Quantum-chemical study on stacking interactions between bioactive polyphenols (trans-resveratrol, trans-piceatannol) and ribonucleosides. Insight into minimum energy geometries of π–π stacked systems

The minimum energy geometries and one-electron properties of the polyphenols (trans-resveratrol and trans-piceatannol) as well as their π–π stacking interactions with ribonucleosides were investigated by means of the M062X/6–311+G(d,p) level of quantum theory in vacuum and water medium. Within the theory level applied, the polyphenols studied exhibit large polarizability. This study presents computed interaction energies of selected complexes ranging from 17.6 to 26.9 kcal mol−1 in vacuum. It has been observed that the stability of the chemical systems decreases in water medium, described by Conductor-like Polarizable Continuum Model (CPCM). For the first time we have predicted that trans-piceatannol binds strongly with ribonucleosides. A complex of trans-piceatannol with adenosine has been found to be the most energetically stable in water medium from among the systems considered within the applied quantum method. All systems studied have been shown to bear π–π stacking interactions and to be bound strongly in the media studied. It is concluded that π–π stacking interactions between ribonucleosides and polyphenols studied play a very important role in binding polyphenols in the complexes investigated. The results reveal that for trans-resveratrol–adenosine (vacuum and water medium) and trans-resveratrol–guanosine (vacuum and water medium), the local energy minima are sandwich structures, and the local energy minima for the other structures are parallel-displaced. This study provides significant insight into the stacked geometries of potential polyphenolic intercalators and can allow other scientist to design new antiviral drugs, basing on a mechanism that hadn’t been used in rational antiviral drug design.