Molecular interaction between a reduced riboflavin derivative and salicylic acid derivatives

The interaction of reduced riboflavin 2', 3', 4', 5'-tetrabutyrate with salicylic acid, aspirin, and salicylamide has been spectroscopically investigated to determine the binding mechanism. Hydrogen-1 and carbon-13 unclear magnetic resonance, infrared, and absoption spectra were measured in chloform-d and chloroform. The association of the reduced riboflavin with salicylic acid derivatives is different from that osidizd one. Salicylic acid and the reduced riboflavin form a cyclic hydrogen bounded complex through the imino (3-N, 5-N) protons and the carbonyl (2-C, 4-C) oxygens of the isolloxazine ring of the latter, and the carboxylic hydroxyl proton and carbonyl oxygen of the former. Aspirin and the reduced riboflavin form a complex by the same mode as salicylic acid. Salicylamide forms a cyclic hydrogen bonded complex with the reduced riboflavin through the imino (3-N, 5-N) protons and the carbonyl (2-C, 4-C) oxygens of the isoalloxazine ring, and the amino proton and the carbonyl oxygen of salic aylmide. It appears that both the oxidized and reduced form of riboflavin are associated with salicylic acid derivatives.