DNA-directed alkylating agents. 7. Synthesis, DNA interaction, and antitumor activity of bis(hydroxymethyl)- and bis(carbamate)-substituted pyrrolizines and imidazoles

Journal of Medicinal Chemistry

Volumn 41, Issue 24, 1998, Pages 4744-4754

  Atwell, Graham J ^a   Fan, Jun Yao ^a   Tan, Karin ^a   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; CARBAMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; PYRROLIZINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DNA ALKYLATION; DNA CROSS LINKING; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ALKYLATION; ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; BASE SEQUENCE; CARBAMATES; CROSS-LINKING REAGENTS; DNA; DNA PRIMERS; DNA, SUPERHELICAL; DRUG SCREENING ASSAYS, ANTITUMOR; ELECTROPHORESIS, AGAR GEL; IMIDAZOLES; KINETICS; LEUKEMIA P388; MOLECULAR SEQUENCE DATA; POLYMERASE CHAIN REACTION; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0032548149     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9803119     Document Type: Article

References (29)

1. Hansson, J.; Lewensohn, R.; Ringborg, U.; Nilsson, B. Formation and removal of DNA cross-links induced by melphalan and nitrogen mustard in relation to drug-induced cytotoxicity in human melanoma cells. Cancer Res. 1987, 47, 2631-2637.
2. Krowicki, K.; Balzarini, J.; De Clercq, E.; Newman, R. A.; Lown, J. W. Novel DNA groove binding alkylators: design, synthesis and biological evaluation. J. Med. Chem. 1988, 31, 341-345.
3. Gourdie, T. A.; Valu, K. K.; Gravatt, G. L.; Boritzki, T. J.; Baguley, B. C.; Wilson, W. R.; Woodgate, P. D.; Denny, W. A. DNA-directed alkylating agents. I. Structure - activity relationships for acridine-linked aniline mustards: consequences of varying the reactivity of the mustard. J. Med. Chem. 1990, 33, 1177-1186.
4. Gravatt, G. L.; Baguley, B. C.; Wilson, W. R.; Denny, W. A. DNA-directed alkylating agents. 6. Synthesis and antitumor activity of DNA minor groove-targeted aniline mustard analogues of pibenzimol (Hoechst 33258). J. Med. Chem. 1994, 37, 4338-4345.
5. Hartley, J. A.; Wyatt, M. D.; Garbiras, B. J.; Richter, C.; Lee, M. Probing the importance of the second chloroethyl arm of a benzoic acid mustard derivative of an imidazole-containing analogue of distamycin. Biorg. Med. Chem. Lett. 1994, 4, 2412-2416.
6. Broggini, M.; Coley, H. M.; Mongelli, N.; Pesenti, E.; Wyatt, M. D.; Hartley, J. A.; D'Incalci, M. DNA sequence-specific adenine alkylation by the novel antitumor drug tallimustine (FCE 24517), a benzoyl nitrogen mustard derivative of distamycin. Nucleic Acids Res. 1995, 23, 81-87.
7. Anderson, W. K.; New, J. S.; Corey, P. F. Tumor inhibitory agents: bis(N-alkylcarbamate) derivatives of 2,3-dihydro-5-(3′,4′-dichlorophenyl)-6,7-bis(hydroxymethyl)-1H- pyrrolizine. Arzneim.-Forsch. 1980, 30 (I), 765-768.
8. Anderson, W. K.; Bhattacharjee, D.; Houston, D. M. Design, synthesis, antineoplastic activity, and chemical properties of bis-(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole. J. Med. Chem. 1989, 32, 119-127.
9. Elliot, W. L.; Fry, D. W.; Anderson, W. K., Nelson, J. M.; Hook, K. E.; Hawkins, P. A.; Leopold, W. R. In vivo and in vitro evaluation of the alkylating agent carmethizole. Cancer Res. 1991, 51, 4581-4587.
10. Anderson, W. K.; Corey, P. F. Synthesis and antileukemic activity of 5-substituted 2,3-dihydro-6,7-bis(hydroxymethyl)-1H-pyrrolizine diesters. J. Med. Chem. 1977, 20, 812-818.
11. Jarosinski, M. A.; Reddy, P. S.; Anderson, W. K. Synthesis, chemical reactivity and antitumor evaluation of congeners of carmethizole hydrochloride; an experimental "acylated vinylogous carbinolamine" tumor inhibitor. J. Med. Chem. 1993, 36, 3618-3627.
12. Woo, J.; Sigurdsson, S. T.; Hopkins, P. B. DNA interstrand cross-linking reactions of pyrrole-derived, bifunctional heterocycles: evidence for a common target site in DNA. J. Am. Chem. Soc. 1993, 115, 3407-3415.
13. (a) Sigurdsson, S. T.; Rink, S. M.; Hopkins, P. B. Affinity cross-linking of duplex DNA by a pyrrole-oligopeptide conjugate. J. Am. Chem. Soc. 1993, 115, 12633-12634.
14. (b) Sigurdsson, S. T.; Hopkins, P. B. Synthesis and reactions with DNA of a family of DNA-DNA affinity cross-linking agents. Tetrahedron 1994, 42, 12065-12084.
15. Waring, M. J. DNA-binding characteristics of acridinylmethane-sulphonanilide drugs: comparison with antitumour properties. Eur. J. Cancer 1976, 12, 995-1001.
16. Braithwaite, A. W.; Baguley, B. C. Existence of an extended series of antitumor compounds which bind to deoxyribonucleic acid by nonintercalative means. Biochemistry 1980, 19, 1101-1106.
17. Espejo, R. T.; Lebowitz, J. A simple electrophoretic method for the determination of superhelical density of closed circular DNAs and for observation of their superhelix density heterogeneity. Anal. Biochem. 1976, 72, 95-103.
18. Stella, V. J.; Anderson, W. K.; Bendetti, A.; Waugh, W. A.; Killion, R. B. Stability of carmethizole hydrochloride (NSC 602668), an experimental cytotoxic agent. Int. J. Pharm. 1991, 71, 157-165.
19. Maniatis, M. Molecular Cloning: A Laboratory Manual; Cold Spring Harbor Press: Plainview, NY 1981.
20. Prakash, A. S.; Denny, W. A.; Gourdie, T. A.; Valu, K. K.; Woodgate, P. D.; Wakelin, L. P. G. DNA-directed alkylating ligands as potential antitumor agents: sequence specificity of alkylation by intercalating aniline mustards. Biochemistry 1990, 29, 9799-9807.
21. Kohn, K. W.; Hartley, J. A.; Mattes, W. B. Mechanisms of DNA sequence selective alkylation of guanine-N7 positions by nitrogen mustards. Nucleic Acids Res. 1987, 15, 1987, 10531-10549.
22. Petrusek, R. L.; Anderson, G. L.; Garner, T. F.; Fannin, Q. L.; Kaplan, D. J.; Zimmer, S. G.; Hurley, L. H. Pyrrolo[1,4]-benzodiazepine antibiotics. Proposed structures and characteristics of the in vitro deoxyribonucleic acid adducts of anthramycin, tomamycin, sibiromycin and neothramycins A and B. Biochemistry 1981, 20, 1111-1119.
23. Lane, M. J.; Dabrowiak, J. C.; Vournakis, J. N. Sequence specificity of actinomycin D and netropsin binding to pBR322 DNA analyzed by protection from DNase I. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 3260-3264.
24. Fox, K. R.; Howarth, N. R. Investigations into the sequence-selective binding of mithramycin and related ligands to DNA. Nucleic Acids Res. 1985, 13, 8695-8714.
25. Gralla, J. D.; Sasse-Dwight, S.; Poljak, L. G. Formation of blocking lesions at identical DNA sequences by the nitrosourea and platinum classes of anticancer drugs. Cancer Res. 1987, 47, 5092-5096.
26. Boritzki, T. J.; Palmer, B. D.; Coddington, J. M.; Denny, W. A. Identification of the major lesion from the reaction of an acridine-targeted aniline mustard with DNA as an adenine N1 adduct. Chem. Res. Toxicol. 1994, 7, 41-46.
27. Fan, J.-Y., Tercel, M.; Denny, W. A. Synthesis, DNA binding and cytotoxicity of 1-[[(-(9-acridiny)lamino]alkyl]carbonyl-3-(chloromethyl)-6-hydroxyindolines, a new class of DNA-targeted alkylating agents. Anti-Cancer Drug Design 1997, 12, 277-293.
28. Fuller, A. T.; Harington, C. R. Rivers, R. P.; Stephens, J. M. L. Some derivatives of p-aminobenzoic acid. J. Chem. Soc. 1948, 241.
29. Baguley, B. C.; Wilson, W. R. Comparison of in vivo and in vitro drug sensitivities of Lewis lung carcinoma and P388 leukemia to analogues of amsacrine. Eur. J. Clin. Oncol. 1987, 23, 607-613.