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Schultz, T.W.; Yarbrough, J.W.; Pilkington, T.B. Aquatic toxicity and abiotic thiol reactivity of aliphatic isothiocyanates: Effects of alkyl-size and -shape. Environ. Toxicol. Pharmacol. 2007, 23, 1, 10–17.

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Schultz, T.W.; Yarbrough, J.W.; Pilkington, T.B. Aquatic toxicity and abiotic thiol reactivity of aliphatic isothiocyanates: Effects of alkyl-size and -shape. Environ. Toxicol. Pharmacol. 2007, 23, 1, 10–17.

QDB archive DOI: 10.15152/QDB.37   DOWNLOAD

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Property IGC50: 40-h Tetrahymena toxicity as IGC50 [mmol/L]

Compounds: 28 | Models: 0 | Predictions: 0

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Title: Schultz, T.W.; Yarbrough, J.W.; Pilkington, T.B. Aquatic toxicity and abiotic thiol reactivity of aliphatic isothiocyanates: Effects of alkyl-size and -shape. Environ. Toxicol. Pharmacol. 2007, 23, 1, 10–17.
Abstract: Aquatic toxicity data in the TETRATOX assay and reactivity data in an abiotic thiol assay were collected for a series of aliphatic isothiocyanates. These compounds can act as Michael-type acceptors with N-hydro-C-mercapto-addition to cellular thiols as a molecular mechanism of action. Comparison of both toxicity and reactivity among the analogues revealed that derivatives with a branch hydrocarbon moiety, especially branched in the β-position were less toxic and less reactive. In contrast, the di-isothiocyanate and the allyl and propargyl derivatives are more toxic than their 1-alkyl homologues. The toxicity and reactivity differences are consistent but except for the tert-butyl-derivative not remarkable. The differences are due to variations in steric hindrance at the reaction center. For the mono-isothiocyanates compounds toxicity (IGC(50)) is linearly related to thiol reactivity (EC(50)): log(1/IGC(50))=1.33(log(1/EC(50)))-0.41; n=23, s=0.24, r(2)=0.911, q(2)=0.907, F=215.
URI: http://hdl.handle.net/10967/37
http://dx.doi.org/10.15152/QDB.37
Date: 2012-05-23


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