Stereochemical features of 1,4-benzodiazepin-2-ones bound to human serum albumin: difference CD and UV studies

The stereochemistry of an achiral (Diazepam) and two chiral (3-methyl and 3-succinyloxy substituted) 1,4-benzodiazepin-2-ones interacting with human serum albumin (HSA) has been investigated by making use of difference absorption (UV) and circular dichroism (CD) spectroscopies. Evidence is obtained for a higher affinity with HSA for one of the two possible conformations of the seven-membered benzodiazepine ring. The red shift revealed by the absorption difference spectrum between the free and the bound drug accounts for the CD difference spectra observed.