QSAR and docking studies of anthraquinone derivatives by similarity cluster prediction

Abstract

Forty anthraquinone derivatives have been downloaded from PubChem database and investigated in a quantitative structure-activity relationships (QSAR) study. The models describing log P and LD50 of this set were built up on the hypermolecule scheme that mimics the investigated receptor space; the models were validated by the leave-one-out procedure, in the external test set and in a new version of prediction by using similarity clusters. Molecular docking approach using Lamarckian Genetic Algorithm was made on this class of anthraquinones with respect to 3Q3B receptor. The best scored molecules in the docking assay were used as leaders in the similarity clustering procedure. It is demonstrated that the LD50 data of this set of anthraquinones are related to the binding energies of anthraquinone ligands to the 3Q3B receptor.

• 3Q3B Receptor
• anthraquinone
• AUTODOCK Vina
• docking
• hypermolecule
• leave-one-out
• log P
• QSAR
• similarity

Acknowledgements

The authors acknowledge to the referees for the valuable suggestions.

Declaration of interest

This paper is a result of a doctoral research made possible by the financial support of the Sectoral Operational Programme for Human Resources Development 2007–2013, co-financed by the European Social Fund, under the project POSDRU/159/1.5/S/137750 – “Doctoral and postdoctoral programs – support for increasing research competitiveness in the field of exact Sciences”.