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Molecular surface area measures of polarity and hydrogen bonding for QSAR

Saunders, Robert Alun. 2004. Molecular surface area measures of polarity and hydrogen bonding for QSAR. PhD Thesis, Cardiff University.

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Modifications were made to the traditional PSA descriptor by decoupling it into its H-bond acidic and basic components. The PSA based descriptors were also scaled according to the known hydrogen bonding characteristics of common functional groups to make them more realistic measures of a molecules hydrogen bonding capacity. Three other surface area descriptors total surface area, total halogen atom surface area and total aromatic carbon surface area were also defined. Various routes to the calculation of these descriptors were explored and it was concluded the best descriptors were those obtained from a single structure generated using the semi empirical-method AMI. It was also shown that descriptors obtained from a vdw surface were more suitable than those obtained from solvent accessible surface area. The scaled PSA descriptors were initially tested against octanol-water, chloroform-water, and cyclohexane-water partition coefficients of 110 organic and drug-like molecules. All of the models produced were seen to be statistically accurate and followed known characteristics of the partition coefficients considered. The scaled PSA descriptors were then applied successfully to a number of important biological processes such as cellular uptake and intestinal absorption models were also produced for important industrial processes such as Fluorophilicity and CMC. The surface area descriptors were also seen to be equally capable of modelling inorganic molecules and excellent models were produced for octanol-water and chloroform-water partitions for a number of platinum containing drugs.

Item Type: Thesis (PhD)
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
ISBN: 9781303224157
Date of First Compliant Deposit: 30 March 2016
Last Modified: 10 Oct 2017 15:26

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