67953-08-6

Basic information

• Product Name: L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE
• Synonyms: n-(4-nitrophenyl)-l-glutaminmonohydrochloride;H-GLU(PNA)-OH HCL;L-GAMMA-GLUTAMYL 4-NITROANILIDE HYDROCHLORIDE;L-GAMMA-GLUTAMYL-P-NITROANILIDE HYDROCHLORIDE;L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE;GAMMA-L-GLUTAMYL-P-NITROANILIDE HYDROCHLORIDE;L-glutamic acid gamma-(P-nitroanilide)*hydrochlor;N-(4-nitrophenyl)-L-glutamine monohydrochloride
• CAS NO: 67953-08-6
• Molecular Formula: C11H14ClN3O5
• Molecular Weight: 303.7
• EINECS: 267-944-5
• Mol File: 67953-08-6.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 659.7 °C at 760 mmHg
• Flash Point: 352.8 °C
• Appearance: /
• Vapor Pressure: 8.57E-15mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Soluble in Water (up to 5 mg/ml).
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 1 month.
• CAS DataBase Reference: L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE(67953-08-6)
• EPA Substance Registry System: L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE(67953-08-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 67953-08-6(Hazardous Substances Data)

Usage

Description

L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE, also known as L-γ-Glutamyl-p-nitroanilide (GPNA), is a substrate for γ-glutamyl transpeptidase. It is primarily used for the determination of γ-glutamyl transpeptidase hydrolytic activity through the spectrophotometric monitoring of p-nitroaniline released by the action of the enzyme on GPNA. Additionally, GPNA has been shown to inhibit glutamine uptake by solute-linked carrier family A1 member 5 (SLC1A5), which plays a crucial role in cancer chemotherapy.

Uses

Used in Pharmaceutical Industry:
L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE is used as a diagnostic tool for monitoring γ-glutamyl transpeptidase hydrolytic activity. This is important in understanding the enzyme's role in various biological processes and its potential as a therapeutic target.
Used in Cancer Research and Treatment:
L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE is used as a therapeutic agent for treating cancers with a deregulated NRF2/KEAP1 pathway. By inhibiting glutamine uptake through SLC1A5, GPNA can potentially disrupt the activation of mTOR, a rate-limiting step in cancer cell growth and proliferation.
Used in Drug Delivery Systems:
L-GLUTAMIC ACID GAMMA-(P-NITROANILIDE) HYDROCHLORIDE may be employed in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. This could involve the use of various organic and metallic nanoparticles as carriers for GPNA delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

References

1) Meister?et al. (1981),?γ-Glutamyl transpeptidase; Methods Enzymol.,?77?237 2) Esslinger?et al. (2005),?N-gamma-aryl glutamine analogues as probes of the ASCT2 neutral amino acid transporter binding site; Bioorg. Med. Chem.,?13?1111 3) Nicklin?et al. (2012),?Bidirectional Transport of Amino Acid Regulates mTOR and Autophagy; Cell,?136?521

InChI:InChI=1/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/t9-;/m0./s1