New sulfurated derivatives of valproic acid with enhanced histone deacetylase inhibitory activity

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 6, 2008, Pages 1893-1897

  Perrino, Elena ^a   Cappelletti, Graziella ^b   Tazzari, Valerio ^a   Giavini, Erminio ^b   Soldato, Piero Del ^a   Sparatore, Anna ^a,b  

^a Progress Srl   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Dithiolethione derivatives; Histone deacetylase inhibitor; Methanethiosulfonate derivatives; Valproic acid derivatives

Indexed keywords

2 AMINOETHYLMETHANETHIOSULFONATE; 2 HYDROXYETHYLMETHANESULFONATE; 5 (4 HYDROXYPHENYL) 3H 1,2 DITHIOLE 3 THIONE; DITHIOLTHIONE; HISTONE DEACETYLASE INHIBITOR; MESYLIC ACID; SULFUR DERIVATIVE; THIOKETONE; UNCLASSIFIED DRUG; VALPROIC ACID;

ACETYLATION; ARTICLE; CANCER INHIBITION; CELL PROLIFERATION; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; IN VITRO STUDY; INHIBITION KINETICS; MOLECULAR MODEL;

ACETYLATION; ADENOCARCINOMA; APOPTOSIS; BLOTTING, WESTERN; CELL PROLIFERATION; ENZYME INHIBITORS; HISTONE DEACETYLASES; HUMANS; LUNG NEOPLASMS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIOSULFONIC ACIDS; TUMOR CELLS, CULTURED; VALPROIC ACID;

EID: 40749117604     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.02.007     Document Type: Article

References (38)

1. Minucci S., and Pelicci P.G. Nat. Rev. Cancer 6 (2006) 38
2. Carraway H.E., and Gore S.D. J. Clin. Oncol. 25 (2007) 1955
3. Moradei O., Maroun C.R., Paquin I., and Vaisburg A. Curr. Med. Chem. 5 (2005) 529
4. Acharya M.R., Sparreboom A., Venits J., and Figg W. Mol. Pharmacol. 68 (2005) 917
5. Gottlicher M., Minucci S., Zhu P., Kramer O.H., Schimpf A., Giavara S., Sleeman J.P., Lo Coco F., Nervi C., Pelicci P.G., and Heinzel T. EMBO J. 20 (2001) 6969
6. Mcintyre J., Moral M.A., and Bozzo J. Drugs Future 32 (2007) 45
7. Wang P.H., and Wiest O. J. Org. Chem. 72 (2007) 5446
8. Lu Q., Yang Y.T., Chen C.S., Davis M., Byrd J.C., Etherton M.R., Umar A., and Chen C.S. J. Med. Chem. 47 (2004) 467
9. Lea M.A., Randolph V.M., Lee J.E., and DesBordes C. Int. J. Cancer 92 (2001) 784
10. Dashwood R.H., and Ho E. Semin. Cancer Biol. 17 (2007) 363
11. Myzak M.C., Ho E., and Dashwood R.H. Mol. Carcinog. 45 (2006) 443
12. Myzak M.C., and Dashwood R.H. Curr. Drug Targets 7 (2006) 443
13. Reddy B.S., Kawamori T., Lubet R., Steele V., Kelloff G., and Rao C.V. Carcinogenesis 20 (1999) 1645
14. Suzuki T., Kouketsu A., Matsuura A., Kohara A., Ninomiya S.-I., Kohda K., and Miyata N. Bioorg. Med. Chem. 14 (2004) 3313
15. Nishino N., Jose B., Okamura S., Ebibusaki S., Kato T., Sumida Y., and Yoshida M. Org. Lett. 5 (2003) 5079
16. Suzuki T., Nagano Y., Kouketsu A., Matsuura A., Maruyama S., Kurotaki M., Nakagawa H., and Miyata N. J. Med. Chem. 48 (2005) 1019
17. Suzuki T., Hisakawa S., Maruyama S., Kurotaki M., Nakagawa H., and Miyata N. Bioorg. Med. Chem. Lett. 17 (2007) 1558
18. Suzuki T., Kouketsu A., Itoh Y., Hisakawa S., Maeda S., Yoshida M., Nakagawa H., and Miyata N. J. Med. Chem. 49 (2006) 4809
19. Anandan S.-K., Ward J.S., Brokx R.D., Bray M.R., Patel D.V., and Xiao X.-X. Bioorg. Med. Chem. Lett. 15 (2005) 1969
20. Chen B., Petukhov P.A., Jung M., Velena A., Eliseeva E., Dritschilo A., and Kozikowski A.P. Bioorg. Med. Chem. Lett. 15 (2005) 1389
21. Suzuki T., Matsuura A., Kouketsu A., Nakagawa H., and Miyata N. Bioorg. Med. Chem. Lett. 15 (2005) 331
22. Gu W., Nusinzon I., Smith Jr. R.D., Horvarth C.M., and Silverman R.B. Bioorg. Med. Chem. 14 (2006) 3320
23. Dehmel F., Ciossek T., Maier T., Weinbrenner S., Schmidt B., Zoche M., and Beckers T. Bioorg. Med. Chem. Lett. 17 (2007) 4746
24. Isenberg J.S., Jia Y., Field L., Ridnour L.A., Sparatore A., Del Soldato P., Sowers A.L., Yeh G.C., Moody T.W., Wink D.A., Ramchandran R., and Roberts D.D. Br. J. Pharmacol. 151 (2007) 142
25. Ruggeri B.A., Robinson C., Angeles T., Wilkinson J., and Clapper M.L. Clin. Cancer Res. 8 (2002) 267
26. Kensler T.W., Curphey T.J., Maxiutenko Y., and Roebuck B.D. Drug Metabol. Drug Interact. 17 (2000) 3
27. Petillon F., and Guerchais J.E. Int. J. Sulf. Chem. 8 (1973) 367
28. Jaffe E.K., Salowe S.P., Chen N.T., and DeHaven P.A. J. Biol. Chem. 259 (1984) 5032
29. Foong L.Y., You S., Jaikaran D.C., Zhang Z., Zunic V., and Woolley G.A. Biochemistry 36 (1997) 1343
30. Bruice T.W., and Kenyon G.L. J. Protein Chem. 1 (1982) 47
31. + 304.10116; found 304.10104.
32. 33 Briefly, HeLa nuclear extracts were incubated with acetylated fluorogenic substrate (100 μM) for 60 min at 37 °C in the presence of test compound dissolved in DMSO or DMSO alone. The deacetylated reaction was stopped by addition of 40 μl of HDAC developer containing 5 μM trichostatin A. After 15 min, fluorescence activity was measured with a Fluorocount™ reader (Packard BioScience, USA) at 360 nm excitation and 465 nm emission. As ADTOH, ACS 2 and ADT still exhibit a low absorbtion at the wavelength of fluorescence emission, appropriate controls were prepared as follows. HeLa nuclear extracts were incubated for 60 min at 37 °C in the absence of these compounds, the reaction was stopped by addition of developer, and, immediately, ADTOH, ACS 2, or ADT were added. After 15 min, the fluorescence was measured. The inhibition of HDAC activity by ADTOH, ACS 2, or ADT was calculated taking this value as the 100% of activity. All experimental data were fitted and analysed by computer using a sigmoidal dose-response function (Sigma Plot, Jandel, CA).
33. Di Renzo F., Cappelletti G., Broccia M., Giavini E., and Menegola E. Toxicol. Appl. Pharmacol. 220 (2007) 178
34. Masoud A.N., and Bueding E. J. Chromatogr. 276 (1983) 111
35. Lubet R.A., Steele V.E., Eto I., Juliana M.M., Kelloff G.J., and Grubb C.J. Int. J. Cancer 72 (1997) 95
36. 33 Data are normalized on the levels of total proteins and expressed as a percentage of control.
37. Chollet M., Legouin B., and Burgot J.-L. J. Chem. Soc., Perkin Trans. 2 2 (1998) 2227
38. Wedel, S. A.; Sparatore, A.; Del Soldato, P.; Al-Batran, S.-E.; Atmaca, A.; Juengel, E.; Hudak, L.; Jonas, D.; Blaheta, R. A. J. Cell. Mol. Med., in press.