Possible chemical mechanisms underlying the antitumor activity of S-deoxyleinamycin

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 10, 2008, Pages 3076-3080

  Sivaramakrishnan, Santhosh ^a   Gates, Kent S ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

Antitumor agent; DNA damage; Hydrogen sulfide; Leinamycin; Polysulfide; Strand cleavage; Superoxide radical; Thiol triggered

Indexed keywords

1,2 DITHIOLAN 3 ONE; DEOXYLEINAMYCIN; HETEROCYCLIC COMPOUND; HYDROGEN PEROXIDE; HYDROGEN SULFIDE; LEINAMYCIN; REACTIVE OXYGEN METABOLITE; SINGLET OXYGEN; SULFIDE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DNA STRAND BREAKAGE; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; HUMAN CELL;

ANTINEOPLASTIC AGENTS; DNA; DNA DAMAGE; LACTAMS; MACROLIDES; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; SULFHYDRYL COMPOUNDS; SULFIDES; THIAZOLES; THIONES;

EID: 43749114238     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.092     Document Type: Article

References (66)

1. Gates K.S. Chem. Res. Toxicol. 13 (2000) 953
2. Hara M., Asano K., Kawamoto I., Takiguchi T., Katsumata S., Takahashi K., and Nakano H. J. Antibiotics 42 (1989) 1768
3. Hara M., Saitoh Y., and Nakano H. Biochemistry 29 (1990) 5676
4. Hara M., Takahashi I., Yoshida M., Kawamoto I., Morimoto M., and Nakano H. J. Antibiotics 42 (1989) 333
5. Bassett S., Urrabaz R., and Sun D. Anti-Cancer Drugs 15 (2004) 689
6. Behroozi S.B., Kim W., and Gates K.S. J. Org. Chem. 60 (1995) 3964
7. Behroozi S.J., Kim W., Dannaldson J., and Gates K.S. Biochemistry 35 (1996) 1768
8. Mitra K., Kim W., Daniels J.S., and Gates K.S. J. Am. Chem. Soc. 119 (1997) 11691
9. Chatterji T., Keerthi K., and Gates K.S. Bioorg. Med. Chem. Lett. 15 (2005) 3921
10. Asai A., Hara M., Kakita S., Kanda Y., Yoshida M., Saito H., and Saitoh Y. J. Am. Chem. Soc. 118 (1996) 6802
11. Nooner T., Dutta S., and Gates K.S. Chem. Res. Toxicol. 17 (2004) 942
12. Shipova K., and Gates K.S. Bioorg. Med. Chem. Lett. 15 (2005) 2111
13. Dutta S., Chowdhury G., and Gates K.S. J. Am. Chem. Soc. 129 (2007) 1852
14. Meister A., and Anderson M.E. Ann. Rev. Biochem. 52 (1983) 711
15. 50 values) against HepG2 cells: cisplatin 3 μM, melphalan 17 μM, bleomycin 1 μM. Nakatsu N., Yoshida Y., Yamazaki K., Nakamura T., Dan S., Fukui Y., and Yamori T. Mol. Cancer. Ther. 4 (2005) 399
16. Chatterji T., and Gates K.S. Bioorg. Med. Chem. Lett. 8 (1998) 535
17. Chatterji T., and Gates K.S. Bioorganic Med. Chem. Lett. 13 (2003) 1349
18. Kim W., and Gates K.S. Chem. Res. Toxicol. 10 (1997) 296
19. Wang Y., Koreeda M., Chatterji T., and Gates K.S. J. Org. Chem. 63 (1998) 8644
20. Halliwell B., and Gutteridge J.M.C. Methods Enzymol. 186 (1990) 1
21. Bagley A.C., Krall J., and Lynch R.E. Proc. Nat. Acad. Sci. U.S.A. 83 (1986) 9189
22. Hassan H.M., and Fridovich I. Arch. Biochem. Biophys. 196 (1979) 385
23. Hassan H.M., and Fridovich I. J. Bacteriol. 141 (1980) 156
24. Sanchez Sellero I., and Lopez-Rivadulla Lamas M. Recent Res. Dev. Drug Metab. Disp. 1 (2002) 275
25. Finkel T., and Holbrook N.J. Nature 408 (2000) 239
26. Davis Jr. W., Ronai Z., and Tew K.D. J. Pharm. Exp. Ther. 296 (2001) 1
27. Arrigo A.-P., Firdaus W.J.J., Mellier G., Moulin M., Paul C., Diaz-Latoud C., and Kretz-Remy C. Methods 35 (2005) 126
28. Chen Y., Jungsuwadee P., Vore M., Butterfield D.A., and Clair St.D.K. Mol. Interventions 7 (2007) 147
29. Pattenden G., and Shuker A.J. J. Chem. Soc. Perkin 1 (1992) 1215
30. Hintermann G., Fischer H.M., Crameri R., and Hutter R. Plasmid 5 (1981) 371
31. Jonson P.H., and Grossman L.I. Biochemistry 16 (1977) 4217
32. Mirabelli C.K., Huang C.H., Fenwick R.G., and Crooke S.T. Antimicrobial Agents Chemother. 27 (1985) 460
33. Oppenheim A. Nucleic Acids Res. 9 (1981) 6805
34. Gates K.S. Covalent modification of DNA by natural products. In: Kool E.T. (Ed). Comprehensive Natural Products Chemistry Vol. 7 (1999), Pergamon, New York 491-552
35. Greenberg M.M. Org. Biomol. Chem. 5 (2007) 18
36. Greenberg M.M. Chem. Res. Toxicol. 11 (1998) 1235
37. Pogozelski W.K., and Tullius T.D. Chem. Rev. 98 (1998) 1089
38. Breen A.P., and Murphy J.A. Free Rad. Biol. Med. 18 (1995) 1033
39. Pratviel G., Bernadou J., and Meunier B. Angew. Chem. Int. Ed. Eng. 34 (1995) 746
40. Gates K.S. Chemical reactions of DNA damage and degradation. In: Platz M.S.M.R.A., and Jones Jr. M. (Eds). Reviews of Reactive Intermediates (2007), John Wiley and Sons, Inc, Hoboken 333-378
41. Hertzberg R.P., and Dervan P.B. Biochemistry 23 (1984) 3934
42. Thiol amounts between 2 and 20 equiv yield comparable levels of strand breaks under these conditions.
43. Daniels J.S., Gates K.S., Tronche C., and Greenberg M.M. Chem. Res. Toxicol. 11 (1998) 1254
44. Hwang J.-T., Greenberg M.M., Fuchs T., and Gates K.S. Biochemistry 38 (1999) 14248
45. 6,8
46. Misra H.P. J. Biol. Chem. 249 (1974) 2151
47. Ross D., Norbeck K., and Moldeus P. J. Biol. Chem. 260 (1985) 15028
48. Wardman P., and von Sonntag C. Methods Enzymol. 251 (1995) 31
49. Schöneich C. Methods Enzymol. 251 (1995) 45
50. Hargrove J.L. J. Biol. Chem. 263 (1988) 17262
51. 4; see:. Vogel A.I. Vogel's Textbook of Macro and Semimicro Quantitative Inorganic Analysis (1985) 195 Control reactions showed that 6 alone or 2 mercaptoethanol alone did not produce the black precipitate
52. Attene-Ramos M.S., Wagner E.D., Gaskins H.R., and Plewa M.J. Mol. Cancer Res. 5 (2007) 455
53. Baskar R., Li L., and Moore P.K. FASEB J. 21 (2007) 247
54. Attene-Ramos M.S., Wagner E.D., Plewa M.J., and Gaskins H.R. Mol. Cancer Res. 4 (2006) 9
55. Truong D.H., Eghbal M.A., Hindmarsh W., Roth S.H., and O'Brien P.J. Drug Metab. Rev. 38 (2006) 733
56. Beauchamp Jr. R.O., Andjelkovich D.A., Kligerman A.D., Morgan K.T., and Heck H. Crit. Rev. Toxicol. 14 (1985) 309
57. Reiffenstein R.J., Hulbert W.C., and Roth S.H. Annu. Rev. Pharmacol. Toxicol. 32 (1992) 109
58. Searcy D.G. Arch. Biochem. Biophys. 334 (1996) 50
59. Vineyard B.D. J. Org. Chem. 32 (1967) 3833
60. Winterbourn C.C., Peskin A.V., and Parsons-Mair H.N. J. Biol. Chem. 277 (2002) 1906
61. 2S (∼0.5 mM) by 29% (0.34 breaks per plasmid). Addition of SOD alone does not generate any strand breaks above background.
62. 29 On a separate note, the inability of 7 to generate strand cleavage may be explained by the inaccessibility and/or instability of the corresponding thiolactone in the benzo series:. Mitra K., and Gates K.S. Tetrahedron Lett. 36 (1995) 1391
63. Mitra K., Pohl M.E., MacGillivray L.R., Barnes C.L., and Gates K.S. J. Org. Chem. 62 (1998) 9361
64. Along these lines, it is worth noting that, in a control there is no evidence that 6 converts spontaneously to 8 under the reaction conditions employed for these studies. Specifically, the reaction of thiol with 6 is complete inside of 1 h. Within this timeframe, in the absence of thiol, there is no detectable oxidative or hydrolytic dcomposition of 6.
65. Tang G.-L., Cheng Y.-Q., and Shen B. Chem. Biol. 11 (2004) 33
66. Wolkenberg S.E., and Boger D.L. Chem. Rev. 102 (2002) 2477