Mutagenicity of N-acetyl and N,N'-diacetyl derivatives of 3 aromatic amines used as epoxy-resin hardeners.
ABSTRACT 3 epoxy-resin hardeners, 4,4'-diaminodiphenyl ether (DDE), 4,4'-diaminodiphenylmethane (DDM), and 4,4'-diaminodiphenylsulfone (DDS), and their N-acetyl and N,N'-diacetyl derivatives were examined for their mutagenicity using Salmonella typhimurium TA98 and TA100 as the tester stains and an S9 mix containing a rat-liver 9000 X g supernatant fraction as the metabolic activation system. DDE and DDM were mutagenic towards TA98 and TA100 in the presence of S9 mix while DDS exhibited no significant mutagenic activity towards these tester strains. These epoxy-resin hardeners were metabolized in vivo and their N-acetyl and N,N'-diacetyl metabolites were found in the urine. Among these acetyl metabolites, only N-acetyl-DDE was found to be mutagenic towards TA98 and TA100 in the presence of S9 mix. None of these acetyl metabolites exhibited significant mutagenic activity towards these tester strains in the absence of S9 mix.
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ABSTRACT: 4,4'-Diaminodiphenyl ether was selected as a lead compound to prepare a novel series of bisimine derivatives bearing polyaromatic hydrocarbon substituents and their reduced benzyl forms. The new compounds were structurally characterized by microanalysis, mass, IR, (1)H, (13)C, DEPT-135, HSQC, g-COSY NMR spectroscopy, UV-visible, fluorescence spectrophotometers and by thermogravimetric analysis. The antitumor activity of these derivatives was evaluated in-vitro against Hep 3B and IMR 32 by the MTT assay and the results were compared with cisplatin. Interestingly, some compounds were found extremely active against both the cell lines and proved to be more potent as cytotoxic agents than cisplatin. Morphological evidences suggest the induction of apoptosis and explain the mode of action of these derivatives as antitumor agents.European Journal of Medicinal Chemistry 01/2014; 74C:552-561. DOI:10.1016/j.ejmech.2013.12.035 · 3.43 Impact Factor
Toxicological Sciences 01/2000; 58(1):102-108. DOI:10.1093/toxsci/58.1.102 · 4.48 Impact Factor
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ABSTRACT: A liquid chromatographic method with UV-detection (λ=246 nm) is presented for determination of 4,4′-methylenedianiline (MDA, C.A.S No 101–77–9) in hydrolysed human urine. The method is based on a two-phase derivatization procedure with isobutylchloroformate. The formed chloroformate derivative was analysed on a octadecylsilyl column using isocratic elution with acetonitrile-water (75:25 v/v). The overall recovery for urine samples spiked with 32 μg MDA/1 was found to be 88 7plusmn; 4%. The calibration graph was linear in the investigated range (3–37 μg/1 urine) with a correlation coefficient of 0.997. The precision was 3.4% for urine samples spiked with 32 μg MDA/1 and the detection limit was 3 μg/1. Methyl-, ethyl-, isobutyl-benzyl-, 2-bromoethyl- and p-nitrobenzylchloroformate as derivatization reagents and clean-up procedures with extraction columns are discussed.Journal of liquid chromatography 02/1990; 13(4):803-820. DOI:10.1080/01483919008051822