Synthesis, DNA-binding ability and evaluation of antitumour activity of triazolo[1,2,4]benzothiadiazine linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 16, 2008, Pages 7804-7810

  Kamal, Ahmed ^a   Khan, M Naseer A ^a   Srikanth, Y V V ^a   Srinivasa Reddy, K ^a   Juvekar, Aarti ^b   Sen, Subrata ^b   Kurian, Nisha ^b   Zingde, Surekha ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b Research and Education in Cancer ACTREC   (India)

Author keywords

Antitumour activity; DNA binding ability; Pyrrolobenzodiazepine; Triazolobenzothiadiazines

Indexed keywords

7 METHOXY 8 [ (3 (10 METHYL 3 SULFANYL 5,10 DIHYDRO 5 BENZO[E] [1,2,4]TRIAZOLO[4,3 B][1,2,4]THIADIAZINE 5,5 DIONE)]PROPYL]OXY(11AS) 1,2,3,11A 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 7 METHOXY 8 [ (4 (10 METHYL 3 SULFANYL 5,10 DIHYDRO 5 BENZO[E][1,2,4]TRIAZOLO[4,3 B][1,2,4]THIADIAZINE 5,5 DIONE)]BUTYL]OXY(11AS) 1,2,3,11A 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA BINDING; DNA DENATURATION; DNA HELIX; DRUG BINDING; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZODIAZEPINES; BENZOTHIADIAZINES; CELL LINE, TUMOR; CELL PROLIFERATION; DNA; DNA, NEOPLASM; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOUTH NEOPLASMS; NUCLEIC ACID DENATURATION; PYRROLES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 49149087266     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.06.056     Document Type: Article

References (42)

1. Wells G., Martin C.R.H., Howard P.W., Sands Z.A., Laughton C.A., Tiberghien A., Woo C.K., Masterson L.A., Stephenson M.J., Hartley J.A., Jenkins T.C., Shnyder S.D., Loadman P.M., Waring M.J., and Thurston D.E. J. Med. Chem. 49 (2006) 5442
2. Wang J.-J., Shen Y.-K., Hu W.-P., Hsieh M.-C., Lin F.-L., Hsu M.-K., and Hsu M.-H. J. Med. Chem. 49 (2006) 1442
3. Larner J. In: Gilman A.G., Goodman L.S., and Gilman A. (Eds). Goodman and Gilman's The Pharmacological Basic of Therapeutics. 6th ed. (1980), Macmillan Publishing Co., Inc., New York 1510
4. Howbert J.J., Grossmann C.S., Crowell T.A., Rieder B.J., Harper R.W., Kramer K.E., Tao E.V., Aikins J., Poore G.A., Riezel S.M., Grindey G.B., Shaw W.W., and Todd G.C. J. Med. Chem. 33 (1990) 2393
5. Houghton P.J., Bailey F.C., Germain G.S., Grindey G.B., Howbert J.J., and Houghton J.A. Biochem. Pharmacol. 39 (1990) 1187
6. Houghton P.J., Bailey F.C., Germain G.S., Grindey G.B., Witt B.C., and Houghton J.A. Cancer Res. 50 (1990) 318
7. Hainsworth J.D., Hande K.R., Satterlee W.G., Kuttesch J., Johnson D.H., Grindey G., Jackson L.E., and Greco F.A. Cancer Res. 49 (1989) 5217
8. Brien M.E., Hardy J., Tan S., Walling J., Peters B., Hatty S., and Wiltshaw E. Cancer Chemother. Pharmacol. 30 (1992) 245
9. Houghton P.J., Bailey F.C., Houghton J.A., Murti K.G., Howbert J.J., and Grindey G.B. Cancer Res. 50 (1990) 664
10. Ruch G.F., Rinzel S., Boder G., Heim R.A., Toth J.E., and Ponsler G.D. Biochem. Pharmacol. 44 (1992) 2387
11. Tang A., Lien E.J., and Lai M.M.C. J. Med. Chem. 28 (1985) 1103
12. Adamson R.H. Nature 236 (1972) 400
13. Buzdar A.U. Breast Cancer Res. Treat 75 (2002) 13
14. Lin R., Connolly P.J., Huang S., Wetter S.K., Murray W.V., Emanuel S.L., Gruninger R.H., Fiemtes-Pesquera A.R., Rugg CA., Middleton S.A., and Jolliffe L.K. J. Med. Chem. 48 (2005) 4208
15. Holla B.S., Poojary K.N., Rao B.S., and Shivananda M.K. Eur. J. Med. Chem. 37 (2002) 511
16. Kamal A., Khan M.N.A., Reddy K.S., Srikanth Y.V.V., and Sridhar B. Chem. Biol. Drug Des. 71 (2008) 78
17. Hurley L.H., and Thurston D.E. Pharm. Res. (1984) 52
18. Hurley L.H. J. Antibiot. 30 (1977) 349
19. Aoki H., Miyairi N., Ajisaka M., and Sakai H. J. Antibiot. 22 (1969) 201
20. Thurston D.E. In: Nieldle D., and Waring M.J. (Eds). Molecular Aspects of Anticancer Drug DNA Interactions (1993), McMillan, London 54
21. Tender M.D., Korman S.H., and Petrusek R.L. Nature 199 (1963) 501
22. Hurley L.H., and Petrusek R.L. Nature 282 (1979) 529
23. Kamal A., Devaiah V., Reddy K.L., and Kumar M.S. Bioorg. Med. Chem. 13 (2005) 2021
24. Kumar R., and Lown J.W. Eur. J. Med. Chem. 40 (2005) 641
25. Gregson S.T., Howard P.W., Gullick D.R., Hamaguchi A., Corcoran K.E., Brooks N.A., Hartley J.A., Jenkins T.C., Patel S., Guille M.J., and Thurston D.E. J. Med. Chem. 47 (2004) 1161
26. Wilson S.C., Howard P.W., Forrow S.M., Hartley J.A., Adams L.J., Jenkins T.C., Kelland L.R., and Thurston D.E. J. Med. Chem. 42 (1999) 4028
27. Tercel M., Stribbling S.M., Sheppard H., Siim B.G., Wu K., Pullen S.M., Botting K.J., Wilson W.R., and Denny W.A. J. Med. Chem. 46 (2003) 2132
28. Kamal A., Laxman E., and Reddy P.S.M.M. Tetrahedron Lett. 41 (2000) 7743
29. Kamal A., Reddy G.S.K., and Raghavan S. Bioorg. Med. Chem. Lett. 13 (2001) 387
30. Kamal A., Reddy P.S.M.M., and Reddy D.R. Tetrahedron Lett. 44 (2003) 2857
31. Kamal A., Ramesh G., Laxman N., Ramulu P., Srinivas O., Neelima K., Kondapi A.K., Srinu V.B., and Nagarajaram H.M. J. Med. Chem. 45 (2002) 4679
32. Kamal A., Ramesh G., Ramulu P., Srinivas O., Rehana T., and Sheelu G. Bioorg. Med. Chem. Lett. 13 (2003) 3451
33. Kamal A., Srinivas O., Ramulu P., Ramesh G., and Kumar P.P. Bioorg. Med. Chem. Lett. 13 (2003) 3577
34. Kamal A., Reddy P.S.M.M., and Reddy D.R. Bioorg. Med. Chem. Lett. 14 (2004) 2669
35. Kamal A., Khan M.N.A., Reddy K.S., Ahmed S.K., Kumar M.S., Juvekar A., Sen S., and Zingde S. Bioorg. Med. Chem. Lett. 17 (2007) 5345
36. Mathew V., Keshavayya J., and Vaidya V.P. Eur. J. Med. Chem. 41 (2006) 1048
37. Vichai V., and Kirtikara K. Nat. Protocols 1 (2006) 1112
38. Skehn P., Storeng R., Scudiero A., Monks J., McMohan D., Vistica D., Jonathan T.W., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107
39. Tatake R.J., Rajaram N., Damle R.N., Balsara B., Bhisey A.N., and Gangal S.G. J. Cancer Res. Clin. Oncol. 116 (1990) 179
40. Jones G.B., Davey C.L., Jenkins T.C., Kamal A., Kneale G.G., Neidle S., Webster G.D., and Thurston D.E. Anti-Cancer Drug Des. 5 (1990) 249
41. McConnaughie A.W., and Jenkins T.C. J. Med. Chem. 38 (1995) 3488
42. Langely D.R., and Thurston D.E. J. Org. Chem. 52 (1987) 91