Pharmacology and structures of the free base of the anaesthetic kazcaine and its complex with β-cyclodextrin

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 68, Issue 3-4, 2010, Pages 323-330

  Kemelbekov, U S ^a   Hagenbach, A ^b   Lentz, D ^b   Imachova, Sh O ^c   Pichkhadze, G M ^c   Rustembekov, Zh I ^a   Beketov, K M ^a   Praliev, K D ^a   Gabdulkhakov, A ^b   Guskov, A ^b   Saenger, W ^b  

^a Institute of Chemical Sciences Academy of Sciences of Kazakhstan   (Kazakhstan)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c ASFENDIYAROV KAZAKH NATIONAL MEDICAL UNIVERSITY   (Kazakhstan)

Author keywords

Anaesthetic; Crystal structure; Cyclodextrin; Kazcaine base; Pharmacological properties; X ray diffraction

Indexed keywords

EID: 78649325975     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9791-7     Document Type: Article

References (21)

1. Saenger, W.: Cyclodextrin inclusion compounds in research and industry. Angew. Chem. Int. Ed. Engl. 19, 344-362 (1980).
2. Dodziuk, H.: Cyclodextrins and Their Complexes. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim (2006).
3. Lindner, K., Saenger, W.: β-Cyclodextrin dodecahydrate: crowding of water molecules within a hydrophobic cavity. Angew. Chem. Int. Ed. Engl. 9, 694-695 (1978).
4. Gröger, M., Kretzer, K. E., Woyke, A.: Cyclodextrine. Science Forum an der Universität Siegen, Siegen (2001).
5. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743-1753 (1998).
6. Challa, R., Ahuja, A., Ali, J., Khar, R. K.: Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech. 6(2), 327-359 (2005).
7. Pinto, L. M. A., Fernandes, F. L., Santana, M. H. A., Pertinhez, T. A., Oyama, S., Junior de Paula, E.: Physico-chemical characterization of benzocaine-β-cyclodextrin inclusion complexes. J. Pharm. Biomed. Anal. 39, 956-963 (2005).
8. Ingle, J. R., Busch, K. W., Busch, M. A.: Chiral analysis by multivariate regression modeling of spectral data using cyclodextrin guest-host complexes-methods for determining enantiomeric composition with varying chiral analyte concentration. Talanta 75, 572-584 (2008).
9. Praliev, K. D., Yu, V. K., Poplavskaya, I. A.: Target synthesis of pharmacologically active derivatives of 4-ethynyl-4-hydroxypiperidine. In: Kartsev, V. G., Tolstikov, G. A. (eds.) Nitrogen-Containing Heterocycles and Alcaloides, pp. 484-489. IBS PRESS, Moscow (2001).
10. Yu, V. K., Nagimova, A. D., Praliev, K. D., Shin, S. N., De Kempe, N.: Synthesis, antibacterial, and analgesic activity of 1-(2-ethoxyethyl)-4-hydroxy(acyloxy)-piperidine-4-carboxylic acids. Pharm. Chem. J. 36(7), 282-284 (2002).
11. Praliev, K. D., Isin, Zh., Yu, V. K., Tarakov, S. A., Bosyakov, Yu. G., Utepbergenova, R. K., Shin, S. N., Kadyrova, D. M.: Hydrochloride of 1-(2-ethoxyethyl)-4-ethynyl-4-benzoyloxy-piperidine possesses anesthetic activity. Patent Ru. 1704415 (1996).
12. Siemens Industrial Automation, Inc., SAINT: Area-Detector Integration Software. Madison, WI, (1995).
13. Siemens Industrial Automation, Inc., SADABS: Area-Detector Absorption Correction. Madison, WI (1995).
14. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A 64, 112-122 (2008).
15. Allen, F. H., Kennard, O., Watson, G. D., Brammer, L., Orpen, A. G., Taylor, R.: Tables of bonds lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. J. Chem. Soc. Perkin Trans. II, 1-17 (1987).
16. Harata, K.: Structural aspects of stereodifferentiation in the solid state. Chem. Rev. 98, 1803-1827 (1998).
17. Mino, R. C., Vivienne, J. G., Luigi, R. N., van Bosch, O.: Synthesis and X-ray crystal structure of β-cyclodextrin diclofenac sodium undecahydrate, a β-CD complex with a unique crystal packing arrangement. J. Chem. Soc. Chem. Commun. 1061-1062 (1994).
18. Bonnet, P., Jaime, C., Morin-Allory, L.: Structure and thermodynamics of a-, b-, and g-cyclodestrin dimers. Molecular dynamics studies of the solvent effect and free binding energies. J. Org. Chem. 67, 8602-8609 (2002).
19. Quevauviller, A.: Local Anaesthethics in Experimental Methods for Comparing Local Anaesthetic Activity-International Encyclopedia of Pharmacology and Therapeutics, pp. 291-318. Pergaman Press, Fayetteville (1971).
20. Dib, B.: Intrathecal chronic cathetarisation in the rat. Pharmacol. Biochem. Behav. 20, 45-48 (1984).
21. Camougis, G., Takman, B. H.: Methods in Pharmacology. Appleton Century Crofts, New York (1971).