Mechanisms of photoinduced electron transfer reactions of lappaconitine with aromatic amino acids. Time-resolved CIDNP study

Abstract

CIDNP techniques were applied to the investigation of the elementary mechanism of photoinduced interaction between anti-arrhythmic drug lappaconitine and amino acids tyrosine and tryptophan. It has been shown that the reactions involve the formation of lappaconitine radical anion. Lappaconitine radical anion is unstable and rapidly eliminates N-acetyl anthranilic acid via protonation and ether bond cleavage. The rate constant of ether bond cleavage was estimated to be equal to 4 × 10⁵ s⁻¹. The role of single electron transfer is discussed in the light of the model of drug–receptor interactions.