Toxicity profile of aromatic compounds towards Scenedesmus obliquus: a QSAR study

Author:

Islam Nasarul1,Pandith Altaf Hussain1

Affiliation:

1. Department of Chemistry, University of Kashmir, Srinagar-190006, (J&K) India.

Abstract

The parameterization of molecular hydrophobicity and electrophilicity, contributing to the overall toxicity of aromatic compounds, has been the subject of many quantitative structure−activity relationship (QSAR) studies. So far, hydrophobicity has been largely described in terms of the logarithm of the octanol−water partition coefficient (log P) and the molecular electrophilicity in terms of the energy of the lowest unoccupied molecular orbital (ELUMO), the maximum acceptor superdeocalizability (Amax), and the electrophilicity index (ω). Here, we report for the first time the parameterization of these properties in terms of cumulative interplay of multiple descriptors. The toxicity data of 68 compounds were compiled in terms of 50% population growth inhibition (pIGC50) of Scenedesmus obliquus. The comparison of the two QSARs (pIGC50 = 0.175ELUMO + 0.057log P + 0.363ω + 0.019V – 3.292, R2adj = 0.761 and pIGC50 = 0.368ELUMO + 0.146α + 0.258ω + 0.021V − 1.170, R2adj = 0.776) reveals that polarizability (α) is a superior descriptor to log P for parameterization of hydrophobicity, when used in conjunction with ELUMO, ω, and V, for profiling of the toxicity of the test compounds. The overall results indicate that ω and α are better descriptors of electrophilicity and hydrophobicity, respectively, for mapping the toxicity profile of aromatic derivatives towards the target organism.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Reference53 articles.

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3. Weinstein, H.; Nombodri, V. K.; Osman, R. In QSAR in Toxicology and Xenobi chemistry; Tichy, M., Ed.; Elsevier: Amsterdam and New York, 1985; pp. 451–463.

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