Shape-dependent catalysis: Insights into the source of catalysis for the CC-1065 and duocarmycin DNA alkylation reaction

Accounts of Chemical Research

Volumn 32, Issue 12, 1999, Pages 1043-1052

  Boger, Dale L ^a   Garbaccio, Robert M ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DUOCARMYCIN A; DUOCARMYCIN B1; DUOCARMYCIN DERIVATIVE; DUOCARMYCIN SA; RACHELMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CONFORMATION; DNA ALKYLATION; DRUG BINDING; DRUG STABILITY; DRUG STRUCTURE; MOLECULAR STABILITY; STRUCTURE ANALYSIS;

EID: 0033377095     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9800946     Document Type: Article

References (61)

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40. Boger, D. L.; Mesini, P. Design, Synthesis and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 2,3,10,10a-Tetrahydro-1H-cyclopropa[d]benzo[f]quinol-5-one (CBQ) Alkylation Subunit: Identification and Structural Origin of Subtle Stereoelectronic Features That Govern Reactivity and Regioselectivity. J. Am. Chem. Soc. 1994, 116, 11335. Boger, D. L.; Mesini, P. DNA Alkylation Properties of CC-1065 and Duocarmycin Analogs Incorporating the 2,3,10,10a-Tetrahydrocyclopropa-[d]benzo[f]quinol-5-one (CBQ) Alkylation Subunit: Identification of Subtle Structural Features That Contribute to the Regioselectivity of the Adenine N3 Alkylation Reaction. J. Am. Chem. Soc. 1995, 117, 11647.
41. Boger, D. L.; Turnbull, P., Synthesis and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 1,2,3,4,11,11a-Hexahydrocyclopropa[c]naphtho[2,1-b]azepin-6-one (CNA) Alkylation Subunit: Structural Features That Govern Reactivity and Reaction Regioselectivity. J. Org. Chem. 1997, 62, 5849.
42. Boger, D. L.; Boyce, C. W.; Johnson, D. S. pH Dependence of the Rate of DNA Alkylation for (+)-Duocarmycin SA and (+)-CCBI-TMI. Bioorg. Med. Chem. Lett. 1997, 7, 233.
43. Boger, D. L.; M. Garbaccio, R. M. Are the Duocarmycin and CC-1065 DNA Alkylation Reactions Acid-catalyzed? Solvolysis pH Rate Profiles Suggest They Arc Not. J. Org. Chem. 1999, 64, 5666.
44. Warpehoski, M. A.; Harper, D. E. Acid-dependent Electrophilicity of Cyclopropylpyrroloindoles. Nature's Masking Strategy for a Potent DNA Alkylator. J. Am. Chem. Soc. 1994, 116, 7573.
45. Warpehoski, M. A.; Harper, D. E. Enzyme-like Rate Acceleration in the DNA Minor Groove. Cyclopropylpyrroloindoles as Mechanism-based Inactivators of DNA. J. Am. Chem. Soc. 1995, 117, 2951.
46. Reynolds, V. L.; Molineux, I. J.; Kaplan, D. J.; Swenson, D. H.; Hurley, L. H. Reaction of the Antitumor Antibiotic CC-1065 with DNA. Location of the Site of Thermally Induced Strand Breakage and Analysis of DNA Sequence Specificity. Biochemistry 1985, 24, 6228. Hurley, L. H.; Lee, C.-S.; McGovren, J. P.; Warpehoski, M. A.; Mitchell, M. A.; Kelly, R. C.; Aristoff, P. A. Molecular Basis for Sequence Specific DNA Alkylation by CC-1065. Biochemistry 1988, 27, 3886. 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, L.; Johnson, P. D.; Bradford, V. S. Sequence Specificity of DNA Alkylation by the Unnatural Enantiomer of CC-1065 and its Synthetic Analogues. J. Am. Chem. Soc. 1990, 112, 4633.
47. Reynolds, V. L.; Molineux, I. J.; Kaplan, D. J.; Swenson, D. H.; Hurley, L. H. Reaction of the Antitumor Antibiotic CC-1065 with DNA. Location of the Site of Thermally Induced Strand Breakage and Analysis of DNA Sequence Specificity. Biochemistry 1985, 24, 6228. Hurley, L. H.; Lee, C.-S.; McGovren, J. P.; Warpehoski, M. A.; Mitchell, M. A.; Kelly, R. C.; Aristoff, P. A. Molecular Basis for Sequence Specific DNA Alkylation by CC-1065. Biochemistry 1988, 27, 3886. 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, L.; Johnson, P. D.; Bradford, V. S. Sequence Specificity of DNA Alkylation by the Unnatural Enantiomer of CC-1065 and its Synthetic Analogues. J. Am. Chem. Soc. 1990, 112, 4633.
48. Reynolds, V. L.; Molineux, I. J.; Kaplan, D. J.; Swenson, D. H.; Hurley, L. H. Reaction of the Antitumor Antibiotic CC-1065 with DNA. Location of the Site of Thermally Induced Strand Breakage and Analysis of DNA Sequence Specificity. Biochemistry 1985, 24, 6228. Hurley, L. H.; Lee, C.-S.; McGovren, J. P.; Warpehoski, M. A.; Mitchell, M. A.; Kelly, R. C.; Aristoff, P. A. Molecular Basis for Sequence Specific DNA Alkylation by CC-1065. Biochemistry 1988, 27, 3886. 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, L.; Johnson, P. D.; Bradford, V. S. Sequence Specificity of DNA Alkylation by the Unnatural Enantiomer of CC-1065 and its Synthetic Analogues. J. Am. Chem. Soc. 1990, 112, 4633.
49. Boger, D. L.; Garbaccio, R. M. A Novel Class of CC-1065 and Duocarmycin Analogues Subject to Mitomycin Related Reductive Activation. J. Org. Chem. 1999, 64, 8350.
50. Boger, D. L.; Santillán, A., Jr.; Searcey, M.; Jin, Q. The Critical Role of the Linking Amide in CC-1065 and the Duocarmycins: Implications on the Source of DNA Alkylation Catalysis. J. Am. Chem. Soc. 1998, 120, 11554.
51. Boger, D. L.; Santillán, A., Jr.; Searcey, M.; Jin, Q. Synthesis and Evaluation of Duocarmycin and CC-1065 Analogues Containing Modifications in the Subunit Linking Amide. J. Org. Chem. 1999, 64, 5241.
52. Boger, D. L.; Han, N.; Tarby, C. M.; Boyce, C. W.; Cai, H.; Jing, Q.; Kitos, P. A. Synthesis, Chemical Properties, and Preliminary Evaluation of Substituted CBI Analogs of CC-1065 and the Duocarmycins Incorporating the 7-Cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CCBI) Alkylation Subunit: Hammett Quantitation of the Magnitude of Electronic Effects on Functional Reactivity. J. Org. Chem. 1996, 61, 4894. Boger, D. L.; McKie, J. A.; Han, N.; Tarby, C. M.; Riggs, H. W.; Kitos, P. A. A Hammett Correlation for CC-1065 and Duocarmycin Analogs: Magnitude of Substituent Electronic Effects on Functional Reactivity. Bioorg. Med. Chem. Lett. 1996, 6, 659.
53. Boger, D. L.; Han, N.; Tarby, C. M.; Boyce, C. W.; Cai, H.; Jing, Q.; Kitos, P. A. Synthesis, Chemical Properties, and Preliminary Evaluation of Substituted CBI Analogs of CC-1065 and the Duocarmycins Incorporating the 7-Cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CCBI) Alkylation Subunit: Hammett Quantitation of the Magnitude of Electronic Effects on Functional Reactivity. J. Org. Chem. 1996, 61, 4894. Boger, D. L.; McKie, J. A.; Han, N.; Tarby, C. M.; Riggs, H. W.; Kitos, P. A. A Hammett Correlation for CC-1065 and Duocarmycin Analogs: Magnitude of Substituent Electronic Effects on Functional Reactivity. Bioorg. Med. Chem. Lett. 1996, 6, 659.
54. 2 Substituent: Validation of a Direct Relationship Between Solvolysis Chemical Stability and in Vitro Biological Potency. J. Am. Chem. Soc. 1994, 116, 5523.
55. Boger, D. L.; McKie, J. A.; Cai, H.; Cacciari, B.; Baraldi, P. G. Synthesis and Properties of Substituted CBI Analogs of CC-1065 and the Duocarmycins Incorporating the 7-Methoxy-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (MCBI) Alkylation Subunit: Magnitude of Electronic Effects on the Functional Reactivity. J. Org. Chem. 1996, 61, 1710.
56. Boger, D. L.; Santillán, A., Jr.; Searcey, M.; Brunette, S. R.; Wolkenberg, S. E.; Hedrick, M.; Jin, Q. Submitted.
57. Schnell, J. R.; Ketchem, R. R.; Boger, D. L.; Chazin, W. J. DNA Binding Induced Alkylation: Insights from the Structure of a DNA Duplex Alkylated by the Indole Derivative of Duocarmycin SA. J. Am. Chem. Soc. 1999, 121, 5645. Eis, P. S.; Smith, J. A.; Rydzewski, J. M.; Case, D. A.; Boger, D. L.; Chazin, W. J. High-Resolution Solution Structure of a DNA Duplex Alkylated by the Antitumor Agent Duocarmycin SA. J. Mol. Biol. 1997, 272, 237. Smith, J. A.; Schnell, J. R.; Chazin, W. J. Unpublished studies.
58. Schnell, J. R.; Ketchem, R. R.; Boger, D. L.; Chazin, W. J. DNA Binding Induced Alkylation: Insights from the Structure of a DNA Duplex Alkylated by the Indole Derivative of Duocarmycin SA. J. Am. Chem. Soc. 1999, 121, 5645. Eis, P. S.; Smith, J. A.; Rydzewski, J. M.; Case, D. A.; Boger, D. L.; Chazin, W. J. High-Resolution Solution Structure of a DNA Duplex Alkylated by the Antitumor Agent Duocarmycin SA. J. Mol. Biol. 1997, 272, 237. Smith, J. A.; Schnell, J. R.; Chazin, W. J. Unpublished studies.
59. Schnell, J. R.; Ketchem, R. R.; Boger, D. L.; Chazin, W. J. DNA Binding Induced Alkylation: Insights from the Structure of a DNA Duplex Alkylated by the Indole Derivative of Duocarmycin SA. J. Am. Chem. Soc. 1999, 121, 5645. Eis, P. S.; Smith, J. A.; Rydzewski, J. M.; Case, D. A.; Boger, D. L.; Chazin, W. J. High-Resolution Solution Structure of a DNA Duplex Alkylated by the Antitumor Agent Duocarmycin SA. J. Mol. Biol. 1997, 272, 237. Smith, J. A.; Schnell, J. R.; Chazin, W. J. Unpublished studies.
60. Boger, D. L.; Yun, W. Reversibility of the Duocarmycin A and SA DNA Alkylation Reaction. J. Am. Chem. Soc. 1993, 115, 9872.
61. Warpehoski, M. A.; Harper, D. H.; Mitchell, M. A.; Monroe, J. J. Reversibility of the Covalent Reaction of CC-1065 and Analogs with DNA. Biochemistry 1992, 31, 2502.