Ultrafast nonradiative deactivation of photoexcited 8-oxo-hypoxanthine: a nonadiabatic molecular dynamics study

Phys Chem Chem Phys. 2021 Jan 21;23(2):1234-1241. doi: 10.1039/d0cp05271j.

Abstract

In the scientific endeavor to understand the chemical origins of life, the photochemistry of the smallest life building blocks, nucleobases, has been a constant object of focus and intense research. Here, we report the results of the first theoretical study on the photo-properties of an 8-oxo-hypoxanthine molecule, the chromophore of 8-oxo-inosine, which is relevant to the recently proposed, prebiotically plausible synthetic routes to the formation of purine- and pyrimidine-nucleotides. With ab initio and semi-empirical OM2/MRCI quantum-chemistry calculations, we predict a strong photostability of the 8-oxo-hypoxanthine system and see the origin of this effect in ultrafast nonradiative relaxation through puckering of the 6-membered heterocyclic ring.

MeSH terms

  • Density Functional Theory
  • Drug Stability
  • Inosine / analogs & derivatives*
  • Inosine / chemistry
  • Inosine / radiation effects
  • Models, Chemical
  • Molecular Dynamics Simulation
  • Ultraviolet Rays

Substances

  • 8-oxoinosine
  • Inosine