Document Report Card

Basic Information

ID: ALA1138109

Journal: Bioorg Med Chem Lett

Title: Semicarbazone-based inhibitors of cathepsin K, are they prodrugs for aldehyde inhibitors?

Authors: Adkison KK, Barrett DG, Deaton DN, Gampe RT, Hassell AM, Long ST, McFadyen RB, Miller AB, Miller LR, Payne JA, Shewchuk LM, Wells-Knecht KJ, Willard DH, Wright LL.

Abstract: Starting from potent aldehyde inhibitors with poor drug properties, derivatization to semicarbazones led to the identification of a series of semicarbazone-based cathepsin K inhibitors with greater solubility and better pharmacokinetic profiles than their parent aldehydes. Furthermore, a representative semicarbazone inhibitor attenuated bone resorption in an ex vivo rat calvarial bone resorption model. However, based on enzyme inhibition comparisons at neutral pH, semicarbazone hydrolysis rates, and 13C NMR experiments, these semicarbazones probably function as prodrugs of aldehydes.

CiteXplore: 16290936

DOI: 10.1016/j.bmcl.2005.10.108