Lethality to leukemia cell lines of DNA interstrand cross-links generated by Cloretazine derived alkylating species

Leukemia Research

Volumn 32, Issue 10, 2008, Pages 1546-1553

  Penketh, Philip G ^a   Baumann, Raymond P ^a   Ishiguro, Kimiko ^a   Shyam, Krishnamurthy ^a   Seow, Helen A ^a   Sartorelli, Alan C ^a  

^a YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

90CE; BCNU; Cloretazine; G C ethane cross links; Leukemia cell lines; O6 Alkylguanine DNA alkyltransferase

Indexed keywords

1,2 BIS(METHYLSULFONYL) 1 (2 CHLOROETHYL)HYDRAZINE; 6 O ALKYLGUANINE DNA ALKYLTRANSFERASE; CLORETAZINE; ETHANE; HYDRAZINE DERIVATIVE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HL 60; CELL STRAIN U937; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA CROSS LINKING; GENOME; HUMAN; HUMAN CELL; LC 50; LETHALITY; LEUKEMIA CELL LINE; LEUKEMIA L 1210; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CROSS-LINKING REAGENTS; CYTOSINE; DNA; ETHANE; GUANINE; HL-60 CELLS; HUMANS; HYDRAZINES; LEUKEMIA; MICE; SULFONAMIDES; U937 CELLS;

EID: 44749092346     PISSN: 01452126     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.leukres.2008.03.005     Document Type: Article

References (35)

1. Penketh P.G., Shyam K., and Sartorelli A.C. Comparison of DNA lesions produced by tumor-inhibitory 1,2-bis(sulfonyl)hydrazines and chloroethylnitrosoureas. Biochem Pharmacol 59 (2000) 283-291
2. Penketh P.G., Shyam K., Baumann R.P., Remack J.S., Brent T.P., and Sartorelli A.C. 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(methylamino)carbonyl]hydrazine (VNP40101M): I. Direct inhibition of O6-alkylguanine-DNA alkyltransferase (AGT) by electrophilic species generated by decomposition. Cancer Chemother Pharmacol 53 (2004) 279-287
3. Teicher B.A. Antitumor alkylating agents. In: DeVita V.T., Hellman S., and Rosenburg S.A. (Eds). Cancer: principles & practice of oncology. 5th ed. (1997), Lippincott-Raven, Philadelphia 405-418
4. Lawley P.D., and Brooks P. Interstrand cross-linking of DNA by difunctional alkylating agents. J Mol Biol 25 (1967) 143-160
5. Teicher B.A. Preclinical models for high-dose therapy. In: Armitage J.O., and Antman K.H. (Eds). High-dose cancer therapy: pharmacology, hematopoietins, stem cells. (1995), Williams and Wilkins, Philadelphia 17
6. Gerson S.L. Clinical relevance of MGMT in the treatment of cancer. J Clin Oncol 20 (2002) 2388-2399
7. 6-alkylguanine-DNA alkyltransferase. In: Cohn W.E., and Moldave K. (Eds). Progress in nucleic acid research and molecular biology vol. 51 (1995), Academic Press, San Diego 167-223
8. Bodell W.J., Tokuda K., and Ludlum D.B. Differences in DNA alkylation products formed in sensitive and resistant human glioma cells treated with N-(2-chloroethyl)-N-nitrosourea. Cancer Res 48 (1988) 4489-4492
9. Ishiguro K., Seow H.A., Penketh P.G., Shyam K., and Sartorelli A.C. Mode of action of the chloroethylating and carbamoylating moieties of the prodrug cloretazine. Mol Cancer Ther 5 (2006) 1-8
10. 6-alkylguanine-DNA alkyltransferase in the cytotoxic activity of cloretazine. Mol Cancer Ther 4 (2005) 1755-1763
11. Ludlum D.B. The chloroethylnitrosoureas: sensitivity and resistance to cancer chemotherapy at the molecular level. Cancer Invest 15 (1997) 588-598
12. Penketh P.G., Shyam K., and Sartorelli A.C. Studies on the mechanism of decomposition and structural factors affecting the aqueous stability of 1,2-bis(sulfonyl)-1-alkylhydrazines. J Med Chem 37 (1994) 2912-2917
13. 6-alkylguanine DNA-alkyltransferase or poly(ADP-ribose) polymerase increases susceptibility of leukemic cells to apoptosis induced by Temozolomide. Mol Pharmacol 52 (1997) 249-258
14. 6-alkylguanine-DNA alkyltransferase. Cancer Res 48 (1988) 1521-1527
15. Yajima N., Hochi S., Miyata N., Kishi T., and Kawanishi G. DNA breaks and repair in the mouse leukemia L1210 cells exposed to three different types of interstrand DNA cross-linkers. Mutat Res 236 (1990) 43-50
16. Thomas Jr. C.A., and MacHattie L.A. The anatomy of viral DNA molecules. Ann Rev Biochem 36 (1967) 485-518
17. Shyam K., Penketh P.G., Divo A.A., Loomis R.H., Patton C.L., and Sartorelli A.C. Synthesis and evaluation of 1,2,3-tris(sulfonyl)hydrazines as antineoplastic and trypanocidal agents. J Med Chem 33 (1990) 2259-22640
18. Penketh P.G., Shyam K., and Sartorelli A.C. Fluorometric assay for the determination of DNA-DNA cross-links utilizing Hoechst 33258 at neutral pH values. Anal Biochem 252 (1997) 210-213
19. Dunn J.J., and Studier F.W. Complete nucleotide sequence of bacteriophage T7 DNA and the locations of T7 genetic elements. J Mol Biol 166 (1983) 477-535
20. Green E.D., and Chakravarti A. The human genome sequence expedition: views from the "base camp". Genome Res 11 (2001) 645-651
21. Mouse Genome Sequencing Consortium. Initial sequencing and comparative analysis of the mouse genome. Nature 2002a;420:520-62.
22. Mouse Genome Sequencing Consortium. Analysis of the mouse transcriptome based on functional annotation of 60,770 full-length cDNAs. Nature 2002b;420:563-73.
23. Schafer F.Q., and Buettner G.R. Singlet oxygen toxicity is cell line-dependent: a study of lipid peroxidation in nine leukemia cell lines. Photochem Photobiol 70 (1999) 858-867
24. Hallows H.R., Packman C.H., and Knauf P.A. Acute cell volume changes in anisotonic media affect F-actin content of HL-60 cells. Am J Physiol 261 (1991) 1154-1161
25. Arrebola F., Canizares J., Cubero M.A., Crespo P.V., Warley A., and Fernandez-Segura E. Biphasic behavior of changes in elemental composition during staurosporine-induced apoptosis. Apoptosis 10 (2005) 1317-1331
26. 6-alkylguanine-DNA alkyltransferase. Cancer Res 44 (1984) 3806-3811
27. D'Atri S., Tentor L., Lacal P.M., Graziani G., Pagani E., Benincasa E., et al. Involvement of the mismatch repair system in temozolomide-induced apoptosis. Mol Pharmacol 54 (1998) 334-341
28. Loveless A. Possible relevance of O-6 alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides. Nature 223 (1969) 206-207
29. - human tumor cell line. Mutat Res 314 (1994) 99-113
30. Bishop R.E., Dunn L.L., Pauly G.T., Dolan M.E., and Moschel R.C. The role of O6 alkylguanine-DNA alkyltransferase in protecting Rat4 cells against the mutagenic effects of O6-substituted guanine residues incorporated in codon 12 of the H-ras gene. Carcinogenesis 4 (1993) 593-598
31. Murren J., Gerson S., Kummar S., Davies M., Remick S., Chu E., et al. A phase I trial of the sulfonylhydrazine alkylator, VNP40101M (101 M), administered weekly in patients with metastatic cancer. J Clin Oncol 22 (2004) 206-207
32. Giles F., Verstovsek S., Thomas D., Gerson S., Cortes J., Faderl S., et al. Phase I study of cloretazine (VNP40101M), a novel sulfonylhydrazine alkylating agent, combined with cytarabine in patients with refractory leukemia. Clin Cancer Res 11 (2005) 7817-7824
33. Spiro T.P., Liu L., Majka S., Haaga J., Willson J.K.V., and Gerson S.L. Temozolomide: the effect of once- and twice-a-day dosing on tumor tissue levels of the DNA repair protein O6-alkylguanine-DNA-alkyltransferase. Clin Cancer Res 7 (2001) 2309-2317
34. 6-alkylguanine-DNA alkyltransferase in cytotoxicity. Cancer Chemother Pharmacol 53 (2004) 288-295
35. Baumann R.P., Seow H.A., Shyam K., Penketh P.G., and Sartorelli A.C. The antineoplastic efficacy of the prodrug Cloretazine is produced by the synergistic interaction of carbamoylating and alkylating products of its activation. Oncol Res 15 (2005) 313-325