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SML2793

Sigma-Aldrich

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
MDL number:
MFCD09971117
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

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

Biochem/physiol Actions

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Tatsuo Yamamoto et al.
The European journal of neuroscience, 20(2), 483-494 (2004-07-06)
The peptide neurotransmitter N-acetylaspartylglutamate (NAAG) acts as an agonist at group II metabotropic glutamate receptors (mGluRs). NAAG is inactivated by extracellular peptidase activity yielding glutamate and N-acetylaspartate. We recently developed a series of potent NAAG peptidase inhibitors, including ZJ-11, ZJ-17
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
Ming Li et al.
Chemical science, 7(11), 6779-6785 (2017-04-30)
Precise visualization of tumor margins with characterization of microscopic tumor invasion are unmet needs in prostate oncology that demand approaches with high sensitivity and specificity. To address those needs we report surface-enhanced Raman scattering (SERS) based optical imaging for prostate
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