Interaction of ibotenic acid with selected small nanographene oxide (GO) models

Ibotenic acid (IA) acts as a psychoactive compound and is one of the toxins, that occurs in certain mushrooms, especially in Amanita muscaria L. This heterocyclic compound is a structural analog of glutamic acid, a well-known neurotransmitter. Mushrooms containing psychotropic compounds are also collected deliberately for their psychedelic effects. Due to their toxicicity designing a sensor capable of detecting and monitoring the presence of ibotenic acid both in mushrooms and biological fluids of patients is of great importance. In order to enable the detection of ibotenic acid with a chemical sensor, we decided to examine interactions between potential sensor materials – small models of graphene oxide (GO) and ibotenic acid. We studied these non-covalent systems using computational methods, including both isolated and implicit solvents, subsequently utilizing semi-empirical method GFN2 (Geometries (vibrational), Frequencies, and Noncovalent interactions) followed by Density Functional Theory (DFT) calculations. The modeled complexes were stabilized mainly by strong and short H-bonds and the highest interaction energy was calculated for graphene oxide models with –COOH substituent and ibotenic acid (up to 20 kcal/mol) whereas benzene formed the weakest π-π type interactions. In comparison to the gas phase, a decrease in interaction was observed in chloroform and water. We confirmed that determining the interaction energy of non-covalent complexes GO-ibotenic acid is not significantly affected by the size of the GO model.