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Volumn 1, Issue 5, 1988, Pages 258-268

Pyrrolo[1,4]benzodiazepine Antitumor Antibiotics: Relationship of DNA Alkylation and Sequence Specificity to the Biological Activity of Natural and Synthetic Compounds

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAMYCIN; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; PYRROLO[1,4]BENZODIAZEPINE DERIVATIVE; TOMAYMYCIN; UNCLASSIFIED DRUG;

EID: 0023755904     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00005a002     Document Type: Article
Times cited : (164)

References (47)
  • 2
    • 0017642450 scopus 로고
    • Pyrrolo[1,4]benzodiazepine antitumor antibiotics
    • Comparative aspects of anthramycin, tomaymycin and sibiromycin
    • Hurley, L. H. (1977) “Pyrrolo[1,4]benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin”. J. Antibiot. 30, 349–370
    • (1977) J. Antibiot. , vol.30 , pp. 349-370
    • Hurley, L.H.1
  • 3
    • 0013852032 scopus 로고
    • Isolation and characterization of anthramycin, a new antitumor antibiotic
    • Leimgruber, W., Stefanovic, V., Schenker, F., Karr, A., and Berger, J. (1965) “Isolation and characterization of anthramycin, a new antitumor antibiotic”. J. Am. Chem. Soc. 87, 5791–5793.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 5791-5793
    • Leimgruber, W.1    Stefanovic, V.2    Schenker, F.3    Karr, A.4    Berger, J.5
  • 4
    • 84943116073 scopus 로고
    • The structures of tomaymycin and oxotomaymycin
    • Kariyone, K., Yazawa, H., and Kohsaka, M. (1971) “The structures of tomaymycin and oxotomaymycin”. Chem. Pharm. Bull. 19, 2289–2293.
    • (1971) Chem. Pharm. Bull. , vol.19 , pp. 2289-2293
    • Kariyone, K.1    Yazawa, H.2    Kohsaka, M.3
  • 6
    • 0021272759 scopus 로고
    • Pyrrolo[1,4]benzodiazepine antitumor antibiotics: chemistry, interaction with DNA and biological implications
    • Hurley, L. H., and Thurston, D. E. (1984) “Pyrrolo[1,4]benzodiazepine antitumor antibiotics: chemistry, interaction with DNA and biological implications”. Pharm. Res. 1, 51–59.
    • (1984) Pharm. Res. , vol.1 , pp. 51-59
    • Hurley, L.H.1    Thurston, D.E.2
  • 7
    • 0016297364 scopus 로고
    • The reaction of anthramycin with DNA II Studies of kinetics and mechanism
    • Kohn, K. W., Glaubiger, D., and Spears, C. L. (1974) “The reaction of anthramycin with DNA II Studies of kinetics and mechanism”. Biochim. Biophys. Acta 361, 288–302.
    • (1974) Biochim. Biophys. Acta , vol.361 , pp. 288-302
    • Kohn, K.W.1    Glaubiger, D.2    Spears, C.L.3
  • 8
    • 0019394787 scopus 로고
    • Pyrrolo-[1,4]benzodiazepine antibiotics
    • Proposed structures and characteristics of the in vitro deoxyribonucleic acid adducts of anthramycin, tomaymycin, sibiromycin and neothramycins A and B
    • Petrusek, R. L., Anderson, G. L., Garner, T. F., Fannin, Q. L., Kaplan, D. J., Zimmer, S. G., and Hurley, L. H. (1981) “Pyrrolo-[1,4]benzodiazepine antibiotics. Proposed structures and characteristics of the in vitro deoxyribonucleic acid adducts of anthramycin, tomaymycin, sibiromycin and neothramycins A and B”. Biochemistry 20, 1111–1119.
    • (1981) Biochemistry , vol.20 , pp. 1111-1119
    • Petrusek, R.L.1    Anderson, G.L.2    Garner, T.F.3    Fannin, Q.L.4    Kaplan, D.J.5    Zimmer, S.G.6    Hurley, L.H.7
  • 9
    • 33845376321 scopus 로고
    • Covalent binding of antitumor antibiotics in the minor groove of DNA
    • Hurley, L. H., and Needham-VanDevanter, D. R. (1986) “Covalent binding of antitumor antibiotics in the minor groove of DNA”. Acc. Chem. Res. 19, 230–237.
    • (1986) Acc. Chem. Res. , vol.19 , pp. 230-237
    • Hurley, L.H.1    Needham-VanDevanter, D.R.2
  • 10
    • 0013798217 scopus 로고
    • Clinical investigation of cancer chemotherapeutic agents for neopl; stic disease
    • Korman, S., and Tendler, M. D. (1965) “Clinical investigation of cancer chemotherapeutic agents for neopl; stic disease”. J. New Drugs 5, 275–285.
    • (1965) J. New Drugs , vol.5 , pp. 275-285
    • Korman, S.1    Tendler, M.D.2
  • 11
    • 84998363591 scopus 로고
    • Noncytotoxic antitumor proteins proliferated by Actinomycete
    • Korman, S., and Tendler, M. D. (1963) “Noncytotoxic antitumor proteins proliferated by Actinomycete”. Abstr. Proc. Am. Assoc. Cancer Res. 4, 135.
    • (1963) Abstr. Proc. Am. Assoc. Cancer Res. , vol.4 , pp. 135
    • Korman, S.1    Tendler, M.D.2
  • 12
    • 0344621684 scopus 로고
    • Interaction of antitumor antibiotics with DNA: studies on sibiromycin
    • Gause, G. F., and Dudnik, Y. V. (1971) “Interaction of antitumor antibiotics with DNA: studies on sibiromycin”. Prog. Mol. Subcell. Biol. 2, 33–39.
    • (1971) Prog. Mol. Subcell. Biol. , vol.2 , pp. 33-39
    • Gause, G.F.1    Dudnik, Y.V.2
  • 14
    • 0016233526 scopus 로고
    • Effects of daunomycin and anthramycin on electrocardiogram and mitochondrial metabolism of the rate heart
    • Cargill, C., Bachmann, E., and Zbinden, G. (1974) “Effects of daunomycin and anthramycin on electrocardiogram and mitochondrial metabolism of the rate heart”. J. Natl. Cancer Inst. (U.S.) 53, 481–486.
    • (1974) J. Natl. Cancer Inst. (U.S.) , vol.53 , pp. 481-486
    • Cargill, C.1    Bachmann, E.2    Zbinden, G.3
  • 15
    • 0344621682 scopus 로고
    • Comparative studies on antitumor activity and toxicity of sibiromycin and its sulfur-containing derivatives
    • Bazhanov, V. S., and Shepelevteva, N. G. (1973) “Comparative studies on antitumor activity and toxicity of sibiromycin and its sulfur-containing derivatives”. Antibiotiki (Moscow) 18, 714–717.
    • (1973) Antibiotiki (Moscow) , vol.18 , pp. 714-717
    • Bazhanov, V.S.1    Shepelevteva, N.G.2
  • 16
    • 0021255897 scopus 로고
    • The reaction of anthramycin with DNA: Proton and carbon nuclear magnetic resonance studies on the structure of the anthramycin-DNA adduct
    • Graves, D. E., Pattaroni, C., Balakrishnan, C., Ostrander, J. M., Hurley, L. H., and Krugh, T. R. (1984) “The reaction of anthramycin with DNA: Proton and carbon nuclear magnetic resonance studies on the structure of the anthramycin-DNA adduct”. J. Biol. Chem. 259, 8202–8209.
    • (1984) J. Biol. Chem. , vol.259 , pp. 8202-8209
    • Graves, D.E.1    Pattaroni, C.2    Balakrishnan, C.3    Ostrander, J.4    Hurley, M.5    Krugh, T.R.6
  • 17
    • 0022310074 scopus 로고
    • 2 adduct from one- and two-dimensional proton NMR experiments in solution
    • 2 adduct from one- and two-dimensional proton NMR experiments in solution”. Biochemistry 24, 7573–7581.
    • (1985) Biochemistry , vol.24 , pp. 7573-7581
    • Graves, D.E.1    Stone, M.P.2    Krugh, T.R.3
  • 18
    • 0023007826 scopus 로고
    • Conformation of complexes between pyrrolo[1,4]benzodiazepines and DNA
    • Remers, W. A., Mabilia, J., and Hopfinger, A. J. (1986) “Conformation of complexes between pyrrolo[1,4]benzodiazepines and DNA”. J. Med. Chem. 29, 2492–2503.
    • (1986) J. Med. Chem. , vol.29 , pp. 2492-2503
    • Remers, W.A.1    Mabilia, J.2    Hopfinger, A.J.3
  • 19
    • 0022995772 scopus 로고
    • Molecular mechanics simulation on covalent complexes between anthramycin and B DNA
    • Rao, S. N., Singh, U. C., and Kollman, P A. (1986) “Molecular mechanics simulation on covalent complexes between anthramycin and B DNA”. J. Med. Chem. 29, 2484–2492.
    • (1986) J. Med. Chem. , vol.29 , pp. 2484-2492
    • Rao, S.N.1    Singh, U.C.2    Kollman, A.3
  • 20
    • 0022446720 scopus 로고
    • A Theoretical investigation of the sequence specificity in the binding of the antitumor drug anthramycin to DNA
    • Zakrzewska, K., and Pullman, B. (1986) “A Theoretical investigation of the sequence specificity in the binding of the antitumor drug anthramycin to DNA”. J. Biomol. Struct. Dyn. 4, 127-136.
    • (1986) J. Biomol. Struct. Dyn. , vol.4 , pp. 127-136
    • Zakrzewska, K.1    Pullman, B.2
  • 21
    • 0020327397 scopus 로고
    • Reaction of anthramycin with DNA
    • Biological consequences of DNA damage in normal and xeroderma pigmentosum cell lines
    • Petrusek, R. L., Uhlenhopp, E. L., Duteau, N., and Hurley, L. H. (1982) “Reaction of anthramycin with DNA. Biological consequences of DNA damage in normal and xeroderma pigmentosum cell lines”. J. Biol. Chem. 257, 6207–6216.
    • (1982) J. Biol. Chem. , vol.257 , pp. 6207-6216
    • Petrusek, R.L.1    Uhlenhopp, E.L.2    Duteau, N.3    Hurley, L.H.4
  • 22
    • 0018122398 scopus 로고
    • Mutagenic and recombinogenic effects of the antitumor antibiotic anthramycin
    • Hannan, M. A., Hurley, L. H., and Gairola, C. (1978) “Mutagenic and recombinogenic effects of the antitumor antibiotic anthramycin”. Cancer Res. 38, 2795–2799.
    • (1978) Cancer Res. , vol.38 , pp. 2795-2799
    • Hannan, M.A.1    Hurley, L.H.2    Gairola, C.3
  • 23
    • 0022519599 scopus 로고
    • Sequence specificity and-biological consequences of drugs that bind covalently in the minor groove of DNA
    • Simic, M. G., Grossman, L., and Upton, A. D., Eds.) Plenum, New York
    • Hurley, L. H., and Needham-VanDevanter, D. R. (1986) “Sequence specificity and-biological consequences of drugs that bind covalently in the minor groove of DNA”. In Mechanisms of DNA Damage and Repair. Implications for Carcinogenesis: a Risk Assessment (Simic, M. G., Grossman, L., and Upton, A. D., Eds.) pp 203–211, Plenum, New York.
    • (1986) In Mechanisms of DNA Damage and Repair. Implications for Carcinogenesis: a Risk Assessment , pp. 203-211
    • Hurley, L.H.1    Needham-VanDevanter, D.R.2
  • 24
    • 0022458567 scopus 로고
    • Pyrrolo[1,4] benzodiazepine antitumor antibiotics
    • Evidence for two forms of tomaymycin bound to DNA
    • Barkley, M., Cheatham, S., Thurston, D. E., and Hurley, L. H. (1986) “Pyrrolo[1,4] benzodiazepine antitumor antibiotics. Evidence for two forms of tomaymycin bound to DNA”. Biochemistry 25,3021-3031.
    • (1986) Biochemistry , vol.25 , pp. 3021-3031
    • Barkley, M.1    Cheatham, S.2    Thurston, D.3    Hurley, L.H.4
  • 25
    • 0022552540 scopus 로고
    • DNA sequence specificity of the pyrrolo[1,4]benzodiazepine antitumor antibiotics
    • MPE. Fe(II) footprinting analysis of DNA binding sites for anthramycin and related drugs
    • Hertzberg, R. P., Hecht, S. M., Reynolds, V. L., Molineux, I. J., and Hurley, L. H. (1986) “DNA sequence specificity of the pyrrolo[1,4]benzodiazepine antitumor antibiotics. MPE.Fe(II) footprinting analysis of DNA binding sites for anthramycin and related drugs”. Biochemistry 25, 1249–1258.
    • (1986) Biochemistry , vol.25 , pp. 1249-1258
    • Hertzberg, R.P.1    Hecht, S.M.2    Reynolds, V.L.3    Molineux, I.J.4    Hurley, L.H.5
  • 26
    • 0021061712 scopus 로고
    • A rational basis for development of antitumor agents in the pyrrolo[1,4]benzodiazepine group
    • Thurston, D. E., and Hurley, L. H. (1983) “A rational basis for development of antitumor agents in the pyrrolo[1,4]benzodiazepine group”. Drugs Future, Correl. Pharmacostruct. 8, 959–971.
    • (1983) Drugs Future, Correl. Pharmacostruct. , vol.8 , pp. 959-971
    • Thurston, D.E.1    Hurley, L.H.2
  • 28
    • 0018745848 scopus 로고
    • Molecular mechanisms of binding of pyrrolo[1,4] benzodiazepine antitumor agents to deoxyribonucleic acid-anthramycin and tomaymycin
    • Lown, J. W., and Josua, A. V. (1979) “Molecular mechanisms of binding of pyrrolo[1,4] benzodiazepine antitumor agents to deoxyribonucleic acid-anthramycin and tomaymycin”. Biochem. Pharmacol. 28, 2017–2026.
    • (1979) Biochem. Pharmacol. , vol.28 , pp. 2017-2026
    • Lown, J.W.1    Josua, A.V.2
  • 29
    • 0021078067 scopus 로고
    • A new and mild method for the reduction of secondary amides to carbinolamine ethers and imines: a conversion of oxotomaymycin to tomamycin
    • Kaneko, T., Wong, H., and Doyle, T. W. (1983) “A new and mild method for the reduction of secondary amides to carbinolamine ethers and imines: a conversion of oxotomaymycin to tomamycin”. Tetrahedron Lett. 24, 5165–5168.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5165-5168
    • Kaneko, T.1    Wong, H.2    Doyle, T.W.3
  • 30
    • 0021345758 scopus 로고
    • A total synthesis of chicamycin A
    • A new pyrrolo[1,4]benzodiazepine
    • Kaneko, T., Wong, H., and Doyle, T. W. (1984) “A total synthesis of chicamycin A. A new pyrrolo[1,4]benzodiazepine”. J. Antibiot. 37, 300–302.
    • (1984) J. Antibiot. , vol.37 , pp. 300-302
    • Kaneko, T.1    Wong, H.2    Doyle, T.W.3
  • 31
    • 0021986987 scopus 로고
    • Bicyclic and tricyclic analogues of anthramycin
    • Kaneko, T., Wong, H., Doyle, T. W., Rose, W. C., and Bradner, W. T. (1985) “Bicyclic and tricyclic analogues of anthramycin”. J. Med. Chem. 28, 388–392.
    • (1985) J. Med. Chem. , vol.28 , pp. 388-392
    • Kaneko, T.1    Wong, H.2    Doyle, T.3    Rose, W.4    Bradner, W.T.5
  • 32
    • 0021270163 scopus 로고
    • Limitations and factors affecting the lactam reduction approach to the synthesis of anthramycin analogs
    • Thurston, D. E., Kaumaya, P. T. P., and Hurley, L. H. (1984) “Limitations and factors affecting the lactam reduction approach to the synthesis of anthramycin analogs”. Tetrahedron Lett. 25, 2649–2652.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2649-2652
    • Thurston, D.E.1    Kaumaya, P.T.P.2    Hurley, L.H.3
  • 33
    • 0022398336 scopus 로고
    • Synthesis and structure of anthramycin analogs via hydride reduction of dilactams
    • Suggs, J. W., Wang, Y., and Lee, K. S. (1985) “Synthesis and structure of anthramycin analogs via hydride reduction of dilactams”. Tetrahedron Lett. 26, 4871–4874.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4871-4874
    • Suggs, J.W.1    Wang, Y.2    Lee, K.S.3
  • 34
    • 0022610872 scopus 로고
    • Synthesis and stereochemistry of carbinolamine-containing pyrrolo [1,4] benzodiazepines by reductive cyclization of N-(2-nitrobenzoyl)-pyrrolidine-2-carboxaldehydes
    • Thurston, D. E., and Langley, D. R. (1986) “Synthesis and stereochemistry of carbinolamine-containing pyrrolo [1,4] benzodiazepines by reductive cyclization of N-(2-nitrobenzoyl)-pyrrolidine-2-carboxaldehydes”. J. Org. Chem. 51, 705–712.
    • (1986) J. Org. Chem. , vol.51 , pp. 705-712
    • Thurston, D.E.1    Langley, D.R.2
  • 35
    • 0023153646 scopus 로고
    • A versatile and efficient synthesis of carbinolamine-containing pyrrolo[1,4]-benzodiazepines via the cyclization of N-(2-aminobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetals: total synthesis of prothracarcin
    • Langley, D. R., and Thurston, D. E. (1987) “A versatile and efficient synthesis of carbinolamine-containing pyrrolo[1,4]-benzodiazepines via the cyclization of N-(2-aminobenzoyl)-pyrrolidine-2-carboxaldehyde diethyl thioacetals: total synthesis of prothracarcin”. J. Org. Chem. 52, 91–97.
    • (1987) J. Org. Chem. , vol.52 , pp. 91-97
    • Langley, D.R.1    Thurston, D.E.2
  • 36
    • 0020645043 scopus 로고
    • New M13 vectors for cloning
    • Messing, J. (1983) “New M13 vectors for cloning”. Methods Enzymol. 101, 20–78.
    • (1983) Methods Enzymol. , vol.101 , pp. 20-78
    • Messing, J.1
  • 37
    • 0018411879 scopus 로고
    • Synthesis of anhydrosibiromycinone: a new method for the direct synthesis of pyrrolo[1,4]benzodiazepin-5-ones
    • Parker, K. A., and Fedynyshyn, T. H. (1979) “Synthesis of anhydrosibiromycinone: a new method for the direct synthesis of pyrrolo[1,4]benzodiazepin-5-ones”. Tetrahedron. Lett. 19, 1657–1660.
    • (1979) Tetrahedron. Lett. , vol.19 , pp. 1657-1660
    • Parker, K.A.1    Fedynyshyn, T.H.2
  • 38
    • 0014233521 scopus 로고
    • Antihypertensive 2-amino-4(3H)-quinazolinones
    • Hess, H.-J., Cronin, T. H., and Scriabine, A. (1968) “Antihypertensive 2-amino-4(3H)-quinazolinones”. J. Med. Chem. 11, 130–136.
    • (1968) J. Med. Chem. , vol.11 , pp. 130-136
    • Hess, H.-J.1    Cronin, T.H.2    Scriabine, A.3
  • 39
    • 0001126454 scopus 로고
    • Mild and efficient methods for the reductive cleavage of nitrogen-oxygen bonds
    • Keck, G. E., Fleming, S., Nickell, D., and Weider, P. (1979) “Mild and efficient methods for the reductive cleavage of nitrogen-oxygen bonds”, Synth. Commun. 9, 281–286.
    • (1979) Synth. Commun. , vol.9 , pp. 281-286
    • Keck, G.E.1    Fleming, S.2    Nickell, D.3    Weider, P.4
  • 40
    • 0021833070 scopus 로고
    • Application of a tissue culture microliter test for the detection of cytoxic agents from natural products
    • Mirabelli, C. K., Bartus, H., Bartus, J. O., Johnson, R., Mong, S.-M., Sung, C.-P., and Crooke, S. T. (1985) “Application of a tissue culture microliter test for the detection of cytoxic agents from natural products”. J. Antibiot. 38, 758–766.
    • (1985) J. Antibiot. , vol.38 , pp. 758-766
    • Mirabelli, C.K.1    Bartus, H.2    Bartus, J.3    Johnson, O.4    Mong, R.5    Sung, C.-P.6    Crooke, S.T.7
  • 41
    • 0018846636 scopus 로고
    • Sequencing end-labeled DNA with base-specific chemical cleavages
    • Maxam, A. M., and Gilbert, W. (1980) “Sequencing end-labeled DNA with base-specific chemical cleavages”. Methods Enzymol. 65, 499–560.
    • (1980) Methods Enzymol. , vol.65 , pp. 499-560
    • Maxam, A.M.1    Gilbert, W.2
  • 42
    • 0019810625 scopus 로고
    • Use of exonuclease III to determine the site of stable lesions in defined sequences of DNA, the cyclobutane dimer and cis- and trans-dichlorodiammineplatinum(II) examples
    • Royer-Pokora, B., Gordon, L. K., and Haseltine, W. A. (1981) “Use of exonuclease III to determine the site of stable lesions in defined sequences of DNA, the cyclobutane dimer and cis- and trans-dichlorodiammineplatinum(II) examples”. Nucleic Acids Res. 9, 4595–4609.
    • (1981) Nucleic Acids Res. , vol.9 , pp. 4595-4609
    • Royer-Pokora, B.1    Gordon, L.K.2    Haseltine, W.A.3
  • 43
    • 0018620965 scopus 로고
    • DNA glycosylases, endonucleases for apurinic/apyrimidinic sites, and base excision-repair
    • Lindahl, T. (1979) “DNA glycosylases, endonucleases for apurinic/apyrimidinic sites, and base excision-repair”. Prog. Nucleic Acid Res. Mol. Biol. 22, 135–192.
    • (1979) Prog. Nucleic Acid Res. Mol. Biol. , vol.22 , pp. 135-192
    • Lindahl, T.1
  • 44
    • 0018223352 scopus 로고
    • Structure of the DNA complexing agent anthramycin
    • Mostad, A., Romming, C., and Storm, B. (1978) “Structure of the DNA complexing agent anthramycin”. Acta Chem. Scand., Ser. B 32, 639–645.
    • (1978) Acta Chem. Scand., Ser. B , vol.32 , pp. 639-645
    • Mostad, A.1    Romming, C.2    Storm, B.3
  • 45
    • 0006343312 scopus 로고    scopus 로고
    • Structural investigations of mode of action of drugs II Molecular structure of anthramycin methyl ether monohydrate
    • Arora, S. K. “Structural investigations of mode of action of drugs II Molecular structure of anthramycin methyl ether monohydrate”. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. B35, 2945–2948.
    • Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. , vol.B35 , pp. 2945-2948
    • Arora, S.K.1
  • 46
    • 0019523349 scopus 로고
    • Chemical conversion of anthramycin 11-methyl ether to didehydroanhydroanthramycin and its utilization in studies of the biosynthesis and mechanism of action of anthramycin
    • Malhotra, R. K., Ostrander, J. M., Hurley, L. H., Mclnnes, A. G., Smith, D. G., Walter, J. A., and Wright, J. L. C. (1981) “Chemical conversion of anthramycin 11-methyl ether to didehydroanhydroanthramycin and its utilization in studies of the biosynthesis and mechanism of action of anthramycin”. J. Nat. Prod. 44, 38–44.
    • (1981) J. Nat. Prod. , vol.44 , pp. 38-44
    • Malhotra, R.K.1    Ostrander, J.M.2    Hurley, L.H.3    Mclnnes, A.G.4    Smith, D.G.5    Walter, J.A.6    Wright, J.L.C.7


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