Publication: 3D-QSAR studies of natural flavonoid compounds as reverse transcriptase inhibitors
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Issued Date
2012
Resource Type
File Type
application/pdf
ISSN
10542523
Other identifier(s)
2-s2.0-84861882886
Rights Holder(s)
Scopus
Bibliographic Citation
Medicinal Chemistry Research. Vol 21, No.5 (2012), p.559-567
Suggested Citation
Phosrithong N., Samee W., Ungwitayatorn J. 3D-QSAR studies of natural flavonoid compounds as reverse transcriptase inhibitors. Medicinal Chemistry Research. Vol 21, No.5 (2012), p.559-567. doi:10.1007/s00044-011-9570-z Retrieved from: https://hdl.handle.net/20.500.14740/7063
Author(s)
Abstract
The three-dimensional quantitative structure-activity relationship (3D-QSAR), comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) were conducted on a series of 44 flavonoid compounds which exhibited in vitro avian myeloblastosis virus-reverse transcriptase (AMVRT) inhibitory activity. The best predictive CoMFA model gives cross-validated r 2 (q 2) = 0.665, non-cross-validated r 2 = 0.983, standard error of estimate (S) = 0.047, and F = 357.438. The best CoMSIA model has q 2 = 0.685, non-cross-validated r 2 = 0.963, S = 0.070, and F = 159.764, including steric, electrostatic, hydrogen bond donor, and acceptor fields. The predictive ability of these models was validated by a set of 11 compounds that were not included in the training set. The calculated (predicted) and experimental inhibitory activities were well correlated. Both CoMFA and CoMSIA models suggest fruitful structural insight to design more active compounds. In order to investigate the activity against HIV 1-RT comparing with AMV-RT, the docking simulation of some flavonoids with HIV 1-RT was performed. The flavonoids with good AMV-RT inhibitory activity also showed good binding energies with HIV 1-RT. © Springer Science+Business Media, LLC 2011.