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Novel β- and γ-Amino Acid-Derived Inhibitors of Prostate-Specific Membrane Antigen.

Abstract：

:Prostate-specific membrane antigen (PSMA) is an excellent biomarker for the early diagnosis of prostate cancer progression and metastasis. The most promising PSMA-targeted agents in the clinical phase are based on the Lys-urea-Glu motif, in which Lys and Glu are α-(l)-amino acids. In this study, we aimed to determine the effect of β- and γ-amino acids in the S1 pocket on the binding affinity for PSMA. We synthesized and evaluated the β- and γ-amino acid analogues with (S)- or (R)-configuration with keeping α-(l)-Glu as the S1'-binding pharmacophore. The structure-activity relationship studies identified that compound 13c, a β-amino acid analogue with (R)-configuration, exhibited the most potent PSMA inhibitory activity with an IC50 value of 3.97 nM. The X-ray crystal structure of PSMA in complex with 13c provided a mechanistic basis for the stereochemical preference of PSMA, which can guide the development of future PSMA inhibitors.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Kim K,Kwon H,Barinka C,Motlova L,Nam S,Choi D,Ha H,Nam H,Son SH,Minn I,Pomper MG,Yang X,Kutil Z,Byun Y

doi

10.1021/acs.jmedchem.9b02022

subject

Has Abstract

pub_date

2020-03-26 00:00:00

pages

3261-3273

issue

6

eissn

0022-2623

issn

1520-4804

journal_volume

63

pub_type

杂志文章

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