Structural alerts for predicting clastogenic activity of pro-oxidant flavonoid compounds: Quantitative structure-activity relationship study

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Yordi, EG (Author) Other; Molina Pérez, E (Author) Other; Joao Matos, M (Author) Other; Uriarte Villares, E (Author) Other

Journal

Title: Journal of Biomolecular Screening

Vol. 17

Pages: 216-224

ISSN: 1087-0571

Publisher: SAGE Publications

Indexing

Scopus - 9 Citations

Other information

Authenticus ID: P-00R-0MN

DOI: 10.1177/1087057111421623

Abstract (EN): Flavonoids have been reported to exert multiple biological effects that include acting as pro-oxidants at very high doses. The authors determined a structural alert to identify the clastogenic activity of a series of flavonoids with pro-oxidant activity. The methodology was based on a quantitative structure-activity relationship (QSAR) study. Specifically, the authors developed a virtual screening method for a clastogenic model using the topological substructural molecular design (TOPS-MODE) approach. It represents a useful platform for the automatic generation of structural alerts, based on the calculation of spectral moments of molecular bond matrices appropriately weighted, taking into account the hydrophobic, electronic, and steric molecular features. Therefore, it was possible to establish the structural criteria for maximal clastogenicity of pro-oxidant flavonoids: the presence of a 3-hydroxyl group and a 4-carbonyl group in ring C, the maximal number of hydroxyl groups in ring B, the presence of methoxyl and phenyl groups, the absence of a 2,3-double bond in ring C, and the presence of 5,7 hydroxyl groups in ring A. The presented clastogenic model may be useful for screening new pro-oxidant compounds. This alert could help in the design of new and efficient flavonoids, which could be used as bioactive compounds in nutraceuticals and functional food. © 2012 Society for Laboratory Automation and Screening.

Language: English

Type (Professor's evaluation): Scientific