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Brominated analogs of 3‐chloro‐4‐(dichloromethyl)‐5‐hydroxy‐2(5 H )‐furanone: Preparation of 3‐chloro‐4‐(bromochloromethyl)‐5‐hydroxy‐2(5 H )‐furanone and mutagenicity studies
Author(s) -
Ramos Isabel,
Lloveras Maia,
Solans Xavier,
Huici Alicia,
Messeguer Angel
Publication year - 2000
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620191103
Subject(s) - mutagen , ames test , chemistry , salmonella , stereochemistry , strain (injury) , biotransformation , carcinogen , biochemistry , biology , enzyme , bacteria , genetics , anatomy
The brominated hydroxyfuranones sructurally related to the potent mutagen MXnamely3‐chloro‐4‐(bromochlorome‐thyl)‐5‐hydroxy‐2(5 H )‐furanone (BMX‐1), has been synthesized and characterized. The mutagenic activity of this bromohydro‐xyfuranone together with those of its analogs BMX‐2 and BMX‐3 has been assessed by employing the Ames test with the Salmonella typhimurium strains TA98 and TA100. The mutagenic potencies in TA100 without S9 metabolic activation were 22.05 ± 3.15 revertants/ng for BMX‐1, 28.64 ± 2.65 revertants/ng for BMX‐2, and 37.29 ± 5.73 revertants/ng for BMX‐3, whereas in the TA98 strain without metabolic activation, they were six‐ to ninefold lower. Studies carried out on the stability of these halogenated furanones suggest that the mutagenic activity observed is more related to the cyclic form of these derivatives.