메뉴 건너뛰기




Volumn 40, Issue 9, 1997, Pages 1327-1339

Studies of Pyrrolo[1,2-α]benzimidazolequinone DT-diaphorase substrate activity, topoisomerase II inhibition activity, and DNA reductive alkylation

Author keywords

[No Author keywords available]

Indexed keywords

6 ACETAMIDOPYRROLO[1,2 A]BENZIMIDAZOLEQUINONE; 6 AZIRIDINYLPYRROLO[1,2 A]BENZIMIDAZOLEQUINONE; DNA TOPOISOMERASE (ATP HYDROLYSING); PYRROLO[1,2 A]QUINOLINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); UNCLASSIFIED DRUG;

EID: 0030968873     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960546p     Document Type: Article
Times cited : (42)

References (35)
  • 1
    • 1542530183 scopus 로고    scopus 로고
    • The Organic Chemistry of the Pyrrolo[1,2-α]benzimidazole Antitumor Agents. An Example of Rational Drug Design
    • For a recent review of the organic chemistry of the pyrrolo[1,2-α]benzimidazoles, see: Skibo, E. B.; Islam, I.; Schulz, W. G.; Zhou, R.; Bess, L.; Boruah, R. The Organic Chemistry of the Pyrrolo[1,2-α]benzimidazole Antitumor Agents. An Example of Rational Drug Design. Synlett 1996, 4, 297-309.
    • (1996) Synlett , vol.4 , pp. 297-309
    • Skibo, E.B.1    Islam, I.2    Schulz, W.G.3    Zhou, R.4    Bess, L.5    Boruah, R.6
  • 2
    • 0025313288 scopus 로고
    • Synthesis and Physical Studies of Azamitosene and Iminoazamitosene Reductive Alkylating Agents. Iminoquinone Hydrolytic Stability, Syn/Anti Isomerization, and Electrochemistry
    • Islam, I.; Skibo, E. B. Synthesis and Physical Studies of Azamitosene and Iminoazamitosene Reductive Alkylating Agents. Iminoquinone Hydrolytic Stability, Syn/Anti Isomerization, and Electrochemistry. J. Org. Chem. 1990, 55, 3195-3205.
    • (1990) J. Org. Chem. , vol.55 , pp. 3195-3205
    • Islam, I.1    Skibo, E.B.2
  • 3
    • 0025931154 scopus 로고
    • Structure-Activity Studies of Antitumor Agents Based on Pyrrolo-[1,2-α]benzimidazoles: New Reductive Alkylating DNA Cleaving Agents
    • Islam, I.; Skibo, E. B.; Dorr, R. T.; Alberts, D. S. Structure-Activity Studies of Antitumor Agents Based on Pyrrolo-[1,2-α]benzimidazoles: New Reductive Alkylating DNA Cleaving Agents. J. Med. Chem. 1991, 34, 2954-2961.
    • (1991) J. Med. Chem. , vol.34 , pp. 2954-2961
    • Islam, I.1    Skibo, E.B.2    Dorr, R.T.3    Alberts, D.S.4
  • 4
    • 0000572792 scopus 로고    scopus 로고
    • The Discovery of the Pyrrolo[1,2-α]benzimidazole Antitumor Agents - The Design of Selective Antitumor Agents
    • For a recent review of the medicinal chemistry of the pyrrolo-[1,2-α]benzimidazoles, see: Skibo, E. B. The Discovery of the Pyrrolo[1,2-α]benzimidazole Antitumor Agents - The Design of Selective Antitumor Agents. Curr. Med. Chem. 1996, 2, 900-931.
    • (1996) Curr. Med. Chem. , vol.2 , pp. 900-931
    • Skibo, E.B.1
  • 5
    • 0027496965 scopus 로고
    • Pyrrolo[1,2-α]benzimidazole-Based Aziridinyl Quinones. A New Class of DNA Cleaving Agent Exhibiting G and A Base Specificity
    • Skibo, E. B.; Schulz, W. G. Pyrrolo[1,2-α]benzimidazole-Based Aziridinyl Quinones. A New Class of DNA Cleaving Agent Exhibiting G and A Base Specificity. J. Med. Chem. 1993, 36, 3050-3055.
    • (1993) J. Med. Chem. , vol.36 , pp. 3050-3055
    • Skibo, E.B.1    Schulz, W.G.2
  • 6
    • 0028010991 scopus 로고
    • Structure-Activity Studies of Benzimidazole-Based DNA-Cleaving Agents. Comparison of Benzimidazole, Pyrrolobenzimidazole and Tetrahydropyrido benzimidazole Analogues
    • Skibo, E. B.; Islam, I.; Heileman, M. J.; Sehulz, W. G. Structure-Activity Studies of Benzimidazole-Based DNA-Cleaving Agents. Comparison of Benzimidazole, Pyrrolobenzimidazole and Tetrahydropyrido benzimidazole Analogues. J. Med. Chem. 1994, 37, 78-92.
    • (1994) J. Med. Chem. , vol.37 , pp. 78-92
    • Skibo, E.B.1    Islam, I.2    Heileman, M.J.3    Sehulz, W.G.4
  • 7
    • 0028340884 scopus 로고
    • A Comparison of the Cytotoxic and Physical Properties of Aziridinyl Quinone Derivatives Based on the Pyrrolo [1,2-α]benzimidazole and Pyrrolo[1,2-α]indole Ring Systems
    • Boruah, R. C.; Skibo, E. B. A Comparison of the Cytotoxic and Physical Properties of Aziridinyl Quinone Derivatives Based on the Pyrrolo [1,2-α]benzimidazole and Pyrrolo[1,2-α]indole Ring Systems. J. Med. Chem. 1994, 37, 1625-1631.
    • (1994) J. Med. Chem. , vol.37 , pp. 1625-1631
    • Boruah, R.C.1    Skibo, E.B.2
  • 10
    • 0029013409 scopus 로고
    • Pyrrolo[1,2-α]benzimidazole-Based Quinones and Iminoquinones. The Role of the 3-Substituent on Cytotoxicity
    • Sehulz, W. G.; Islam, E.; Skibo, E. B. Pyrrolo[1,2-α]benzimidazole-Based Quinones and Iminoquinones. The Role of the 3-Substituent on Cytotoxicity. J. Med. Chem. 1995, 38, 109-118.
    • (1995) J. Med. Chem. , vol.38 , pp. 109-118
    • Sehulz, W.G.1    Islam, E.2    Skibo, E.B.3
  • 11
    • 0029797555 scopus 로고    scopus 로고
    • Chemistry of the Pyrrolo[1,2-α]benzimidazole Antitumor Agents: Influence of the 7-Substituent on the Ability to Alkylate DNA and Inhibit Topoisomerase II
    • Zhou, R.; Skibo, E. B. Chemistry of the Pyrrolo[1,2-α]benzimidazole Antitumor Agents: Influence of the 7-Substituent on the Ability to Alkylate DNA and Inhibit Topoisomerase II. J. Med. Chem. 1996, 39, 4321-4331.
    • (1996) J. Med. Chem. , vol.39 , pp. 4321-4331
    • Zhou, R.1    Skibo, E.B.2
  • 12
    • 0029610076 scopus 로고
    • Evidence for DNA Phosphate Backbone Alkylation and Cleavage by Pyrrolo[1,2-α] benzimidazoles, Small Molecules Capable of Causing Sequence Specific Phosphoester Bond Hydrolysis
    • Schulz, W. G.; Nieman, R. A.; Skibo, E. B. Evidence for DNA Phosphate Backbone Alkylation and Cleavage by Pyrrolo[1,2-α] benzimidazoles, Small Molecules Capable of Causing Sequence Specific Phosphoester Bond Hydrolysis. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 11854-11858.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 11854-11858
    • Schulz, W.G.1    Nieman, R.A.2    Skibo, E.B.3
  • 13
    • 37049167943 scopus 로고
    • The Formation of 2-Substituted Benzimidazoles
    • Phillips, M. A. The Formation of 2-Substituted Benzimidazoles. J. Chem. Soc. 1928, 2393-2399.
    • (1928) J. Chem. Soc. , pp. 2393-2399
    • Phillips, M.A.1
  • 14
    • 0029067854 scopus 로고
    • Catalytic Properties of NAD(P)H: Quinone Acceptar Oxidoreductase: Study Involving Mouse, Rat, Human, and Mouse-Rat Chimeric Enzymes
    • Chen, S.; Knox, R.; Lewis, A. D.; Friedlos, F.; Workman, P.; Deng, P. S. K.; Fung, M.; Ebenstein, D.; Wu, K.; Tsai, T.-M. Catalytic Properties of NAD(P)H: Quinone Acceptar Oxidoreductase: Study Involving Mouse, Rat, Human, and Mouse-Rat Chimeric Enzymes. Mol. Pharmacol. 1995, 47, 934-939.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 934-939
    • Chen, S.1    Knox, R.2    Lewis, A.D.3    Friedlos, F.4    Workman, P.5    Deng, P.S.K.6    Fung, M.7    Ebenstein, D.8    Wu, K.9    Tsai, T.-M.10
  • 15
    • 0028243181 scopus 로고
    • Metabolism of Bioreductive Antitumor Compounds by Purified Rat and Human DT-Diaphorases
    • Beall, H. D.; Mulcahy, R. T.; Siegel, D.; Traver, R. D.; Gibson, N. W.; Ross, D. Metabolism of Bioreductive Antitumor Compounds by Purified Rat and Human DT-Diaphorases. Cancer Res. 1994, 54, 3196-3201.
    • (1994) Cancer Res. , vol.54 , pp. 3196-3201
    • Beall, H.D.1    Mulcahy, R.T.2    Siegel, D.3    Traver, R.D.4    Gibson, N.W.5    Ross, D.6
  • 16
    • 0029121481 scopus 로고
    • Nicotinamide Adenine Dinucleotide (Phosphate): Quinone Oxidoreductase (DT-Diaphorase) as a Target for Bioreductive Antitumor Quinones: Quinone Cytotoxicity and Selectivity in Human Lung and Breast Cancer Cell Lines
    • Beall, H. D.; Murphy, A. M.; Siegel, D.; Hargreaves, R. H. J.; Butler, J.; Ross, D. Nicotinamide Adenine Dinucleotide (Phosphate): Quinone Oxidoreductase (DT-Diaphorase) as a Target for Bioreductive Antitumor Quinones: Quinone Cytotoxicity and Selectivity in Human Lung and Breast Cancer Cell Lines. Mol. Pharmacol. 1995, 48, 499-504.
    • (1995) Mol. Pharmacol. , vol.48 , pp. 499-504
    • Beall, H.D.1    Murphy, A.M.2    Siegel, D.3    Hargreaves, R.H.J.4    Butler, J.5    Ross, D.6
  • 17
    • 0029068515 scopus 로고
    • The Three-Dimensional structure of NAD(P)H: Quinone Reductase, a Flavoprotein Involved in Cancer Chemoprotection and Chemotherapy; Mechanism of the Two-Electron Reduction
    • Li, R.; Bianchet, M. A.; Taladay, P.; Amzel, L. M. The Three-Dimensional structure of NAD(P)H: Quinone Reductase, a Flavoprotein Involved in Cancer Chemoprotection and Chemotherapy; Mechanism of the Two-Electron Reduction. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8846-8850.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 8846-8850
    • Li, R.1    Bianchet, M.A.2    Taladay, P.3    Amzel, L.M.4
  • 19
    • 0028861748 scopus 로고
    • Subunit Functional Studies of NAD(P)H: Quinone Oxidoreductase with a Heterodimer Approach
    • Cui, K.; Lu, A. Y. H.; Yang, C. S. Subunit Functional Studies of NAD(P)H: Quinone Oxidoreductase with a Heterodimer Approach. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 1043-1047.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 1043-1047
    • Cui, K.1    Lu, A.Y.H.2    Yang, C.S.3
  • 20
    • 0024316466 scopus 로고
    • Topoisomerase Poisons as Antitumor Drugs
    • Liu, L. F. Topoisomerase Poisons as Antitumor Drugs. Annu. Rev. Biochem. 1989, 58, 351-375.
    • (1989) Annu. Rev. Biochem. , vol.58 , pp. 351-375
    • Liu, L.F.1
  • 21
    • 0025264034 scopus 로고
    • Human DNA Topoisomerase II: Evaluation of Enzyme Activity in Normal and Neoplastic Tissue
    • (a) Holden, J. A.; Rolfson, D. H.; Wittwer, C. T. Human DNA Topoisomerase II: Evaluation of Enzyme Activity in Normal and Neoplastic Tissue. Biochemistry 1990, 29, 2127-2134.
    • (1990) Biochemistry , vol.29 , pp. 2127-2134
    • Holden, J.A.1    Rolfson, D.H.2    Wittwer, C.T.3
  • 23
    • 0025037693 scopus 로고
    • Sequence-Selective Topoisomerase II Inhibition by Anthracycline Derivatives in SV-40 DNA: Relationship with DNA Binding Affinity and Cytotoxicity
    • Capranico, G.; Zunino, F.; Kohn, K. W.; Pommier, Y. Sequence-Selective Topoisomerase II Inhibition by Anthracycline Derivatives in SV-40 DNA: Relationship with DNA Binding Affinity and Cytotoxicity. Biochemistry 1990, 29, 562-569.
    • (1990) Biochemistry , vol.29 , pp. 562-569
    • Capranico, G.1    Zunino, F.2    Kohn, K.W.3    Pommier, Y.4
  • 25
    • 0021153767 scopus 로고
    • Formation and Rejoining of Deoxyribonucleic Acid Double-Stranded Breaks induced in Isolated Nuclei by Antineoplastic Intercalating Agents
    • Pommier, Y.; Schwartz, R. E.; Kohn, K. W.; Zwelling, L. A. Formation and Rejoining of Deoxyribonucleic Acid Double-Stranded Breaks induced in Isolated Nuclei by Antineoplastic Intercalating Agents. Biochemistry 1984, 23, 3194-3201.
    • (1984) Biochemistry , vol.23 , pp. 3194-3201
    • Pommier, Y.1    Schwartz, R.E.2    Kohn, K.W.3    Zwelling, L.A.4
  • 26
    • 0021688805 scopus 로고
    • Role of Topoisomerase II in Mediating Epipodophyllotoxin-Induced DNA Cleavage
    • Ross, W.; Rowe, T.; Glisson, F.; Yalowich, J.; Siu, L. Role of Topoisomerase II in Mediating Epipodophyllotoxin-Induced DNA Cleavage. Cancer Res. 1984, 44, 5857-5860.
    • (1984) Cancer Res. , vol.44 , pp. 5857-5860
    • Ross, W.1    Rowe, T.2    Glisson, F.3    Yalowich, J.4    Siu, L.5
  • 27
    • 0027379549 scopus 로고
    • A Pyrimido-[1,6-α]benzimidazole that Enhances DNA Cleavage Mediated by Eukaryotic Topoisomerase II: A Novel Class of Topoisomerase II-Targeted Drugs with Cytotoxic Potential
    • Corbett, A. H.; Guerry, P.; Pflieger, P.; Osheroff, N. A Pyrimido-[1,6-α]benzimidazole that Enhances DNA Cleavage Mediated by Eukaryotic Topoisomerase II: A Novel Class of Topoisomerase II-Targeted Drugs With Cytotoxic Potential. Antimicrob. Agents Chemother. 1993, 37, 2599-2605.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 2599-2605
    • Corbett, A.H.1    Guerry, P.2    Pflieger, P.3    Osheroff, N.4
  • 28
    • 0027167775 scopus 로고
    • Novel Cytotoxic Topoisomerase II Inhibiting Pyrroloiminoquinones from Fijian Sponges of the Genus Zyzzya
    • Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. Novel Cytotoxic Topoisomerase II Inhibiting Pyrroloiminoquinones from Fijian Sponges of the Genus Zyzzya. J. Am. Chem. Soc. 1993, 115, 1632-1638.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1632-1638
    • Radisky, D.C.1    Radisky, E.S.2    Barrows, L.R.3    Copp, B.R.4    Kramer, R.A.5    Ireland, C.M.6
  • 29
    • 0026458552 scopus 로고
    • Induction of Topoisomerase II-Mediated DNA Cleavage by the Plant Naphthoquinones Plumbagin and Shikonin
    • Fujii, N.; Yamashita, Y.; Arima, Y.; Nagashima, M.; Nakano, H. Induction of Topoisomerase II-Mediated DNA Cleavage by the Plant Naphthoquinones Plumbagin and Shikonin. Antimicrob. Agent Chemother. 1992, 36, 2589-2594.
    • (1992) Antimicrob. Agent Chemother. , vol.36 , pp. 2589-2594
    • Fujii, N.1    Yamashita, Y.2    Arima, Y.3    Nagashima, M.4    Nakano, H.5
  • 30
    • 0028027335 scopus 로고
    • Quinobenoxazines: A Class of Novel Antitumor Quinolones and Potent Mammalian DNA Topoisomerase II Catalytic Inhibitors
    • Permana, P. A.; Snapka, R. M.; Shen, L. L.; Chu, D. T. W.; Clement, J. J.; Plattner, J. J. Quinobenoxazines: A Class of Novel Antitumor Quinolones and Potent Mammalian DNA Topoisomerase II Catalytic Inhibitors. Biochemistry 1994, 33, 11333-11339.
    • (1994) Biochemistry , vol.33 , pp. 11333-11339
    • Permana, P.A.1    Snapka, R.M.2    Shen, L.L.3    Chu, D.T.W.4    Clement, J.J.5    Plattner, J.J.6
  • 32
    • 0022587259 scopus 로고
    • Nonintercalating DNA-Binding Ligands: Specificity of the Intercalation and Their Use as Tools in Biophysical, Biochemical and Biological Investigations of the Genetic Material
    • Zimmer, C.; Wahnert, U. Nonintercalating DNA-Binding Ligands: Specificity of the Intercalation and Their Use as Tools in Biophysical, Biochemical and Biological Investigations of the Genetic Material. Prog. Biophys. Mol. Biol. 1986, 47, 31-112.
    • (1986) Prog. Biophys. Mol. Biol. , vol.47 , pp. 31-112
    • Zimmer, C.1    Wahnert, U.2
  • 33
    • 0019405822 scopus 로고
    • Biospecific Absorption of Hepatic DT-Diaphorase on Immobilized Dicoumarol
    • (a) Höjeberg, B.; Blomberg, K.; Stenberg, L.; Lind, C. Biospecific Absorption of Hepatic DT-Diaphorase on Immobilized Dicoumarol. Arch. Biochem. Biophys. 1981, 207, 205-216.
    • (1981) Arch. Biochem. Biophys. , vol.207 , pp. 205-216
    • Höjeberg, B.1    Blomberg, K.2    Stenberg, L.3    Lind, C.4
  • 34
    • 0024386604 scopus 로고
    • Purification by Cibacron Blue F3GA Dye Affinity Chromatography and Comparison of NAD(P)H: Quinone Reductase (E.C.1.6.99.2) from Rat Liver Cytosol and Microsomes
    • (b) Sharkis, D. H.; Swenson, R. P. Purification by Cibacron Blue F3GA Dye Affinity Chromatography and Comparison of NAD(P)H: Quinone Reductase (E.C.1.6.99.2) from Rat Liver Cytosol and Microsomes. Biochem, Biophys. Res. Commun. 1989, 161, 434-441.
    • (1989) Biochem, Biophys. Res. Commun. , vol.161 , pp. 434-441
    • Sharkis, D.H.1    Swenson, R.P.2
  • 35
    • 0017184389 scopus 로고
    • A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding
    • Bradford, M. M. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 1976, 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.