Effects of structural modification on the DNA binding properties and photo-induced cleavage reactivity of propargylic sulfones conjugated with an anthraquinone structure

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 13, 2006, Pages 4427-4432

  Haruna, Ken ichi ^a   Kanezaki, Hiroshi ^a   Tanabe, Kazuhito ^a   Dai, Wei Min ^b   Nishimoto, Sei ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

DNA cleavage; Intercalation; Photooxidation; Propargylic sulfone

Indexed keywords

3 ANTHRAQUINYLSULFONYL PROPYNE; ANTHRAQUINONE DERIVATIVE; DNA; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG; ALKYLATING AGENT; ALKYNE; DRUG DERIVATIVE; ISATIN; PROPARGYLIC SULFONE;

ARTICLE; CHROMATOPHORE; CONTROLLED STUDY; CYTOTOXICITY; DNA ALKYLATION; DNA BINDING; DNA CLEAVAGE; DNA MODIFICATION; DRUG DNA BINDING; DRUG EFFECT; DRUG STRUCTURE; HUMAN; HUMAN CELL; IRRADIATION; OXIDATION; ANIMAL; CELL CULTURE; CHEMISTRY; LIGHT; MOUSE; PHOTOLYSIS; RADIATION EXPOSURE; SYNTHESIS;

ALKYNES; ANIMALS; ANTHRAQUINONES; ANTINEOPLASTIC AGENTS, ALKYLATING; DNA; ISATIN; LIGHT; MICE; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; TUMOR CELLS, CULTURED;

EID: 33747362691     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.02.036     Document Type: Article

References (24)

1. Nicolaou K.C., Skokotas G., Maligres P., Zuccarello G., Schweiger E.J., Toshima K., and Wendeborn S. Angew. Chem. Int., Ed. Engl. 28 (1989) 1272
2. Nicolaou K.C., Wendeborn S., Maligres P., Isshiki K., Zein N., and Ellestad G. Angew. Chem., Int. Ed. Engl. 30 (1991) 418
3. Dai W.-M., Fong K.C., Danjo H., Nishimoto S., Solow M., Mak W.L., and Yeung M.L. Bioorg. Med. Chem. Lett. 6 (1996) 1093
4. Dai W.-M., Li Q., Fong K.C., Chow C.W., Zhou L., Hamaguchi W., and Nishimoto S. Bioorg. Med. Chem. Lett. 8 (1998) 169
5. Dai W.-M., Chow C.-W., Zhou L., Ishii A., Lau C.-W., Li Q., Hamaguchi W., and Nishimoto S. Bioorg. Med. Chem. Lett. 9 (1999) 2789
6. Haruna K., Tanabe K., Ishii A., Dai W.-M., Hatta H., and Nishimoto S. Bioorg. Med. Chem. 11 (2003) 5311
7. Saito I., Takayama M., Sugiyama H., and Nakatani K. J. Am. Chem. Soc. 117 (1995) 6406
8. Breslin D.T., and Schuster G.B. J. Am. Chem. Soc. 118 (1996) 2311
9. Breslin D.T., Coury J.E., Anderson J.R., McFail-Isom L., Kan Y., Williams L.D., Bottomely L.A., and Schuster G.B. J. Am. Chem. Soc. 119 (1997) 5043
10. -1) suggest that propargylic sulfone 2 favors intercalation of anthraquinone chromophore into DNA duplex rather than naphthalene chromophore. Upon intercalation of anthraquinone chromophore, activated allenic site of 2 would be located far from nucleobases in the complex of 2 with DNA duplex. This unfavorable orientation of the activated allene resulted in low DNA alkylating activity (see Ref. 3d).
11. Yoshimoto S., Hirakawa N., Nishiyama K., and Taniguchi I. Langmuir 16 (2000) 4399
12. 3.
13. Kenneth G.S., and Ronald E.S. J. Chem. Edu. 71 (1994) 77
14. Lown M.J. The Chemistry of DNA Damage by Antitumor Drugs. In: Neidles S., and Waring M.J. (Eds). Molecular Aspects of Anticancer Drug action (1983), Verlag Chemie, Weinheim 283
15. Sakai Y., Bando Y., Shishido K., and Shibuya M. Tetrahedron Lett. 33 (1992) 957
16. Xie G., Morgan A.R., and Lown J.W. Bioorg. Med. Chem. Lett. 3 (1993) 1565
17. Toshima K., Ohta K., Otsuka A., Matsumura S., and Nakata M. J. Chem. Soc., Chem. Commun. 18 (1993) 1406
18. Kerwin S.M. Tetrahedron Lett. 35 (1994) 1023
19. McPhee M.M., Kern J.T., Hoster B.C., and Kerwin S.M. Bioorg. Chem. 28 (2000) 98
20. McPhee M.M., and Kerwin S.M. Bioorg. Med. Chem. 9 (2001) 2809
21. Maxam A.M., and Gilbert W. Proc. Natl. Acad. Sci. U.S.A. 74 (1977) 569
22. Maniatis T., Fritsch E.F., and Sambrook J. Molecular Cloning (1982), Cold Spring Harbor Laboratory Press, Plainview, New York
23. Sambrook J., Fritsch E.F., and Maniatis T. Molecular Cloning: A Laboratory Manual. 2nd ed. (1989), Cold Spring Harbor Laboratory Press, New York
24. Mosmann T. J. Immunol. Methods 65 (1983) 55