메뉴 건너뛰기




Volumn 72, Issue 5, 2000, Pages 619-624

N-hydroxy-4-(4-chlorophenyl)thiazole-2(3H)-thione as a photochemical hydroxyl-radical source: Photochemistry and oxidative damage of DNA (strand breaks) and 2′-deoxyguanosine (8-oxodG formation)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; 7,8 DIHYDRO 8 OXO 2' DEOXYGUANOSINE; DEOXYGUANOSINE; DISULFIDE; GUANOSINE DERIVATIVE; HYDROXYL RADICAL; KETONE DERIVATIVE; N HYDROXY 4 (4 CHLOROPHENYL)THIAZOLE 2(3H) THIONE; SINGLET OXYGEN; THIAZOLE DERIVATIVE; THIAZOLETHIONE; UNCLASSIFIED DRUG;

EID: 0034335284     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2000)072<0619:NHCTHT>2.0.CO;2     Document Type: Article
Times cited : (27)

References (35)
  • 1
    • 0002738322 scopus 로고
    • Formation of 8-hydroxy-deoxyguanosine in DNA by oxygen radicals and its biological significance
    • Edited by H. Sies. Academic Press, New York
    • Kasai, H. and S. Nishimura (1991) Formation of 8-hydroxy-deoxyguanosine in DNA by oxygen radicals and its biological significance. In Oxidative Stress: Oxidants and Antioxidants (Edited by H. Sies), pp. 99-116. Academic Press, New York.
    • (1991) Oxidative Stress: Oxidants and Antioxidants , pp. 99-116
    • Kasai, H.1    Nishimura, S.2
  • 2
    • 4243545125 scopus 로고    scopus 로고
    • Oxidative nucleobase modifications leading to strand scission
    • Burrows, C. J. and J. G. Muller (1998) Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98, 1109-1151.
    • (1998) Chem. Rev. , vol.98 , pp. 1109-1151
    • Burrows, C.J.1    Muller, J.G.2
  • 3
    • 0025344870 scopus 로고
    • Phthalimides hydroperoxides as efficient photochemical hydroxyl radical generators. A novel DNA-cleaving agent
    • Saito, I., M. Takayama and T. Matsuura, (1990) Phthalimides hydroperoxides as efficient photochemical hydroxyl radical generators. A novel DNA-cleaving agent. J. Am. Chem. Soc. 112, 883-884.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 883-884
    • Saito, I.1    Takayama, M.2    Matsuura, T.3
  • 6
    • 33748227289 scopus 로고
    • N-Hydroxypyridinethiones as photochemical hydroxyl radical source for oxidative DNA damage
    • Adam, W., D. Ballmaier, B. Epe, G. N. Grimm and C. R. Saha-Möller (1995) N-Hydroxypyridinethiones as photochemical hydroxyl radical source for oxidative DNA damage. Angew. Chem. Int. Ed. Engl. 34, 2156-2158.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2156-2158
    • Adam, W.1    Ballmaier, D.2    Epe, B.3    Grimm, G.N.4    Saha-Möller, C.R.5
  • 7
    • 0029664335 scopus 로고    scopus 로고
    • Photolysis of N-hydroxypyridinethiones: A new source of hydroxyl radicals for the direct damage of cell-free and cellar DNA
    • Epe, B., D. Ballmaier, W. Adam, G. N. Grimm and C. R. Saha-Möller (1996) Photolysis of N-hydroxypyridinethiones: a new source of hydroxyl radicals for the direct damage of cell-free and cellar DNA. Nucleic Acids Res. 24, 1625-1631.
    • (1996) Nucleic Acids Res , vol.24 , pp. 1625-1631
    • Epe, B.1    Ballmaier, D.2    Adam, W.3    Grimm, G.N.4    Saha-Möller, C.R.5
  • 8
    • 0031975262 scopus 로고    scopus 로고
    • DNA cleavage induced by alkoxyl radicals generated in the photolysis of N-alkoxylpyridinethiones
    • Adam, W., G. N. Grimm and C. R. Saha-Möller (1998) DNA cleavage induced by alkoxyl radicals generated in the photolysis of N-alkoxylpyridinethiones. Free Radic. Biol. Med. 24, 234-238.
    • (1998) Free Radic. Biol. Med. , vol.24 , pp. 234-238
    • Adam, W.1    Grimm, G.N.2    Saha-Möller, C.R.3
  • 10
    • 0029138513 scopus 로고
    • Photosensitized formation of 8-hydroxy-2′-deoxyguanosine in salmon testes DNA by furocoumarin hydroperoxides: A novel, intercalating "photo-Fenton reagent" for oxidative DNA damage
    • Adam, W., J. Cadet, F. Dall'Acqua, B. Epe, D. Ramaiah and C. R. Saha-Möller (1995) Photosensitized formation of 8-hydroxy-2′-deoxyguanosine in salmon testes DNA by furocoumarin hydroperoxides: a novel, intercalating "photo-Fenton reagent" for oxidative DNA damage. Angew. Chem. Int. Ed. Engl. 34, 107-110.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 107-110
    • Adam, W.1    Cadet, J.2    Dall'Acqua, F.3    Epe, B.4    Ramaiah, D.5    Saha-Möller, C.R.6
  • 11
    • 0001292229 scopus 로고    scopus 로고
    • Photochemistry and photobiology of furocoumarin hydroperoxides derived from imperatorin: Novel intercalating photo-Fenton reagents for oxidative DNA modification by hydroxyl radicals
    • Adam, W., M. Berger, J. Cadet, F. Dall'Acqua, B. Epe, S. Frank, D. Ramaiah, S. Raoul, C. R. Saha-Möller and D. Vedaldi (1996) Photochemistry and photobiology of furocoumarin hydroperoxides derived from imperatorin: novel intercalating photo-Fenton reagents for oxidative DNA modification by hydroxyl radicals. Photochem. Photobiol. 63, 768-778.
    • (1996) Photochem. Photobiol. , vol.63 , pp. 768-778
    • Adam, W.1    Berger, M.2    Cadet, J.3    Dall'Acqua, F.4    Epe, B.5    Frank, S.6    Ramaiah, D.7    Raoul, S.8    Saha-Möller, C.R.9    Vedaldi, D.10
  • 12
    • 0029905868 scopus 로고    scopus 로고
    • Photochemistry of N-hydroxy-2(1H)-pyridone, a more selective source of hydroxyl radicals than N-hydroxypyridine-2(1H)-thione
    • Aveline, B. M., I. E. Kochevar and R. W. Redmond (1996) Photochemistry of N-hydroxy-2(1H)-pyridone, a more selective source of hydroxyl radicals than N-hydroxypyridine-2(1H)-thione. J. Am. Chem. Soc. 118, 10 124-10 133.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10124-10133
    • Aveline, B.M.1    Kochevar, I.E.2    Redmond, R.W.3
  • 13
    • 0001242324 scopus 로고    scopus 로고
    • Oxidative DNA damage in the photolysis of N-hydroxy-2-pyridone, a specific hydroxyl-radical source
    • Adam, W., S. Marquardt and C. R. Saha-Möller (1999) Oxidative DNA damage in the photolysis of N-hydroxy-2-pyridone, a specific hydroxyl-radical source. Photochem. Photobiol. 70, 287-291.
    • (1999) Photochem. Photobiol. , vol.70 , pp. 287-291
    • Adam, W.1    Marquardt, S.2    Saha-Möller, C.R.3
  • 14
    • 0033577012 scopus 로고    scopus 로고
    • Are pyridinethiones reliable photochemical oxyl-radical sources for photobiological studies? The importance of secondary photolysis products in the guanine oxidation of 2′-deoxyguanosine and cell-free DNA
    • Adam, W., G. N. Grimm, S. Marquardt and C. R. Saha-Möller (1999) Are pyridinethiones reliable photochemical oxyl-radical sources for photobiological studies? The importance of secondary photolysis products in the guanine oxidation of 2′-deoxyguanosine and cell-free DNA. J. Am. Chem. Soc. 121, 1179-1185.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1179-1185
    • Adam, W.1    Grimm, G.N.2    Marquardt, S.3    Saha-Möller, C.R.4
  • 15
    • 0001309354 scopus 로고    scopus 로고
    • Hydroxyl radical-induced degradation of 2′-deoxyguanosine under reducing conditions
    • Douki, T., S. Spinelli, J.-L. Ravanat and J. Cadet (1999) Hydroxyl radical-induced degradation of 2′-deoxyguanosine under reducing conditions. J. Chem. Soc., Perkin Trans. 2, 1875-1880.
    • (1999) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1875-1880
    • Douki, T.1    Spinelli, S.2    Ravanat, J.-L.3    Cadet, J.4
  • 16
    • 0001663042 scopus 로고    scopus 로고
    • N-hydroxypyridine-2(1H)-thione: Not a selective generator of hydroxyl radicals in aqueous solution
    • Aveline, B. M., I. E. Kochevar and R. W. Redmond (1996) N-hydroxypyridine-2(1H)-thione: not a selective generator of hydroxyl radicals in aqueous solution. J. Am. Chem. Soc. 118, 289-290.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 289-290
    • Aveline, B.M.1    Kochevar, I.E.2    Redmond, R.W.3
  • 17
    • 0029855489 scopus 로고    scopus 로고
    • Photochemistry of the nonspecific hydroxyl radical generator, N-hydroxypyridine-2(1H)-thione
    • Aveline, B. M., I. E. Kochevar and R. W. Redmond (1996) Photochemistry of the nonspecific hydroxyl radical generator, N-hydroxypyridine-2(1H)-thione. J. Am. Chem. Soc. 118, 10 113-10 123.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10113-10123
    • Aveline, B.M.1    Kochevar, I.E.2    Redmond, R.W.3
  • 18
    • 0001690152 scopus 로고
    • Formation of carbon-carbon bonds with radicals derived from the esters of thiohydroxamic acids
    • Barton, D. H. R., D. Crich and G. Kretzschmar (1984) Formation of carbon-carbon bonds with radicals derived from the esters of thiohydroxamic acids. Tetrahedron Lett. 25, 1055-1058.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1055-1058
    • Barton, D.H.R.1    Crich, D.2    Kretzschmar, G.3
  • 19
    • 0000879554 scopus 로고
    • On the mechanism of the decarboxylative rearrangement of thiohydroxamic esters
    • Barton, D. H. R., D. Crich and P. Potier (1985) On the mechanism of the decarboxylative rearrangement of thiohydroxamic esters. Tetrahedron Lett. 26, 5943-5946.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5943-5946
    • Barton, D.H.R.1    Crich, D.2    Potier, P.3
  • 20
    • 37049075025 scopus 로고
    • The invention of new radical chain reactions. Part 9. Further radical chemistry of thiohydroxamic esters; formation of carbon-carbon bonds
    • Barton, D. H. R., D. Crich and G. Kretzschmar (1986) The invention of new radical chain reactions. Part 9. Further radical chemistry of thiohydroxamic esters; formation of carbon-carbon Bonds. J. Chem. Soc., Perkin Trans. 1, 39-53.
    • (1986) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 39-53
    • Barton, D.H.R.1    Crich, D.2    Kretzschmar, G.3
  • 21
    • 0002640062 scopus 로고    scopus 로고
    • Towards improved alkoxy radical precursors - The synthesis of N-alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones
    • Hartung, J. and M. Schwarz (1997) Towards improved alkoxy radical precursors - the synthesis of N-alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones. Synlett 848-850.
    • (1997) Synlett , pp. 848-850
    • Hartung, J.1    Schwarz, M.2
  • 22
    • 0032792040 scopus 로고    scopus 로고
    • A new generation of alkoxyl radical precursors - Preparation and properties of N-(alkoxy)-4-arylthiazole-2(3H)-thiones
    • Hartung, J., M. Schwarz, I. Svoboda, H. Fueß and M. T. Duarte (1999) A new generation of alkoxyl radical precursors - preparation and properties of N-(alkoxy)-4-arylthiazole-2(3H)-thiones. Eur. J. Org. Chem. 1275-1290.
    • (1999) Eur. J. Org. Chem. , pp. 1275-1290
    • Hartung, J.1    Schwarz, M.2    Svoboda, I.3    Fueß, H.4    Duarte, M.T.5
  • 23
    • 0032771203 scopus 로고    scopus 로고
    • On the selective O-alkylation of ambident nucleophiles - The synthesis of thiohydroxamic acid O-esters by phase-transfer reactions
    • Hartung, J., R. Kneuer, M. Schwarz, I. Svoboda and H. Fueß (1999) On the selective O-alkylation of ambident nucleophiles - the synthesis of thiohydroxamic acid O-esters by phase-transfer reactions. Eur. J. Org. Chem. 97-106.
    • (1999) Eur. J. Org. Chem. , pp. 97-106
    • Hartung, J.1    Kneuer, R.2    Schwarz, M.3    Svoboda, I.4    Fueß, H.5
  • 24
    • 0009955787 scopus 로고
    • Über einige unsymmerishe heterocyclische disulfide. II
    • Runge, F., A. Jumar and F. Koehler (1965) Über einige unsymmerishe heterocyclische Disulfide. II. J. Prakt. Chem. 21, 39-47.
    • (1965) J. Prakt. Chem. , vol.21 , pp. 39-47
    • Runge, F.1    Jumar, A.2    Koehler, F.3
  • 25
    • 0000251878 scopus 로고
    • Über die tuberkulostatische wirkung von derivaten der 3 isomeren phenylthiazole
    • Erlenmeyer, H., J. Eckenstein, E. Sorkin and H. Meyer (1950) Über die tuberkulostatische Wirkung von Derivaten der 3 isomeren Phenylthiazole. Helv. Chim. Acta 33, 1271-1276.
    • (1950) Helv. Chim. Acta , vol.33 , pp. 1271-1276
    • Erlenmeyer, H.1    Eckenstein, J.2    Sorkin, E.3    Meyer, H.4
  • 26
    • 0001329321 scopus 로고
    • Synthèses d'aryl-4 thiazoles substitués ou non en position-2
    • Vernin, G. and J. Metzger (1963) Synthèses d'aryl-4 thiazoles substitués ou non en position-2. Bull. Soc. Chim. Fr. 2498-2503.
    • (1963) Bull. Soc. Chim. Fr. , pp. 2498-2503
    • Vernin, G.1    Metzger, J.2
  • 27
    • 0001014503 scopus 로고
    • Phthalocyanine and naphthalocyanine photosensitized oxidation of 2′-deoxyguanosine: Distinct type I and type II products
    • Ravanat, J.-L., M. Berger, F. Bernard, R. Langlois, R. Ouellet, J. E. van Lier and J. Cadet (1992) Phthalocyanine and naphthalocyanine photosensitized oxidation of 2′-deoxyguanosine: distinct type I and type II products. Photochem. Photobiol. 55, 809-814.
    • (1992) Photochem. Photobiol. , vol.55 , pp. 809-814
    • Ravanat, J.-L.1    Berger, M.2    Bernard, F.3    Langlois, R.4    Ouellet, R.5    Van Lier, J.E.6    Cadet, J.7
  • 28
    • 84949415861 scopus 로고
    • Photochemistry of pesticides, 12. On the photoconversion of 1,3-dihydro-2 H-benzimidazole-2-thione, 2(3H)-benzothiazole thione, and 2-chlorobezothiazole
    • Abdou, W. M., M. M. Sidky and H. Wamhoff (1987) Photochemistry of pesticides, 12. On the photoconversion of 1,3-dihydro-2 H-benzimidazole-2-thione, 2(3H)-benzothiazole thione, and 2-chlorobezothiazole. Z. Naturforsch. 42b, 1153-1158.
    • (1987) Z. Naturforsch. , vol.42 B , pp. 1153-1158
    • Abdou, W.M.1    Sidky, M.M.2    Wamhoff, H.3
  • 29
    • 0013160712 scopus 로고
    • Sulfur containing chromophores
    • Blackwell Scientific Publications, Oxford, UK
    • Gilbert, A. and J. Baggott (1991) Sulfur containing chromophores. In Essentials of Molecular Photochemistry, pp. 477-479. Blackwell Scientific Publications, Oxford, UK.
    • (1991) Essentials of Molecular Photochemistry , pp. 477-479
    • Gilbert, A.1    Baggott, J.2
  • 30
    • 0018992113 scopus 로고
    • Spin trapping of superoxide and hydroxyl radicals: Practical aspects
    • Finkelstein, E., G. M. Rosen and E. J. Rauckman (1980) Spin trapping of superoxide and hydroxyl radicals: practical aspects. Arch. Biochem. Biophys. 200, 1-16.
    • (1980) Arch. Biochem. Biophys. , vol.200 , pp. 1-16
    • Finkelstein, E.1    Rosen, G.M.2    Rauckman, E.J.3
  • 31
    • 84989711049 scopus 로고
    • Photochemistry of 2-mercaptopyridines. Part 1. An EPR and spin-trapping investigation using 5,5-dimethyl-1-pyrroline N-oxide in aqueous solutions
    • Reszka, K. J. and C. F. Chignell (1994) Photochemistry of 2-mercaptopyridines. Part 1. An EPR and spin-trapping investigation using 5,5-dimethyl-1-pyrroline N-oxide in aqueous solutions. Photochem. Photobiol. 60, 442-449.
    • (1994) Photochem. Photobiol. , vol.60 , pp. 442-449
    • Reszka, K.J.1    Chignell, C.F.2
  • 32
    • 0000989226 scopus 로고
    • - radicals with organic substrates in aqueous and toluene solution
    • - radicals with organic substrates in aqueous and toluene solution. J. Phys. Chem. 79, 1-6.
    • (1975) J. Phys. Chem. , vol.79 , pp. 1-6
    • Neta, P.1    Schuler, R.H.2
  • 33
    • 0000322425 scopus 로고
    • g) in liquid water as determined by time-resolved infrared luminescence measurements
    • g) in liquid water as determined by time-resolved infrared luminescence measurements. J. Am. Chem. Soc. 104, 5541-5543.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 5541-5543
    • Rodgers, M.A.J.1    Snowden, P.T.2
  • 34
    • 0026749724 scopus 로고
    • Model studies for damage to nucleic acids mediated by thiyl radicals
    • Griffith, J. and J. A. Murphy (1992) Model studies for damage to nucleic acids mediated by thiyl radicals. Tetrahedron 48, 5543-5556.
    • (1992) Tetrahedron , vol.48 , pp. 5543-5556
    • Griffith, J.1    Murphy, J.A.2
  • 35
    • 85008025188 scopus 로고
    • Iron-catalyzed autooxidation of cholesterol in the presence of unsaturated long-chain fatty acid
    • Muto, T., J. Tanaka, T. Miura and M. Kimura (1982) Iron-catalyzed autooxidation of cholesterol in the presence of unsaturated long-chain fatty acid. Chem. Pharm. Bull. 30, 3172-3177.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 3172-3177
    • Muto, T.1    Tanaka, J.2    Miura, T.3    Kimura, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.