Vinyl phosphonates as photopharmacological agents – laser induced cis‐trans isomerization and butyrylcholinesterase activity

Photoswitchable molecules are highly requested compounds in various fields and in particular biomedicine. The urgent modern task of photopharmacology (emerging approach in medicine) is design of molecules that have both photoswitchable and bioactive properties. In this study, we present vinyl phosphonates – diene compounds with ethyl and isopropyl substituents on phosphonate group. Both compounds demonstrated laser‐induced cis‐trans isomerization via C=C bond after irradiation with 266 nm wavelength. Photoisomerisation quantum yield was found to be 17% and 20% for compounds with ethyl and isopropyl groups, respectively. The main advantage of the presented vinyl phosphonates is their bioactivity unlike other photoswitchable molecules. Rather efficient butyrylcholinesterase inhibition by both presented compounds was demonstrated by IPC‐Micro analysis. The notable butyrylcholinesterase inhibition increase by 5 and 9 times was found for the vinyl phosphonates after laser irradiation. Such a sizeable difference in inhibition values for different isomeric states is a critical factor, which opens the way toward promising applications of vinyl phosphonates as photopharmacological agents.