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  • Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (HAA) mutagenicity.

Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (HAA) mutagenicity.

Bioorganic & medicinal chemistry (2008-04-15)
Alfonso Pérez-Garrido, Maykel Pérez González, Amalio Garrido Escudero
ABSTRACT

The risk of the presence of haloacetic acids in drinking water as chlorination by-products and the shortage of experimental mutagenicity data for most of them requires a research work. This paper describes a QSAR model to predict direct mutagenicity for these chemicals. The model, able to describe more than 90% of the variance in the experimental activity, was developed with the use of the spectral moment descriptors. The model, using these descriptors with multiplicative effects provides better results than other linear descriptors models based on Geometrical, RDF, WHIM, eigenvalue-based indices, 2D-autocorrelation ones, and information descriptors, taking into account the statistical parameters of the model and the cross-validation results. The structural alerts and the mutagenicity-predicted values from the model output are in agreement with references from other authors. The mutagenicity predicted values for the three haloacetic acids, which have available experimental data (TCAA-Trichloroacetic acid, BDCAA-Bromodichloroacetic acid, and TBAA-Tribromoacetic acid), are reasonably close to their experimental values, specially for the latest two.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Bromoacetic acid, reagent grade, 97%
Sigma-Aldrich
1,2-Dibromoethane, 98%
Sigma-Aldrich
Tribromoacetic acid, 99%
Sigma-Aldrich
Bromoacetic acid, ReagentPlus®, ≥99.0%
Supelco
Dichloroacetic acid, PESTANAL®, analytical standard
Sigma-Aldrich
Trichloroacetic acid, ACS reagent, for the determination of Fe in blood according to Heilmeyer, ≥99.5%
Sigma-Aldrich
2-Chloroethanol, puriss. p.a., ≥99.0% (GC)
Sigma-Aldrich
1,2-Dibromoethane, ≥99%
Sigma-Aldrich
Allyl chloride, ReagentPlus®, 99%
Sigma-Aldrich
Allyl chloride, reagent grade, 98%
Sigma-Aldrich
2-Chloroethanol, 99%
Sigma-Aldrich
Dichloroacetic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
1,2-Dibromoethane, purum, ≥98.0% (GC)
Sigma-Aldrich
Iodoacetic acid, ≥98.0% (T)
Sigma-Aldrich
Trichloroacetic acid, suitable for electrophoresis, suitable for fixing solution (for IEF and PAGE gels), ≥99%
Sigma-Aldrich
Trichloroacetic acid, BioXtra, ≥99.0%
Sigma-Aldrich
Trichloroacetic acid, ≥99.0% (titration)
Sigma-Aldrich
Trichloroacetic acid, ACS reagent, ≥99.0%
Sigma-Aldrich
Chloroacetic acid, ACS reagent, ≥99.0%
Sigma-Aldrich
Chloroacetic acid, 99%
Supelco
Chloroacetic acid, PESTANAL®, analytical standard
Sigma-Aldrich
(R)-(−)-Epichlorohydrin, 99%
Sigma-Aldrich
Trichloroacetic acid, BioUltra, ≥99.5% (T)
Sigma-Aldrich
Chloroacetaldehyde solution, produced by Wacker Chemie AG, Burghausen, Germany, ≥45.0% in H2O (density determination)
Sigma-Aldrich
1,3-Dichloropropene, 90%, technical grade
Sigma-Aldrich
trans-1,4-Dichloro-2-butene, technical grade, 85%, remainder predominantly cis isomer
Sigma-Aldrich
1,3-Dichloro-2-propanol, 97%
Sigma-Aldrich
2,3-Dichloro-1-propene, 98%
Sigma-Aldrich
Dichloroacetyl chloride, 98%
Sigma-Aldrich
Chloroacetaldehyde solution, ~55 wt. % in H2O