A molecular electrostatic potential mapping study of some fluoroquinolone anti-bacterial agents

Santhosh Chidangil, Manoj K. Shukla, Phool C. Mishra

Research output: Contribution to journalArticle

95 Citations (Scopus)

Abstract

Molecular electrostatic potential (MEP) maps of some fluoroquinolones having varying degrees of activity against the bacterium Staphylococcus Aureus have been studied using the optimized hybridization displacement charges (HDC) combined with Löwdin charges obtained by the AM1 method. The roles of different substitutions at the N1-position in the parent quinolone ring have been studied. The conformation of the carboxylic group attached to the quinolone ring was shown to be such that there is an intramolecular hydrogen bonding between the hydrogen atom of this group and the oxygen atom of the carbonyl group of the quinolone moiety. The carbonyl oxygen atom of the quinolone moiety, hydroxyl oxygen atom of the carboxylic group and the terminal nitrogen atom of the piperazin ring attached to the quinolone ring appear to be involved in the action of the drugs through electrostatic interactions while the N1-alkyl substituents seem to be involved in the same through hydrophobic interactions.

Original languageEnglish
Pages (from-to)250-258
Number of pages9
JournalJournal of Molecular Modeling
Volume4
Issue number8
Publication statusPublished - 01-01-1998

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Bactericides
Quinolones
Fluoroquinolones
Electrostatics
electrostatics
Anti-Bacterial Agents
oxygen atoms
Atoms
rings
Oxygen
staphylococcus
nitrogen atoms
bacteria
hydrogen atoms
Coulomb interactions
drugs
Hydroxyl Radical
interactions
Conformations
substitutes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Computational Theory and Mathematics
  • Inorganic Chemistry

Cite this

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A molecular electrostatic potential mapping study of some fluoroquinolone anti-bacterial agents. / Chidangil, Santhosh; Shukla, Manoj K.; Mishra, Phool C.

In: Journal of Molecular Modeling, Vol. 4, No. 8, 01.01.1998, p. 250-258.

Research output: Contribution to journalArticle

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