G6133

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

Name: <SC>L</SC>-Glutamic acid γ-(p-nitroanilide) hydrochloride
Brand: SIGMA

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

Sinónimos:

L-γ-Glutamyl-p-nitroanilide

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Fórmula empírica (notación de Hill):

C₁₁H₁₃N₃O₅ · HCl

Número CAS:

67953-08-6

Peso molecular:

303.70

Número CE:

267-944-5

Número MDL:

MFCD00039054

Código UNSPSC:

12352204

ID de la sustancia en PubChem:

24895247

NACRES:

NA.83

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Nombre del producto

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

Ensayo

≥98% (HPLC)

Formulario

powder

solubilidad

water: 5 mg/mL, clear, yellow

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

OJEVFSFTVARWQX-UHFFFAOYSA-N

Categorías relacionadas

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Este artículo	G1135	49525	G2505
Sigma-Aldrich G6133 L-Glutamic acid γ-(p-nitroanilide) hydrochloride	Sigma-Aldrich G1135 L-Glutamic acid γ-(4-nitroanilide)	Sigma-Aldrich 49525 L-Glutamic acid γ-(3-carboxy-4-nitroanilide) ammonium salt	Sigma-Aldrich G2505 N-Glutaryl-L-phenylalanine p-nitroanilide
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥99.0% (TLC)	assay ≥98% (HPLC)
solubility water: 5 mg/mL, clear, yellow	solubility formic acid: 50 mg/mL, clear to slightly hazy	solubility H₂O: 100 mg/mL, clear, yellow-green	solubility methanol with 1 M NH₄OH: 50 mg/mL, clear to slightly hazy
Quality Level 300	Quality Level 200	Quality Level 200	Quality Level 100
form powder	form powder	form powder	form powder
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C

Descripción general

Substrate for γ-glutamyl transpeptidase

Aplicación

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)[1]
in glutamine ELISA assay to treat confluent differentiated uninfected human colonoid monolayer (HCM) in apical and basolateral compartments to study its effects[2]
to study its effect on SLC1A5_var-mediated mitochondrial glutamine transport inhibition[3]
to study its effects on cellular glutathione levels, cellular reactive oxygen species (ROS) levels, and mitochondrial ROS levels[3]

Acciones bioquímicas o fisiológicas

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).[2]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Cross-Talk between Probiotic Nissle 1917 and Human Colonic Epithelium Affects the Metabolite Composition and Demonstrates Host Antibacterial Effect.

Karol Dokladny et al.

Metabolites, 11(12) (2021-12-24)

Colonic epithelium-commensal interactions play a very important role in human health and disease development. Colonic mucus serves as an ecologic niche for a myriad of commensals and provides a physical barrier between the epithelium and luminal content, suggesting that communication

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

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)

Induction of Thioredoxin-Interacting Protein by a Histone Deacetylase Inhibitor, Entinostat, Is Associated with DNA Damage and Apoptosis in Esophageal Adenocarcinoma.

Paul L Feingold et al.

Molecular cancer therapeutics, 17(9), 2013-2023 (2018-06-24)

In 2017, an estimated 17,000 individuals were diagnosed with esophageal adenocarcinoma (EAC), and less than 20% will survive 5 years. Positron emission tomography avidity is indicative of high glucose utilization and is nearly universal in EAC. TXNIP blocks glucose uptake

Overexpression, one-step purification, and biochemical characterization of a recombinant gamma-glutamyltranspeptidase from Bacillus licheniformis.

Long-Liu Lin et al.

Applied microbiology and biotechnology, 73(1), 103-112 (2006-07-20)

A truncated gene from Bacillus lichenifromis ATCC 27811 encoding a recombinant gamma-glutamyltranspeptidase (BLrGGT) was cloned into pQE-30 to generate pQE-BLGGT, and the overexpressed enzyme was purified from the crude extract of IPTG-induced E. coli M15 (pQE-BLGGT) to homogeneity by nickel-chelate

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