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Merck
CN

SML2793

ZJ43

≥98% (HPLC)

Synonym(s):

(S)-2-(3-((S)-1-Carboxy-3-methylbutyl)ureido)pentanedioic acid, N-[[[(1S)-1-Carboxy-3-methylbutyl]amino]carbonyl]-L-glutamic acid, ZJ 43, ZJ-43

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About This Item

Empirical Formula (Hill Notation):
C12H20N2O7
CAS Number:
723331-20-2
Molecular Weight:
304.30
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD09971117

Key Documents

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SMILES string

N([C@@H](CC(C)C)C(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)O

InChI

1S/C12H20N2O7/c1-6(2)5-8(11(19)20)14-12(21)13-7(10(17)18)3-4-9(15)16/h6-8H,3-5H2,1-2H3,(H,15,16)(H,17,18)(H,19,20)(H2,13,14,21)/t7-,8-/m0/s1

InChI key

BSGWCSGMXAVYRT-YUMQZZPRSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

Potent glutamate carboxypeptidase II (GCPII; NAAG peptidase; NAALADase I; PSMA) inhibitor that suppresses PCP-induced motor activity in vivo.
ZJ43 is a urea-based N-acetylaspartylglutamate (NAAG) analog and a potent glutamate carboxypeptidase II (GCPII; NAAG peptidase; N-acetylaspartylglutamate peptidase I; NAALADase I; prostate-specific membrane antigen; PSMA) inhibitor (Ki = 0.8 nM/hGCPII vs 23 nM/hGCPIII) with no affinity toward NMDAR or mGluRs. ZJ43 effectively suppresses phencyclidine-induced motor activity (150 mg ZJ43/kg, 10 mg PCP/kg i.p.) and displays antinociceptive efficacy (100 mg/kg i.v.) in rats in vivo. Comparing to Quisqualate and 2-PMPA, ZJ43 shows human species-selectivity over murine GCPII (Ki = 0.58 nM/h vs. 5.9 nM/m using respective avi-tagged extracellular GCPII).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000119365
0000119366
0000106934

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Tomáš Knedlík et al.
FEBS open bio, 7(9), 1362-1378 (2017-09-15)
Glutamate carboxypeptidase II (GCPII), also known as prostate-specific membrane antigen (PSMA) or folate hydrolase, is a metallopeptidase expressed predominantly in the human brain and prostate. GCPII expression is considerably increased in prostate carcinoma, and the enzyme also participates in glutamate excitotoxicity
Rafal T Olszewski et al.
Journal of neurochemistry, 89(4), 876-885 (2004-05-14)
Phencyclidine (PCP) administration elicits positive and negative symptoms that resemble those of schizophrenia and is widely accepted as a model for the study of this human disorder. Group II metabotropic glutamate receptor (mGluR) agonists have been reported to reduce the
[Insulin therapy today and tomorrow].
F Kuntschen
Revue medicale de la Suisse romande, 115(9), 713-716 (1995-09-01)
Chunlong Zhong et al.
Journal of neurotrauma, 22(2), 266-276 (2005-02-18)
Traumatic brain injury (TBI) produces a rapid and excessive elevation in extracellular glutamate associated with excitotoxicity and secondary brain pathology. The peptide neurotransmitter Nacetylaspartylglutamate (NAAG) suppresses glutamate transmission through selective activation of presynaptic Group II metabotropic glutamate receptor subtype 3
Sangeeta Ray Banerjee et al.
Bioconjugate chemistry, 27(6), 1447-1455 (2016-04-15)
(68)Ga-labeled, low-molecular-weight imaging agents that target the prostate-specific membrane antigen (PSMA) are increasingly used clinically to detect prostate and other cancers with positron emission tomography (PET). The goal of this study was to compare the pharmacokinetics of three PSMA-targeted radiotracers:
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