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Volumn 40, Issue 8, 1997, Pages 1276-1286

Redox pathway leading to the alkylation of DNA by the anthracycline, antitumor drugs adriamycin and daunomycin

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE ANTIBIOTIC AGENT; DAUNORUBICIN; DITHIOTHREITOL; DNA; DOXORUBICIN; FORMALDEHYDE; HYDROGEN PEROXIDE; SPERMINE;

EID: 0030991136     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960835d     Document Type: Article
Times cited : (129)

References (41)
  • 1
    • 0019501881 scopus 로고
    • Medical Progress: The anthracycline antineoplastic drugs
    • Young, R. C.; Ozols, R. F.; Myers, C. E. Medical Progress: The anthracycline antineoplastic drugs. New Engl. J. Med. 1981, 305, 139-153.
    • (1981) New Engl. J. Med. , vol.305 , pp. 139-153
    • Young, R.C.1    Ozols, R.F.2    Myers, C.E.3
  • 3
    • 0024316466 scopus 로고
    • DNA topoisomerase poisons as antitumor drugs
    • Liu, L. F. DNA 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
  • 4
    • 0002786613 scopus 로고
    • DNA topoisomerases and their inhibition by anthracyclines
    • Priebe, W., Ed.; ACS Symposium Series 574; American Chemical Society: Washington, DC
    • Pommier, Y. DNA topoisomerases and their inhibition by anthracyclines. In Anthracycline Antibiotics: New Analogues, Methods of Delivery, and Mechanisms of Action; Priebe, W., Ed.; ACS Symposium Series 574; American Chemical Society: Washington, DC, 1995; pp 183-203.
    • (1995) Anthracycline Antibiotics: New Analogues, Methods of Delivery, and Mechanisms of Action , pp. 183-203
    • Pommier, Y.1
  • 5
    • 0020036939 scopus 로고
    • Further studies on the generation of reactive oxygen species from activated anthracyclines and the relationship to cytotoxic action and cardiotoxic effects
    • Lown, W. J.; Chen, J. A.; Plambeck, J. A.; Acton, E. M. Further studies on the generation of reactive oxygen species from activated anthracyclines and the relationship to cytotoxic action and cardiotoxic effects. Biochem. Pharmacol. 1982, 31, 575-581.
    • (1982) Biochem. Pharmacol. , vol.31 , pp. 575-581
    • Lown, W.J.1    Chen, J.A.2    Plambeck, J.A.3    Acton, E.M.4
  • 6
    • 0000301953 scopus 로고
    • Role of reactive-oxygen metabolism in cardiac toxicity of anthracycline antibiotics
    • Priebe, W., Ed.; ACS Symposium Series 574, American Chemical Society: Washington, DC
    • Doroshow, J. H. Role of reactive-oxygen metabolism in cardiac toxicity of anthracycline antibiotics. In Anthracycline Antibiotics: New Analogues, Methods of Delivery, and Mechanisms of Action; Priebe, W., Ed.; ACS Symposium Series 574, American Chemical Society: Washington, DC, 1995; pp 259-267.
    • (1995) Anthracycline Antibiotics: New Analogues, Methods of Delivery, and Mechanisms of Action , pp. 259-267
    • Doroshow, J.H.1
  • 7
    • 0025966717 scopus 로고
    • Redox chemistry of anthracycline antitumor drugs and use of captodative radicals as tools for its elucidation and control
    • Gaudiano, G.; Koch, T. H. Redox chemistry of anthracycline antitumor drugs and use of captodative radicals as tools for its elucidation and control. Chem. Res. Toxicol. 1991, 4, 2-16.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 2-16
    • Gaudiano, G.1    Koch, T.H.2
  • 8
    • 0024376508 scopus 로고
    • Coupling of the anthracycline antitumor drug menogaril to 2′-deoxyguanosine through reductive activation
    • Egholm, M.; Koch, T. H. Coupling of the anthracycline antitumor drug menogaril to 2′-deoxyguanosine through reductive activation. J. Am. Chem. Soc. 1989, 111, 8291-8293.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8291-8293
    • Egholm, M.1    Koch, T.H.2
  • 9
    • 0028212923 scopus 로고
    • Does adriamycin induce interstrand cross-links in DNA?
    • Cullinane, C.; van Rosmalen, A.; Phillips, D. R. Does adriamycin induce interstrand cross-links in DNA? Biochemistry 1994, 33, 4632-4638.
    • (1994) Biochemistry , vol.33 , pp. 4632-4638
    • Cullinane, C.1    Van Rosmalen, A.2    Phillips, D.R.3
  • 10
    • 0029863539 scopus 로고    scopus 로고
    • Adriamycin-induced DNA adducts inhibit the DNA interactions of transcription factors and RNA polymerase
    • Cutts, S. M.; Parsons, P. G.; Sturm, R. A.; Phillips, D. R. Adriamycin-induced DNA adducts inhibit the DNA interactions of transcription factors and RNA polymerase. J. Biol. Chem. 1996, 271, 5422-5429.
    • (1996) J. Biol. Chem. , vol.271 , pp. 5422-5429
    • Cutts, S.M.1    Parsons, P.G.2    Sturm, R.A.3    Phillips, D.R.4
  • 11
    • 0029030672 scopus 로고
    • Use of oligonuclcotides to define the site of interstrand cross-links induced by Adriamycin
    • Cutts, S. M.; Phillips, D. R. Use of oligonuclcotides to define the site of interstrand cross-links induced by Adriamycin. Nucleic Acids Res. 1995, 23, 2450-2456.
    • (1995) Nucleic Acids Res. , vol.23 , pp. 2450-2456
    • Cutts, S.M.1    Phillips, D.R.2
  • 13
    • 0029840013 scopus 로고    scopus 로고
    • Alkylation of DNA by the Anthracycline, Antitumor Drugs Adriamycin and Daunomycin
    • Taatjes, D. J.; Gaudiano, G.; Resing, K.; Koch, T. H. Alkylation of DNA by the Anthracycline, Antitumor Drugs Adriamycin and Daunomycin. J. Med. Chem. 1996, 39, 4135-4138.
    • (1996) J. Med. Chem. , vol.39 , pp. 4135-4138
    • Taatjes, D.J.1    Gaudiano, G.2    Resing, K.3    Koch, T.H.4
  • 14
    • 0017261550 scopus 로고
    • Adriamycin Analogs. Periodate Oxidation of Adriamycin
    • Tong, G.; Lee, W. W.; Black, D. R.; Henry, D. W. Adriamycin Analogs. Periodate Oxidation of Adriamycin. J. Med. Chem. 1976, 19, 395-398.
    • (1976) J. Med. Chem. , vol.19 , pp. 395-398
    • Tong, G.1    Lee, W.W.2    Black, D.R.3    Henry, D.W.4
  • 16
    • 77049138167 scopus 로고
    • The colorimetric estimation of formaldehyde by means of the Hantzsch reaction
    • Nash, T. The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J. 1953, 55, 416-421.
    • (1953) Biochem. J. , vol.55 , pp. 416-421
    • Nash, T.1
  • 17
    • 0025869558 scopus 로고
    • Formaldehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray driffraction studies
    • Wang, A. H. J.; Gao, Y. G.; Liaw, Y. C.; Li, Y. k. Formaldehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray driffraction studies. Biochemistry 1991, 30, 3812-3815.
    • (1991) Biochemistry , vol.30 , pp. 3812-3815
    • Wang, A.H.J.1    Gao, Y.G.2    Liaw, Y.C.3    Li, Y.K.4
  • 18
    • 0025845286 scopus 로고
    • Facile formation of a crosslinked adduct between DNA and the daunorubicin derivative MAR70 mediated by formaldehyde: Molecular structure of the MAR70-d(CGT-nACG) covalent adduct
    • Gao, Y. G.; Liaw, Y. C.; Li, Y. k.; van der Marel, G.; van Boom, J. H.; Wang, A. H. J. Facile formation of a crosslinked adduct between DNA and the daunorubicin derivative MAR70 mediated by formaldehyde: molecular structure of the MAR70-d(CGT-nACG) covalent adduct. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 4845-4849.
    • (1991) Proc. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 4845-4849
    • Gao, Y.G.1    Liaw, Y.C.2    Li, Y.K.3    Van Der Marel, G.4    Van Boom, J.H.5    Wang, A.H.J.6
  • 19
    • 0027299132 scopus 로고
    • Simultaneous incorporations of two anticancer drugs into DNA. The structures of formaldehyde-cross-linked adducts of daunorubicin-d(CG(araC)GCG) and doxorubicin-d(CA(araC)GTG) complexes at high resolution
    • Zhang, H.; Gao, Y. G.; van der Marel, G. A.; van Boom, J. H.; Wang, A. H. Simultaneous incorporations of two anticancer drugs into DNA. The structures of formaldehyde-cross-linked adducts of daunorubicin-d(CG(araC)GCG) and doxorubicin-d(CA(araC)GTG) complexes at high resolution. J. Biol. Chem. 1993, 268, 10095-10101.
    • (1993) J. Biol. Chem. , vol.268 , pp. 10095-10101
    • Zhang, H.1    Gao, Y.G.2    Van Der Marel, G.A.3    Van Boom, J.H.4    Wang, A.H.5
  • 20
    • 0027726002 scopus 로고
    • Interaction of hydroxyl radicals with tris(hydroxymethyl)aminomethane and Good's buffers containing hydroxylmethyl or hydroxylethyl residues produce formaldehyde
    • Shiraishi, H.; Kataoka, M.; Morta, Y.; Umemoto, J. Interaction of hydroxyl radicals with tris(hydroxymethyl)aminomethane and Good's buffers containing hydroxylmethyl or hydroxylethyl residues produce formaldehyde. Free Rad. Res. Commun. 1993, 19, 315.
    • (1993) Free Rad. Res. Commun. , vol.19 , pp. 315
    • Shiraishi, H.1    Kataoka, M.2    Morta, Y.3    Umemoto, J.4
  • 23
    • 0028341010 scopus 로고
    • Relevance of interstrand DNA crosslinking induced by anthracyclines for their biological activity
    • Skladanowski, A.; Konopa, J. Relevance of interstrand DNA crosslinking induced by anthracyclines for their biological activity. Biochem. Pharmacol. 1994, 47, 2279-2287.
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 2279-2287
    • Skladanowski, A.1    Konopa, J.2
  • 24
    • 0028236904 scopus 로고
    • Interstrand DNA crosslinking induced by anthracyclines in tumour cells
    • Skladanowski, A.; Konopa, J. Interstrand DNA crosslinking induced by anthracyclines in tumour cells. Biochem. Pharmacol. 1994, 47, 2269-2278.
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 2269-2278
    • Skladanowski, A.1    Konopa, J.2
  • 25
    • 0019992950 scopus 로고
    • Oxidative destruction of erythrocyte ghost membranes catalyzed by the doxorubicin-iron complex
    • Myers, C. E.; Gianni, L.; Simone, C. B.; Klecker, R.; Greene, R. Oxidative destruction of erythrocyte ghost membranes catalyzed by the doxorubicin-iron complex. Biochemistry 1982, 21, 1707-1712.
    • (1982) Biochemistry , vol.21 , pp. 1707-1712
    • Myers, C.E.1    Gianni, L.2    Simone, C.B.3    Klecker, R.4    Greene, R.5
  • 27
    • 0029922702 scopus 로고    scopus 로고
    • Base specific and regiospecific chemical cross-linking of Daunorubicin to DNA
    • Leng, F.; Savkur, R.; Fokt, I.; Przewloka, T.; Priebe, W.; Chaires, J. B. Base specific and regiospecific chemical cross-linking of Daunorubicin to DNA. J. Am. Chem. Soc. 1996, 118, 4731-4738.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4731-4738
    • Leng, F.1    Savkur, R.2    Fokt, I.3    Przewloka, T.4    Priebe, W.5    Chaires, J.B.6
  • 28
    • 0017367565 scopus 로고
    • Production of formaldehyde from N5-methyltetrahydrofolate by normal and leukemic leukocytes
    • Thorndike, J.; Beck, W. S. Production of formaldehyde from N5-methyltetrahydrofolate by normal and leukemic leukocytes. Cancer Res. 1977, 37, 1125-1132.
    • (1977) Cancer Res. , vol.37 , pp. 1125-1132
    • Thorndike, J.1    Beck, W.S.2
  • 29
    • 84920291018 scopus 로고
    • Tumor-bearing transgenic mice and cancer patients have elevated levels of expired formaldehyde
    • Ebeler, S. E.; Zulim, R. A.; Hinrichs, S. H.; Clifford, A. J.; Shibamoto, T. Tumor-bearing transgenic mice and cancer patients have elevated levels of expired formaldehyde. Faseb J. 1993, 7, A716.
    • (1993) Faseb J. , vol.7
    • Ebeler, S.E.1    Zulim, R.A.2    Hinrichs, S.H.3    Clifford, A.J.4    Shibamoto, T.5
  • 30
    • 0028909048 scopus 로고
    • Adriamycin-induced hepatic and myocardial lipid peroxidation and DNA damage, and enhanced excretion of urinary lipid metabolites in rats
    • Bagchi, D.; Bagchi, M.; Hassoun, E. A.; Kelly, J.; Stohs, S. J. Adriamycin-induced hepatic and myocardial lipid peroxidation and DNA damage, and enhanced excretion of urinary lipid metabolites in rats. Toxicology 1995, 95, 1-9.
    • (1995) Toxicology , vol.95 , pp. 1-9
    • Bagchi, D.1    Bagchi, M.2    Hassoun, E.A.3    Kelly, J.4    Stohs, S.J.5
  • 31
    • 0019515713 scopus 로고
    • Mammary tumor induction in male and female Sprague-Dawley rats by Adriamycin and daunomycin
    • Bucciarelli, E. Mammary tumor induction in male and female Sprague-Dawley rats by Adriamycin and daunomycin. J. Natl. Cancer Inst. 1981, 66, 81-84.
    • (1981) J. Natl. Cancer Inst. , vol.66 , pp. 81-84
    • Bucciarelli, E.1
  • 32
    • 0027520065 scopus 로고
    • Covalent modification of DNA by daunorubicin
    • Purewal, M.; Liehr, J. G. Covalent modification of DNA by daunorubicin. Cancer Chemother. Pharmacol. 1993, 33, 239-244.
    • (1993) Cancer Chemother. Pharmacol. , vol.33 , pp. 239-244
    • Purewal, M.1    Liehr, J.G.2
  • 33
    • 0026504081 scopus 로고
    • Enhancement of doxorubicin toxicity following activation by NADPH cytochromeP450 reductase
    • Bartoszek, A.; Wolf, C. R. Enhancement of doxorubicin toxicity following activation by NADPH cytochromeP450 reductase. Biochem. Pharmacol. 1992, 43, 1449-1457.
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 1449-1457
    • Bartoszek, A.1    Wolf, C.R.2
  • 34
    • 0022353528 scopus 로고
    • Radical dimer rescue of toxicity and improved therapeutic index of Adriamycin in tumor-bearing mice
    • Averbuch, S. D.; Gaudiano, G.; Koch, T. H.; Bachur, N. R. Radical dimer rescue of toxicity and improved therapeutic index of Adriamycin in tumor-bearing mice. Cancer Res. 1985, 45, 6200-6204.
    • (1985) Cancer Res. , vol.45 , pp. 6200-6204
    • Averbuch, S.D.1    Gaudiano, G.2    Koch, T.H.3    Bachur, N.R.4
  • 37
    • 7144241394 scopus 로고
    • Synthesis of 3″-dehydro-4-O-methylbarminomycin II having an eight-membered acetal-azomethine ring
    • Ikeda, D.; Ajito, K.; Kondo, S.; Takeuchi, T. Synthesis of 3″-dehydro-4-O-methylbarminomycin II having an eight-membered acetal-azomethine ring. Chem. Lett. 1990, 1431-1432.
    • (1990) Chem. Lett. , pp. 1431-1432
    • Ikeda, D.1    Ajito, K.2    Kondo, S.3    Takeuchi, T.4
  • 38
    • 0029965293 scopus 로고    scopus 로고
    • High yield conversion of doxorubicin to 2-pyrrolinodoxorubicin, an analog 500-1000 times more potent: Structure-activity relationship of daunosamine-modified derivatives of doxorubicin
    • Nagy, A.; Armatis, P.; Schally, A. V. High yield conversion of doxorubicin to 2-pyrrolinodoxorubicin, an analog 500-1000 times more potent: Structure-activity relationship of daunosamine-modified derivatives of doxorubicin. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 2464-2469.
    • (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 2464-2469
    • Nagy, A.1    Armatis, P.2    Schally, A.V.3
  • 39
    • 0026325629 scopus 로고
    • N-(5,5-Diacetoxypentyl)doxorubicin: A novel anthracycline producing DNA interstrand cross-linking and rapid endonucleolytic cleavage in human leukemia cells
    • Zwelling, L. A.; Altschuler, E.; Cherif, A.; Farquhar, D. N-(5,5-Diacetoxypentyl)doxorubicin: A novel anthracycline producing DNA interstrand cross-linking and rapid endonucleolytic cleavage in human leukemia cells. Cancer Res. 1991, 57, 6704-6707.
    • (1991) Cancer Res. , vol.57 , pp. 6704-6707
    • Zwelling, L.A.1    Altschuler, E.2    Cherif, A.3    Farquhar, D.4
  • 40
    • 0026737732 scopus 로고
    • N-(5,5-Diacetoxypent-1-yl)doxorubicin: A New Intensely Potent Doxorubicin Analogue
    • Cherif, A.; Farquhar, D. N-(5,5-Diacetoxypent-1-yl)doxorubicin: A New Intensely Potent Doxorubicin Analogue. J. Med. Chem. 1992, 35, 3208-3214.
    • (1992) J. Med. Chem. , vol.35 , pp. 3208-3214
    • Cherif, A.1    Farquhar, D.2


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