Design, synthesis, and anticancer activity of phosphonic acid diphosphate derivative of adenine-containing butenolide and its water-soluble derivatives of paclitaxel with high antitumor activity

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 20, 2003, Pages 4303-4313

  Moosavi Movahedi, Ali A ^a   Hakimelahi, Shahram ^b   Chamani, Jamshid ^a   Khodarahmi, Ghadam Ali ^c   Hassanzadeh, Farshid ^c   Luo, Fen Tair ^d   Ly, Tai Wei ^d   Shia, Kak Shan ^e   Yen, Chi Feng ^e   Jain, Moti L ^f   Kulatheeswaran, Ramasamy ^d   Xue, Cuihua ^d   Pasdar, Manijeh ^b   Hakimelahi, Gholam Hossein ^a,d,e  

^a UNIVERSITY OF TEHRAN   (Iran)

^b UNIVERSITY OF ALBERTA   (Canada)

^c ISFAHAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d INSTITUTE OF CHEMISTRY   (Taiwan)

^e TaiGen Biotechnology   (Taiwan)

^f UNIVERSITY OF ARKANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 [2 (PACLITAXEL 2' O CARBO ALPHA CHLOROMETHYL)TRIPHOSPHONO 2 (ADENIN 9 YL)ETHYLIDENE] 2,3 DIMETHOXY DELTA DELTA ALPHA BETA BUTENOLIDE; 4 [2 (PACLITAXEL 2' O CARBOMETHYL)TRIPHOSPHONO 2 (ADENIN 9 YL)ETHYLIDENE] 2,3 DIMETHOXY DELTA ALPHA BETA BUTENOLIDE; 4 [2 (PACLITAXEL 2' O TRIPHOSPHONO) 2 (ADENIN 9 YL)ETHYLIDENE] 2,3 DIMETHOXY DELTA ALPHA BETA BUTENOLIDE; ADENINE DERIVATIVE; ANTINEOPLASTIC AGENT; BUTENOLIDE; OXIDOREDUCTASE INHIBITOR; PACLITAXEL; PACLITAXEL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORIBOSYL PYROPHOSPHATE; RIBONUCLEOSIDE DIPHOSPHATE REDUCTASE; RIBOSEPHOSPHATE PYROPHOSPHOKINASE; TRIPHOSPHONO GAMMA ETHYLIDENE 2,3 DIMETHOXYBUTENOLIDE; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG DESIGN; DRUG SOLUBILITY; DRUG SYNTHESIS; ENZYME INACTIVATION; ESCHERICHIA COLI; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; LIPOPHILICITY; MICROTUBULE ASSEMBLY; NONHUMAN; STOICHIOMETRY; T LYMPHOBLAST;

ESCHERICHIA COLI; MURINAE;

EID: 12444250003     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00524-8     Document Type: Article

References (30)

1. Silverman, R. B. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC: Boca Raton, FL, 1988, p 3.
2. Thelander L., Reichard P. Annu. Rev. Biochem. 48:1979;133.
3. Sando G.N., Hogenkamp H.P.C. Biochemistry. 12:1973;3316.
4. Berglund O. J. Biol. Chem. 247:1972;7270.
5. Hakimelahi G.H., Nemer M. J. Sci. Tech. (Shiraz). 10:1985;1.
6. Blakley R.L. J. Biol. Chem. 241:1966;176.
7. Goldberg I.H. Acc. Chem. Res. 24:1991;191.
8. Meier C., Lorey M., De Clercq E., Balzarini J. J. Med. Chem. 41:1998;1417. and references cited therein.
9. (a) Souto A.A., Acuna A.U., Andreu J.M., Barasoain I., Abal M., Amat-Guerri F. Angew. Chem., Int. Ed. Engl. 34:1995;2710. and references cited therein.
10. (b) Schiff P.B., Fant J., Horwitz S.B. Nature. 277:1979;665.
11. (c) Wiernik P.H., Schwartz E.L., Strauman J.J., Dutcher J.P., Lipton R.B., Phase E. Cancer Res. 47:1987;2486. and references cited therein.
12. (d) Schiff P.B., Horwitz S.B. Proc. Natl. Acad. Sci. U.S.A. 77:1980;1561.
13. Greenwald R.B., Gilbert C.W., Pendri A., Conover C.D., Xia J., Martinez A. J. Med. Chem. 39:1996;424. and references cited therein.
14. Oliyai R., Stella V.J. Annu. Rev. Pharmacol. Taxicol. 32:1993;521.
15. Hakimelahi G.H., Mei N.-W., Moosavi-Movahedi A.A., Davari H., Hakimelahi S., King K.-Y., Hwu J.R., Wen Y.-S. J. Med. Chem. 44:2001;1749.
16. Balzarini J., De Clercq E. J. Biol. Chem. 266:1991;8686. and references cited therein.
17. Baker D.C., Haskell T.H., Putt S.R. J. Med. Chem. 21:1978;1218.
18. (a) Baker C.H., Banzon J., Bollinger J.M., Stubbe J., Samano V., Robins M.J., Lippert B., Jarvi E., Resvick R. J. Med. Chem. 34:1991;1879 (b) Salowe S.P., Stubbe J. J. Bacteriol. 165:1986;363.
19. (a) Baker C.H., Banzon J., Bollinger J.M., Stubbe J., Samano V., Robins M.J., Lippert B., Jarvi E., Resvick R. J. Med. Chem. 34:1991;1879 (b) Salowe S.P., Stubbe J. J. Bacteriol. 165:1986;363.
20. Steeper J.R., Steuart C.D. Anal. Biochem. 34:1970;123.
21. For stoichiometric mechanism-based inhibitors, see: Salowe S.P., Ator M.A., Stubbe J. Biochemistry. 26:1987;3408.
22. Mathew A.E., Mejillano M.R., Nath J.P., Himes R.H., Stella V.J. J. Med. Chem. 35:1992;145. and references cited therein.
23. (a) Raić-Malić S., Hergold-Brundić A., Nagl A., Grdisa M., Pavelić K., De Clercq E., Mintas M. J. Med. Chem. 42:1999;2673.
24. (b) Raić-Malić S., Svedruzić D., Gazivoda T., Marunović A., Hergold-Brundić A., Nagl A., Balzarini J., De Clercq E., Mintas M. J. Med. Chem. 43:2000;4806.
25. (a) Schinazi R.F., Peters J., Williams C.C., Chance D., Nahmias A. J. Antimicrob. Agents Chemother. 22:1982;499.
26. (b) Hakimelahi G.H., Ly T.W., Moosavi-Movahedi A.A., Jain M.L., Zakerinia M., Davari H., Mei H.-C., Sambaiah T., Moshfegh A.A., Hakimelahi S. J. Med. Chem. 44:2001;3710. and references cited therein.
27. Hakimelahi G.H., Moosavi-Movahedi A.A., Sadegi M.M., Tsay S.-C., Hwu J.R. J. Med. Chem. 38:1995;4648. and references cited therein.
28. Bradford M.M. Anal. Biochem. 72:1970;248.
29. Swindell C.S., Krauss N.E., Horwitz S.B., Ringel I. J. Med. Chem. 34:1991;1176. and references cited therein.
30. Hakimelahi S., Parker H.R., Gilchrist A.J., Barry M., Li Z., Bleackley R.C., Pasdar M. J. Biol. Chem. 275:2000;10905.