Synthesis and biological evaluation of the suberoylanilide hydroxamic acid (SAHA) β-glucuronide and β-galactoside for application in selective prodrug chemotherapy

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 4, 2007, Pages 983-986

  Thomas, Mickaël ^a   Rivault, Freddy ^a   Tranoy Opalinski, Isabelle ^a   Roche, Joëlle ^a   Gesson, Jean Pierre ^a   Papot, Sébastien ^a  

^a UNIVERSITÉ DE POITIERS   (France)

Author keywords

ADEPT; Galactoside; Glucuronide; HDAC; Prodrug; SAHA

Indexed keywords

BETA GALACTOSIDE; BETA GLUCURONIDASE; GLUCURONIDE; PRODRUG; VORINOSTAT;

ARTICLE; CANCER CHEMOTHERAPY; DRUG RELEASE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, NON-SMALL-CELL LUNG; CATTLE; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLINICAL TRIALS; GALACTOSIDES; GLUCURONIDES; HUMANS; HYDROLYSIS; HYDROXAMIC ACIDS; PRODRUGS;

BOVINAE; ESCHERICHIA COLI;

EID: 33846578183     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.11.042     Document Type: Article

References (31)

1. Rooseboom M., Commandeur J.N.M., and Vermeulen N.P.E. Pharmacol. Rev. 56 (2004) 53
2. P.M.T.: Prodrug Mono-Therapy. Bosslet K., Czech J., and Hoffman D. Tumor Target. 1 (1995) 45
3. Bosslet K., Straub R., Blumrich M., Czech J., Gerken M., Sperker B., Kroemer H.K., Gesson J.-P., Koch M., and Monneret C. Cancer Res. 58 (1998) 1195
4. deGroot F.M.H., Damen E.W.P., and Scheeren H.W. Curr. Med. Chem. 8 (2001) 1093
5. A.D.E.P.T.: Antibody-Directed Enzyme Prodrug Therapy. Niculescu-Duvaz I., and Springer C.J. Adv. Drug Deliv. Rev. 26 (1997) 151
6. Bagshawe K.D., Sharma S.K., and Begent R.H. Expert Opin. Biol. Ther. 4 (2004) 1777
7. G.D.E.P.T.: Gene-Directed Enzyme Prodrug Therapy. Springer C.J., and Niculescu-Duvaz I. Adv. Drug Deliv. Rev. 22 (1996) 351
8. Niculescu-Duvaz I., and Springer C.J. Mol. Biotechnol. 30 (2005) 71
9. L.E.A.P.T.: Lectin-Directed Enzyme-Activated Prodrug Therapy. Robinson M.A., Charlton S.T., Garnier P., Wang X., Davis S.S., Perkins A.C., Frier M., Duncan R., Savage T.J., Wyatt D.A., Watson S.A., and Davis B.G. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 14527
10. Bosslet K., Czech J., and Hoffman D.. Cancer Res. 54 (1994) 2151
11. Fang L., Battisti R.F., Cheng H., Reigan P., Xin Y., Shen J., Ross D., Chan K.K., Martin Jr. E., Wang P.G., and Sun D. J. Med. Chem. 49 (2006) 6290
12. Xiao J., Horst S., Hinkle G., Cao X., Kocak E., Fanq J., Young D., Khazaeli M., Agnese D., Sun D., and Martin Jr. E. Cancer Biother. Radiopharm. 20 (2005) 16
13. Monneret C. Eur. J. Med. Chem. 40 (2005) 1
14. Miller T.A., Witter D.J., and Belvedere S. J. Med. Chem. 46 (2003) 5097
15. McLaughlin F., and La Thangue N.B. Biochem. Pharmacol. 68 (2004) 1139
16. Richon V.M., Webb Y., Merger R., Sheppard T., Jursic B., Ngo L., Civoli F., Breslow R., Rifkind R.A., and Marks P.A. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 5705
17. Richon V.M., Emiliani S., Verdin E., Webb Y., Breslow R., Rifkind R.A., and Marks P.A. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 3003
18. Breslow R., Belvedere S., and Gershell L. Helv. Chim. Acta 83 (2000) 1685
19. Butler L.M., Agus D.B., Scher H.I., Higgins B., Rose A., Cordon-Cardo C., Thaler H.T., Rifkind R.A., Marks P.A., and Richon V.M. Cancer Res. 60 (2000) 5165
20. Cohen L.A., Amin S., Marks P.A., Rifkind R.A., Desai D., and Richon V.M. Anticancer Res. 19 (1999) 4999
21. Kelly W.K., Richon V.M., O'Connor O., Curley T., MacGregor-Curtelli B., Tong W., Klang M., Schwartz L., Richardson S., Rosa E., Drobnjak M., Cordon-Cordo C., Chiao J.H., Rifkind R., Marks P.A., and Scher H. Clin. Cancer Res. 9 (2003) 3578
22. Krug L.M., Curley T., Schwartz L., Richardson S., Marks P., Chiao J., and Kelly W.K. Clin. Lung Cancer 7 (2006) 257
23. Finnin M.S., Donigian J.R., Cohen A., Richon V.M., Rifkind R.A., Marks P.A., Breslow R., and Pavletich N.P. Nature 401 (1999) 188
24. Vannini A., Volpari C., Filocamo G., Casavola E.C., Brunetti M., Renzoni D., Chakravarty P., Paolini C., De Francesco R., Gallinari P., Steinkühler C., and Di Marco S. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 15064
25. Somoza J.R., Skene R.J., Katz B.A., Mol C., Ho J.D., Jennings A.J., Luong C., Arvai A., Buggy J.J., Chi E., Tang J., Sang B.-C., Verner E., Wynands R., Leahy E.M., Dougan D.R., Snell G., Navre M., Knuth M.W., Swanson R.V., McRee D.E., and Tari L.W. Structure 12 (2004) 1325
26. Mitchell M.B., and Whitcombe I.W.A. Tetrahedron Lett. 41 (2000) 8829
27. Hosokawa S., Ogura T., Togashi H., and Tatsuta K. Tetrahedron Lett. 46 (2005) 333
28. Suzuki T., Matsuura A., Kouketsu A., Hisakawa S., Nakagawa H., and Miyata N. Bioorg. Med. Chem. 13 (2005) 4332
29. 3OD) δ (ppm): 25.2, 25.6, 28.6, 28.7, 32.4, 36.7, 61.4, 68.9, 69.3, 73.4, 76.1, 107.0, 120.1, 124.0, 128.6, 138.7, 172.2, 173.5.
30. 2O/TFA 3:7:0.028. Retention times for compounds 2, 3 and SAHA, respectively, were 3.40, 3.31 and 4.15 min. E. coli β-glucuronidase, bovine liver β-glucuronidase and β-galactosidase were purchased from Sigma-Aldrich (reference Sigma: G2513-1KU, G0501-100KU and G7896-2KU, respectively).
31. Du, L.; Musson, D. G.; Wang, A. Q. Abstracts of papers, 229th ACS National Meeting, San Diego, CA, United States, March 13-17, 2005.