Structure-activity relationship study on N-glycosyl moieties through model building of DNA and ellipticine N-glycoside complex

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 12, 1996, Pages 1331-1334

  Shimamoto, Tetsuo ^a   Imajo, Seiichi ^a   Honda, Tadashi ^a   Yoshimura, Satomichi ^a   Ishiguro, Masaji ^a,b  

^a SUNTORY LTD   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DAUNORUBICIN; DAUNOSAMINE; DNA; DOXORUBICIN; ELLIPTICINE; ELLIPTINIUM; GLYCOSIDE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DNA DRUG COMPLEX; DRUG DNA BINDING; DRUG SYNTHESIS; INTRAPERITONEAL DRUG ADMINISTRATION; LEUKEMIA L 1210; MOLECULAR RECOGNITION; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALIA;

EID: 0029892584     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00219-3     Document Type: Article

References (21)

1. Lima, C.D.; Wang, J.C.; Mondragon, A. Nature, 1994, 367, 138.
2. Berger, J.M.; Gamblin, S.J.; Harrison, S.C.; Wang, J.C. Nature, 1996, 379, 225.
3. Honda, T.; Kato, M.; Inoue, M.; Shimamoto, T.; Shima, K.; Nakanishi, T.; Yoshida, T.; Noguchi T. J. Med. Chem., 1988, 31, 31295.
4. 5.
5. Yoshimura, S.; Nakanishi, T.; Honda, T.; Tsuruo, T. Jap. J. Can. Res., 1989, 2141.
6. Capranico, G.; Palumbo, M.; Tinelli, S.; Mabilia, M.; Pozzan, A.; Zunico, F. J. Mol. Biol., 1994, 235, 1218.
7. Gros, E.G.; Mastronardi, I.O. Carbohydr. Res., 1969, 10, 318.
8. Batey, J.F.; Bullock, C.; O'Brien, E.; Williams, J.M. Carbohydr. Res., 1975, 43, 43.
9. Honda, T.; Inoue, M.; Kato, M.; Shima, K.; Shimamoto, T. Chem. Pharm. Bull., 1987, 35, 3975.
10. The compound 1 did not show a particular base-pair specificity upon intercalation.
11. Jain, S.C.; Bhandary, K.K.; Sobell, H.M. J. Mol. Biol., 1975, 135, 813.
12. Quigley, G.J.; Wang, A.H.; Ughetto, G.; Marel, G.; Boom, J.H. Rich, A. Proc. Natl. Acad. Sci., 1980, 77, 7204.
13. Alden, C.J.; Aruott, S. Nucl. Acids Res., 1975, 2, 1701.
14. Lybrand, T.; Kollman, P.A. Biopolymers., 1985, 24, 1863.
15. Weiner, S.J.; Kollman, P.A.; Case, D.A.; Singh, U.C.; Ghio, C.; Alagona, G.; Profeta, Jr. S.; Weiner, P.E. J. Am. Chem. Soc., 1984, 106, 765.
16. The atoms of both ends of base pair were constrained (1000kJ/mol/Å2) in order to maintain the helical structure.
17. Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem., 1990, 11, 440.
18. 1′.
19. A-T base pair has the same hydrogen bond at the major groove.
20. All the DNA atoms were fixed for the minimization of the complex structure of the methylated ellipticine derivatives with the DNA.
21. Complex models of DNA and O-methylated derivatives for the other conformations (A, B, and D) were also examined. A similar structural change of the 2′-O-methylated derivative was obtained from the conformation A. However, no significant conformational change was observed in the other remaining models.