Determining chemical reactivity driving biological activity from SMILES transformations: the bonding mechanism of anti-HIV pyrimidines

Assessing the molecular mechanism of a chemical-biological interaction and bonding stands as the ultimate goal of any modern quantitative structure-activity relationship (QSAR) study. To this end the present work employs the main chemical reactivity structural descriptors (electronegativity, chemica...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-07, Vol.18 (8), p.9061-9116
Main Authors: Putz, Mihai V, Dudaş, Nicoleta A
Format: Article
Language:English
Subjects:
1,3-disubstituted uracil derivatives
anti-HIV activity
Anti-HIV Agents - chemistry
Anti-HIV Agents - therapeutic use
Biological activity
chemical hardness
chemical power
chemical reactivity principles
electronegativity
electrophilicity
HIV
HIV Infections - drug therapy
HIV Infections - pathology
HIV-1 - chemistry
HIV-1 - drug effects
Human immunodeficiency virus
Humans
lipophilicity
Molecular Structure
Monte Carlo Method
Organic chemicals
Principles
QSAR
Quantitative Structure-Activity Relationship
SMILES
Software
Toxicity
Toxicology
Uracil - analogs & derivatives
Uracil - chemistry
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Summary:Assessing the molecular mechanism of a chemical-biological interaction and bonding stands as the ultimate goal of any modern quantitative structure-activity relationship (QSAR) study. To this end the present work employs the main chemical reactivity structural descriptors (electronegativity, chemical hardness, chemical power, electrophilicity) to unfold the variational QSAR though their min-max correspondence principles as applied to the Simplified Molecular Input Line Entry System (SMILES) transformation of selected uracil derivatives with anti-HIV potential with the aim of establishing the main stages whereby the given compounds may inhibit HIV infection. The bonding can be completely described by explicitly considering by means of basic indices and chemical reactivity principles two forms of SMILES structures of the pyrimidines, the Longest SMILES Molecular Chain (LoSMoC) and the Branching SMILES (BraS), respectively, as the effective forms involved in the anti-HIV activity mechanism and according to the present work, also necessary intermediates in molecular pathways targeting/docking biological sites of interest.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules18089061