A model based on molecular structure descriptors for predicting mutagenicity of organic compounds

Flora, Silvio De; Koch, R.; Strobel, K.; Nagel, M.

doi:10.1080/02772248509357099

Cited by 11 publications

(1 citation statement)

References 28 publications

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“…• E: 112 nitrobenzoic compounds of which 53 were musk odorants and 59 were non-musks [29]. • F: 114 organic compounds of which 66 were mutagenic and 48 non-mutagenic in the Ames reversion test [30]. • G: 109 cyclic nitrogeneous compounds of which 63 were mutagenic and 46 were non-mutagenic [31].…”

Section: Methodsmentioning

confidence: 99%

Techniques for the calculation of three-dimensional structural similarity using inter-atomic distances

Pepperrell

Willett

1991

J Computer-Aided Mol Des

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This paper reports a comparison of several methods for measuring the degree of similarity between pairs of 3-D chemical structures that are represented by inter-atomic distance matrices. The methods that have been tested use the distance information in very different ways and have very different computational requirements. Experiments with 10 small datasets, for which both structural and biological activity data are available, suggest that the most cost-effective technique is based on a mapping procedure that tries to match pairs of atoms, one from each of the molecules that are being compared, that have neighbouring atoms at approximately the same distances.

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Section: Methodsmentioning

confidence: 99%

Techniques for the calculation of three-dimensional structural similarity using inter-atomic distances

Pepperrell

Willett

1991

J Computer-Aided Mol Des

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A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the ames test: 1. Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100

Debnath

Shusterman

et al. 1992

Environ and Mol Mutagen

169

172

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Quantitative structure-activity relationships (QSAR) have been derived for the mutagenic activity of 88 aromatic and heteroaromatic amines acting on Salmonella typhimurium TA98 + S9 and 67 amines acting on TA100 + S9. Mutagenic activity is linearly dependent on hydrophobicity, the energy of the highest occupied molecular orbital, and the energy of the lowest unoccupied molecular orbital of the amine. The dependence of mutagenic activity on hydrophobicity and electronic effects is nearly identical for TA98 and TA100. Mutagenic activity in TA98 is also found to depend on the size of the aromatic ring system. Different QSARs are derived for the mutagenic activity of hydrophilic amines (log P less than 1) acting on either TA98 or TA100. The mechanism of amine activation and reaction with DNA is considered in light of these findings.

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Comparison of Fragment Weighting Schemes for Substructural Analysis

Ormerod

Willett

Bawden

1989

Quant. Struct.‐Act. Relat.

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Several methods have been described in the literature for the calculation of weights which represent the contribution of fragments to the overall activity or inactivity of molecules which contain them. These weighting schemes are based on fragment occurrence data in training sets of molecules for which the activity is known. This paper reports a comparison of several such schemes (fourteen fragment weights in all), using small datasets for which structural and activity data are available. The comparison reveals that the most effective weight seems to be one derived from research into document retrieval systems (where indexing terms are used to discriminate between relevant and non‐relevant documents).

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A model based on molecular structure descriptors for predicting mutagenicity of organic compounds

Cited by 11 publications

References 28 publications

Techniques for the calculation of three-dimensional structural similarity using inter-atomic distances

Techniques for the calculation of three-dimensional structural similarity using inter-atomic distances

A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the ames test: 1. Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100

Comparison of Fragment Weighting Schemes for Substructural Analysis

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