Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 34, Pages 8832-8845Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101229
Keywords
DNA; G-quadruplexes; resveratrol; stilbenoids; viniferin
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Funding
- FIRC-AIRC fellowship for Italy
- AIRC - Associazione Italiana per la Ricerca sul Cancro [25046]
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The natural compound stilbenoids, including (+/-)-trans-delta-viniferin, have shown the ability to bind to both DNA duplex and G-quadruplex structures, with higher affinity for the DNA targets compared to their monomeric counterparts. These compounds exhibit cytotoxicity and DNA damaging activity on cancer cell lines.
Stilbenoids are natural compounds endowed with several biological activities, including cardioprotection and cancer prevention. Among them, (+/-)-trans-delta-viniferin, deriving from trans-resveratrol dimerization, was investigated in its ability to target DNA duplex and G-quadruplex structures by exploiting NMR spectroscopy, circular dichroism, fluorescence spectroscopy and molecular docking. (+/-)-trans-delta-Viniferin proved to bind both the minor and major grooves of duplexes, whereas it bound the 3'- and 5'-ends of a G-quadruplex by stacking on the outer quartets, accompanied by rearrangement of flanking residues. Specifically, (+/-)-trans-delta-viniferin demonstrated higher affinity for the investigated DNA targets than its monomeric counterpart. Additionally, the methoxylated derivatives of (+/-)-trans-delta-viniferin and trans-resveratrol, i. e. (+/-)-pterostilbene-trans-dihydrodimer and trans-pterostilbene, respectively, were evaluated, revealing similar binding modes, affinities and stoichiometries with the DNA targets as their parent analogues. All tested compounds were cytotoxic at mu M concentration on several cancer cell lines, showing DNA damaging activity consistent with their ability to tightly interact with duplex and G-quadruplex structures.
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