메뉴 건너뛰기




Volumn 163, Issue 1, 2005, Pages 85-89

The release of 5-methylene-2-furanone from irradiated DNA catalyzed by cationic polyamines and divalent metal cations

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYRIBONOLACTONE; 5 METHYLENE 2 FURANONE; BERYLLIUM; COPPER; DNA; FURANONE DERIVATIVE; LACTONE DERIVATIVE; MAGNESIUM; METAL ION; NICKEL; PHOSPHATE; POLYAMINE DERIVATIVE; POLYLYSINE; PUTRESCINE; SPERMINE; UNCLASSIFIED DRUG; ZINC;

EID: 11144260160     PISSN: 00337587     EISSN: None     Source Type: Journal    
DOI: 10.1667/RR3288     Document Type: Article
Times cited : (40)

References (37)
  • 1
    • 0023052463 scopus 로고
    • Nuclease activity of 1,10-phenanthroline-copper ion: Reaction with CGCGAATTCGCG and its complexes with netropsin and EcoRI
    • M. Kuwabara, C. Yoon, T. Goyne, T. Thederahn and D. S. Sigman, Nuclease activity of 1,10-phenanthroline-copper ion: Reaction with CGCGAATTCGCG and its complexes with netropsin and EcoRI. Biochemistry 25, 7401-7408 (1986).
    • (1986) Biochemistry , vol.25 , pp. 7401-7408
    • Kuwabara, M.1    Yoon, C.2    Goyne, T.3    Thederahn, T.4    Sigman, D.S.5
  • 2
    • 33845282765 scopus 로고
    • Nuclease activity of 1,10-phenanthroline-copper ion. Chemistry of deoxyribose oxidation
    • T. E. Goyne and D. S. Sigman, Nuclease activity of 1,10-phenanthroline- copper ion. Chemistry of deoxyribose oxidation. J. Am. Chem. Soc. 109, 2846-2848 (1987).
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2846-2848
    • Goyne, T.E.1    Sigman, D.S.2
  • 3
    • 0031019030 scopus 로고    scopus 로고
    • Chemical mechanism of DNA scission by (1,10-phenanthroline)copper. Carbonyl oxygen of 5-methylenefuranone is derived from water
    • M. M. Meijler, O. Zelenko and D. S. Sigman, Chemical mechanism of DNA scission by (1,10-phenanthroline)copper. Carbonyl oxygen of 5-methylenefuranone is derived from water. J. Am. Chem. Soc. 119, 1135-1136 (1997).
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1135-1136
    • Meijler, M.M.1    Zelenko, O.2    Sigman, D.S.3
  • 4
    • 0000578776 scopus 로고    scopus 로고
    • Chemical nuclease activity of 1,10-henanthroline-copper. Isotopic probes of mechanism
    • O. Zelenko, J. Gallagher, Y. Xu and D. S. Sigman, Chemical nuclease activity of 1,10-henanthroline-copper. Isotopic probes of mechanism. Inorg. Chem. 37, 2198-2204 (1998).
    • (1998) Inorg. Chem. , vol.37 , pp. 2198-2204
    • Zelenko, O.1    Gallagher, J.2    Xu, Y.3    Sigman, D.S.4
  • 5
    • 0032557199 scopus 로고    scopus 로고
    • Model studies indicate that copper phenanthroline induces direct strand breaks via β-elimination of the 2′-deoxyribonolactone intermediate observed in enediyene mediated DNA damage
    • T. Chen and M. M. Greenberg, Model studies indicate that copper phenanthroline induces direct strand breaks via β-elimination of the 2′-deoxyribonolactone intermediate observed in enediyene mediated DNA damage. J. Am. Chem. Soc. 120, 3815-3816 (1998).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3815-3816
    • Chen, T.1    Greenberg, M.M.2
  • 6
    • 0034608974 scopus 로고    scopus 로고
    • Mechanism of DNA strand scission induced by (1,10-phenanthroline)copper complex: Major direct DNA cleavage is not through 1′,2′- dehydronucleotide intermediate nor β-elimination of forming ribonolactone
    • T. Oyoshi and H. Sugiyama, Mechanism of DNA strand scission induced by (1,10-phenanthroline)copper complex: Major direct DNA cleavage is not through 1′,2′-dehydronucleotide intermediate nor β-elimination of forming ribonolactone. J. Am. Chem. Soc. 122, 6313-6314 (2000).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6313-6314
    • Oyoshi, T.1    Sugiyama, H.2
  • 7
    • 0034671836 scopus 로고    scopus 로고
    • Mechanisms of DNA cleavage by copper complexes of 3-clip-Phen and of its conjugate with a distamycin analogue
    • M. Pitie, C. J. Burrows and B. Meunier, Mechanisms of DNA cleavage by copper complexes of 3-clip-Phen and of its conjugate with a distamycin analogue. Nucleic Acids Res. 28, 4856-4864 (2000).
    • (2000) Nucleic Acids Res. , vol.28 , pp. 4856-4864
    • Pitie, M.1    Burrows, C.J.2    Meunier, B.3
  • 8
    • 0037036739 scopus 로고    scopus 로고
    • A minor groove binding copper-phenanthroline conjugate produces direct strand breaks via β-elimination of 2-deoxyribonolactone
    • B. C. Bales, M. Pitie, B. Meunier and M. M. Greenberg, A minor groove binding copper-phenanthroline conjugate produces direct strand breaks via β-elimination of 2-deoxyribonolactone. J. Am. Chem. Soc. 124, 9062-9063 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9062-9063
    • Bales, B.C.1    Pitie, M.2    Meunier, B.3    Greenberg, M.M.4
  • 9
    • 0024501789 scopus 로고
    • Identification of 2-deoxyribonolactone at the site of neocarzinostatin-induced cytosine release in the sequence d(AGC)
    • L. S. Kappen and I. H. Goldberg, Identification of 2-deoxyribonolactone at the site of neocarzinostatin-induced cytosine release in the sequence d(AGC). Biochemistry 28, 1027-1032 (1989).
    • (1989) Biochemistry , vol.28 , pp. 1027-1032
    • Kappen, L.S.1    Goldberg, I.H.2
  • 10
    • 12044260107 scopus 로고
    • Mechanism of neocarzinostatin action: Role of DNA microstructure in determination of chemistry of bistranded oxidative damage
    • I. H. Goldberg, Mechanism of neocarzinostatin action: Role of DNA microstructure in determination of chemistry of bistranded oxidative damage. Acc. Chem. Res. 24, 191-198 (1991).
    • (1991) Acc. Chem. Res. , vol.24 , pp. 191-198
    • Goldberg, I.H.1
  • 11
    • 0026695943 scopus 로고
    • Neocarzinostatin acts as a sensitive probe of DNA microheterogeneity: Switching of chemistry from C-1′ to C-4′ by a G.T mismatch 5′ to the site of DNA damage
    • L. S. Kappen and I. H. Goldberg, Neocarzinostatin acts as a sensitive probe of DNA microheterogeneity: Switching of chemistry from C-1′ to C-4′ by a G.T mismatch 5′ to the site of DNA damage. Proc. Natl. Acad. Sci. USA 89, 6706-6710 (1992).
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 6706-6710
    • Kappen, L.S.1    Goldberg, I.H.2
  • 12
    • 0034830066 scopus 로고    scopus 로고
    • The 2-deoxyribonolactone lesion produced in DNA by neocarzinostatin and other damaging agents forms cross-links with the base-excision repair enzyme endonuclease III
    • M. Hashimoto, M. M. Greenberg, Y. W. Kow, J. T. Hwang and R. P. Cunningham, The 2-deoxyribonolactone lesion produced in DNA by neocarzinostatin and other damaging agents forms cross-links with the base-excision repair enzyme endonuclease III. J. Am. Chem. Soc. 123, 3161-3162 (2001).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3161-3162
    • Hashimoto, M.1    Greenberg, M.M.2    Kow, Y.W.3    Hwang, J.T.4    Cunningham, R.P.5
  • 13
    • 0025990957 scopus 로고
    • Mechanism of DNA cleavage by cationic manganese porphyrins: Hydroxylations at the 1′-carbon and 5′-carbon atoms of deoxyriboses as initial damages
    • G. Pratviel, M. Pitie, J. Bernadou and B. Meunier, Mechanism of DNA cleavage by cationic manganese porphyrins: Hydroxylations at the 1′-carbon and 5′-carbon atoms of deoxyriboses as initial damages. Nucleic Acids Res. 19, 6283-6288 (1991).
    • (1991) Nucleic Acids Res. , vol.19 , pp. 6283-6288
    • Pratviel, G.1    Pitie, M.2    Bernadou, J.3    Meunier, B.4
  • 14
    • 0029140468 scopus 로고
    • 5 system results from a cytochrome P-450-type hydroxylation reaction
    • 5 system results from a cytochrome P-450-type hydroxylation reaction. J. Am. Chem. Soc. 117, 2935-2936 (1995).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2935-2936
    • Pitie, M.1    Bernadou, J.2    Meunier, B.3
  • 16
    • 0033562760 scopus 로고    scopus 로고
    • Oxidative damage of DNA by chromium(V) complexes: Relative importance of base versus sugar oxidation
    • R. N. Bose, S. Moghaddas, P. A. Mazzer, L. P. Dudones, L. Joudah and D. Stroup, Oxidative damage of DNA by chromium(V) complexes: Relative importance of base versus sugar oxidation. Nucleic Acids Res. 27, 2219-2226 (1999).
    • (1999) Nucleic Acids Res. , vol.27 , pp. 2219-2226
    • Bose, R.N.1    Moghaddas, S.2    Mazzer, P.A.3    Dudones, L.P.4    Joudah, L.5    Stroup, D.6
  • 17
    • 0028846227 scopus 로고
    • Kinetics and mechanism of the oxidation of sugars and nucleotides by oxoruthenium(IV): Model studies for predicting cleavage patterns in polymeric DNA and RNA
    • G. A. Neyhart, C. C. Cheng and H. H. Thorp, Kinetics and mechanism of the oxidation of sugars and nucleotides by oxoruthenium(IV): Model studies for predicting cleavage patterns in polymeric DNA and RNA. J. Am. Chem. Soc. 117, 1463-1471 (1995).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 1463-1471
    • Neyhart, G.A.1    Cheng, C.C.2    Thorp, H.H.3
  • 18
    • 0024830828 scopus 로고
    • A 2-deoxyribonolactone-containing nucleotide: Isolation and characterization of the alkali-sensitive photoproduct of the trideoxyribonucleotide d(ApCpA)
    • H. Urata, K. Yamamoto, M. Akagi, H. Hiroaki and S. Uesugi, A 2-deoxyribonolactone-containing nucleotide: Isolation and characterization of the alkali-sensitive photoproduct of the trideoxyribonucleotide d(ApCpA). Biochemistry 28, 9566-9569 (1989).
    • (1989) Biochemistry , vol.28 , pp. 9566-9569
    • Urata, H.1    Yamamoto, K.2    Akagi, M.3    Hiroaki, H.4    Uesugi, S.5
  • 19
    • 0000957104 scopus 로고
    • Radiolyse gamma de la thymidine en solution aqueuse aerée. III. Aspects quantitatifs et mecanisme
    • J. Cadet and R. Teoule, Radiolyse gamma de la thymidine en solution aqueuse aerée. III. Aspects quantitatifs et mecanisme. Bull. Soc. Chim. Fr. 891-895 (1975).
    • (1975) Bull. Soc. Chim. Fr. , pp. 891-895
    • Cadet, J.1    Teoule, R.2
  • 20
    • 0017556605 scopus 로고
    • Isolation of 2-deoxy-D-erythro-pentonic acid from an alkali-labile site in γ-irradiated DNA
    • M. Dizdaroglu, D. Schulte-Frohlinde and C. von Sonntag, Isolation of 2-deoxy-D-erythro-pentonic acid from an alkali-labile site in γ-irradiated DNA. Int. J. Radiat. Biol. 32, 481-483 (1977).
    • (1977) Int. J. Radiat. Biol. , vol.32 , pp. 481-483
    • Dizdaroglu, M.1    Schulte-Frohlinde, D.2    Von Sonntag, C.3
  • 22
    • 0029999641 scopus 로고    scopus 로고
    • Direct effects of γ-radiation on 2′-deoxycytidine in frozen aqueous solution
    • A. A. Shaw and J. Cadet, Direct effects of γ-radiation on 2′-deoxycytidine in frozen aqueous solution. Int. J. Radiat. Biol. 70, 1-6 (1996).
    • (1996) Int. J. Radiat. Biol. , vol.70 , pp. 1-6
    • Shaw, A.A.1    Cadet, J.2
  • 23
    • 0037036761 scopus 로고    scopus 로고
    • Chemistry of the 2-deoxyribonolactone lesion in oligonucleotides: Cleavage kinetics and products analysis
    • Y. Roupioz, J. Lhomme and M. Kotera, Chemistry of the 2-deoxyribonolactone lesion in oligonucleotides: Cleavage kinetics and products analysis. J. Am. Chem. Soc. 124, 9129-9135 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9129-9135
    • Roupioz, Y.1    Lhomme, J.2    Kotera, M.3
  • 24
    • 0032544035 scopus 로고    scopus 로고
    • DNA strand breaking by the hydroxyl radical is governed by the accessible surface areas of the hydrogen atoms of the DNA backbone
    • B. Balasubramanian, W. K. Pogozelski and T. D. Tullius, DNA strand breaking by the hydroxyl radical is governed by the accessible surface areas of the hydrogen atoms of the DNA backbone. Proc. Natl. Acad. Sci. USA 95, 9738-9743 (1998).
    • (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 9738-9743
    • Balasubramanian, B.1    Pogozelski, W.K.2    Tullius, T.D.3
  • 25
    • 0028274695 scopus 로고
    • Theoretical study on the deoxyribose radicals formed by hydrogen abstraction
    • K. Miaskiewicz and R. Osman, Theoretical study on the deoxyribose radicals formed by hydrogen abstraction. J. Am. Chem. Soc. 116, 232-238 (1994).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 232-238
    • Miaskiewicz, K.1    Osman, R.2
  • 26
    • 0029274078 scopus 로고
    • Structure and relative stability of deoxyribose radicals in a model DNA backbone: Ab initio molecular orbital calculations
    • A-O. Colson and M. D. Sevilla, Structure and relative stability of deoxyribose radicals in a model DNA backbone: ab initio molecular orbital calculations. J. Phys. Chem. 99, 3867-3874 (1995).
    • (1995) J. Phys. Chem. , vol.99 , pp. 3867-3874
    • Colson, A.-O.1    Sevilla, M.D.2
  • 27
    • 0001473346 scopus 로고
    • An improved synthesis of protoanemonin
    • C. Grundmann and E. Kober, An improved synthesis of protoanemonin. J. Am. Chem. Soc. 77, 2332-2333 (1955).
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 2332-2333
    • Grundmann, C.1    Kober, E.2
  • 28
    • 0037382913 scopus 로고    scopus 로고
    • Radiation-activated nuclease activity of o,o′-diphenyleneiodonium cations (DPI): A reductively initiated chain reaction involving the C1′ chemistry
    • Y. Razskazovskiy, Radiation-activated nuclease activity of o,o′-diphenyleneiodonium cations (DPI): A reductively initiated chain reaction involving the C1′ chemistry. Radiat. Res. 159, 543-549 (2003).
    • (2003) Radiat. Res. , vol.159 , pp. 543-549
    • Razskazovskiy, Y.1
  • 29
    • 11544314893 scopus 로고    scopus 로고
    • Oxidative strand scission of nucleic acids: Routes initiated by hydrogen abstraction from the sugar moiety
    • W. K. Pogozelski and T. D. Tullius, Oxidative strand scission of nucleic acids: routes initiated by hydrogen abstraction from the sugar moiety. Chem. Rev. 98, 1089-1107 (1998).
    • (1998) Chem. Rev. , vol.98 , pp. 1089-1107
    • Pogozelski, W.K.1    Tullius, T.D.2
  • 30
    • 0034110914 scopus 로고    scopus 로고
    • Direct radiation damage to crystalline DNA: What is the source of unaltered base release?
    • Y. Razskazovskiy, M. G. Debije and W. A. Bernhard, Direct radiation damage to crystalline DNA: What is the source of unaltered base release? Radiat. Res. 153, 436-441 (2000).
    • (2000) Radiat. Res. , vol.153 , pp. 436-441
    • Razskazovskiy, Y.1    Debije, M.G.2    Bernhard, W.A.3
  • 31
    • 0029050296 scopus 로고
    • DNA strand breakage is correlated with unaltered base release
    • E. S. Henle, R. Roots, W. R. Holley and A. Chatterjee, DNA strand breakage is correlated with unaltered base release. Radiat. Res. 143, 144-150 (1995).
    • (1995) Radiat. Res. , vol.143 , pp. 144-150
    • Henle, E.S.1    Roots, R.2    Holley, W.R.3    Chatterjee, A.4
  • 32
    • 0028927261 scopus 로고
    • Reactions of oxyl radicals with DNA
    • A. Breen and J. Murphy, Reactions of oxyl radicals with DNA. Free Radic. Biol. Med. 18, 1033-1077 (1995).
    • (1995) Free Radic. Biol. Med. , vol.18 , pp. 1033-1077
    • Breen, A.1    Murphy, J.2
  • 33
    • 0026600950 scopus 로고
    • Radiation-induced DNA damage as a function of hydration. I. Release of unaltered bases
    • S. G. Swarts, M. D. Sevilla, D. Becker, C. J. Tokar and K. T. Wheeler, Radiation-induced DNA damage as a function of hydration. I. Release of unaltered bases. Radiat. Res. 129, 333-344 (1992).
    • (1992) Radiat. Res. , vol.129 , pp. 333-344
    • Swarts, S.G.1    Sevilla, M.D.2    Becker, D.3    Tokar, C.J.4    Wheeler, K.T.5
  • 34
    • 0033215488 scopus 로고    scopus 로고
    • The reactivity of the 2-deoxyribonolactone lesion in single-stranded DNA and its implication in reaction mechanisms of DNA damage and repair
    • J. T. Hwang, K. A. Tallman and M. M. Greenberg, The reactivity of the 2-deoxyribonolactone lesion in single-stranded DNA and its implication in reaction mechanisms of DNA damage and repair. Nucleic Acids Res. 27, 3805-3810 (1999).
    • (1999) Nucleic Acids Res. , vol.27 , pp. 3805-3810
    • Hwang, J.T.1    Tallman, K.A.2    Greenberg, M.M.3
  • 35
    • 0032572092 scopus 로고    scopus 로고
    • Release of superoxide from nucleoside peroxyl radicals, a double-edged sword?
    • K. A. Tallman, C. Tronche, D. J. Yoo and M. M. Greenberg, Release of superoxide from nucleoside peroxyl radicals, a double-edged sword? J. Am. Chem. Soc. 120, 4903-4909 (1998).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4903-4909
    • Tallman, K.A.1    Tronche, C.2    Yoo, D.J.3    Greenberg, M.M.4
  • 37
    • 0034605431 scopus 로고    scopus 로고
    • Models of DNA C1′ radicals. Structural, spectral, and chemical properties of the thyminylmethyl radical and the 2′-deoxyuridin-1′- yl radical
    • C. Chatgilialoglu, C. Ferreri, R. Bazzanini, M. Guerra, S-Y. Choi, C. J. Emanuel, J. H. Horner and M. Newcomb, Models of DNA C1′ radicals. Structural, spectral, and chemical properties of the thyminylmethyl radical and the 2′-deoxyuridin-1′-yl radical. J. Am. Chem. Soc. 122, 9525-9533 (2000).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9525-9533
    • Chatgilialoglu, C.1    Ferreri, C.2    Bazzanini, R.3    Guerra, M.4    Choi, S.-Y.5    Emanuel, C.J.6    Horner, J.H.7    Newcomb, M.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.