Document Report Card

Basic Information

ID: ALA1770077

Journal: Bioorg Med Chem Lett

Title: Synthesis, modelling and kinetic assays of potent inhibitors of purple acid phosphatase.

Authors: Mohd-Pahmi SH, Hussein WM, Schenk G, McGeary RP.

Abstract: Purple acid phosphatases (PAPs) are binuclear metallohydrolases that have been isolated from various mammals, plants, fungi and bacteria. In mammals PAP activity is associated with bone resorption and can lead to bone metabolic disorders such as osteoporosis; thus human PAP is an attractive target to develop anti-osteoporotic drugs. Based on a previous lead compound and rational drug design, acyl derivatives of α-aminonaphthylmethylphosphonic acid were synthesised and tested as PAP inhibitors. Kinetic analysis showed that they are good PAP inhibitors whose potencies improve with increasing acyl chain length. Maximum potency is reached when the number of carbons in the acyl chain is between 12 and 14. The most potent inhibitor of red kidney bean PAP is the dodecyl-derivative with K(ic)=5 μM, while the most potent pig PAP inhibitor is the tetradecyl-derivative with K(ic)=8 μM, the most potent inhibitor of a mammalian PAP yet reported.

CiteXplore: 21459576

DOI: 10.1016/j.bmcl.2011.03.024