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Study on the interaction of homoisoflavonoids with RNA

Paper ID Volume ID Publish Year Pages File Format Full-Text
30473 44480 2013 7 PDF Available
Title
Study on the interaction of homoisoflavonoids with RNA
Abstract

•Homoisoflavonoids bind RNA via hydrophobic and hydrophilic contacts.•The bindings are via N7 guanine, adenine, O2 uracil and the PO2 group.•RNA aggregation occurs at high polyphenol concentrations.•Polyphenols induce RNA structural changes, while RNA remains in A-from.

Homoisoflavonoids (3-benzylidene-4-chromanones) are isomers of flavonoids and exhibit different biological activities because of hydroxyl groups attaching to different positions. This study is the first attempt to locate the binding sites of four synthetic homoisoflavonoids: (E)-3-(3,4-dihydroxybenzylidene)-7-methoxychroman-4-one (BMC), (E)-3-(3,4-dihydroxybenzylidene)-7-propoxychroman-4-one (BPC), (E)-3-(4-hydroxybenzylidene)-7-methoxychroman-4-one (HBMC) and (E) 3-(4-hydroxybenzylidene)-chroman-4-one (HBC) to RNA. The effect of the ligand complexation on RNA aggregation was investigated in aqueous solution at physiological conditions, using constant RNA concentration (6.25 mM) and various ligand/polynucleotide (phosphate) ratios of 1/120, 1/80, 1/40, 1/20, 1/10 and 1/5. Fourier transform infrared (FTIR) and UV–Visible spectroscopic methods were used to determine the ligand binding modes, the binding constants, and the stability of ligand–RNA complexes in aqueous solution. Spectroscopic evidence showed external binding of homoisoflavonoids to RNA duplex with overall binding constants of KBMC–RNA = 1.06(±0.09) × 104 M−1, KBPC-RNA = 1.11(±0.15) × 104 M−1, KHBC-RNA = 3.82(±0.09) × 103 M−1 and KHBMC–RNA = 5.82(±0.04) × 103 M−1. The affinity of homoisoflavonoid–RNA binding is in the order of BPC > BMC > HBMC > HBC. No biopolymer secondary structural changes were observed upon homoisoflavonoids interaction and RNA remains in the A-family structure in these complexes.

Keywords
RNA; Homoisoflavonoids; 3-Benzylidenechroman-4-ones; FTIR; UV–Visible spectroscopy
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 128, 5 November 2013, Pages 100–106
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us