Synthesis and Antitumor Cytotoxicity Evaluation of Novel Pyrrolo[2,1-c][1,4]benzodiazepine Imidazole Containing Polyamide Conjugates

Oncology Research

Volumn 13, Issue 4, 2002, Pages 221-233

  Kumar, Rohtash ^a   Lown, J William ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Cytotoxicity; DNA minor groove binders; PBD polyamide conjugate; Polyamide; Pyrrolo 2,1 c 1,4 henzodiazepines

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; PYRROLO[2,1 C][1,4]BENZODIAZEPINE IMIDAZOLE; THIOACETALDEHYDE; UNCLASSIFIED DRUG; BENZODIAZEPINE DERIVATIVE; IMIDAZOLE; NYLON; PYRROLE DERIVATIVE; PYRROLO(2,1 C)(1,4)BENZODIAZEPINE; PYRROLO(2,1-C)(1,4)BENZODIAZEPINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; COLON CANCER; CONTROLLED STUDY; CYCLIZATION; CYTOTOXICITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; KIDNEY CANCER; MELANOMA; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; ANIMAL; CELL CULTURE; DRUG EFFECT; DRUG SCREENING; HELA CELL; METHODOLOGY; MOUSE; PHYSIOLOGY; SYNTHESIS;

ANIMALS; BENZODIAZEPINES; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; IMIDAZOLES; MICE; NYLONS; PYRROLES; TUMOR CELLS, CULTURED;

EID: 0142061772     PISSN: 09650407     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Dervan, P. B. Design of sequence specific DNA binding molecules. Science 232:464; 1986.
2. Hurley, L. H.; Petrusek, R. Proposed structure of the anthramycin-DNA adduct. Nature 282:529; 1979.
3. Hurley, L. H.; Allen, C. S.; Feola, J. M.; Lubawy, W. C. In vitro and in vivo stability of anthramycin-DNA conjugate and its potential application as an anthramycin prodrug. Cancer Res. 39:3134; 1979.
4. Hurley, L. H. Pyrrolo (1,4) benzodizepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin. J. Antibiot. 30:349; 1977.
5. Hurley, L. H.; Rokem, J. S.; Petrusek, R. L. Proposed structures of the pyrrolo (1,4) benzodizepine antibiotic-deoxynucleic acid adducts. Biochem. Pharmacol. 29:1307; 1980.
6. Reddy, B. S. P.; Sondhi, S. M.; Lown, J. W. Synthetic DNA minor groove-binding drugs. Pharmacol. Therapeut. 84:1; 1999.
7. Thurston, D. E.; Bose, D. S. Synthesis of DNA-interactive pyrrolo [2,1-c][1,4] benzodiazepines. Chem. Rev. 94:433; 1994.
8. Kopka, M. L.; Goodsel, D. S.; Baikalov, I.; Grzeskowaik, K.; Cascio, D.; Dickerson, R. E. Crystal structure of a covalent DNA-drug adduct: Anthramycin bound to C-C-A-A-C-G-T-T-G-G and a molecular explanation of specificity. Biochemistry 33:13593; 1994.
9. Kamal, A.; Damayanthi, Y.; Reddy, B. S. N.; Lakminarayana, B.; Reddy, B. S. P. Novel biocatalytic reduction of aryl azides: Chemoenzymatic synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics. Chem. Commun. 11:1015; 1997.
10. Kamal, A.; Reddy, B. S. N.; Reddy, B. S. P. An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via reductive cyclization. Biorg. Med. Chem. Lett. 7:1825: 1997.
11. Miyamoto, M.; Kondo, S.; Naganawa, H.; Maeda, K.; Ohno, M.; Umezawa, H. Structure and synthesis of neothramycin. J. Antibiot. 30:340; 1977.
12. Thurston, D. E.; Thompson, A. S. The molecular recognition of DNA. Chemische Berichte 26:767; 1990.
13. Hurley, L. H.; Reck, T.; Thurston, D. E.; Longley, D. R.; Holden, K. G.; Faucette, F., Jr.; Mong, S. M.; Johnson, R. K. Pyrrolo[1,4]-benzodiazepine antitumor antibiotics: Relationship of DNA alkylation and sequences specificity to the biological activity of natural and synthetic compounds. Chem. Res. Toxicol. 1, 258; 1988.
14. Wang, J. J.; Hill, G. C.; Hurley, L. H. Template-directed design of a DNA-DNA cross-linker based upon bis-tomaymycin duplex adduct. J. Med. Chem. 35:2995: 1992.
15. Bose, D. S.; Jones, G. B. New approaches to the pyrrolo [2.1-c][1,4] benzodiazepines: Synthesis, DNA binding and cytotoxicity of DC-81. Tetrahedron 48:751; 1992.
16. Jenkins, T. C.; Hurley, L. H.; Neidle, S.; Thurston, D. E. Structure of a conalent DNA minor groove adduct with pyrrolobenzodiazepine dimmer: Evidence for sequence specific inter-strand crossing. J. Med. Chem. 37:4529; 1994.
17. Farmer, J. D., Jr.; Gustafson, G. R.; Conti, A.; Zimmt, M. B.; Suggs, J. W. DNA binding properties of a new class of linked anthramycin analogues. Nucleic Acids Res. 19:899; 1991.
18. Bose, D. S.; Thompson, A. S.; Ching, J.; Hartley, J. A.; Berardini, M. D.; Jenkins, T. C.; Neidle, S.; Hurley, L. H.; Thurston, D. E. Rational design of a highly efficient irreversible DNA inter-strand cross-linking agents based on the pyrrolo-benzodiazepine ring system. J. Am. Chem. Soc. 114:4939; 1992.
19. Mountzouris, J. A.; Wang, J. J.; Thurston, D. E.; Hurley, L. H. Comparison of a DSB-120 DNA interstrand cross linked adduct with the corresponding bis-tomaymycin adduct: An example of a successful template directed approach to drug design based upon the monoalkylating compound tomaymycin. J. Med. Chem. 37: 3132; 1994.
20. Sondhi, S. M.; Reddy, B. S. P.; Lown, J. W. Lexitropsin conjugates: Action on DNA targets. Curr. Med. Chem. 4:313; 1997.
21. Lown, J. W.; Joshua, A. V. Molecular mechanism of binding of pyrrolo (1,4) benzodizepine antitumor agents to deoxyribonucleic acid: Anthramycin and tomaymycin. Biochem. Pharmacol. 28: 2017; 1979.
22. Damayanthi, Y.; Reddy, B. S. P.; Lown, J. W. Design and synthesis of novel pyrrolo[2,1-c][1,4] henzodiazepines-lexitropsin conjugates. J. Organic Chem. 64:290; 1999.
23. Kumar, R.; Lown, J. W. Design and synthesis of novel DNA inter strand cross-linking agents: C2-linked pyrrolo [2,1-c][1,4] benzodiazepines polyamide conjugates. Heterocyclic Commun. 8(2): 115; 2002.
24. Reddy, B. S. P.; Damayanthi, Y.; Lown, J. W. Design and efficient synthesis of novel DNA inter strand cross-linking agents: C2-linked pyrrolo[2,1-c][1,4] benzodiazepines dimers. Synthetic Lett. 1112: 1999.
25. Reddy, B. S. P.; Damayanthi, Y.; Reddy, B. S. N.; Lown, J. W. Design, synthesis and in vitro cytotoxicity studies of novel pyrrolo [2,1-c][1,4] benzodiazepines (PBD)-polyamide conjugates and 2,2′-PBD dimmers. Anti-Cancer Drug Design 15:225; 2000.
26. Rao, K. E.; Lown, J. W. Lexitropsins: Sequence selective DNA binding and anticancer agents. Trends Organic Chem. 3:141; 1992.
27. Gupta, R.; Wang, H. Huang, L.; Lown, J. W. Design, synthesis, DNA sequence preferential alkylation and biological evaluation of N-mustard derivatives of Hoechst 33258 analogs. Anti-Cancer Drug Design 10:25; 1994.
28. Gupta, R.; Xie, G.; Lown, J. W. Hybrid molecules containing propargylic sulfones and DNA minor groove-binding lexitropsins: Synthesis, sequence specificity of reaction with DNA and biological evaluation. Gene 149:81; 1994.
29. Dervan, P. B.; Baird, E. E. Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids. J. Am. Chem. Soc. 118:6141; 1996.
30. Maruyama, I. N.; Tanaka, N.; Kondo, S.; Umezawa, H. Fluorometric studies on neothramycin and its reaction with DNA. J. Antibot. 34:427; 1981.
31. Maruyama, I. N.; Suzuki, H.; Tanaka, N. Mechanism of action of neothramycin: The effect of macromolecular synthesis. J. Antibot. 31:761; 1978.