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Solvation and Intermolecular Exploration of Drug Molecule Fragments

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Abstract

The paramagnetic contributions from dioxygen to solute proton spin-lattice relaxation rate constants are reported for a series of aromatic hydrocarbons and drug molecule fragments, in order to examine the energetic factors for intermolecular exploration in solution. The measurements provide differences in local oxygen concentration at different sites on the solute molecule. The relaxation rate differences caused by steric factors are taken into account using a lattice model calculation to normalize the relaxation rates for intermolecular contact. The measurements reveal small differences in oxygen accessibility for aromatic solutes in aqueous acetone and for aliphatic drug fragments in chloroform. Larger differences are observed for aliphatic protons in dimethyl sulfoxide; however, the differences are generally small compared with previous measurements on amino acids in water. Concentration ratios between local oxygen concentrations and the solvent references are all smaller than 2.2 and high local concentrations are favored by bulky adjacent groups such as alkane chains.

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Author notes

  1. M. L. Brown

    Present address: Lombardi Comprehensive Cancer Center, New Research Building EP-07, Washington, DC, 20057-1468, USA

Authors and Affiliations

  1. Chemistry Department, University of Virginia, Charlottesville, VA, 22901-4319, USA

    K. Fumino, G. Diakova, J. D. Andersen, M. L. Brown & R. G. Bryant

Authors
  1. K. Fumino
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  2. G. Diakova
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  3. J. D. Andersen
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  4. M. L. Brown
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  5. R. G. Bryant
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Correspondence to R. G. Bryant.

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Fumino, K., Diakova, G., Andersen, J.D. et al. Solvation and Intermolecular Exploration of Drug Molecule Fragments. J Solution Chem 36, 715–722 (2007). https://doi.org/10.1007/s10953-007-9142-5

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  • DOI: https://doi.org/10.1007/s10953-007-9142-5

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