Synthesis of 2-phenylbenzotriazole-type mutagens, PBTA-5 and PBTA-6, and their detection in river water from Japan

Watanabe, Tetsushi; Nukaya, Haruo; Terao, Yoshiyasu; Takahashi, Yoshifumi; Tada, Atsuko; Takamura, Takeji; Sawanishi, Hiroyuki; Ohe, Takeshi; Hirayama, Teruhisa; Sügimura, Takashi; Wakabayashi, Keiji

doi:10.1016/s1383-5718(01)00273-x

Cited by 43 publications

(43 citation statements)

References 20 publications

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“…Uma nova classe de compostos genotóxicos, os 2-fenilbenzotriazóis (PBTAs) foi descoberta e identificada em extratos obtidos através das técnicas de Blue rayon e Blue cotton in situ em rios do Japão, que recebiam efluentes de indústrias têxteis ou que continham corantes 5,6,8,9,31 , tendo sido esta técnica também utilizada no monitoramento destes contaminantes 32 . Os PBTAs são produtos formados a partir de dinitrofenilazo corantes, usados em processos industriais como, por ex., em unidades de tingimento.…”

Section: Métodos De Utilização Do Blue Rayon Blue Rayon In Situunclassified

“…Ainda como continuação do trabalho de Nukaya et al 9 foi identificado um outro composto, responsável por outros 12% da atividade mutagênica total dos extratos obtidos, como sendo o 2-[2-(acetilamino)-4-amino-5-metoxifenil]-5-amino-7-bromo-4-cloro-2H-benzotriazol (PBTA-4) 6 . Watanabe et al 5 Um ano mais tarde, Watanabe et al 31 …”

Section: Métodos De Utilização Do Blue Rayon Blue Rayon In Situunclassified

“…Neste grupo de contaminantes, os produtos químicos tóxicos ou cancerígenos têm recebido grande atenção 3 . Para análise dos contaminantes presentes em ambientes aquáti-cos, os procedimentos de extração/concentração são muito utilizados, pois estes normalmente estão em concentrações baixas, diluí-dos em grandes volumes de amostra, e os métodos seletivos de extração/concentração de amostras têm se mostrado bastante úteis no direcionamento das análises químicas de identificação, bem como na descoberta de novas classes de contaminantes ambientais [3][4][5][6][7][8][9] . Em 1983 foi descoberto que fibras de algodão ligadas covalentemente ao pigmento ftalocianina de cobre tiossulfato, denominadas Blue cotton (Figura 1), formavam um adsorvente seletivo para compostos policíclicos 10,11 .…”

Section: Introductionunclassified

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Uso do Blue Rayon para extração/concentração de compostos policíclicos em amostras ambientais

Kummrow

Umbuzeiro

2006

Quím. Nova

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Section: Métodos De Utilização Do Blue Rayon Blue Rayon In Situunclassified

Section: Introductionunclassified

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Uso do Blue Rayon para extração/concentração de compostos policíclicos em amostras ambientais

Kummrow

Umbuzeiro

2006

Quím. Nova

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“…Four hundred and sixtyseven (87z) of the water concentrates were mutagenic, and most of the positive water concentrates showed the highest activities in YG1024 with S9 mix. To date, we have detected seven 2-[2-(acetylamino)-4-amino-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA) congeners, which show strong mutagenicities toward YG1024 with S9 mix, as major mutagenic constituents in highly mutagenic river water concentrates collected in Kyoto, Aichi, and Fukui Prefectures, Japan (9)(10)(11)(12)(13)(14). Moreover, four non-chlorinated derivatives of PBTA, i.e.…”

Section: Introductionmentioning

confidence: 99%

Detection of 3,3′-Dichlorobenzidine in Water from the Waka River in Wakayama, Japan

Watanabe

Hasei

Ohe

et al. 2006

Genes and Environment

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In a previous study, we found that water concentrate from the Waka River, which ‰ows through an industrial area in Wakayama, Japan, showed signiˆcant mutagenicity in Salmonella typhimurium YG1024 without a mammalian metabolic system (S9 mix), and 4-amino-3,3?-dichloro-5,4?-dinitrobiphenyl (ADDB) was identiˆed as a major direct-acting mutagenic constituent in the water concentrate. ADDB induced 428,000 revertants/mg in YG1024 without S9 mix, and this activity was 48 times as high as that with S9 mix. In this study, to clarify whether other mutagenic contaminants were present in the river, water concentrates were collected at three sites along the Waka River and examined for mutagenicity by the Ames test using YG1024 and YG1029 with and without S9 mix. All water concentrates showed potent mutagenicity in YG1024 with and/or without S9 mix. ADDB was detected in water concentrate that was extremely mutagenic without S9 mix. An indirect-acting mutagen, which accounted for more than 30% of the total mutagenicity of the water concentrates in YG1024 with S9 mix, was isolated from two extremely mutagenic water concentrates by HPLC separation. On the basis of spectral data and co-chromatography using authentic chemicals, this mutagen was identiˆed as 3,3?-dichlorobenzidine (DCB). DCB showed strong mutagenicity in YG1024 with S9 mix, inducing 5,186 revertants/mg. DCB was detected in water concentrates collected on the other three sampling dates in the range from 15.8 to 28.5 mg/g of blue rayon. These results suggest that Waka River water might be continually contaminated with mutagens, and DCB was thought to be the major mutagenic constituent of the river water.

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“…Between 2000 and 2002, six PBTAtype compounds, i.e. 2- -8) were conˆrmed and were suggested to be formed from the corresponding dinitrophenylazo dyes via reduction with sodium hydrosulˆte and subsequent chlorination with sodium hypochlorite (17)(18)(19)(20). In fact, these PBTA-type compounds with the exclusion PBTA-5 were detected in concentrates collected at sites downstream from municipal sewage plants or textile-dying factories along several rivers ‰owing in geographically diŠerent areas in Japan (16)(17)(18)(19)(20)(21)(22)(23).…”

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confidence: 99%

Mutagenicity and Levels of 2-Phenylbenzotriazole (PBTA)-type Mutagens in Sewaga Effluent, River Water, Sediment and Drinking Water Collected from the Yodo River System, Japan

Ohe

Mizuno

Morisawa

et al. 2006

Genes and Environment

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In order to assess the potential hazards to human health and aquatic ecosystem, we examined the mutagenic activity of sewage eOEuents, river waters, sediments and drinking water collected from the Yodo River system, Japan. We also compared the levels of mutagenic activity with the levels of 2-phenylbenzotriazole (PBTA)-type mutagens formed from corresponding dinitrophenylazo dyes via reduction and subsequent chlorination. We assessed mutagenicity in the O-acetyltransferase-overexpressing frameshift strain YG1024 of Salmonella with S9 mix. Sixty-six samples among 133 adsorbates (50%) obtained by the blue rayon hanging method collected from 1996 to 2005 were classiˆed as extreme mutagenicity with more than 100,000 revertants per g blue rayon equivalent (BRE). The average mutagenicity of both sewage eOEuents and river waters at sites located below sewage plants was 382,400 revertants per g BRE (n＝86), which was 4.4 times as higher than the downstream river waters (87,900 revertants per g BRE, n＝47). PBTA-1 was detected in 33 samples among 76 (43%), and PBTA-2 was detected in 66 samples among 76 (87%), however, the concentration of these compounds ‰uctuated widely among the samples. Average concentrations of PBTA-1 and PBTA-2 were also much higher in sewage eOEuents and river waters at sites located below sewage plants (n＝50, PBTA-1, 24.1 ng/g BRE; PBTA-2, 88.4 ng/g BRE) than they were in downstream river water samples (n＝26, PBTA-1; 1.3 ng/g BRE, PBTA-2; 19.7 ng/g BRE). PBTA-1 and PBTA-2 accounted for 6% and 26% on average, respectively, of the total mutagenicity in all samples analyzed. Based on the concentrations of the PBTA-type mutagens and the eOEuent volume discharged from three sewage plants, we estimated that ¿5 kg/year of PBTAtype mutagens including PBTA-1, PBTA-2, PBTA-3, PBTA-4, PBTA-6, PBTA-7 and PBTA-8, were discharged from three sewage plants into rivers. Further studies showed that these PBTA-type mutagens in river water might not easily accumulate in the river sediment and these PBTAtype mutagens were not detected in drinking water. In thê nal study, we monitored quantitatively the mutagenic potency of water samples collected at twelve sites, including six sites mentioned above, from the Yodo River system using Sep-Pak C18 cartridge columns and Blue-Chitin columns. The average mutagenic activities recovered by these columns were 10,000 and 5,800 revertants/L. Theseˆndings demonstrate that the Yodo River system has been continually and heavily polluted with not only polycyclic planar mutagens, but also by a wide range of chemical mutagens released from sewage plants located along the tributaries for many years.

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Synthesis of 2-phenylbenzotriazole-type mutagens, PBTA-5 and PBTA-6, and their detection in river water from Japan

Cited by 43 publications

References 20 publications

Uso do Blue Rayon para extração/concentração de compostos policíclicos em amostras ambientais

Uso do Blue Rayon para extração/concentração de compostos policíclicos em amostras ambientais

Detection of 3,3′-Dichlorobenzidine in Water from the Waka River in Wakayama, Japan

Mutagenicity and Levels of 2-Phenylbenzotriazole (PBTA)-type Mutagens in Sewaga Effluent, River Water, Sediment and Drinking Water Collected from the Yodo River System, Japan

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