Cytotoxicity and DNA interaction of the enantiomers of 6-amino-3- (chloromethyl)-1-[(5,6,7-trimethoxyindol-2-yl)-carbonyl]indoline (amino-seco- CI-TMI)

Chemical Research in Toxicology

Volumn 12, Issue 8, 1999, Pages 700-706

  Tercel, Moana ^a   Gieseg, Michael A ^a   Milbank, Jared B ^a   Boyd, Maruta ^a   Fan, Jun Yao ^a   Tan, L Karin ^a   Wilson, William R ^a   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINO 3 (CHLOROMETHYL) 1 [(5,6,7 TRIMETHOXYINDOL 2 YL) CARBONYL]INDOLINE; ADENINE; DNA; INDOLE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ARTICLE; CATTLE; CYTOTOXICITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN INTERACTION; THYMUS;

ALKYLATION; ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; DNA ADDUCTS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NUCLEIC ACID CONFORMATION; STEREOISOMERISM; TUMOR CELLS, CULTURED;

EID: 0032809160     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990069o     Document Type: Article

References (26)

1. Boger, D. L., and Johnson, D. S. (1996) CC-1065 and the duocarmycins: understanding their biological function through mechanistic studies. Angew. Chem., Int. Ed. 35, 1438-1474.
2. Kobayashi, E., Okamoto, A., Asada, M., Okabe, M., Nagamura, S., Asai, A., Saito, H., Gomi, K., and Hirata, T. (1994) Characteristics of antitumor activity of KW-2189, a novel water-soluble derivative of duocarmycin, against murine and human tumors. Cancer Res. 54, 2404-2410.
3. Nagamura, S., Asai, A., Amishiro, N., Kobayashi, E., Gomi, K., and Saito, H. (1997) Synthesis and antitumor activity of duocarmycin derivatives: A-ring pyrrole compounds bearing cinnamoyl groups. J. Med. Chem. 40, 972-979.
4. Boger, D. L., Ishizaki, T., Zarrinmayeh, H., Munk, S. A., Kitos, P. A., and Suntornwat, O. (1990) Duocarmycin-pyrindamycin DNA alkylation properties and identification, synthesis and evaluation of agents incorporating the pharmacophore of the duocarmycin-pyrindamycin alkylation subunit. Identification of the CC-1065-duocarmycin common pharmacophore. J. Am. Chem. Soc. 112, 8961-8971.
5. Boger, D. L., Ishizaki, T., Zarrinmayeh, H., Munk, S. A., Kitos, P. A., and Suntornwat, O. (1990) Synthesis and preliminary evaluation of agents incorporating the pharmacophore of the duocarmycin/pyrindamycin alkylation subunit: identification of the CC-1065-duocarmycin common pharmacophore. J. Org. Chem. 55, 4499-4502.
6. Tercel, M., Wilson, W. R., and Denny, W. A. (1996) Nitrogen and sulfur analogues of the seco-CI alkylating agent: synthesis and cytotoxicity. Bioorg. Med. Chem. Lett. 6, 2735-2740.
7. Tercel, M., Wilson, W. R., and Denny, W. A. (1996) A novel nitro-substituted seco-CI: application as a reductively activated ADEPT prodrug. Bioorg. Med. Chem. Lett. 6, 2741-2744.
8. Tercel, M., and Denny, W. A. (1998) Synthesis of nitrogen and sulfur analogues of the seco-CI alkylating agent. J. Chem. Soc., Perkin Trans. 1, 509-519.
9. Atwell, G. J., Wilson, W. R., and Denny, W. A. (1997) Synthesis of amino analogues of the potent DNA alkylating agent seco-CBI-TMI. Bioorg. Med. Chem. Lett. 7, 1493-1496.
10. Atwell, G. J., Tercel, M., Boyd, M., Wilson, W. R., and Denny, W. A. (1998) Synthesis and cytotoxicity of 5-amino-1-(chloromethyl)-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro- 3H-benz[e]indole (amino-seco-CBI-TMI) and related 5-alkylamino analogues: new DNA minor groove alkylating agents. J. Org. Chem. 63, 9414-9420.
11. Tercel, M., Gieseg, M. A., Denny, W. A., and Wilson, W. R. (1999) Synthesis and cytotoxicity of amino-seco-DSA, an amino analogue of the DNA alkylating agent duocarmycin SA. J. Org. Chem. 64 (in press).
12. 1 epoxide. J. Am. Chem. Soc. 116, 8863-8869.
13. Gieseg, M. A., Matejovic, J., and Denny, W. A. (1999) Comparison of the patterns of DNA alkylation by phenol and amino seco-CBI-TMI compounds: use of a PCR method for the facile preparation of single end-labelled double-stranded DNA. Anti-Cancer Drug Des. 14 (in press).
14. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82, 1107-1112.
15. Boger, D. L., and Yun, W. (1994) CBI-TMI: synthesis and evaluation of a key analogue of the duocarmycins. Validation of a direct relationship between chemical solvolytic stability and cytotoxic potency, and confirmation of the structural features responsible for the distinguishing behaviour of enantiomeric pairs of agents. J. Am. Chem. Soc. 116, 7996-8006.
16. Boger, D. L., Boyce, C. W., Garbaccio, R. M., and Goldberg, J. A. (1997) CC-1065 and the duocarmycins: synthetic studies. Chem. Rev. 97, 787-828.
17. Hurley, L. H., Reynolds, V. L., Swenson, D. H., Petzold, G. L., and Scahill, T. A. (1984) Reaction of the antitumor antibiotic CC-1065 with DNA: structure of a DNA adduct with DNA sequence selectivity. Science 226, 843-844.
18. Scahill, T. A., Jensen, R. M., Swenson, D. H., Hatzenbuhler, N. T., Petzold, G., Wierenga, W., and Brahme, N. D. (1990) An NMR study of the covalent and noncovalent interactions of CC-1065 and DNA. Biochemistry 29, 2852-2860.
19. Hurley, L. H., Warpehoski, M. A., Lee, C.-S., McGovren, J. P., Scahill, T. A., Kelly, R. C., Mitchell, M. A., Wicnienski, N. A., Gebhard, I., Johnson, P. D., and Bradford, V. S. (1990) Sequence specificity of DNA alkylation by the unnatural enantiomer of CC-1065 and its synthetic analogues. J. Am. Chem. Soc. 112, 4633-4649.
20. Boger, D. L., Ishizaki, T., and Zarrinmayeh, H. (1991) Isolation and characterization of the duocarmycin-adenine adduct. J. Am. Chem. Soc. 113, 6645-6649.
21. Asai, A., Nagamura, S., and Saito, H. (1994) A novel property of duocarmycin and its analogues for covalent reactions with DNA. J. Am. Chem. Soc. 116, 4171-4177.
22. Boger, D. L., Johnson, D. S., and Yun, W. (1994) (+)- and ent-(-)-Duocarmycin SA and (+)- and ent-(-)-N-BOC-DSA DNA alkylation properties. Alkylation site models that accommodate the offset AT-rich adenine N3 alkylation selectivity of the enantiomeric agents. J. Am. Chem. Soc. 116, 1635-1656.
23. Boger, D. L., and Mésini, P. (1995) DNA alkylation properties of CC-1065 and duocarmycin analogs incorporating the 2,3,10,10a-tetrahydrocyclopropa[d]benzo[f]quinol-5-one alkylation subunit: identification of subtle structural features that contribute to the regioselectivity of the adenine N3 alkylation reaction. J. Am. Chem. Soc. 117, 11647-11655.
24. Boger, D. L., Garbaccio, R. M., and Jin, Q. (1997) Synthesis and evaluation of CC-1065 and duocarmycin analogues incorporating the Iso-CI and Iso-CBI alkylation subunits: impact of relocation of the C-4 carbonyl. J. Org. Chem. 62, 8875-8891.
25. 32P-end-labelled double-stranded DNA for binding studies: development of a protocol for examination of functional features of (+)-CC-1065 and the duocarmycins that contribute to their sequence-selective DNA alkylation properties. Tetrahedron 47, 2661-2682.
26. Hoy, C. A., Salazar, E. P., and Thompson, L. H. (1984) Rapid detection of DNA-damaging agents using repair-deficient CHO cells. Mutat. Res. 180, 321-332.