plieninger H. Verfahren zur Herstellung von einschlussverbindungen physiologisch wirksamer organischer verbindungen // German Pat. 1953. 895.769.
6. Loftsson T., Duchêne D. Cyclodextins and their pharmaceutical applications: historical perspectives // Int. J. Pharm. 2007. V. 329. P. 1-11.
7. Qi Q., Zimmermann W. Cyclodextrin glucanotransferase: from gene to application // Appl. Microbiol. Biotechnol.2005. V. 66. P. 475-485.
8. Belikov V.G., Kompanceva E.V., Botezat-Belyjj JU.K. Ciklodekstriny i ikh soedinenija vkljuchenija s lekarstvennymi veshhestvami // KHimiko-farmacevticheskijj zhurnal. 1986. V. 20. № 5. P. 525-532.
9. Loftsson T., Brewster M.E. Pharmaceutical applications of cyclodextrins: 1. Drug solubilisation and stabilization // J. Pharm. Sci. 1996. V. 85. P. 1017-1025.
10. Saenger W. Cyclodextrin inclusion compounds in research and industry // Angew. Chem. Int. Ed. Engl. 1980. V. 19. № 5. P. 344-362.
11. Uekama K. Design and evaluation of cyclodextrin-based drug formulation // Chem. Pharm. Bull. 2004. V. 52. P. 900-915.
12. Zia V., Rajewski V., Stella V.J. Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)_7m-β-CD to HP-β-CD // Pharm. Res. 2001. V. 18. № 5. P. 667-673.
13. Gabelica V., Galic N., De Pauw E.J. On the specificity of cyclodextrin complexes detected by electrospray mass spectroscopy // Am. Soc. Mass. Spectrom. V. 13. № 8. P. 946-953.
14. Bikádi Z., Iványl R., Szente L., Hazai E.Cyclodextrin complexes: chiral recognition and complexation behavior // Curr. Drug Discov. Technol. 2007. V. 4. № 4. V. 282-294.
15. Ramstad T., Hadden C.E., Martin G.E., Speaker S.M., Teagarden D.L., Thamann T.J. Determination by NMR of the binding constant for the molecular complex between alprostadil and alpha-cyclodextrin. Implications for a freeze-dried formulation // Int. J. Pharm. 2005. V. 296. № 1-2. P. 55-63.
16. Loftsson T., Ólafsdóttir B.J., Fridriksdóttir H., Jónsdóttir S. Cyclodextrin complexation of NSAIDS: physicochemical characteristics // Eur. J. Pharm. Sci. 1993. V. 1. № 2. P. 95-101.
17. Husain N., Ndou T.T., De La Peña A.M., Warner I.M.Complexation of Doxorubicin with β- and γ-Cyclodextrins // Appl. Spectrosc. 1992. V. 46. № 4. P. 652-658.
18. Ali S.M., Maheshwari A. Proton magnetic resonance study of fexofenadine/β-cyclodextrin inclusion complexes in aqueous solution // Bull. Korean Chem. Soc. 2005. V. 26. № 12. P. 2061-2064.
19. Loftsson T., Matthíasson K., Másson M. The effects of organic salts on the cyclodextrin solubilization of drugs // Int. J. Pharm. 2002. V. 43. № 1-2. P. 101-107.
20. Loftsson T., Magnúsdóttir A., Másson M., Sigurjónsdóttir J.F. Self-association and cyclodextrin solubilization of drugs // J. Pharm. Sci. 2002. V. 91. № 11. P. 2307-2316.
21. Loftsson T., Másson M., Sigurdsson H.H. Cyclodextrins and drug permeability through semi-permeable cellophane membranes // Int. J. Pharm. 2002. V. 232. № 1-2. P. 35-43.
22. Al-Marzouqi A.H., Jobe B., Dowaidar A., Maestrelli F., Mura P. Evaluation of supercritical fluid technology as preparative technique of benzocaine-cyclodextrin complexes; comparison with conventional methods // J. Pharm. Biomed. Anal. 2007. V. 43. № 2. P. 566-574.
23. Ribeiro. A., Figueiras A., Santos D., Veiga F. Preparation and solid state characterization on inclusion complexes formed between miconazole and methyl-b-cyclodextrin // AAPS PharmSciTech. 2009. V. 9. №4. P. 1102-1109.
24. Badr-Eldin S.M., Elkheshen S.A., Ghorab M.M.Inclusion complexes of tadalafil with natural and chemically modified β-cyclodextrins: I. Preparation and in-vitro evaluation // Eur. J. Pharm. Biopharm. 2008. V. 70. № 3. P. 819-827.
25. Figueiras A., Carvalho R.A., Ribeiro L., Torres-Labandeira J.J., Veiga F.J.B. Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified β-cyclodextrin // Eur. J. Pharm. Biopharm. 2007. V. 67. № 2. P. 531-539.
26. Al-Marzouqi A.H., Elwy H.M., Shehadi I., Adem A. Physicochemical properties of antifungal drug-cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques // J. Pharm. Biomed. Anal. 2009. V. 49. № 2. P. 227-233.
27. Salústio P.J., Feio G., Figueirinhas J.L., Pinto J.F., Cabral Marques H.M. The influence of the preparation methods on the inclusion of model drugs in a β-cyclodextrin cavity //Eur. J. Pharm. Biopharm. 2009. V. 71. № 2. P. 377-386.
28. Higashi K., Tozuka Y., Moribe K., Yamamoto K.Salicylic acid/gamma-cyclodextrin 2:1 and 4:1 complex formation by sealed-heating method // J. Pharm. Sci. 2010. V. 99. № 10. P. 4192-4200.
29. Zhao D.G., Liao K.I., Ma X.Y., Yan X.H.Study of the supramolecular inclusion of β-cyclodextrin with andrographolide // J. Inclusion Phenom. Macrocyclic Chem. 2002. V. 43. № 3-4. P. 259-264.
30. Nacsa Á., Ambrus R., Berkesi O. J. Szabó-Révész P., Aigner Z. Water-soluble loratadine inclusion complex: analytical control of the preparation by microwave irradiation // Pharm. Biomed. Anal. 2008. V. 48. № 3. P. 1020-1023.
31. Cirri M., Maestrelli F., Mennini N., Mura P.Physical-chemical characterization of binary and ternary systems of ketoprofen with cyclodextins and phospholipids // J. Pharm. Biomed. Anal. 2009. V. 50. № 5. P. 683-689.
32. Van Hees T., Piel G., Evrard B., Otte X., Thunus L., Delattre L. Application of supercritical carbon dioxide for the preparation of a piroxicam-β-cyclodextrin inclusion compound // Pharm. Res. 1999. V. 16. № 12. P. 1864-1870.
33. Toropainen T., Velaga S., Heikkilä T., Matilainen L., Jarho P., Carlfors J., Lehto V.P., Järvinen T., Järvinen K. Preparation of budesonide/γ-cyclodextrin complexes in supercritical fluids with a novel SEDS method // J. Pharm. Sci. 2006. V. 95. № 10. P. 2235-2245.
34. Pentin JU.A., Vilkov L.V. Fizicheskie metody issledovanija v khimii. M.: Mir. 2003. 683 s.
35. BelyakovaL.A., LyashenkoD.Yu., GrebenyukA.G., DzyubenkoL.S., OranskayaE.I.Studyof ?β-cyclodextrin-benzenecarboxylicacid - supramolecularcomplexe // Phis. Chem.  Solidstate. 2011. V. 12. № 3. P. 690-700.
36. Iacovino R., Caso J.V., Rapuano F., Russo A., Isidori M., Lavorgna M., Malgieri G., Isernia C. Physicochemical characterization and cytotoxic activity evaluation of hydroxyme-thylferrocene:β-cyclodextrin inclusion complex // Molecules. 2012. V. 17. № 5. P. 6056-6070.
37. Bershtejjn V.A., Egorov V.M. Differencialnaja skanirujushhaja kalorimetrija v fizikokhimii polimerov P.: KHimija. 1990. 256 s.
38. Ansari K.A., Vavia P.R., Trotta F., Cavalli R. Cyclodextrin-based nanosponges for delivery of resveratrol: in vitro characterisation, rtability,c and permeation study // AAPS Pharm. Sci. Tech. V. 12. № 1. P. 279-286.
39. KHejjker D.M., Zevin L.S. Rentgenovskaja difraktometrija. M.: Fizmatgiz. 1961. 380 s.
40. Borisov R.S., Zaikin V.G., Varlamov A.V., Kulikova L.N. Metody ionizacii i razdelenija ionov v mass-spektrometrii. M.: RUDN. 2011. 62 c.
41. Guernelli S., Lagana M.F., Mezzina E., Ferroni F., Siani G. Supramolecular complex formation: a study of the interactions between β-cyclodextrin and some different classes of organic compounds by ESI-MS, surface tension measurements,and UV/Vis and ¹H NMR spectroscopy // Eur. J. Org. Chem. 2003. V. 2003. № 24. P. 4765-4776.
42. Suvorov EH.V. Fizicheskie osnovy ehksperimentalnykh metodov issledovanija realnojj struktury kristallov. CHernogolovka: IPKHF RAN. 1999. 231 s.
43. Karataeva F.KH.. Klochkov V.V. Spektroskopija JAMR v organicheskojj khimii. Kazan: KFU. 2012. 96 s.
44. Schneider H.-J., Hacket F., Rüdiger V., IkedaH. NMR studies of cyclodextrins and cyclodextrin complexes // Chem. Rev.1998. V. 98. № 5. P. 1755-1786.