Pyrrolo[2,1-c][1,4]benzodiazepine and indole conjugate (IN6CPBD) has better efficacy and superior safety than the mother compound DC-81 in suppressing the growth of established melanoma in vivo

Chemico-Biological Interactions

Volumn 180, Issue 3, 2009, Pages 360-367

  Lee, Chih Hung ^a,b,d   Hu, Wan Ping ^a   Hong, Chien Hui ^c   Yu, Hsin Su ^a   Liao, Wei Ting ^a   Chen, Chung Yu ^a   Chen, Yeh Long ^a   Chen, Bai Hsiun ^a   Chen, Gwo Shing ^a   Wang, Jeh Jeng ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^c Veterans General Hospital   (Taiwan)

^d KAOHSIUNG MUNICIPAL HSIAO KANG HOSPITAL   (Taiwan)

Author keywords

Apoptosis; Indole; Melanoma; Metastasis; Pyrrolo 2,1 c 1,4 benzodiazepine

Indexed keywords

(11AS) 8 [3 (1H 2 INDOLYCARBOXAMIDO)]HEXOXY 7 METHOXY 1,2,3,11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 1,2,3,11A TETRAHYDRO 8 HYDROXY 7 METHOXY 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; LIPOCORTIN 5; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; APOPTOSIS; ARTICLE; CARDIOTOXICITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DOSE RESPONSE; DRUG DOSE COMPARISON; DRUG EFFICACY; DRUG SAFETY; DRUG SELECTIVITY; FEMALE; IN VIVO STUDY; LIVER DYSFUNCTION; LIVER TOXICITY; LUNG METASTASIS; MELANOMA; MELANOMA B16; METASTASIS INHIBITION; MITOCHONDRIAL MEMBRANE POTENTIAL; MOUSE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; AZEPINES; BENZODIAZEPINES; INDOLES; LIVER; LUNG NEOPLASMS; MELANOMA; MICE; MICE, INBRED BALB C; ORGANOPHOSPHORUS COMPOUNDS; REACTIVE OXYGEN SPECIES; SKIN NEOPLASMS; TRANSPLANTATION, HETEROLOGOUS;

MURINAE; MUS;

EID: 67349095662     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2009.05.001     Document Type: Article

References (33)

1. Jemal A., Devesa S.S., Hartge P., and Tucker M.A. Recent trends in cutaneous melanoma incidence among whites in the United States. J. Natl. Cancer. Inst. 93 9 (2001) 678-683
2. Allen A.C., and Spitz S. Malignant melanoma; a clinicopathological analysis of the criteria for diagnosis and prognosis. Cancer 6 1 (1953) 1-45
3. Balch C.M., Buzaid A.C., Soong S.J., Atkins M.B., Cascinelli N., Coit D.G., Fleming I.D., Gershenwald J.E., Houghton Jr. A., Kirkwood J.M., McMasters K.M., Mihm M.F., Morton D.L., Reintgen D.S., Ross M.I., Sober A., Thompson J.A., and Thompson J.F. Final version of the American Joint Committee on Cancer staging system for cutaneous melanoma. J. Clin. Oncol. 19 16 (2001) 3635-3648
4. Breslow A. Thickness, cross-sectional areas and depth of invasion in the prognosis of cutaneous melanoma. Ann. Surg. 172 5 (1970) 902-908
5. Veronesi U., Cascinelli N., Adamus J., Balch C., Bandiera D., Barchuk A., Bufalino R., Craig P., De Marsillac J., Durand J.C., et al. Thin stage I primary cutaneous malignant melanoma. Comparison of excision with margins of 1 or 3 cm. N. Engl. J. Med. 318 18 (1988) 1159-1162
6. Bellett R.E., Mastrangelo M.J., Laucius J.F., and Bodurtha A.J. Randomized prospective trial of DTIC (NSC-45388) alone versus BCNU (NSC-409962) plus vincristine (NSC-67574) in the treatment of metastatic malignant melanoma. Cancer Treat. Rep. 60 5 (1976) 595-600
7. Atkins M.B., Lotze M.T., Dutcher J.P., Fisher R.I., Weiss G., Margolin K., Abrams J., Sznol M., Parkinson D., Hawkins M., Paradise C., Kunkel L., and Rosenberg S.A. High-dose recombinant interleukin 2 therapy for patients with metastatic melanoma: analysis of 270 patients treated between 1985 and 1993. J. Clin. Oncol. 17 7 (1999) 2105-2116
8. Rosenberg S.A., Lotze M.T., Yang J.C., Topalian S.L., Chang A.E., Schwartzentruber D.J., Aebersold P., Leitman S., Linehan W.M., Seipp C.A., et al. Prospective randomized trial of high-dose interleukin-2 alone or in conjunction with lymphokine-activated killer cells for the treatment of patients with advanced cancer. J. Natl. Cancer Inst. 85 8 (1993) 622-632
9. Panka D.J., Wang W., Atkins M.B., and Mier J.W. The Raf inhibitor BAY 43-9006 (Sorafenib) induces caspase-independent apoptosis in melanoma cells. Cancer Res. 66 3 (2006) 1611-1619
10. Smalley K.S., and Herlyn M. Targeting intracellular signaling pathways as a novel strategy in melanoma therapeutics. Ann. N.Y. Acad. Sci. 1059 (2005) 16-25
11. Alley M.C., Hollingshead M.G., Pacula-Cox C.M., Waud W.R., Hartley J.A., Howard P.W., Gregson S.J., Thurston D.E., and Sausville E.A. SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity. Part 2. Efficacy evaluations. Cancer. Res. 64 18 (2004) 6700-6706
12. Hartley J.A., Spanswick V.J., Brooks N., Clingen P.H., McHugh P.J., Hochhauser D., Pedley R.B., Kelland L.R., Alley M.C., Schultz R., Hollingshead M.G., Schweikart K.M., Tomaszewski J.E., Sausville E.A., Gregson S.J., Howard P.W., and Thurston D.E. SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity. Part 1. Cellular pharmacology, in vitro and initial in vivo antitumor activity. Cancer Res. 64 18 (2004) 6693-6699
13. Hurley L.H., and Petrusek R. Proposed structure of the anthramycin-DNA adduct. Nature 282 5738 (1979) 529-531
14. Kohn K.W. Anthramycin. In: Corcoran J.W., and Hahn F.E. (Eds). Antibiotics III Mechanism of Action of Antimicrobial and Antitumor Agents (1975), Springer-Verlag 3-11
15. Thurston D.E. Advances in the study of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) antitumor antibiotics, I. In: Neidle S., and Waring M. (Eds). Molecular Aspects of Anticancer Drug-DNA Interactions (1993), Macmillan Press 54-88
16. Thurston D.E., and Bose D.S. Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines. Chem. Rev. 94 (1994) 433
17. Hurley L.H., and Draves P.H. Advances in the study of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) antitumor antibiotics. In: Neidle S., and Waring M. (Eds). Molecular Aspects of the Interaction of (+)-CC-1065 with DNA (1993), Macmillan Press 89-133
18. Kase H., Iwahashi K., and Matsuda Y. K-252a, a potent inhibitor of protein kinase C from microbial origin. J. Antibiot. (Tokyo) 39 8 (1986) 1059-1065
19. Mitchell M.A., Kelly R.C., Wicnienski N.A., Hatzenbuhler N.T., Williams M.G., Petzold G.L., Slightom J.L., and Siemieniak D.R. Synthesis and DNA crosslinking by a rigid CPI dimer. J. Am. Chem. Soc. 113 (1991) 8994-8995
20. Zhou Q., Duan W., Simmons D., Shayo Y., Raymond M.A., Dorr R.T., and Hurley L.H. Design and synthesis of a novel DNA-DNA interstrand adenine-guanine cross-linking agent. J. Am. Chem. Soc. 123 20 (2001) 4865-4866
21. Wang J.J., Shen Y.K., Hu W.P., Hsieh M.C., Lin F.L., Hsu M.K., and Hsu M.H. Design, synthesis, and biological evaluation of pyrrolo[2,1-c][1,4]benzodiazepine and indole conjugates as anticancer agents. J. Med. Chem. 49 4 (2006) 1442-1449
22. Hu W.P., Yu H.S., Sung P.J., Tsai F.Y., Shen Y.K., Chang L.S., and Wang J.J. DC-81-Indole conjugate agent induces mitochondria mediated apoptosis in human melanoma A375 cells. Chem. Res. Toxicol. 20 6 (2007) 905-912
23. Salvesen G.S., and Dixit V.M. Caspases: intracellular signaling by proteolysis. Cell 91 4 (1997) 443-446
24. Shi Y. Mechanisms of caspase activation and inhibition during apoptosis. Mol. Cell 9 3 (2002) 459-470
25. Deng W., Li R., and Ladisch S. Influence of cellular ganglioside depletion on tumor formation. J. Natl. Cancer Inst. 92 11 (2000) 912-917
26. Garcia A.F., Heindl P., Voigt H., Buttner M., Butz P., Tauber N., Tauscher B., and Pfaff E. Dual nature of the infectious prion protein revealed by high pressure. J. Biol. Chem. 280 11 (2005) 9842-9847
27. Kikkawa H., Imafuku H., Tsukada H., and Oku N. Possible role of immune surveillance at the initial phase of metastasis produced by B16BL6 melanoma cells. FEBS Lett. 467 2-3 (2000) 211-216
28. Lee C.H., Kakinuma T., Wang J., Zhang H., Palmer D.C., Restifo N.P., and Hwang S.T. Sensitization of B16 tumor cells with a CXCR4 antagonist increases the efficacy of immunotherapy for established lung metastases. Mol. Cancer Ther. 5 10 (2006) 2592-2599
29. Baraldi P.G., Cacciari B., Guiotto A., Romagnoli R., Spalluto G., Leoni A., Bianchi N., Feriotto G., Rutigliano C., Mischiati C., and Gambari R. [2,1-c][1,4]benzodiazepine (PBD)-distamycin hybrid inhibits DNA binding to transcription factor Sp1. Nucleosides Nucleotides Nucleic Acids 19 8 (2000) 1219-1229
30. Hu W.P., Tsai F.Y., Yu H.S., Sung P.J., Chang L.S., and Wang J.J. Induction of apoptosis by DC-81-indole conjugate agent through NF-kappaB and JNK/AP-1 pathway. Chem. Res. Toxicol. 21 7 (2008) 1330-1336
31. Campiani G., Garofalo A., Fiorini I., Botta M., Nacci V., Tafi A., Chiarini A., Budriesi R., Bruni G., and Romeo M.R. Pyrrolo[2,1-c][1,4]benzothiazines: synthesis, structure-activity relationships, molecular modeling studies, and cardiovascular activity. J. Med. Chem. 38 22 (1995) 4393-4410
32. Kelsall S.R., and Mintz B. Metastatic cutaneous melanoma promoted by ultraviolet radiation in mice with transgene-initiated low melanoma susceptibility. Cancer Res. 58 18 (1998) 4061-4065
33. Zaidi M.R., Day C.P., and Merlino G. From UVs to metastases: modeling melanoma initiation and progression in the mouse. J. Invest. Dermatol. 128 10 (2008) 2381-2391