메뉴 건너뛰기




Volumn 90, Issue 2, 2016, Pages 433-448

The mycotoxin patulin reacts with DNA bases with and without previous conjugation to GSH: implication for related α,β-unsaturated carbonyl compounds?

Author keywords

Adducts; Glutathione; Nucleoside; Patulin

Indexed keywords

ADENINE; ALPHA,BETA UNSATURATED CARBONYL GROUP; AMIDE; CARBONYL DERIVATIVE; DNA BASE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; NUCLEIC ACID BASE; NUCLEOSIDE; PATULIN; PURINE; UNCLASSIFIED DRUG; DNA; DNA ADDUCT; MUTAGENIC AGENT;

EID: 84958124897     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-014-1443-z     Document Type: Article
Times cited : (21)

References (43)
  • 3
    • 0034067139 scopus 로고    scopus 로고
    • Induction of micronuclei and chromosomal aberrations by the mycotoxin patulin in mammalian cells: role of ascorbic acid as a modulator of patulin clastogenicity
    • COI: 1:CAS:528:DC%2BD3cXjs1CqtL8%3D, PID: 10792015
    • Alves I, Oliveira NG, Laires A, Rodrigues AS, Rueff J (2000) Induction of micronuclei and chromosomal aberrations by the mycotoxin patulin in mammalian cells: role of ascorbic acid as a modulator of patulin clastogenicity. Mutagenesis 15:229–234
    • (2000) Mutagenesis , vol.15 , pp. 229-234
    • Alves, I.1    Oliveira, N.G.2    Laires, A.3    Rodrigues, A.S.4    Rueff, J.5
  • 4
    • 0024337954 scopus 로고
    • Classification according to chemical structure, mutagenicity to Salmonella and level of carcinogenicity of a further 42 chemicals tested for carcinogenicity by the US National Toxicology Program
    • COI: 1:CAS:528:DyaL1MXksFahtLw%3D, PID: 2662004
    • Ashby J, Tennant RW, Zeiger E, Stasiewicz S (1989) Classification according to chemical structure, mutagenicity to Salmonella and level of carcinogenicity of a further 42 chemicals tested for carcinogenicity by the US National Toxicology Program. Mutat Res 223:73–103
    • (1989) Mutat Res , vol.223 , pp. 73-103
    • Ashby, J.1    Tennant, R.W.2    Zeiger, E.3    Stasiewicz, S.4
  • 5
    • 84877627216 scopus 로고    scopus 로고
    • Antioxidative and antigenotoxic effect of vitamin E against patulin cytotoxicity and genotoxicity in HepG2 cells
    • COI: 1:CAS:528:DC%2BC3sXntVaqt7c%3D, PID: 21656641
    • Ayed-Boussema I, Abassi H, Bouaziz C, Hlima WB, Ayed Y, Bacha H (2013) Antioxidative and antigenotoxic effect of vitamin E against patulin cytotoxicity and genotoxicity in HepG2 cells. Environ Toxicol 28:299–306
    • (2013) Environ Toxicol , vol.28 , pp. 299-306
    • Ayed-Boussema, I.1    Abassi, H.2    Bouaziz, C.3    Hlima, W.B.4    Ayed, Y.5    Bacha, H.6
  • 6
    • 0027205012 scopus 로고
    • Mass spectrometry in the analysis of glutathione conjugates
    • COI: 1:CAS:528:DyaK3sXltFams7k%3D, PID: 8329460
    • Baillie TA, Davis MR (1993) Mass spectrometry in the analysis of glutathione conjugates. Biol Mass Spectrom 22:319–325
    • (1993) Biol Mass Spectrom , vol.22 , pp. 319-325
    • Baillie, T.A.1    Davis, M.R.2
  • 7
    • 26844473978 scopus 로고    scopus 로고
    • Kinetic analysis of the chronology of patulin- and gossypol-induced cytotoxicity in vitro
    • COI: 1:CAS:528:DyaK28XitlSmtL8%3D, PID: 8812278
    • Barhoumi R, Burghardt RC (1996) Kinetic analysis of the chronology of patulin- and gossypol-induced cytotoxicity in vitro. Fundam Appl Toxicol 30:290–297
    • (1996) Fundam Appl Toxicol , vol.30 , pp. 290-297
    • Barhoumi, R.1    Burghardt, R.C.2
  • 8
    • 0028036292 scopus 로고
    • Detoxication of base propenals and other α, β-unsaturated aldehyde products of radical reactions and lipid peroxidation by human glutathione transferases
    • COI: 1:CAS:528:DyaK2cXhvVGitbw%3D, PID: 8108434
    • Berhane K, Widersten M, Engström A, Kozarich JW, Mannervik B (1994) Detoxication of base propenals and other α, β-unsaturated aldehyde products of radical reactions and lipid peroxidation by human glutathione transferases. Proc Natl Acad Sci USA 91:1480–1484
    • (1994) Proc Natl Acad Sci USA , vol.91 , pp. 1480-1484
    • Berhane, K.1    Widersten, M.2    Engström, A.3    Kozarich, J.W.4    Mannervik, B.5
  • 9
    • 0039469984 scopus 로고
    • Studies on structurally simple α, β-butenolides V. Reactions of protoanemonin with piperidine and C-nucleophiles. A general approach to its behaviour as electrophilic acceptor
    • COI: 1:CAS:528:DyaL28XltFCnsL0%3D
    • Bigorra J, Font J, Jaime C, Ortuno RM, Sanchez-Ferrando F (1985) Studies on structurally simple α, β-butenolides V. Reactions of protoanemonin with piperidine and C-nucleophiles. A general approach to its behaviour as electrophilic acceptor. Tetrahedron 41:5577–5587
    • (1985) Tetrahedron , vol.41 , pp. 5577-5587
    • Bigorra, J.1    Font, J.2    Jaime, C.3    Ortuno, R.M.4    Sanchez-Ferrando, F.5
  • 10
    • 0001394763 scopus 로고
    • Studies on structurally simple a, ß-butenolides I. New syntheses of racemic γ-hydroxymethyl- α, β-butenolide and derivatives
    • COI: 1:CAS:528:DyaL3sXitFGnsLs%3D
    • Cardellach J, Estopa C, Font J, Moreno-Mañas M, Ortuño RM, Sanchez-Ferrando F, Valle S, Vilamajo L (1982) Studies on structurally simple a, ß-butenolides I. New syntheses of racemic γ-hydroxymethyl- α, β-butenolide and derivatives. Tetrahedron 38:2377–2394
    • (1982) Tetrahedron , vol.38 , pp. 2377-2394
    • Cardellach, J.1    Estopa, C.2    Font, J.3    Moreno-Mañas, M.4    Ortuño, R.M.5    Sanchez-Ferrando, F.6    Valle, S.7    Vilamajo, L.8
  • 11
    • 0018640307 scopus 로고
    • DNA crosslinking, sister-chromatid exchange and specific-locus mutations
    • COI: 1:CAS:528:DyaL3cXlt1Oktw%3D%3D, PID: 522865
    • Carrano AV, Thompson LH, Stetka DG, Minkler JL, Mazrimas JA, Fong S (1979) DNA crosslinking, sister-chromatid exchange and specific-locus mutations. Mutat Res 63:175–188
    • (1979) Mutat Res , vol.63 , pp. 175-188
    • Carrano, A.V.1    Thompson, L.H.2    Stetka, D.G.3    Minkler, J.L.4    Mazrimas, J.A.5    Fong, S.6
  • 12
    • 0028090617 scopus 로고
    • Mutagenicity of trans, trans-muconaldehyde and its metabolites in V79 cells
    • COI: 1:CAS:528:DyaK2cXmt1Cju7s%3D, PID: 7925324
    • Chang RL, Wong CQ, Kline SA, Conney AH, Goldstein BD, Witz G (1994) Mutagenicity of trans, trans-muconaldehyde and its metabolites in V79 cells. Environ Mol Mutagen 24:112–115
    • (1994) Environ Mol Mutagen , vol.24 , pp. 112-115
    • Chang, R.L.1    Wong, C.Q.2    Kline, S.A.3    Conney, A.H.4    Goldstein, B.D.5    Witz, G.6
  • 14
    • 0042978647 scopus 로고    scopus 로고
    • Mycotoxins in fruits, fruit juices, and dried fruits
    • COI: 1:CAS:528:DC%2BD3sXmvF2ktLw%3D, PID: 12929850
    • Drusch S, Ragab W (2003) Mycotoxins in fruits, fruit juices, and dried fruits. J Food Prot 66:1514–1527
    • (2003) J Food Prot , vol.66 , pp. 1514-1527
    • Drusch, S.1    Ragab, W.2
  • 15
    • 0027291213 scopus 로고
    • Identification and characterization of deoxyguanosine adducts of mutagenic beta-alkyl-substituted acrolein congeners
    • COI: 1:CAS:528:DyaK3sXltlehsbY%3D, PID: 8374046
    • Eder E, Hoffman C (1993) Identification and characterization of deoxyguanosine adducts of mutagenic beta-alkyl-substituted acrolein congeners. Chem Res Toxicol 6:486–494
    • (1993) Chem Res Toxicol , vol.6 , pp. 486-494
    • Eder, E.1    Hoffman, C.2
  • 16
    • 84958136077 scopus 로고    scopus 로고
    • EU SCOOP (2002) Scientific Cooperation (SCOOP) Task Reports. Task 3.2.8. Assessment of dietary intake of patulin by the population of EU member states. Directorate-General Health and Consumer Protection, March 2002. Accessed Nov 27, 2013
    • EU SCOOP (2002) Scientific Cooperation (SCOOP) Task Reports. Task 3.2.8. Assessment of dietary intake of patulin by the population of EU member states. Directorate-General Health and Consumer Protection, March 2002. http://ec.europa.eu/food/fs/scoop/3.2.8_en.pdf. Accessed Nov 27, 2013
  • 17
    • 0032703307 scopus 로고    scopus 로고
    • The mycotoxin patulin induces intra- and intermolecular protein crosslinks in vitro involving cysteine, lysine, and histidine side chains, and alpha-amino groups
    • COI: 1:CAS:528:DyaK1MXntVeqtLc%3D, PID: 10597903
    • Fliege R, Metzler M (1999) The mycotoxin patulin induces intra- and intermolecular protein crosslinks in vitro involving cysteine, lysine, and histidine side chains, and alpha-amino groups. Chem Biol Interact 123:85–103
    • (1999) Chem Biol Interact , vol.123 , pp. 85-103
    • Fliege, R.1    Metzler, M.2
  • 18
    • 0034128518 scopus 로고    scopus 로고
    • Electrophilic properties of patulin. N-acetylcysteine and glutathione adducts
    • COI: 1:CAS:528:DC%2BD3cXisVelsrY%3D, PID: 10813654
    • Fliege R, Metzler M (2000a) Electrophilic properties of patulin. N-acetylcysteine and glutathione adducts. Chem Res Toxicol 13:373–381
    • (2000) Chem Res Toxicol , vol.13 , pp. 373-381
    • Fliege, R.1    Metzler, M.2
  • 19
    • 0034039154 scopus 로고    scopus 로고
    • Electrophilic properties of patulin. Adduct structures and reaction pathways with 4-bromothiophenol and other model nucleophiles
    • COI: 1:CAS:528:DC%2BD3cXisVelsrk%3D, PID: 10813653
    • Fliege R, Metzler M (2000b) Electrophilic properties of patulin. Adduct structures and reaction pathways with 4-bromothiophenol and other model nucleophiles. Chem Res Toxicol 13:363–372
    • (2000) Chem Res Toxicol , vol.13 , pp. 363-372
    • Fliege, R.1    Metzler, M.2
  • 20
    • 72749086094 scopus 로고    scopus 로고
    • An overview of chemical processes that damage cellular DNA: spontaneous hydrolysis, alkylation, and reactions with radicals
    • COI: 1:CAS:528:DC%2BD1MXhtFemu7bI, PID: 19757819
    • Gates KS (2009) An overview of chemical processes that damage cellular DNA: spontaneous hydrolysis, alkylation, and reactions with radicals. Chem Res Toxicol 22:1747–1760
    • (2009) Chem Res Toxicol , vol.22 , pp. 1747-1760
    • Gates, K.S.1
  • 21
    • 84859813375 scopus 로고    scopus 로고
    • Patulin: mechanism of genotoxicity
    • COI: 1:CAS:528:DC%2BC38XmtVCit7g%3D, PID: 22425938
    • Glaser N, Stopper H (2012) Patulin: mechanism of genotoxicity. Food Chem Toxicol 50:1796–1801
    • (2012) Food Chem Toxicol , vol.50 , pp. 1796-1801
    • Glaser, N.1    Stopper, H.2
  • 23
    • 0000356602 scopus 로고
    • The reaction of diazomethane and its derivatives with aldehydes and ketones
    • Gutsche CD (1954) The reaction of diazomethane and its derivatives with aldehydes and ketones. Org React 8:364–429
    • (1954) Org React , vol.8 , pp. 364-429
    • Gutsche, C.D.1
  • 24
    • 0041377897 scopus 로고    scopus 로고
    • α, β-unsaturated carbonyl compounds: induction of oxidative DNA damage in mammalian cells
    • COI: 1:CAS:528:DC%2BD3sXnt1Kisrw%3D, PID: 12960416
    • Janzowski C, Glaab V, Mueller C, Straesser U, Kamp HG, Eisenbrand G (2003) α, β-unsaturated carbonyl compounds: induction of oxidative DNA damage in mammalian cells. Mutagenesis 18:465–470
    • (2003) Mutagenesis , vol.18 , pp. 465-470
    • Janzowski, C.1    Glaab, V.2    Mueller, C.3    Straesser, U.4    Kamp, H.G.5    Eisenbrand, G.6
  • 25
    • 0034671702 scopus 로고    scopus 로고
    • Specific DNA adducts induced by some mono-substituted epoxides in vitro and in vivo
    • COI: 1:CAS:528:DC%2BD3MXnslWntg%3D%3D, PID: 11137062
    • Koskinen M, Plná K (2000) Specific DNA adducts induced by some mono-substituted epoxides in vitro and in vivo. Chem Biol Interact 129:209–229
    • (2000) Chem Biol Interact , vol.129 , pp. 209-229
    • Koskinen, M.1    Plná, K.2
  • 27
    • 0043234938 scopus 로고    scopus 로고
    • Evaluation of genotoxic risk and oxidative DNA damage in mammalian cells exposed to mycotoxins, patulin and citrinin
    • COI: 1:CAS:528:DC%2BD3sXnt1amu70%3D, PID: 13678658
    • Liu BH, Yu FY, Wu TS, Li SY, Su MC, Wang MC, Shih SM (2003) Evaluation of genotoxic risk and oxidative DNA damage in mammalian cells exposed to mycotoxins, patulin and citrinin. Toxicol Appl Pharmacol 191:255–263
    • (2003) Toxicol Appl Pharmacol , vol.191 , pp. 255-263
    • Liu, B.H.1    Yu, F.Y.2    Wu, T.S.3    Li, S.Y.4    Su, M.C.5    Wang, M.C.6    Shih, S.M.7
  • 28
    • 0031927107 scopus 로고    scopus 로고
    • Aneuploidogenic and clastogenic potential of the mycotoxins citrinin and patulin
    • COI: 1:CAS:528:DyaK1cXkvV2gsLc%3D, PID: 9683194
    • Pfeiffer E, Gross K, Metzler M (1998) Aneuploidogenic and clastogenic potential of the mycotoxins citrinin and patulin. Carcinogenesis 19:1313–1318
    • (1998) Carcinogenesis , vol.19 , pp. 1313-1318
    • Pfeiffer, E.1    Gross, K.2    Metzler, M.3
  • 29
    • 84863920443 scopus 로고    scopus 로고
    • Contributions of human enzymes in carcinogen metabolism
    • COI: 1:CAS:528:DC%2BC38XlvFGjsrY%3D, PID: 22531028
    • Rendic S, Guengerich FP (2012) Contributions of human enzymes in carcinogen metabolism. Chem Res Toxicol 25:1316–1383
    • (2012) Chem Res Toxicol , vol.25 , pp. 1316-1383
    • Rendic, S.1    Guengerich, F.P.2
  • 30
    • 67449149687 scopus 로고    scopus 로고
    • Analysis of glutathione adducts of patulin by means of liquid chromatography (HPLC) with biochemical detection (BCD) and electrospray ionization tandem mass spectrometry (ESI–MS/MS)
    • COI: 1:CAS:528:DC%2BD1MXkvFGjsbY%3D, PID: 19390846
    • Schebb NH, Faber H, Maul R et al (2009) Analysis of glutathione adducts of patulin by means of liquid chromatography (HPLC) with biochemical detection (BCD) and electrospray ionization tandem mass spectrometry (ESI–MS/MS). Anal Bioanal Chem 394:1361–1373
    • (2009) Anal Bioanal Chem , vol.394 , pp. 1361-1373
    • Schebb, N.H.1    Faber, H.2    Maul, R.3
  • 31
    • 14644408151 scopus 로고    scopus 로고
    • Mutagenicity of the mycotoxin patulin in cultured Chinese hamster V79 cells, and its modulation by intracellular glutathione
    • COI: 1:CAS:528:DC%2BD2MXhtF2gt7k%3D, PID: 15536543
    • Schumacher DM, Metzler M, Lehmann L (2005a) Mutagenicity of the mycotoxin patulin in cultured Chinese hamster V79 cells, and its modulation by intracellular glutathione. Arch Toxicol 79:110–121
    • (2005) Arch Toxicol , vol.79 , pp. 110-121
    • Schumacher, D.M.1    Metzler, M.2    Lehmann, L.3
  • 32
    • 33646758269 scopus 로고    scopus 로고
    • Influence of decreased intracellular glutathione level on the mutagenicity of patulin in cultured mouse lymphoma cells
    • COI: 1:CAS:528:DC%2BD2MXhtlWqsbfJ, PID: 23605280
    • Schumacher DM, Wagner J, Metzler M, Lehmann L (2005b) Influence of decreased intracellular glutathione level on the mutagenicity of patulin in cultured mouse lymphoma cells. Mycotoxin Res 21:150–152
    • (2005) Mycotoxin Res , vol.21 , pp. 150-152
    • Schumacher, D.M.1    Wagner, J.2    Metzler, M.3    Lehmann, L.4
  • 33
    • 33748802756 scopus 로고    scopus 로고
    • DNA–DNA cross-links contribute to the mutagenic potential of the mycotoxin patulin
    • COI: 1:CAS:528:DC%2BD28XpvV2lt7c%3D, PID: 16978808
    • Schumacher DM, Müller C, Metzler M, Lehmann L (2006) DNA–DNA cross-links contribute to the mutagenic potential of the mycotoxin patulin. Toxicol Lett 166:268–275
    • (2006) Toxicol Lett , vol.166 , pp. 268-275
    • Schumacher, D.M.1    Müller, C.2    Metzler, M.3    Lehmann, L.4
  • 34
    • 31544440695 scopus 로고    scopus 로고
    • Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection
    • COI: 1:CAS:528:DC%2BD28Xmslyrug%3D%3D, PID: 16272169
    • Singh R, Farmer PB (2006) Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection. Carcinogenesis 27:178–196
    • (2006) Carcinogenesis , vol.27 , pp. 178-196
    • Singh, R.1    Farmer, P.B.2
  • 35
    • 0030754684 scopus 로고    scopus 로고
    • Adenine adducts with diepoxybutane: isolation and analysis in exposed calf thymus DNA
    • COI: 1:CAS:528:DyaK2sXmslWiurg%3D, PID: 9348440
    • Tretyakova N, Sangaiah R, Yen TY, Gold A, Swenberg JA (1997) Adenine adducts with diepoxybutane: isolation and analysis in exposed calf thymus DNA. Chem Res Toxicol 10:1171–1179
    • (1997) Chem Res Toxicol , vol.10 , pp. 1171-1179
    • Tretyakova, N.1    Sangaiah, R.2    Yen, T.Y.3    Gold, A.4    Swenberg, J.A.5
  • 36
    • 0031921976 scopus 로고    scopus 로고
    • Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry
    • COI: 1:CAS:528:DyaK1cXjtV2jsr8%3D, PID: 9597770
    • Tretyakova N, Chiang SY, Walker VE, Swenberg JA (1998) Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry. J Mass Spectrom 33:363–376
    • (1998) J Mass Spectrom , vol.33 , pp. 363-376
    • Tretyakova, N.1    Chiang, S.Y.2    Walker, V.E.3    Swenberg, J.A.4
  • 37
    • 84876110558 scopus 로고    scopus 로고
    • Mass spectrometry of structurally modified DNA
    • COI: 1:CAS:528:DC%2BC3sXjtVCks7s%3D, PID: 23441727
    • Tretyakova N, Villalta PW, Kotapati S (2013) Mass spectrometry of structurally modified DNA. Chem Rev 113:2395–2436
    • (2013) Chem Rev , vol.113 , pp. 2395-2436
    • Tretyakova, N.1    Villalta, P.W.2    Kotapati, S.3
  • 38
    • 0021236745 scopus 로고
    • Counter-irritant and other medicinal uses of plants in Ranunculaceae by native peoples in British Columbia and neighbouring areas
    • COI: 1:STN:280:DyaL2M%2FjsFSmsQ%3D%3D, PID: 6387285
    • Turner NJ (1984) Counter-irritant and other medicinal uses of plants in Ranunculaceae by native peoples in British Columbia and neighbouring areas. J Ethnopharmacol 11:181–201
    • (1984) J Ethnopharmacol , vol.11 , pp. 181-201
    • Turner, N.J.1
  • 39
    • 84976224886 scopus 로고    scopus 로고
    • Toxicological evaluation of certain food additives and contaminants. WHO Food Additives Series 35; 847. Patulin. Prepared by: The 44th meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). World Health Organization
    • WHO (1996) Toxicological evaluation of certain food additives and contaminants. WHO Food Additives Series 35; 847. Patulin. Prepared by: The 44th meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). World Health Organization, Geneva 1996
    • (1996) Geneva , pp. 1996
  • 41
    • 80053368007 scopus 로고    scopus 로고
    • 6-Gingerol prevents patulin-induced genotoxicity in HepG2 cells
    • COI: 1:CAS:528:DC%2BC3MXht1amtb7J, PID: 21953711
    • Yang G, Zhong L, Jiang L, Geng C, Cao J, Sun X, Liu X, Chen M, Ma Y (2011) 6-Gingerol prevents patulin-induced genotoxicity in HepG2 cells. Phytother Res 25:1480–1485
    • (2011) Phytother Res , vol.25 , pp. 1480-1485
    • Yang, G.1    Zhong, L.2    Jiang, L.3    Geng, C.4    Cao, J.5    Sun, X.6    Liu, X.7    Chen, M.8    Ma, Y.9
  • 42
    • 61449262757 scopus 로고    scopus 로고
    • Patulin-induced genotoxicity and modulation of glutathione in HepG2 cells
    • COI: 1:CAS:528:DC%2BD1MXislKmsrk%3D, PID: 19673104
    • Zhou SM, Jiang LP, Geng CY, Cao J, Zhong LF (2009) Patulin-induced genotoxicity and modulation of glutathione in HepG2 cells. Toxicon 53:584–586
    • (2009) Toxicon , vol.53 , pp. 584-586
    • Zhou, S.M.1    Jiang, L.P.2    Geng, C.Y.3    Cao, J.4    Zhong, L.F.5
  • 43
    • 72749095740 scopus 로고    scopus 로고
    • Patulin-induced oxidative DNA damage and p53 modulation in HepG2 cells
    • COI: 1:CAS:528:DC%2BC3cXjs1Gm, PID: 19744505
    • Zhou SM, Jiang LP, Geng CY, Cao J, Zhong LF (2010) Patulin-induced oxidative DNA damage and p53 modulation in HepG2 cells. Toxicon 55:390–395
    • (2010) Toxicon , vol.55 , pp. 390-395
    • Zhou, S.M.1    Jiang, L.P.2    Geng, C.Y.3    Cao, J.4    Zhong, L.F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.