Effect of a-ring modifications on the DNA-binding behavior and cytotoxicity of pyrrolo[2,1-c][1,4]benzodiazepines

Journal of Medicinal Chemistry

Volumn 42, Issue 11, 1999, Pages 1951-1964

  Thurston, David E ^b   Bose, D Subhas ^a,b   Howard, Philip W ^b   Jenkins, Terence C ^c   Leoni, Alberto ^b   Baraldi, Pier G ^d   Guiotto, Andrea ^d   Cacciari, Barbara ^d   Kelland, Lloyd R ^e   Foloppe, Marie Paule ^f   Rault, Sylvain ^f  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b UNIVERSITY OF PORTSMOUTH   (United Kingdom)

^c UNIVERSITY OF GREENWICH   (United Kingdom)

^d UNIVERSITY OF FERRARA   (Italy)

^e INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^f UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,11A TETRAHYDRO 8 HYDROXY 7 METHOXY 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 11 METHOXY 1,2,3,10,11,11A HEXAHYDRO 5H PYRROLO[2,1 C][1,4] PYRIDO[3,2F]DIAZEPIN 5 ONE; ANTHRAMYCIN; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; SIBIROMYCIN; TOMAYMYCIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYCLIZATION; DNA DENATURATION; DRUG BINDING SITE; DRUG CYTOTOXICITY; DRUG DNA BINDING; DRUG OXIDATION; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; NITRATION; NONHUMAN; OVARY CELL; PLASMACYTOMA; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033519732     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981117p     Document Type: Article

References (47)

1. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
2. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
3. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
4. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
5. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
6. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
7. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
8. Trauger, J. W.; Baird, E. E.; Dervan, P. B. Recognition of 16 Base Pairs in the Minor Groove of DNA by a Pyrrole-Imidazole Polyamide Dimer. J. Am. Chem. Soc. 1998, 720, 3534-3535. White, S,; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the Four Watson-Crick Base Pairs in the DNA Minor Groove by Synthetic Ligands. Nature 1998, 391, 468-471. Kielkopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. A Structural Basis for Recognition of A•T and T•A Base Pairs in the Minor Groove of B-DNA. Science 1998, 282, 111-115. Dervan, P. B. Gene-Specific Transcription Inhibition In Vivo by Designed Ligands. FASEB 1997,11, 2546. Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of Seven Base Pair Sequences in the Minor Groove of DNA by Ten-Ring Pyrrole-Imidazole Polyamide Hairpins. J. Am. Chem. Soc. 1997, 119, 7636-7644. Wemmer, D. E.; Dervan, P. B. Targeting the Minor Groove of DNA. Curr. Opin. Struct. Biol. 1997, 7, 355-361. Gottesfeld, J. M.; Neely, L.; Trauger, J. W,; Baird, E. E.; Dervan, P. B. Regulation of Gene Expression by Small Molecules. Nature 1997, 387, 202-205. Szewczyk, J. W.; Baird, E. E.; Dervan, P. B. Sequence-Specific Recognition of DNA by a Major and Minor Groove Binding Ligand. Angew. Chem., Int. Ed. Engl. 1996, 35, 1487-1489.
9. Neidle, S.; Puvvada, M. S.; Thurston, D. E. The Relevance of Drug-DNA Sequence-Specificity to Antitumour Activity. Eur. J. Cancer 1994, 30A, 567-568. Neidle, S.; Thurston, D. E. DNA Sequences as Targets for New Anticancer Agents. In New Targets for Cancer Chemotherapy; Kerr, D. J., Workman, P., Eds.; CRC Press Ltd.: Boca Raton, FL, 1994; pp 159-175. Thurston, D. E. Advances in the Study of Pyrrolo[2,1-c][1,4]-benzodiazepine (PBD) Antitumour Antibiotics. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M. J., Eds.; The Macmillan Press Ltd.: London, 1993; pp 54-88.
10. Neidle, S.; Puvvada, M. S.; Thurston, D. E. The Relevance of Drug-DNA Sequence-Specificity to Antitumour Activity. Eur. J. Cancer 1994, 30A, 567-568. Neidle, S.; Thurston, D. E. DNA Sequences as Targets for New Anticancer Agents. In New Targets for Cancer Chemotherapy; Kerr, D. J., Workman, P., Eds.; CRC Press Ltd.: Boca Raton, FL, 1994; pp 159-175. Thurston, D. E. Advances in the Study of Pyrrolo[2,1-c][1,4]-benzodiazepine (PBD) Antitumour Antibiotics. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M. J., Eds.; The Macmillan Press Ltd.: London, 1993; pp 54-88.
11. Neidle, S.; Puvvada, M. S.; Thurston, D. E. The Relevance of Drug-DNA Sequence-Specificity to Antitumour Activity. Eur. J. Cancer 1994, 30A, 567-568. Neidle, S.; Thurston, D. E. DNA Sequences as Targets for New Anticancer Agents. In New Targets for Cancer Chemotherapy; Kerr, D. J., Workman, P., Eds.; CRC Press Ltd.: Boca Raton, FL, 1994; pp 159-175. Thurston, D. E. Advances in the Study of Pyrrolo[2,1-c][1,4]-benzodiazepine (PBD) Antitumour Antibiotics. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M. J., Eds.; The Macmillan Press Ltd.: London, 1993; pp 54-88.
12. Hertzberg, R. P.; Hecht, S. M.; Reynolds, V. L.; Molineux, I. J.; Hurley, L. H. DNA Sequence Specificity of the Pyrrolo[l,4]-benzodiazepine Antitumor Antibiotics. Methidiumpropyl-EDTA-Iron(II) Footprinting Analysis of DNA Binding Sites for Anthramycin and Related Drugs. Biochemistry 1986, 25, 1249-1258.
13. Hurley, L. H.; Reck, T.; Thurston, D. E.; Langley, D. R.; Holden, K. G.; Hertzberg, R. P.; Hoover, J. R. E.; Gallagher, G., Jr.; Faucette, L. F.; Mong, S.-M.; Johnson, R. K. Pyrrolo[1,4]-benzodiazepine Antitumour Antibiotics; Relationship of DNA Alkylation and Sequence Specificity to the Biological Activity of Natural and Synthetic Compounds. Chem. Res. Toxicol. 1988, 1, 258-268.
14. Barkley, M. D.; Cheatham, S. F.; Thurston, D. E.; Hurley, L. H. Pyrrolo[1,4]benzodiazepine Antitumour Antibiotics: Evidence for Two Forms of Tomaymycin Bound to DNA. Biochemistry 1986, 25, 3021-3031.
15. Jenkins, T. C.; Hurley, L. H.; Neidle, S.; Thurston, D, E. Structure of a Covalent DNA Minor Groove Adduct with a Pyrrolobenzodiazepine Dimer: Evidence for Sequence-Specific Interstrand Cross-Linking. J. Med. Chem. 1994, 37, 4529-4537.
16. 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. 1994, 37, 3132-3140.
17. Remers, W. A. The Chemistry of Antitumor Antibiotics; Wiley: New York, 1988; Vol. 2, pp 28-92.
18. Farmer, J. D.; Rudnicki, S. M.; Suggs, J. W. Synthesis and DNA Cross-linking Ability of a Dimeric Anthramycin Analogue. Tetrahedron Lett. 1988, 29, 5105-5108. Farmer, J. D.; 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. 1991, 19, 899-903.
19. Farmer, J. D.; Rudnicki, S. M.; Suggs, J. W. Synthesis and DNA Cross-linking Ability of a Dimeric Anthramycin Analogue. Tetrahedron Lett. 1988, 29, 5105-5108. Farmer, J. D.; 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. 1991, 19, 899-903.
20. 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 Interstrand Cross-Linking Agent based on the Pyrrolobenzodiazepine Ring System. J. Am. Chem. Soc. 1992, 114, 4939-4941. Bose, D. S.; Thompson, A. S.; Smellie, M.; Berardini, M. D.; Hartley, J. A.; Jenkins, T. C.; Neidle, S.; Thurston, D. E. Effect of Linker Length on DNA-Binding Affinity, Cross-Linking Efficiency and Cytotoxicity of C8-Linked Pyrrolobenzodiazepine Dimers. J. Chem. Soc., Chem. Commun. 1992, 14, 1518-1520. Thurston, D. E.; Bose, D. S.; Thompson, A. S.; Howard, P. W.; Leoni, A.; Croker, S. J.; Jenkins, T. C.; Neidle, S.; Hartley, J. A.; Hurley, L. H. Synthesis of Sequence-Selective C8-Linked Pyrrolo[2,1-c][1,4]benzodiazepine DNA Interstrand Cross-Linking Agents. J. Org. Chem. 1996, 61, 8141-8147.
21. 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 Interstrand Cross-Linking Agent based on the Pyrrolobenzodiazepine Ring System. J. Am. Chem. Soc. 1992, 114, 4939-4941. Bose, D. S.; Thompson, A. S.; Smellie, M.; Berardini, M. D.; Hartley, J. A.; Jenkins, T. C.; Neidle, S.; Thurston, D. E. Effect of Linker Length on DNA-Binding Affinity, Cross-Linking Efficiency and Cytotoxicity of C8-Linked Pyrrolobenzodiazepine Dimers. J. Chem. Soc., Chem. Commun. 1992, 14, 1518-1520. Thurston, D. E.; Bose, D. S.; Thompson, A. S.; Howard, P. W.; Leoni, A.; Croker, S. J.; Jenkins, T. C.; Neidle, S.; Hartley, J. A.; Hurley, L. H. Synthesis of Sequence-Selective C8-Linked Pyrrolo[2,1-c][1,4]benzodiazepine DNA Interstrand Cross-Linking Agents. J. Org. Chem. 1996, 61, 8141-8147.
22. 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 Interstrand Cross-Linking Agent based on the Pyrrolobenzodiazepine Ring System. J. Am. Chem. Soc. 1992, 114, 4939-4941. Bose, D. S.; Thompson, A. S.; Smellie, M.; Berardini, M. D.; Hartley, J. A.; Jenkins, T. C.; Neidle, S.; Thurston, D. E. Effect of Linker Length on DNA-Binding Affinity, Cross-Linking Efficiency and Cytotoxicity of C8-Linked Pyrrolobenzodiazepine Dimers. J. Chem. Soc., Chem. Commun. 1992, 14, 1518-1520. Thurston, D. E.; Bose, D. S.; Thompson, A. S.; Howard, P. W.; Leoni, A.; Croker, S. J.; Jenkins, T. C.; Neidle, S.; Hartley, J. A.; Hurley, L. H. Synthesis of Sequence-Selective C8-Linked Pyrrolo[2,1-c][1,4]benzodiazepine DNA Interstrand Cross-Linking Agents. J. Org. Chem. 1996, 61, 8141-8147.
23. Smellie, M.; Kelland, L. R.; Thurston, D. E.; Souhami, R. L.; Hartley, J. A. Cellular Pharmacology of Novel C8-Linked Anthramycin-based Sequence-Selective DNA Minor-Groove Cross-Linking Agents. Br. J. Cancer 1994, 70, 48-53.
24. Puvvada, M. S.; Hartley, J. A.; Jenkins, T. C.; Thurston, D. E. A Quantitative Assay to Measure the Relative DNA-Binding Affinity of Pyrrolo[2,1-c][1,4]benzodiazepine (PBD) Antitumour Antibiotics Based on the Inhibition of Restriction Endonuclease BamHI. Nucleic Acids Res. 1993, 21, 3671-3675.
25. Puvvada, M. S.; Hartley, J. A.; Gibson, I.; Stephenson, P.; Jenkins, T. C.; Thurston, D. E. Inhibition of Bacteriophage T7 RNA Polymerase In Vitro Transcription by the DNA-Binding Pyrrolo[2,1-c][1,4]benzodiazepine (PBD) Antitumour Antibiotics. Biochemistry 1997, 36, 2478-2484.
26. Thurston, D. E.; Bose, D. S. Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines. Chem. Rev. 1994, 94, 433-465. Hurley, L. H.; Thurston, D. E. Pyrrolo(1,4)Benzodiazepine Antitumor Antibiotics - Chemistry, Interaction With DNA, and Biological Implications. Pharm. Res. 1984, 52-59.
27. Thurston, D. E.; Bose, D. S. Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines. Chem. Rev. 1994, 94, 433-465. Hurley, L. H.; Thurston, D. E. Pyrrolo(1,4)Benzodiazepine Antitumor Antibiotics - Chemistry, Interaction With DNA, and Biological Implications. Pharm. Res. 1984, 52-59.
28. Thurston, D. E.; Hurley, L. H. A Rational Basis for the Development of Antitumour Agents in the Pyrrolo[1,4]benzodiazepine Group. Drugs Future 1983, 8, 957-971.
29. Kaneko, T.; Wong, H.; Doyle, T. W.; Rose, W. C.; Bradner, W. T. Bicyclic and Tricyclic Analogues of Anthramycin. J. Med. Chem. 1985, 28, 388-392.
30. Baraldi, P. G.; Leoni, A.; Cacciari, B.; Manfredini, S.; Simoni, D.; Bergomi, M.; Menta, E.; Spinelli, S. Synthesis and Antitumor-Activity of a New Class of Pyrazolo[4,3-e]pyrrolo[1,2-a][1,4]-diazepinone Analogues of Pyrrolo[1,4][2,1-c]Benzodiazepines. J. Med. Chem. 1994, 37, 4329-4337.
31. Courtney, S. M.; Thurston, D. E. A New Convenient Procedure for the Synthesis of Pyrrolo[2,1-c][1,4]benzodiazepines. Tetrahedron Lett. 1993, 34, 5327-5328; and unpublished data for 53.
32. Langley, D. R.; Thurston, D. E. A Versatile and Efficient Synthesis of Carbinolamine-Containing Pyrrolo[1,4]benzodiazepines via the Cyclization of N-(2-Aminobenzoyl)pyrrolidine-2-carboxaldehyde Diethylthioacetals: Total Synthesis of Prothracarcin. J. Org. Chem. 1987, 52, 91-97.
33. Bock, L. H.; Wash, S. Polyesters from Hydroxyalkyl Ethers of Vanillic Acid and Esters Thereof. U.S. Patent 2755273, 1956.
34. Althuis, T. H.; Hess, H. J. Synthesis and Identification of the Major Metabolites of Prazosin Formed in Dog and Rat. J. Med. Chem. 1976, 20, 146-149.
35. 2-Induced Regiospecific Opening of the 1,3-Benzodioxazole Ring System: A Route to the Novel DNA Interactive Ligand Iso-DC-81. Tetrahedron Lett. 1993, 34, 1377-1378.
36. Foloppe, M. P.; Caballero, E.; Rault, S.; Robba, M. Synthese et etude de l'activite cytotoxique in vitro et antimorle in vivo de nouvelles pyrrolo[2,1-c][1,4]benzodiazepines. Eur. J. Med. Chem. 1992, 27, 291-295.
37. Thurston, D. E.; Murty, V. S.; Langley, D. R.; Jones, G. B. O-Debenzylation of a Pyrrolo[2,1-c][1,4]benzodiazepine in the Presence of a Carbinolamine Functionality: Synthesis of DC-81. Synthesis 1990, 1, 81-84.
38. Thurston, D. E.; Jones, G. B.; Davis, M. E. Synthesis and Reactivity of a Novel Oxazolo[2,1-c][1,4]benzodiazepine Ring System with DNA-Recognition Potential: A New Class of Anthramycins. J. Chem. Soc., Chem. Commun. 1990, 12, 874-876.
39. Bose, D. S.; Jones, G. B.; Thurston, D. E. New Approaches to Pyrrolo[2,1-c][1,4]benzodiazepines: Synthesis, DNA-Binding and cytotoxicity of DC-81. Tetrahedron 1992, 48, 751-758.
40. Coppola, G. M. The Chemistry of Isatoic Anhydrides. Synthesis 1980, 505-536.
41. Beckwith, A. L. J.; Hickman, R. J. Reaction of Lead Tetra-Acetate. Part III. Formation of Pyrimidinones and Related Compounds From Dicarboxylic Acid Amides. J. Chem. Soc. C 1968, 2756-2759.
42. Dallaker, Von F.; Steiner, G. Darstellung und Reaktionen von 2-Amino-pyrazin-carbonsaure-3-methylester. Ann. 1962, 98-103.
43. Ellingson, R. C.; Henry, R. L.; McDonald, F. Pyrazine Chemistry. I. Derivatives of 3-Aminopyrazinoic Acid. J. Am. Chem. Soc. 1945, 61, 1711-1715.
44. Gershon, H. Pyrimidines. II. Chlorinated Pyrimidines Derived From Orotic Acid. J. Org. Chem. 1962, 27, 3507-3510.
45. Jones, G. B.; Davey, C. L.; Jenkins, T. C.; Kamal, A.; Kneale, G. G.; Neidle, S.; Webster, G. D.; Thurston, D. E. The Non-Covalent Interaction of Pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones with DNA. Anti-Cancer Drug Des. 1990, 5, 249-264.
46. Suggs, J. W.; Wang, Y. S.; Lee, K. S. Synthesis and Structure of Anthramycin Analogues Via Hydride Reduction of Dilactams. Tetrahedron Lett. 1985, 26, 4871-4874.
47. Manzini, G.; Barcellona, M. L.; Avitabile, M.; Quadrifoglio, F. Interaction of Diamidino-2-phenylindole (DAPI) with Natural and Synthetic Nucleic Acids. Nucleic Acids Res. 1983, 11, 8861-8876.