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Molecules 2013, 18(5), 5032-5050; doi:10.3390/molecules18055032

Identification of Electronic and Structural Descriptors of Adenosine Analogues Related to Inhibition of Leishmanial Glyceraldehyde-3-Phosphate Dehydrogenase

1
Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP 13566-590, Brazil
2
Departamento de Química, Universidade Federal da Paraiba, João Pessoa, PB 13083-970, Brazil
3
Centro de Ciência Naturais e Humanas, Universidade Federal do ABC, Santo Andre, SP 09210-170, Brazil
4
Escola de Artes, Ciências e Humanidades, Universidade de São Paulo, São Paulo, SP 03828-000, Brazil
5
Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, SP 13560-590, Brazil
*
Author to whom correspondence should be addressed.
Received: 10 September 2012 / Revised: 27 April 2013 / Accepted: 28 April 2013 / Published: 29 April 2013
(This article belongs to the Special Issue QSAR and Its Applications)
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Abstract

Quantitative structure–activity relationship (QSAR) studies were performed in order to identify molecular features responsible for the antileishmanial activity of 61 adenosine analogues acting as inhibitors of the enzyme glyceraldehyde 3-phosphate dehydrogenase of Leishmania mexicana (LmGAPDH). Density functional theory (DFT) was employed to calculate quantum-chemical descriptors, while several structural descriptors were generated with Dragon 5.4. Variable selection was undertaken with the ordered predictor selection (OPS) algorithm, which provided a set with the most relevant descriptors to perform PLS, PCR and MLR regressions. Reliable and predictive models were obtained, as attested by their high correlation coefficients, as well as the agreement between predicted and experimental values for an external test set. Additional validation procedures were carried out, demonstrating that robust models were developed, providing helpful tools for the optimization of the antileishmanial activity of adenosine compounds.
Keywords: adenosine compounds; antileishmanial activity; glyceraldehyde 3-phosphate dehydrogenase; DFT; multivariate regression adenosine compounds; antileishmanial activity; glyceraldehyde 3-phosphate dehydrogenase; DFT; multivariate regression
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Lozano, N.B.H.; Oliveira, R.F.; Weber, K.C.; Honorio, K.M.; Guido, R.V.; Andricopulo, A.D.; Silva, A.B.F.D. Identification of Electronic and Structural Descriptors of Adenosine Analogues Related to Inhibition of Leishmanial Glyceraldehyde-3-Phosphate Dehydrogenase. Molecules 2013, 18, 5032-5050.

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