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G6133

L-Glutamic acid γ-(p-nitroanilide) hydrochloride

Name: <SC>L</SC>-Glutamic acid &#947;-(p-nitroanilide) hydrochloride
Brand: SIGMA

≥98% (HPLC), glutamine (Gln) transporter alanine-serine-cysteine transporter 2 (ASCT2) blocker, powder

Synonym(s):

L-γ-Glutamyl-p-nitroanilide

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₃N₃O₅ · HCl

CAS Number:

67953-08-6

Molecular Weight:

303.70

NACRES:

NA.83

PubChem Substance ID:

24895247

UNSPSC Code:

12352204

EC Number:

267-944-5

MDL number:

MFCD00039054

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Properties

Product Name

L-Glutamic acid γ-(p-nitroanilide) hydrochloride, γ-glutamyl transpeptidase substrate

Quality Level

300

assay

≥98% (HPLC)

form

powder

solubility

water: 5 mg/mL, clear, yellow

storage temp.

2-8°C

SMILES string

Cl.NC(CCC(=O)Nc1ccc(cc1)N(=O)=O)C(O)=O

InChI

1S/C11H13N3O5.ClH/c12-9(11(16)17)5-6-10(15)13-7-1-3-8(4-2-7)14(18)19;/h1-4,9H,5-6,12H2,(H,13,15)(H,16,17);1H

InChI key

OJEVFSFTVARWQX-UHFFFAOYSA-N

Description

General description

Substrate for γ-glutamyl transpeptidase

Application

L-Glutamic acid γ-(p-nitroanilide) hydrochloride has been used as a solute carrier family 1 member 5 (SLC1A5) inhibitor:

or an inhibitor of the cell membrane glutamine transporter to study the effects of blocking glutamine uptake on esophageal adenocarcinoma (EACC) and thioredoxin-interacting protein (TXNIP)
in glutamine ELISA assay to treat confluent differentiated uninfected human colonoid monolayer (HCM) in apical and basolateral compartments to study its effects
to study its effect on SLC1A5_var-mediated mitochondrial glutamine transport inhibition
to study its effects on cellular glutathione levels, cellular reactive oxygen species (ROS) levels, and mitochondrial ROS levels

Biochem/physiol Actions

L-Glutamyl-p-nitroanilide (GPNA) is commonly used to block the glutamine (Gln) transporter alanine-serine-cysteine transporter 2 (ASCT2). It can also inhibit sodium-dependent and independent amino acid transporters. GPNA, γ-glutamyltransferase (GGT) substrate plays a key role in the hydrolysis of its γ-glutamyl bond and the subsequent release of the chromogen, p-nitroaniline (PNA).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Computational models applied to metabolomics data hints at the relevance of glutamine metabolism in breast cancer.

Lucía Trilla-Fuertes et al.

BMC cancer, 20(1), 307-307 (2020-04-16)

Metabolomics has a great potential in the development of new biomarkers in cancer and it has experiment recent technical advances. In this study, metabolomics and gene expression data from 67 localized (stage I to IIIB) breast cancer tumor samples were

γ-Glutamyltransferase enzyme activity of cancer cells modulates L-γ-glutamyl-p-nitroanilide (GPNA) cytotoxicity.

Alessandro Corti et al.

Scientific reports, 9(1), 891-891 (2019-01-31)

L-γ-Glutamyl-p-nitroanilide (GPNA) is widely used to inhibit the glutamine (Gln) transporter ASCT2, but recent studies have demonstrated that it is also able to inhibit other sodium-dependent and independent amino acid transporters. Moreover, GPNA is a well known substrate of the