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Química Nova

Print version ISSN 0100-4042On-line version ISSN 1678-7064


SILVA, Thais Horta Álvares da et al. Molecular modeling study of complexes between ferriprotoporphyrin IX and antimalarial 4-quinolinecarbinolamines: a proposal of pharmacophore. Quím. Nova [online]. 2005, vol.28, n.2, pp.244-249. ISSN 0100-4042.

Quinine and quinidine are well-known 4-quinolinecarbinolamines that exhibit antimalarial activity, but, in contrast, their epimers 9-epiquinine and 9-epiquinidine are almost inactive. Literature data are conflicting in describing the 4-quinolinecarbinolamine interaction mode with the molecular target, the ferriprotoporphyrin IX [Fe(III)PPIX]. In the present paper, a pharmacophore is proposed based on the binding of the non-aromatic nitrogen to the iron atom. The 4-quinolinecarbinolamine antimalarials were superimposed on the pharmacophore under consideration and complexes with Fe(III)PPIX were constructed. Conformational analyses of the complexes were performed applying the MM+ molecular mechanics method. The analysis of the complexes showed that the proposed ligand mode is possible although it does not explain the activity differences between epimers. A discussion of the structural aspects is also provided.

Keywords : antimalarial; quinine; pharmacophore.

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