Molecular design, chemical synthesis and biological evaluation of quinoxaline-carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

Tetrahedron

Volumn 59, Issue 35, 2003, Pages 7057-7066

  Toshima, Kazunobu ^a   Kimura, Tomonori ^a   Takano, Ryusuke ^a   Ozawa, Tomohiro ^a   Ariga, Akiko ^a   Shima, Yutaka ^a   Umezawa, Kazuo ^a   Matsumura, Shuichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Carbohydrate; Cytotoxicity; DNA photocleavage; Quinoxaline

Indexed keywords

ANTINEOPLASTIC AGENT; CARBOHYDRATE DERIVATIVE; CYTOTOXIC AGENT; DOUBLE STRANDED DNA; QUINOXALINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DNA CLEAVAGE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IRRADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET RADIATION;

EID: 0043160197     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00820-2     Document Type: Article

References (26)

1. Demeunynck M., Bailly C., Wilson W.D. DNA and RNA Binders. 2003;Wiley-VCH, Weinheim.
2. Armitage B. Chem. Rev. 98:1998;1171-1200.
3. (a) Brown J.E., Brown S.B., Vernon D.I. J. Soc. Dyers Colour. 115:1999;249-353.
4. (b) Morgan A.R. Curr. Med. Chem. 2:1995;604-615.
5. (c) Bonnett R. Chem. Soc. Rev. 1995;19-33.
6. (d) Henderson R.W., Dougherty T.J. Photodynamic Therapy: Basic Principles and Clinical Applications. 1992;Marcel Dekker, New York.
7. A preliminary communication of this work Toshima K., Takano R., Ozawa T., Matsumura S. Chem. Commun. 2002;212-213.
8. Waring M.J., Fox K.R. Niedle S., Waring M.J. Molecular Aspects of Anti-cancer Drug Action. 1983;127-156 Macmillan, New York.
9. Waring M.J., Wakelin L.P.G. Nature. 252:1974;653-657.
10. (a) Toshima K., Ouchi H., Okazaki Y., Kano T., Moriguchi M., Asai A., Matsumura S. Angew. Chem. Int. Ed. Engl. 36:1997;2748-2750.
11. (b) Toshima K., Takano R., Maeda Y., Suzuki M., Asai A., Matsumura S. Angew. Chem. Int. Ed. Engl. 38:1999;3733-3735.
12. (c) Toshima K., Maeda Y., Ouchi H., Asai A., Matsumura S. Bioorg. Med. Chem. Lett. 10:2000;2163-2165.
13. (d) Toshima K., Takai S., Maeda Y., Takano R., Matsumura S. Angew. Chem. Int. Ed. 39:2000;3656-3658.
14. (e) Toshima K., Okuno Y., Nakajima Y., Matsumura S. Bioorg. Med. Chem. Lett. 12:2002;671-673.
15. Bartner P., Boxier D.L., Brambilla R., Mallams A.K., Morton J.B., Reichert P., Sancilio F.D., Surprenant H., Tomalesky G., Lukacs G., Olesker A., Thang T.T., Valente L., Omura S. J. Chem. Soc. Perkin Trans. 1. 1979;1600-1624.
16. Nicolaou K.C., Seitz S.P., Papahatjis D.P. J. Am. Chem. Soc. 105:1983;2430-2434.
17. Fukuyama T., Jow C.-K., Cheung M. Tetrahedron Lett. 36:1995;6373-6374.
18. (a) Chaires J.B., Leng F., Prewloka T., Fokt I., Ling Y.-H., Perez-Soler R., Priebe W. J. Med. Chem. 40:1997;261-266
19. (b) Hu G.G., Shui X., Leng F., Priebe W., Chaires J.B., William L.D. Biochemistry. 36:1997;5940-5946.
20. Sanger F., Nicklen S., Coulsen A.R. Proc. Natl Acad. Sci. USA. 74:1977;5463-5467.
21. (a) Boger D.L., Munk S.A., Zarrinmayeh H., Ishizaki T., Haught J., Bina M. Tetrahedron. 47:1991;2661-2682
22. (b) Toshima K., Ohta K., Ohashi A., Nakamura T., Nakata M., Tatsuta K., Matsumura S. J. Am. Chem. Soc. 117:1995;4822-4831.
23. (a) Saito I., Takayama M., Sugiyama H., Nakatani K., Tsuchida A., Yamamoto M. J. Am. Chem. Soc. 117:1995;6406-6407.
24. (b) Sugiyama H., Saito I. J. Am. Chem. Soc. 118:1996;7063-7068.
25. DNA Unwinding Kit available from TopoGEN, Inc. was used.
26. Scudieero D.A., Shoemaker R.H., Paull K.D., Monks A., Tierney S., Nofziger T.H., Currens M.J., Seniff D., Boyd M.R. Cancer Res. 48:1988;4827-4833.