Table 2 Mutagenicity of heterocyclic amines in Salmonella typhimurium YG strains
Chemical | Strain | Metabolic activation | Remarks | Reference |
|---|---|---|---|---|
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) | TA98, TA98NR, YG1024, TA98/1,8-DNP6 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024 > TA98 = TA98/1,8-DNP6 = TA98NR | [46] |
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) | TA98, YG1024 | W | The sensitivity was about 3 times higher in YG1024 than in TA98. The mutagenic potency (induced revertants/μg) was more than 100 times lower than that of MeIQx. | [47] |
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) | YG1024 | W | The mutagenicity of PhIP was enhanced up to six times by the presence of ethylparathion, methylparathion or methyl paraoxon. | [48] |
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) | TA98, YG1024 | W* | PhIP was negative in both strains in the presence of colon S9 prepared from 3-MC-treated rats. | [49] |
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) | TA1538, YG1019 | W | The mutagenic potency (revertants/ng) was in the order of MeIQx = IQ > 4,8-diMeIQx>> > PhIP>MeAαC>AαC in YG1019. | [50] |
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) | YG1024 | W* | The mutagenic potency was IQ = MeIQ>Trp-P-1 = MeIQx>PhIP in the presence of HepG2 cell homogenates. The order was unchanged when rat S9 was used although the mutagenic potency was much more enhanced with rat S9. | [51] |
2-nitro-1-methyl-6-phenylimidazo [4,5-b]pyridine (NO2-PhIP) | TA98, TA98NR, YG1024, TA98/1,8-DNP6 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1024 = TA98 > TA98/1,8-DNP6 > TA98NR. | [46] |
2-azido-1-methyl-6-phenylimidazo [4,5-b]pyridine (azido-PhIP) | TA98, TA98NR, YG1024, TA98/1,8-DNP6 | W* | Near UV light was used for activation. The sensitivity (induced revertants/nmol) was in the order of YG1024 = TA98 = TA98NR > TA98/1,8-DNP6. | [46] |
2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1) | YG1020, YG1024, YG1025, YG1029 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024> > YG1020 > YG1029 > YG1025. | [16] |
2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1) | TA98, TA98NR, TA98/1,8-DNP6, YG1021, YG1024 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024 > YG1021 > TA98 > TA98NR > TA98/1,8-DNP6. | [36] |
2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1) | YG1020, YG1024, YG1012, YG1019 | W | The sensitivity (induced revertants/nmol) was in the order of YG1012 > YG1019 = YG1024 > YG1020. | [23] |
2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1) | TA98, YG1021, YG1024, YG1041 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024 = YG1041 > TA98 > YG1021. | [26] |
2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1) | YG1024 | W | YG1024 may lose plasmid pYG219 under highly toxic conditions. | [52] |
2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1) | YG1006, TA98 | W* | Ram seminal vesicle microsomes (prostaglandin H synthase) activated Glu-P-1 for mutagenesis in YG1006. | [53] |
2-hydroxyamino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (N-OH-Glu-P-1) | YG1020, YG1024, YG1025, YG1029 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1024> > YG1020 > YG1029 > YG1025. S9 was not needed for the mutagenicity. | [16] |
2-hydroxyamino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (N-OH-Glu-P-1) | TA98, TA98NR, TA98/1,8-DNP6, YG1021, YG1024 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1024 > TA98 = YG1021 = TA98NR > TA98/1,8-DNP6. S9 was not needed for the mutagenicity. | [36] |
2-hydroxyamino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (N-OH-Glu-P-1) | TA98, YG1021, YG1024, YG1041 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1041 > YG1024 > YG1021 = TA98. | [26] |
2-nitro-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (NO2-Glu-P-1) | TA98, YG1021, YG1024, YG1041 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1041> > YG1024 > YG1021 > TA98. | [26] |
2-nitro-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (NO2-Glu-P-1) | TA98, TA98NR, TA98/1,8-DNP6, YG1021, YG1024 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1024 > YG1021 > TA98 > TA98/1,8-DNP6 > TA98NR. | [36] |
3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) | YG1024 | W* | The mutagenic potency was IQ = MeIQ>Trp-P-1 = MeIQx>PhIP in the presence ofI HepG2 cell homogenates. The order was unchanged when rat S9 was used although the mutagenic potency was much more enhanced with rat S9. | [51] |
3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) | TA98, YG1024 | W | Trp-P-1 was identified in samples from the Danube River in Vienna. | [43] |
3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) | TA98, TA98NR, TA98/1,8-DNP6, YG1021, YG1024 | W | The sensitivity (induced revertants/nmol) was in the order of TA98/1,8-DNP6 > YG1021 = TA98 > YG1024 = TA98NR. | [36] |
3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) | TA98, YG1021, YG1024, YG1041 | W | The sensitivity (induced revertants/nmol) was not substantially different among the four strains. | [26] |
3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) | TA98, YG1024 | W* | Untreated rat liver S12 fraction was used for metabolic activation. The sensitivity was similar between TA98 and YG1024. | [54] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1012 | W* | Human or rat cytochrome P-450 1A2 plus hydrogen peroxide supported metabolic activation of IQ | [55] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | TA1538, YG1019 | W | The mutagenic potency (revertants/ng) was in the order of MeIQx = IQ > 4,8-diMeIQx>> > PhIP>MeAαC>AαC in YG1019. | [50] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | TA98, YG1024, TA98/1,8-DNP6 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024> > TA98> > TA98/1,8-DNP6. | [46] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1024 | W* | Ram seminal vesicle microsomes(supplemented with arachidonic acid) activated IQ for mutagenesis. | [56] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1024, TA98 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024 > TA98. | [57] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1024 | W* | The mutagenic potency was IQ = MeIQ>Trp-P-1 = MeIQx>PhIP in the presence of HepG2 cell homogenates. The order was unchanged when rat S9 was used although the mutagenic potency was much more enhanced with rat S9. | [51] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1024 | W* | The C8-dG-IQ-adduct N-(deoxyguanosin-8-yl)-IQ was the major adduct when IQ was incubated with YG1024 either in ovine seminal vesicle cells (prostaglandin H synthase) or hepatocytes (monooxygenases). | [58] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1024 | W | Urinary metabolites of IQ-treated rats were investigated with improved extraction methods and assay conditions. | [59] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1006, TA98 | W* | Ram seminal vesicle microsomes (prostaglandin H synthase) activated IQ for mutagenesis in YG1006. | [53] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1024 | W | The mutagenicity of IQ was enhanced about two times by the presence of methyl parathion and methyl paraoxon. | [48] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1012 | W* | Ram seminal vesicle microsomes (prostaglandin H synthase) activated IQ for mutagenesis in YG1012. | [25] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | TA98, YG1024 | W | IQ was identified in samples from the Danube River in Vienna. | [43] |
2-amino-3-methylimidazo[4,5-f]quinoline (IQ) | YG1024, TA98 | W | The mutagenic potency of IQ (revertants/μg) was more than 5 times higher than that of IQx. | [60] |
2-nitro-3-methylimidazo[4,5-f]quinoline (NO2-IQ) | TA98, YG1024, TA98/1,8-DNP6 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1024> > TA98> > TA98/1,8-DNP6. | [46] |
2-nitro-3-methylimidazo[4,5-f]quinoline (NO2-IQ) | YG1024 | W/O | NO2-IQ and NO-IQ exhibited similar mutagenicity to YG1024. | [56] |
2-nitro-3-methylimidazo[4,5-f]quinoline (NO2-IQ) | YG1012, YG1024, YG1024NR | W/O | NO2-IQ was a metabolite of IQ by ram seminal vesicle microsomes (prostaglandin H synthase). YG1012 exhibited similar or slightly higher sensitivity to NO2-IQ than YG1024. | [25] |
2-nitroso-3-methylimidazo[4,5-f]quinoline (NO-IQ) | YG1024 | W/O | NO2-IQ and NO-IQ showed similar mutagenicity to YG1024. | [56] |
7-hydroxy-2-amino-3-methylimidazo[4,5-f]quinoline (7-OH-IQ) | YG1012, YG1024NR | W/O | 7-OH-IQ was a possible metabolite of IQ by ram seminal vesicle microsomes. The mutagenicity was substantially lower than that of NO2-IQ. | [25] |
2, 2′-azo-bis-3-methylimidazo[4,5-f]quinoline (azo-IQ) | YG1024, TA98 | W/O | azo-IQ was a metabolite of IQ in the presence of ram seminal vesicle microsomes. The mutagenicity was much weaker than NO-IQ or NO2-IQ. | [56] |
2-amino-3-methylimidazo[4,5-f]quinoxaline (IQx) | YG1024, TA98 | W | The mutagenic potency of IQx (revertants/μg) was more than 50 times higher than that of 1-methynaphtho[2,3-d]imidazole-2-amine (Linear-NI). | [60] |
2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) | YG1024, TA98 | W | YG1024 may lose plasmid pYG219 under highly toxic conditions. | [52] |
2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) | YG1024, TA98 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024 > TA98. | [57] |
2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) | YG1024, TA98 | W* | Untreated rat liver S12 fraction was used for metabolic activation. The sensitivity was similar between TA98 and YG1024 because of the high toxicity. | [54] |
2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) | YG1024 | W* | The mutagenic potency was IQ = MeIQ>Trp-P-1 = MeIQx>PhIP in the presence of HepG2 cell homogenates. The order was unchanged when rat S9 was used although the mutagenic potency was much more enhanced with rat S9. | [51] |
2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) | YG1006, TA98 | W* | Ram seminal vesicle microsomes (prostaglandin H synthase) activated MeIQ for mutagenesis in YG1006. | [53] |
2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) | TA1538, YG1019 | W | The mutagenic potency (revertants/ng) was in the order of MeIQx = IQ > 4,8-diMeIQx>> > PhIP>MeAαC>AαC in YG1019. | [50] |
2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) | YG1024, TA98 | W* | MeIQx was mutagenic to YG1024 in the presence of human liver microsomes. YG1024 was more sensitive than TA98. N-OH-MeIQx was a major oxidation product by human liver microsomes. | [62] |
2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) | YG1024, TA98 | W | The sensitivity (induced revertants/nmol) was in the order of YG1024 > TA98. | [57] |
2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) | YG1024 | W* | The mutagenic potency was IQ = MeIQ>Trp-P-1 = MeIQx>PhIP in the presence of HepG2 cell homogenates. The order was unchanged when rat S9 was used although the mutagenic potency was much more enhanced with rat S9. | [51] |
2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) | YG1024, TA98 | W | The sensitivity (induced revertants/μg) was about 12 times higher in YG1024 than in TA98. | [47] |
2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) | YG1024 | W | The mutagenicity of MeIQx was suppressed by the urinary phenolics in humans. | [61] |
2-hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline (N-OHMeIQx) | TA98, YG1024, TA98/1,8-DNP6 | W/O | The sensitivity (induced revertants/nmol) was in the order of YG1024 > TA98 > TA98/1,8-DNP6. N-OH-MeIQx was identified as a major metabolite of MeIQx by human CYP1A2. | [62] |
2-amino-4-hydroxymethyl-3,8-dimethylimidazo[4,5-f]quinoxaline (4-CH2OH-8-MeIQx) | YG1024, TA98, TA100 | W | The sensitivity was in the order of YG1024 > TA98> > TA100. | [63] |
2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx) | TA1538, YG1019 | W | The mutagenic potency (revertants/ng) was in the order of MeIQx = IQ > 4,8-diMeIQx>> > PhIP>MeAαC>AαC in YG1019. | [50] |
2-amino-1,7,9-trimethylimidazo[4,5-g]quinoxaline (7,9-diMeIQx) | YG1024, TA98 | W | The sensitivity was in the order of YG1024 > TA98. The mutagenic potency (induced revertants/μg) of 7,9-diMeIQx was 250 times lower than those of MeIQx and 4,8-diMeIQx and 3 times lower than that of PhIP. | [64] |
2-amino-1,6-dimethylimidazo[4,5-g]quinoxaline (6-MeIQx) | YG1024, TA98 | W | The sensitivity was about 8 fold higher in YG1024 than in TA98. 6-MeIQx was a weak mutagen. | [47] |
2-amino-1,7-dimethylimidazo[4,5-g]quinoxaline (7-MeIQx) | YG1024, TA98 | W | The sensitivity was about 16 times higher in YG1024 than in TA98. The mutagenic potency (induced revertants/μg) was more than 4000 times lower than that of MeIQx. | [47] |
2-amino-1,7,9-trimethylimidazo[4,5-g]quinoxaline (7,9-diMeIQx) | YG1024, TA98 | W | The sensitivity was about 4 times higher in YG1024 than in TA98. The mutagenic potency (induced revertants/μg) was more than 100 times lower than that of MeIQx. | [47] |
9-(4′-aminophenyl)-9H-pyrido[3,4-b]indole (aminophenylnorharman, APNH) | TA98, YG1024, TA100, YG1029 | W | APNH was formed from aniline and norharman in the presence of S9 mix. The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency of APNH (revertants/μg) was comparable to those of MeIQx and Glu-P-1. | [65] |
9-(4′-hydroxyaminophenyl)-9H-pyrido[3,4-b]indole (hydroxyaminophenylnorharman) | YG1024 | W/O | N-hydroxy derivative of APNH. | [65] |
9-(4′-amino-3′-methylphenyl)-9H-pyrido[3,4-b]indole (amino-3′-methylphenylnorharman) | TA98, TA100, YG1024, YG1029 | W | Amino-3′-methylphenylnorharman was formed from aniline and o-toluidine in the presence of S9 mix.. The sensitivity was YG1024> > TA98 > YG1029 > TA100. The mutagenic potency (revertants/μg) was weaker than that of aminophenylnorharman. | [66] |
9-(4′-amino-2′-methylphenyl)-9H-pyrido[3,4-b]indole (amino-2′-methylphenylnorharman) | TA98, TA100, YG1024, YG1029 | W | Amino-2′-methylphenylnorharman was formed from aniline and m-toluidine in the presence of S9 mix. The sensitivity was YG1024> > TA98 > YG1029 > TA100. The mutagenic potency (revertants/μg) was weaker than that of amino-3′-methylphenylnorharman. | [66] |
5-amino-6-hydroxy-8H-benzo[6,7]azepino[5,4,3-de]quinolin-7-one (ABAQ) | TA98, TA100, YG1024, YG1029 | W | ABAQ was formed by the Maillard reaction of glucose and amino acids. The sensitivity was YG1024> > TA98 > YG1029 > TA100. The mutagenic potency of ABAQ (revertants/μg) was comparable to that of PhIP. | [67] |
2-amino-9H-pyrido[2,3-b]indole (AαC) | TA1538, YG1019 | W | The mutagenic potency (revertants/ng) was in the order of MeIQx = IQ > 4,8-diMeIQx>> > PhIP>MeAαC>AαC in YG1019. | [50] |
2-amino-9H-pyrido[2,3-b]indole (AαC) | YG1019, TA1538 | W | AαC is a mutagen detected in panfried or grilled meat. YG1019 exibited higher sensitivity to AαC than TA1538. | [68] |
2-amino-9H-pyrido[2,3-b]indole (AαC) | TA98, YG1024 | W | AαC was identified in samples from the Danube River in Vienna. | [43] |
2-nitro-9H-pyrido[2,3-b]indole (NαC) | YG1019 | W/O | NαC was a direct-acting mutagen. The mutagenic potency in the absence of S9 was lower than that of AαC in the presence of S9. | [68] |
2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeAαC) | TA1538, YG1019 | W | The mutagenic potency (revertants/ng) was in the order of MeIQx = IQ > 4,8-diMeIQx>> > PhIP>MeAαC>AαC in YG1019. | [50] |
1-methylimidazo[4,5-b][1,8]naphthyridin-2-amine (compound 1) | YG1024, TA98 | W | The mutagenic potency (revertants/μg) was IQ> > IQx> > Linear-NI > compound 2 > compound 5 > compound 3 = compound 4 > compound 1. The sensitivity was YG1024 > > TA98. | [60] |
1-methylimidazo[4,5-b][1,7]naphthyridin-2-amine (compound 2) | YG1024, TA98 | W | ||
1-methylimidazo[4,5-b][1,6]naphthyridin-2-amine (compound 3) | YG1024, TA98 | W | ||
1-methylimidazo[4,5-g][1,5]naphthyridin-2-amine (compound 4) | YG1024, TA98 | W | ||
1-methylimidazo[4,5-b]quinoline-2-amine (compound 5) | YG1024, TA98 | W | ||
1-methynaphtho[2,3-d]imidazole-2-amine (linear-NI) | YG1024, TA98 | W | ||
2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-1) | YG1024 | W | PBTA-1 was a novel aromatic amine mutagen isolated from river water in Kyoto. The mutagenicity potency (revertants/μg) was comparable to that of Glu-P-1. | [69] |
2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-1) | TA98, TA100, YG1024, YG1029 | W | The sensitivity was in the order of YG1024 > > TA98 > YG1029> > TA100. | [70] |
2-[(2-bromo-4,6-dinitrophenyl)azo]-4-methoxy-5-[bis(2-methoxyethyl)amino]acetoanilide (AZO DYE-1) | TA98, TA100, YG1024, YG1029 | W | AZO DYE-1 was converted to PBTA-1 through deClPBTA-1. The potency of AZO DYE-1 (revertants/μg) was 1000-fold lower than that of PBTA-1. | [70] |
2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-6-amino-4-bromo-2H-benzotriazole (deClPBTA-1) | TA98, TA100, YG1024, YG1029 | W | deClPBTA-1 was an intermediate from AZO-DYE-1 to PBTA-1. The potency of deClPBTA-1 (revertants/μg) was lower than that of PBTA-1 but higher than that of AZO-DYE-1. | [70] |
2-[2-(acetylamino)-4-[N-(2-cyanoethyl)ethylamino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-2) | TA98, TA100, YG1024, YG1029 | W | PBTA-2 was a novel aromatic amine mutagen isolated from river water in Kyoto. The sensitivity was YG1024> > TA98. The mutagen may be produced from an azo dye in dyeing factories and treatment at sewage plants. | [71] |
2-[(2-bromo-4,6-dinitrophenyl)azo]-5-[N-(2-cyanoethyl)ethylamino]-4-methoxyacetoanilide (AZO DYE-2) | TA98, TA100, YG1024, YG1029 | W | AZO DYE-2 was converted to PBTA-2 through deClPBTA-2. The potency of AZO DYE-2 (revertants/μg) was 1000-fold lower than that of PBTA-1. | [71] |
2-[2-(acetylamino)-4-[N-(2-cyanoethyl)ethylamino]-5-methoxyphenyl]-6-amino-4-bromo-2H-benzotriazole (deClPBTA-2) | TA98, TA100, YG1024, YG1029 | W | deClPBTA-2 was an intermediate from AZO-DYE-2 to PBTA-2. The potency of deClPBTA-2 (revertants/μg) was lower than PBTA-2 but higher than AZO-DYE-2. | [71] |
PBTA-1, PBTA-2 | YG1024 | W | PBTA-1 and PBTA-2 were released from sewage plants into the Yodo river in Japan. | [72] |
2-[2-(acetylamino)-4-[(2-hydroxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-3) | TA98, YG1024 | W | The sensitivity was YG1024> > TA98. The mutagenic potency of PBTA-3(revertants/μg) was comparable to those of PBTA-1 and PBTA-2. | [73] |
2-[2-(acetylamino)-4-amino-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-4) | TA98, TA100, YG1024, YG1029 | W | The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency of PBTA-4 (revertants/μg) was about twice as high as those of PBTA-1, PBTA-2 and PBTA-3. | [74] |
2-[2-(acetylamino)-4-amino-5-methoxyphenyl]-6-amino-4-bromo-2H-benzotriazole (non-ClPBTA-4) | TA98, TA100, YG1024, YG1029 | W | The sensitivity was YG1024> > YG1029 > TA98> > TA100. The mutagenic potency (revertants/μg) was about 20 times lower than that of PBTA-4. | [74] |
5-amino-2-[(2-bromo-4,6-dinitrophenyl)azo]-5-amino-4-methoxyacetoanilide (AZO DYE-4) | TA98, TA100, YG1024, YG1029 | W | AZO DYE-4 was converted to PBTA-4 through deClPBTA-4. The potency of AZO DYE-4 (revertants/μg) was more than 2000-fold lower than that of PBTA-4. | [74] |
2-[4-[bis(2-acetoxyethyl)amino]-2-(acetylamino)-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-5) | TA98, TA100, YG1024, YG1029 | W | The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency of PBTA-5 (revertants/μg) was about 10 times lower than that of PBTA4. | [75] |
2-[2-(acetylamino)-4-[bis-(2-hydroxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-6) | TA98, TA100, YG1024, YG1029 | W | The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency of PBTA-6 (revertants/μg) was two to three times lower than that of PBTA5. | [75] |
PBTA-3, PBTA-4, PBTA-6 | YG1024, YG1029 | W | PBTA-3, PBTA-4 and PBTA-6 substantially contributed to the mutagenicity of river water in Fukui, Japan. | [76] |
PBTA-2, PBTA-3, PBTA-4, PBTA-6 | YG1024 | W | PBTA2, PBTA-3, PBTA-4 and PBTA-6 were generated in a sawage treatment plant and released to the Uji River, Japan. | [77] |
2-[2-(acetylamino)-4-(diethylamino)-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-7) | TA98, TA100, YG1024, YG1029 | W | PBTA-7 was detected in river water In Japan. The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency (revertants/nmol) was comparable to that of PBTA-1. | [78] |
2-[2-(acetylamino)-4-(diallylamino)-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-8) | TA98, TA100, YG1024, YG1029 | W | PBTA-8 was detected in river water In Japan. The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency (revertants/nmol) was comparable to that of PBTA-1. | [78] |
PBTA-1, PBTA-2, PBTA-3, PBTA-4, PBTA-6, PBTA-7, PBTA-8 | YG1024 | W | About 5 kg PBTA-type mutagens are released per year from sewage plants in the Yodo river in Japan. | [79] |
2-[2-(acetylamino)-4-[(2-hydroxyethyl)amino]-5-methoxyphenyl]-6-amino-4-bromo-2H-benzotriazole (non-ClPBTA-3) | TA98, TA100, YG1024, YG1029 | W | The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency (revertants/μg) was more than 10 times lower than that of PBTA-3. | [80] |
2-[2-(acetylamino)-4-(diethylamino)-5-methoxyphenyl]-6-amino-4-bromo-2H-benzotriazole (non-ClPBTA-7) | TA98, TA100, YG1024, YG1029 | W | The sensitivity was YG1024> > TA98> > YG1029 > TA100. The mutagenic potency (revertants/μg) was more than 5 times lower than that of PBTA-7. | [80] |