Density functional and ab initio studies on N-acetyl-duocarmycin SA: Insight into its DNA interaction properties

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 2, 2000, Pages 329-335

  Kirschner, Karl N ^a   Lee, Moses ^b   Stanley, Robert C ^b   Bowen, J Phillip ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b FURMAN UNIVERSITY   (United States)

Author keywords

Antitumor compound; Duocarmycin; Ground state destabilization; Molecular modeling

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DUOCARMYCIN SA; RACHELMYCIN;

ANALYTIC METHOD; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; DRUG CONFORMATION; DRUG DNA BINDING; X RAY ANALYSIS;

BASE SEQUENCE; DNA; DNA PRIMERS; INDOLES; PYRROLIDINONES;

EID: 0034005227     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00278-3     Document Type: Article

References (28)

1. Dickerson, R. E.; Kopka, M. L.; Pjura P. E. In DNA-Ligand Interactions From Drugs to Proteins; Guschlbauer, W.; Saenger W., Eds.; Plenum Publishing: New York, 1987; pp 45-62.
2. Boger D.L., Boyce C.W., Johnson D.S. Bioorg. Med. Chem. Lett. 7:1997;233.
3. Boger D.L., Goldberg J., McKie J.A. Bioorg. Med. Chem. Lett. 6:1996;1955.
4. Boger D.L., Johnson D.S. Angew Chem., Int. Ed. Engl. 351:1996;1438.
5. Hurley L.H., Warpehoski M.A., Lee C.-S., McGovren J.P., Scahill T.A., Kelly R.C., Mitchell M.A., Wicnienski N.A., Gebhard I., Johnson P.D., Bradford V.S. J. Am. Chem. Soc. 112:1990;4633.
6. Hurley L.H., Lee C.-S., McGovren J.P., Warpehoski M.A., Mitchell M.A., Kelly R.C., Aristoff P.A. Biochem. 27:1988;3886.
7. Chidester C.G., Krueger W.C., Mizsak S.A., Duchamp D.J., Martin D.G. J. Am. Chem. Soc. 103:1981;7629.
8. Ichimura M., Ogawa T., Takahashi K., Kawamoto E., Yasuzawa T., Takahashi I., Nakano H. J. Antibiot. 43:1990;1037.
9. Takahashi I., Takahashi K., Ichimura M., Morimoto M., Asano K., Kawamoto I., Tomita F., Nakano H. J. Antibiot. 41:1988;1915.
10. Yasuzawa T., Muroi K., Ichimura M., Takahashi I., Ogawa T., Takahashi K., Sano H., Saitoh S.H. Chem. Pharm. Bull. 43:1995;378.
11. Boger D.L., Bollinger B., Hertzog D.L., Johnson D.S., Cai H., Mesini P., Garbaccio R.M., Jin Q., Kitos P.A. J. Am. Chem. Soc. 119:1997;4987.
12. Boger D.L., Garbaccio R.M. Bioorg. Med. Chem. 5:1997;263.
13. Boger D.L., Hetzog D.L., Bollinger B., Johnson D.S., Cai H., Goldberg J., Turnbull P. J. Am. Chem. Soc. 119:1997;4977.
14. Lin C.H., Beale J.M., Hurley L.H. Biochem. 30:1991;3597.
15. Boger D.L., Invergo B.J., Coleman R.S., Zarrinmayeh H., Kitos P.A., Thompson S.C., Leong T., McLaughlin L.W. Chem.-Biol. Interact. 73:1990;29.
16. Boger D.L., Sakya S.M. J. Org. Chem. 57:1992;1277.
17. Boger D.L., Zhou J., Cai H. Bioorg. Med. Chem. 4:1996;859.
18. Boger D.L., Munk S.A., Zarrinmayeh H. J. Am. Chem. Soc. 113:1991;3980.
19. Boger D.L., Yun W. J. Am. Chem. Soc. 116:1994;5523.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2; Gaussian, Inc., Pittsburgh PA, 1995.
21. Becke A.D. J. Chem. Phys. 98:1993;5648.
22. Mulliken R.S. J. Chem. Phys. 23:1955;1833.
23. Hehre, W. J.; Radom, L.; Schleyer, R. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986; pp 25-29.
24. Breneman C.M., Wiberg K.B. J. Comp. Chem. 11:1990;361.
25. Eis P.S., Smith J.A., Rydzewski J.M., Case D.A., Boger D.L., Chazin W.J. J. Mol. Biol. 272:1997;237.
26. Eis, P. S.; Smith, J. A.; Case, D. A.; Chazin, W. J. Protein Data Bank structure 1DSA.
27. Colored graphical depictions of the HOMO and LUMO orbitals for the neutral N-Ac-DSA can be obtained from the authors.
28. Stowasser, R.; Hoffman, R. J. Am. Chem. Soc. 1999, 121, 3414.