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An Y , Doney AC , Andrade RB , Wheeler SE
Stacking Interactions between 9-Methyladenine and Heterocycles Commonly Found in Pharmaceuticals
J Chem Inf Model. 2016 May 23;56(5) :906-14
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Complexes of 9-methyladenine with 46 heterocycles commonly found in drugs were located using dispersion-corrected density functional theory, providing a representative set of 408 unique stacked dimers. The predicted binding enthalpies for each heterocycle span a broad range, highlighting the strong dependence of heterocycle stacking interactions on the relative orientation of the interacting rings. Overall, the presence of NH and carbonyl groups lead to the strongest stacking interactions with 9-methyadenine, and the strength of pi-stacking interactions is sensitive to the distribution of heteroatoms within the ring as well as the specific tautomer considered. Although molecular dipole moments provide a sound predictor of the strengths and orientations of the 28 monocyclic heterocycles considered, dipole moments for the larger fused heterocycles show very little correlation with the predicted binding enthalpies.
1549-960x An, Yi Doney, Analise C Andrade, Rodrigo B Wheeler, Steven E Journal Article United States J Chem Inf Model. 2016 May 23;56(5):906-14. doi: 10.1021/acs.jcim.5b00651. Epub 2016 Apr 27.