Isolation and chemical-structural determination of a novel aromatic amine mutagen in water from the Nishitakase River in Kyoto
| Autor: | Masakatsu Tezuka, Atsuko Oguri, Jun Yamashita, Kuniro Tsuji, Takashi Sugimura, Hiroyuki Sawanishi, Yoshiyasu Terao, Takao Katsuhara, Keiji Wakabayashi, Haruo Nukaya, Kiyoka Kiyokawa, Takeshi Ohe |
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| Rok vydání: | 1998 |
| Předmět: |
chemistry.chemical_classification
Chemistry Aromatic amine Mutagen Fresh Water General Medicine Toxicology medicine.disease_cause High-performance liquid chromatography Ames test chemistry.chemical_compound Adsorption Column chromatography Japan Sephadex medicine Organic chemistry Amines Derivative (chemistry) Water Pollutants Chemical Nuclear chemistry Mutagens |
| Zdroj: | Chemical research in toxicology. 10(10) |
| ISSN: | 0893-228X |
| Popis: | Water samples from the Nishitakase River in Kyoto, Japan, especially taken at sites below sewage plants, show significantly high mutagenicity in the Ames test. In the present study, mutagens in the river water were adsorbed to 24 g of blue rayon, extracted, and separated by HPLC on ODS columns. Five mutagenic compounds (I-V) were isolated, and they accounted for 21%, 17%, 11%, 12%, and 6%, respectively, of the total mutagenicity of the blue rayon-adsorbed materials. With compound I obtained from adsorbate to 24 g of blue rayon as a marker, a large quantity (1.1 mg) of mutagenic compound I was isolated by Sephadex LH-20 column chromatography and HPLC on ODS columns from material adsorbed to 27 kg of blue cotton. X-ray crystal analysis was carried out with the debrominated derivative of compound I. Based on this X-ray crystallography data and the UV, mass, and 1H-NMR spectra of both the derivative and compound I, the structure of compound I was determined to be 2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-5-amino - 7-bromo-4-chloro-2H-benzotriazole (PBTA-1). PBTA-1 is a newly identified potent mutagen, inducing 1,200,000 revertants of Salmonella typhimurium YG1024 per microgram in the presence of S9 mix. |
| Databáze: | OpenAIRE |
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