Chemical and structural properties of the inclusion complex of euplotin C with heptakis(2,6-di-O-methyl)-β-cyclodextrin through NMR spectroscopy, electrospray mass spectrometry and molecular mechanics investigations

European Journal of Organic Chemistry

Volumn , Issue 6, 2004, Pages 1308-1317

  Guella, Graziano ^a   Callone, Emanuela ^a   Mancini, Ines ^a   Uccello Barretta, Gloria ^b   Balzano, Federica ^b   Dini, Fernando ^b  

^a UNIVERSITY OF TRENTO   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

Cyclodextrins; Electrospray ionization; Euplotin C; Hydrolysis; NMR spectroscopy

Indexed keywords

ACETIC ACID DERIVATIVE; CYCLODEXTRIN DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; EUPLOTIN C; HEPTAKIS(2,5 DI O METHYL) BETA CYCLODEXTRIN; METHYL GROUP; PROTOZOAL PROTEIN; SESQUITERPENOID; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOTOXICITY; DEGRADATION KINETICS; ELECTROSPRAY MASS SPECTROMETRY; EUPLOTES; EUPLOTES CRASSUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOST PARASITE INTERACTION; HYDROLYSIS; MASS SPECTROMETRY; MATHEMATICAL COMPUTING; MOLECULAR EVOLUTION; MOLECULAR MECHANICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT; RING OPENING; STATISTICAL SIGNIFICANCE; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 4544349597     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300502     Document Type: Article

References (31)

1. [1a] F. Dini, G. Guella, P. Giubbilini, I. Mancini, F. Pietra, Naturwissenschaften 1993, 80, 84-86.
2. [1b] G. Guella, F. Dini, T. Tomei, F. Pietra, J. Chem. Soc., Perkin Trans, 1 1994, 161-166.
3. [1c] G. Guella, F. Dini, T. Tomei, F. Pietra, Helv. Chim. Acta 1996, 79, 710-717.
4. F. Trielli, G. Guella, G. Di Giuseppe, B. Burlando, A. V. Corrado, T. Kruppel, A. Viarengo, F. Dini, manuscript submitted.
5. D. Savoia, G. Guella, E. Gallone, F. Dini, work in progress.
6. T. Nakatsu, B. N. Ravi, D. J. Faulkner, J. Org. Chem. 1981, 46, 2435-2438.
7. R. A. Aungst Jr., R. L. Funk, J. Am. Chem. Soc. 2001, 123, 9455-9456.
8. K. A. Connors, Chem. Rev. 1997, 97, 1325-1357.
9. K. Miyake, F. Hirayama, K. Ukeama, J. Pharm. Sci. 1999, 88, 39-45.
10. A. M. C. Myles, D. J. Barlow, G. France, M. J. Lawrence, Bioch. Bioph. Acta 1994, 1199, 27-36.
11. N. Nesnas, J. Lou, R. Breslow, Bioorg. Med. Chem. Lett. 2000, 10, 1931-1933.
12. I. Tabushi, Acc. Chem. Res. 1982, 15, 66-72.
13. S. Li, W. C. Purdy, Chem. Rev. 1992, 92, 1457-1470.
14. K. Lipkowitz, Chem. Rev. 1998, 98, 1829-1873.
15. W. Saenger, Angew. Chem. 1980, 92, 343-361; Angew. Chem. Int. Ed. Engl. 1980, 19, 344-362.
16. W. Saenger, Angew. Chem. 1980, 92, 343-361; Angew. Chem. Int. Ed. Engl. 1980, 19, 344-362.
17. M. Taghvaei, G. H. Stewart, Anal. Chem. 1991, 63, 1902-1904.
18. T. Wang, J. S. Bradshaw, R. M. Izatt, J. Heterocycl. Chem. 1994, 31, 1097-1114.
19. H. A. Benesi, J. H. Hildebrand, J. Am. Chem. Soc. 1949, 71, 2703-2707.
20. L. Fielding, Tetrahedron 2000, 56, 6151-6170.
21. C. Frassineti, S. Ghelli, P. Gans, A. Sabatini, M. S. Moruzzi, A. Vacca, Anal. Biochem. 1995, 231, 374-382.
22. [19a] P. Job, Ann Chim Appl. 1928, 9, 113-134.
23. [19b] F. Djeaini, S. Z. Lin, B. Perly, D. Wouessidjewe, J. Pharm. Sci. 1990, 79, 643-646.
24. J. B. Cunniff, P. Kouros, J. Am. Soc., Mass Spectrom. 1995, 6, 437-443.
25. M. Shahgholi, C. L. Copper, J. Callahan, Supramol. Chem. 1998, 9, 263-276.
26. C. Siethoff, W. Wagner-Redeker, M. Schaefer, M. Lindscheid, Chimia 1999, 53, 484-491.
27. J. B. Fenn, M. Mann, C. K. Meng, S. F. Wong, C. M. Whitehouse, Science 1989, 246, 64-71.
28. R. B. Cole, Electrospray Ionization Mass Spectroscopy, Wiley-Interscience, New York, 1997.
29. P. Bonnet, C. Jaime, L. Morin-Allory, J. Org. Chem. 2001, 66, 689-692.
30. S. Tascioglu, Tetrahedron 1996, 52, 11113-11152.
31. G. Uccello-Barretta, C. Chiavacci, C. Bertucci, P. Salvadori, Carbohydr. Res. 1993, 243, 1-10.