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Molecular modeling and chemometric study of anticancer derivatives of artemisinin

2011; Serbian Chemical Society; Volume: 76; Issue: 9 Linguagem: Inglês

10.2298/jsc111227111b

1820-7421

Jardel Pinto Barbosa, João Elias Vidueira Ferreira, António J. Figueiredo, Ruth Catarine O. de Almeida, Osmarina Silva, José Carlos Tavares Carvalho, Cristino da, José Ciríaco-Pinheiro, José Vieira, Raymony Tayllon Alves Serra,

Statistical Methods and Applications

In this work, a molecular modeling and multivariate study involving artemisinin and 28 derivatives with activity against human hepatocellular carcinoma HepG2 is reported. The studied calculations of the compounds were performed at the B3LYP/6-31G level. MEP maps were used in an attempt to identify key structural features of artemisinin and its derivatives that are necessary for their activities, and to investigate their interaction with the transferrin. The chemometrics methods PCA, HCA, KNN, SIMCA and SDA were employed in order to reduce dimensionality and to investigate which subset of variables could be more effective for classification of the compounds according to their degree of anticancer activity. Chemometric studies revealed that the ALOGPS_logs, Mor29m, IC5 and the Gap energy descriptors are responsible for the separation into more active and less active compounds. In addition, molecular docking was used to investigate the interaction between ligands and receptor. The results showed that the ligands approached the receptor through the endoperoxide bond.