Literature DB >> 24354364

δ-Thiolactones as prodrugs of thiol-based glutamate carboxypeptidase II (GCPII) inhibitors.

Dana V Ferraris1, Pavel Majer, Chiyou Ni, C Ethan Slusher, Rana Rais, Ying Wu, Krystyna M Wozniak, Jesse Alt, Camilo Rojas, Barbara S Slusher, Takashi Tsukamoto.   

Abstract

δ-Thiolactones derived from thiol-based glutamate carboxypeptidase II (GCPII) inhibitors were evaluated as prodrugs. In rat liver microsomes, 2-(3-mercaptopropyl)pentanedioic acid (2-MPPA, 1) was gradually produced from 3-(2-oxotetrahydrothiopyran-3-yl)propionic acid (5), a thiolactone derived from 1. Compound 1 was detected in plasma at concentrations well above its IC50 for GCPII following oral administration of 5 in rats. Consistent with the oral plasma pharmacokinetics, thiolactone 5 exhibited efficacy in a rat model of neuropathic pain following oral administration.

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Year:  2013        PMID： 24354364      PMCID： PMC3932958          DOI： 10.1021/jm401703a

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  17 in total

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3.  Structural optimization of thiol-based inhibitors of glutamate carboxypeptidase II by modification of the P1' side chain.

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4.  Enantiospecificity of glutamate carboxypeptidase II inhibition.

Authors:  Takashi Tsukamoto; Pavel Majer; Dilrukshi Vitharana; Chiyou Ni; Bunda Hin; Xi-Chun M Lu; Ajit G Thomas; Krystyna M Wozniak; David C Calvin; Ying Wu; Barbara S Slusher; David Scarpetti; George W Bonneville
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  5 in total

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