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Our laboratory has recently reported the development of a coumarin-based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated the clinical potential of this prodrug system. However, the original synthetic method used required a long sequence of reactions with a relatively low...
To study the structural effects on the release kinetics of a coumarin-based esterase-sensitive prodrug system, two series of compounds with varying structural features of the ester ‘trigger’ part and the amine ‘drug’ part were synthesized. The half-lives of the nine model prodrugs in the presence of porcine liver esterase ranged from about 2min to 190min. The steric bulkiness of the acyl group seems...
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