Hydration structure of cocaine and its metabolites: a molecular dynamics study

David A. Rincon, Miguel Jorge, M. Natalia D. S. Cordeiro, Ricardo A. Mosquera, Fernanda Borges

Research output: Contribution to journalArticle

Abstract

We present molecular dynamics simulations of solvated cocaine and its metabolites in water, using both the Optimized Potentials for Liquid Simulations (OPLS) force field and the same force field but with Quantum Theory of Atoms In Molecules (QTAIM) atomic charges. We focus on the microscopic aspects of solvation, e.g. hydrogen bonds, and investigate influence of partial charges applied. Hydrophobicity or hydrophicility of these molecules were analyzed in terms of solute-solvent radial distribution functions and, for their most hydrophilic atoms, by spatial density functions. These hydration studies allowed us to classify these molecules according to their total coordination numbers, from the most hydrated metabolite to least hydrated, and this trend matches the degree of each metabolite is excreted in urine of patients with a high consumption of cocaine. Finally, we observed that QTAIM charges provide a more physically reasonable description of electrostatic environment of these solvated molecules than those of OPLS charges.

LanguageEnglish
Pages656-679
Number of pages24
JournalJournal of Solution Chemistry
Volume40
Issue number4
DOIs
Publication statusPublished - Apr 2011

Fingerprint

Quantum Theory
metabolites
Molecular Dynamics Simulation
Metabolites
Cocaine
Hydration
hydration
Molecular dynamics
molecular dynamics
Molecules
Static Electricity
Hydrophobic and Hydrophilic Interactions
Quantum theory
molecules
Hydrogen
quantum theory
Atoms
field theory (physics)
Urine
Water

Keywords

  • cocaine metabolites
  • cocaine
  • hydration structure
  • OPLS
  • QTAIM charges
  • molecular dynamics

Cite this

Rincon, David A. ; Jorge, Miguel ; Cordeiro, M. Natalia D. S. ; Mosquera, Ricardo A. ; Borges, Fernanda. / Hydration structure of cocaine and its metabolites : a molecular dynamics study. In: Journal of Solution Chemistry. 2011 ; Vol. 40, No. 4. pp. 656-679.
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Hydration structure of cocaine and its metabolites : a molecular dynamics study. / Rincon, David A.; Jorge, Miguel; Cordeiro, M. Natalia D. S.; Mosquera, Ricardo A.; Borges, Fernanda.

In: Journal of Solution Chemistry, Vol. 40, No. 4, 04.2011, p. 656-679.

Research output: Contribution to journalArticle

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