Theoretical Investigation of Molecular and Electronic Properties of 2,4'-Bithiazole Isomer in Bleomycin, an Antitumor Drug

• Autorzy: Abedi A. , Safari N. , Bahrami H.
• Języki publikacji: EN

Abstrakty

EN

Bithiazole moiety of bleomycin, a DNA cutting agent has been investigated using ab initio method. B3LYP/6-31G* level has been shown to be suitable for optimizing structural properties of bithiazole compounds. Mother nature has chosen the 2,4'-bithiazole isomer, which has interesting bioactivity. Other isomers such as 2,2c-bithiazole and 4,4'-bithiazole, which have similar structures and reactivity in vitro chemistry, were studied and compared with 2,4'-bithiazole isomer to find out what is special about this isomer in order to illustrate its bioactivity. These studies have confirmed that 2,4'-bithiazole isomeris more stable, its electron affinity is higher and has special electrostatic charac eristics compared to other isomers. These properties of 2,4'-bithiazole can be related to the roles of this part of drug in DNA cleavage.

Słowa kluczowe

EN

bithiazole; bleomycin; DNA cleavage; ab initio methods; isomers comparison

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 4
• Strony: 669--679
• Opis fizyczny: Bibliogr. 34 poz., rys.

Twórcy

autor

Abedi A.

autor

Safari N.

autor

Bahrami H.

• Department of Chemistry, North Tehran Branch, Islamic Azad University, No. 9, darabnia al., daftari-sharghi, al., Zafar-shariati cross, Tehran, Iran,

Bibliografia

• 1. Umezawa H, Maeda K, Takeuchi T. and Okami Y, J. Antibiot., 19, 200 (1966).
• 2. Umezawa H., Fed. Proc, 33, 2296 (1974).
• 3. Kuroda R, Neidle S, Riordan J.M. and Sakai T.T., Nucl. Acids Res., 10, 4753 (1982).
• 4. Wu W, Vanderwall D.E., Stubbe J, Kozarich J.W. and Turner C.J, J. Am. Chem. Soc, 116, 10843 (1994).
• 5. Houssin R, Helbecque N.. Bernier J.L. and Henichart J.P, J. Biomol. Struct. Dyn., 4, 219 (1986).
• 6. Sugiyama M, Kumagai T, Hayashida M, Maruyama M. and Matoba Y, J. Biol. Chem., 277, 2311 (2002) .
• 7. Lin S.Y and Grollman A.P, Biochemistry, 20, 7589 (1981).
• 8. Sakai T.T., Riordan J.M, Booth T.E. and Glickson J.D., J. Med. Chem., 24, 279 (1981).
• 9. Kuwahara J. and Sugiura Y, Proc. Natl. Acad. Sci. U. S. A., 85, 2459 (1988).
• 10. Khavasi H.R., Abedi A, Amani V, Notash B. and Safari N, Polyhedron, 21, 1848 (2008).
• 11. Sugiyama M. and Kumagai T, J. Biosci. Bioeng., 93, 105 (2002).
• 12. Frisch M.J, Trucks G.W., Schlegel H.B., Scuseria G.E, et al, Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT (2004).
• 13. Weinhold F. and Landis C.R, Chem. Ed. Res. Pract., 2, 91 (2001).
• 14. Ma B, Lii J.H., Schaefer H.F. and Allinger N.L., J. Phys. Chem. B, 100, 8763 (1996).
• 15. Zahedi M, Bahrami H, Shahbazian S, Safari N. and Weng S, J. Mol. Struct. (Theochem), 633, 21 (2003) .
• 16. Merrill G, Gronert S. and Kass S.R, J. Phys. Chem. A, 101, 208 (1997).
• 17. Stephens P.J, Delvin F.J, Chabalowski C.R and Frisch M.J, J. Phys. Chem., 98, 11623 (1994).
• 18. Muchall H.M., WerstiukN.H. and Choudhury B, Can. J. Chem., 16, 221 (1998).
• 19. Ghosh A. and Vangberg T, Theor. Chem. Ace, 97, 143 (1997).
• 20. Benassi R, Ferrarini P., Fontanesi C, Benedetti L. and Paolucci F, J. Electroanal. Chem., 564, 231 (2004) .
• 21. Tian Y.-N, Yang P. and Wang H.-F, Polyhedron, 15, 2771 (1996).
• 22. Onggo D, Scudder M.L., Craig D.C. and Goodwin H.A, Aust. J. Chem., 53, 153 (2000).
• 23. Besler B.H., Merz K. M., Jr. and Kollman P.A., J. Comput. Chem., 11, 431 (1990).
• 24. Becker O.M, Mackerell A.D.J, Roux B. and Watanabe M, Computational Biochemistry and Biophysics, M. Dekker, NY, 2001.
• 25. ZuccaA, CinelluMA, Minghetti G, Stoccoro S. and ManasseroM.,Eur. J. Inorg. Chem.,4484 (2004).
• 26. Villanueva-Garcia M, Huerta-Salazar N, Martinez-Richa A. and Robles J, Arkivoc, xi, 149 (2003).
• 27. Amant A.S, Cornell W.D., Halgren T.A. and Kollman PA, J. Comput. Chem., 16, 1483 (1995).
• 28. Scheiner A.C., Baker J. and Andzelm J.W, J. Comput. Chem., 18, 775 (1997).
• 29. Bailly C, Colson P., Houssier C, Houssin R, et al., Biochemistry, 31, 8349 (1992).
• 30. Henichart J.-P, Bernier J.-L, Helbecque N. and Houssin R, Nucl. Acids Res., 13, 6703 (1985).
• 31. Breen A.P. and Murphy J.A, Free Radic. Biol. Med., 18, 1033 (1995).
• 32. Quada J.C, Boturyn D. and Hecht S.M., Bioorg. Med. Chem., 9, 2303 (2001).
• 33. Manderville R.A, Ellena J.F. and Hecht S.M, J. Am. Chem. Soc, 116, 10851 (1994).
• 34. Lehmann T.E, Ming L.-J, Rosen M.E. and Que L, Biochemistry, 36, 2807 (1997).2, 4857 (1998).