Structural characterization of P1'-diversified urea-based inhibitors of glutamate carboxypeptidase II
Language English Country Great Britain, England Media print-electronic
Document type Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.
Grant support
R01 CA134675
NCI NIH HHS - United States
PubMed
24731280
PubMed Central
PMC4077459
DOI
10.1016/j.bmcl.2014.03.066
PII: S0960-894X(14)00293-5
Knihovny.cz E-resources
- Keywords
- GCPII, Metallopeptidase, PSMA, Prostate-specific membrane antigen, Structure-based drug design, Urea-based inhibitor, X-ray crystallography,
- MeSH
- Antigens, Surface chemistry MeSH
- Glutamate Carboxypeptidase II antagonists & inhibitors chemistry MeSH
- Enzyme Inhibitors chemistry pharmacology MeSH
- Kinetics MeSH
- Protein Conformation MeSH
- Crystallography, X-Ray MeSH
- Humans MeSH
- Urea analogs & derivatives chemistry pharmacology MeSH
- Molecular Conformation MeSH
- Models, Molecular MeSH
- Drug Design MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Research Support, N.I.H., Extramural MeSH
- Research Support, U.S. Gov't, Non-P.H.S. MeSH
- Names of Substances
- Antigens, Surface MeSH
- FOLH1 protein, human MeSH Browser
- Glutamate Carboxypeptidase II MeSH
- Enzyme Inhibitors MeSH
- Urea MeSH
Urea-based inhibitors of human glutamate carboxypeptidase II (GCPII) have advanced into clinical trials for imaging metastatic prostate cancer. In parallel efforts, agents with increased lipophilicity have been designed and evaluated for targeting GCPII residing within the neuraxis. Here we report the structural and computational characterization of six complexes between GCPII and P1'-diversified urea-based inhibitors that have the C-terminal glutamate replaced by more hydrophobic moieties. The X-ray structures are complemented by quantum mechanics calculations that provide a quantitative insight into the GCPII/inhibitor interactions. These data can be used for the rational design of novel glutamate-free GCPII inhibitors with tailored physicochemical properties.
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