Sulphonamide-based bombesin prodrug analogues for glutathione transferase, useful in targeted cancer chemotherapy

European Journal of Medicinal Chemistry

Volumn 44, Issue 5, 2009, Pages 2009-2016

  Axarli, I ^a   Labrou, N E ^a   Petrou, C ^b   Rassias, N ^c   Cordopatis, P ^b   Clonis, Y D ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^b UNIVERSITY OF PATRAS   (Greece)

^c RAFARM SA   (Greece)

Author keywords

Alkylating agents; Antineoplastic therapy; Detoxification; Drug resistance; Enzyme activated prodrug; Glutathione transferase

Indexed keywords

BOMBESIN [LEUCINE 13]; BOMBESIN [PHENYLALANINE 13]; BOMBESIN [SERINE 3 ARGININE 10 PHENYLALANINE 13]; BOMBESIN DERIVATIVE; GLUTATHIONE; GLUTATHIONE TRANSFERASE A1; PRODRUG; SULFONAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CANCER CHEMOTHERAPY; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MALE; MOLECULAR RECOGNITION; MOUSE; NONHUMAN; RAT; TUMOR CELL;

ANTINEOPLASTIC AGENTS; BOMBESIN; GLUTATHIONE TRANSFERASE; HUMANS; PRODRUGS; SULFONAMIDES;

EID: 62749159756     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.10.009     Document Type: Article

References (50)

1. Mannervik B., and Danielson U.H. CRC Crit. Rev. Biochem. 23 (1988) 283-337
2. Frova C. Biomol. Eng. 23 (2006) 149-169
3. Dulhunty A., Gage P., Curtis S., Chelvanayagam G., and Board P. J. Biol. Chem. 276 (2001) 3319-3323
4. Alias Z., and Clark A.G. Proteomics 7 (2007) 3618-3628
5. Dixon D.P., Davis B.G., and Edwards R. J. Biol. Chem. 277 (2002) 30859-30869
6. Allocati N., Favaloro B., Masulli M., Alexeyev M.F., and Di Ilio C. Biochem. J. 373 (2002) 305-311
7. Wiktelius E., and Stenberg G. Biochem. J. 406 (2007) 115-123
8. Oakley A.J. Curr. Opin. Struct. Biol. 15 (2005) 716-723
9. Cusack Jr. J.C., and Tanabe K.K. Surg. Oncol. Clin. N. Am. 11 (2002) 497-519
10. Sehgal A. Curr. Opin. Drug Discov. Devel 5 (2002) 245-250
11. Hayes J.D., and Pulford D.J. Crit. Rev. Biochem. Mol. Biol. 30 (1995) 445-600
12. Batist G., Tulpule A., Sinha B.K., Katki A.G., Myers C.E., and Cowan K.H. J. Biol. Chem. 261 (1986) 15544-15549
13. Sargent J.M., Williamson C., Hall A.G., Elgie A.W., and Taylor C.G. Exp. Med. Biol. 457 (1999) 205-209
14. Kodera Y., Isobe K., Yamauchi M., Kondo K., Akiyama S., Ito K., Nakashima I., and Takagi H. Cancer. Chemother. Pharmacol. 34 (1994) 203-208
15. Adler V., Yin Z., Fuchs S.Y., Benezra M., Rosario L., Tew K.D., Pincus M.R., Sardana M., Henderson C.J., Wolf C.R., Davis R.J., and Ronai Z. EMBO J. 18 (1999) 1321-1334
16. Sweeney C., Coles B.F., Nowell S., Lang N.P., and Kadlubar F.F. Toxicology 181-182 (1988) 83-87
17. Reubi J.C., Wenger S., Schmuckli-Maurer J., Schaer J.C., and Gugger M. Clin. Cancer Res. 8 (2002) 1139-1146
18. Nagy A., Armatis P., Cai R.Z., Szepeshazi K., Halmos G., and Schally A.V. Proc. Natl. Acad. Sci. USA 94 (1997) 652-656
19. Labrou N.E., Mello L.V., and Clonis Y.D. Eur. J. Biochem. 268 (2001) 3950-3957
20. Meyer D.J., and Thomas M. Biochem. J. 311 (1995) 739-742
21. McGonigle B., Keeler S.J., Lau S.M., Koeppe M.K., and O'Keefe D.P. Plant Physiol. 124 (2000) 1105-1120
22. Fields B.G., and Noble L.R. Int. J. Pept. Prot. Res. 35 (1990) 161-214
23. S. Aventis, European Patent 3,22,348 and US Patent 5,124,478.
24. Köning W., and Geiger R. Chem. Ber. 103 (1970) 788-798
25. Kaiser E., Colescott R.L., Bossinger C.D., and Cook P.I. Anal. Biochem. 34 (1970) 595-598
26. Vojkovsky T. Detection of secondary amines on solid phase. Pept. Res. 8 (1995) 236-237
27. Katusz R.M., Bono B., and Colman R.F. Biochemistry 30 (1991) 11230-11238
28. Bradford M.M. Anal. Biochem 72 (1976) 248-258
29. Cameron A.D., Sinning I., L`Hermite G., Olin B., Board P.G., Mannervik B., and Jones T.A. Structure 3 (1995) 717-727
30. ChemDraw Software [Available from: http://www.cambridgesoft.com/software/ChemDraw/].
31. Thompson M.A. ArgusLab 4.0.1. [Available from: ]. Planaria Software LLC, Seattle, WA.
32. Erve A., Saoudi Y., Thirot S., Guetta-Landras C., Florent J.C., Nguyen C.H., Grierson D.S., and Popov A.V. Nucleic Acids Res. 34 (2006) (e43)
33. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639-1662
34. DeLano W.L. The PyMOL Molecular Graphics System (2002), DeLano Scientific, San Carlos, USA
35. Mukanganyama S., Widersten M., Naik Y.S., Mannervik B., and Hasler J.A. Int. J. Cancer 97 (2002) 700-705
36. Zhao Z., Koeplinger K.A., Peterson T., Conradi R.A., Burton P.S., Suarato A., Heinrikson R.L., and Tomasselli A.G. Drug Metab. Dispos. 27 (1999) 992-998
37. Koeplinger K.A., Zhao Z., Peterson T., Leone J.W., Schwende F.S., Heinrikson R.L., and Tomasselli A.G. Drug Metab. Dispos. 27 (1999) 986-991
38. Czerwinski M., Gibbs J.P., and Slattery J.T. Drug Metab. Dispos. 24 (1996) 1015-1019
39. Dirven H.A.A.M., van Ommen B., and van Bladeren P. J. Chem. Res. Toxicol. 9 (1996) 351-360
40. Chatzistamou I., Schally A.V., Szepeshazi K., Groot K., Hebert F., and Arencibia J.M. Cancer Lett. 171 (2001) 37-45
41. Darker J.G., Brough S.J., Heath J., and Smart D. J. Pept. Sci. 7 (2001) 598-605
42. Meyer D.J. Xenobiotica 23 (1993) 823-834
43. Chang M., Zhang F., Shen L., Pauss N., Alam I., van Breemen R.B., Blond S.Y., and Bolton J.L. Chem. Res. Toxicol. 11 (1998) 758-765
44. McHugh T.E., Atkins W.M., Racha J.K., Kunze K.L., and Eaton D.L. J. Biol. Chem. 271 (1996) 27470-27474
45. O'Dwyer P.J., LaCreta F., Nash S., Tinsley P.W., Schilder R., Clapper M.L., Tew K.D., Panting L., Litwin S., Comis R.L., and Ozols R.F. Cancer Res. 51 (1991) 6059-6065
46. Morgan A.S., Ciaccio P.J., Tew K.D., and Kauvar L.M. Cancer Chemother. Pharmacol. 37 (1996) 363-370
47. Lyttle M.H., Satyam A., Hocker M.D., Bauer K.E., Caldwell C.G., Hui H.C., Morgan A.S., Mergia A., and Kauvar L.M. J. Med. Chem. 37 (1994) 1501-1507
48. Satyam A., Hocker M.D., Kane-Maguire K.A., Morgan A.S., Villar H.O., and Lyttle M.H. J. Med. Chem. 39 (1996) 1736-1747
49. Tew K.D. Expert. Opin. Investig. Drugs 14 (2005) 1047-1054
50. Saavedra J.E., Bohle D.S., Smith K.N., George C., Deschamps J.R., Parrish D., Ivanic J., Wang Y.N., Citro M.L., and Keefer L.K. J. Am. Chem. Soc. 126 (2004) 12880-12887