GPNA hydrochloride | CAS# 67953-08-6 | ASCT2 (SLC1A5) Inhibitor

MedKoo Cat#: 564043 | Name: GPNA hydrochloride

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

GPNA, also known as L-γ-Glutamyl-p-nitroanilide, is a potent, competitive inhibitor of the neutral amino acid transporter ASCT2 (SLC1A5).

Chemical Structure

GPNA hydrochloride

CAS#67953-08-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 564043

Name: GPNA hydrochloride

CAS#: 67953-08-6 (HCl)

Chemical Formula: C11H14ClN3O5

Exact Mass: 0.0000

Molecular Weight: 303.70

Elemental Analysis: C, 43.50; H, 4.65; Cl, 11.67; N, 13.84; O, 26.34

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 350.00	2 Weeks
1g	USD 650.00	2 Weeks

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Related CAS #

7300-59-6 (free base) 67953-08-6 (HCl)

Synonym

GPNA hydrochloride; GPNA HCl; GPNA (hydrochloride)

IUPAC/Chemical Name

N5-(4-nitrophenyl)-L-glutamine hydrochloride

InChi Key

OJEVFSFTVARWQX-FVGYRXGTSA-N

InChi Code

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/t9-;/m0./s1

SMILES Code

OC([C@@H](N)CCC(NC1=CC=C([N+]([O-])=O)C=C1)=O)=O.Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

GPNA hydrochloride is a well known substrate of the enzyme γ-glutamyltransferase (GGT). GPNA hydrochloride is a specific glutamine (Gln) transporter ASCT2 inhibitor. GPNA hydrochloride also inhibit Na+-dependent carriers, such as SNAT family (SNAT1/2/4/5), and the Na+-independent leucine transporters LAT1/2. GPNA reversibly induces apoptosis in A549 cells.

In vitro activity:

As presented in Figure 3d, glutamine consumption was inhibited after GPNA treatment. Comparatively, GPNA treatment induced proliferation repression of MDA-MB-231 and BT-549 cells (Figure 3e-G). On the opposite, the apoptosis of MDA-MB-231 and BT-549 cells was promoted after GPNA treatment (Figure 3h). In support, GPNA induced cell arrest at G0/G1 phase (Figure 3i), which also indicated the repressing role of SLC1A5 knockdown in cell proliferation. Reference: Bioengineered. 2021 Dec;12(2):10624-10637. https://pubmed.ncbi.nlm.nih.gov/34738502/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	65.0	214.03
	Water	1.5	4.94

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 303.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wang J, Yang K, Cao J, Li L. Knockdown of circular RNA septin 9 inhibits the malignant progression of breast cancer by reducing the expression of solute carrier family 1 member 5 in a microRNA-149-5p-dependent manner. Bioengineered. 2021 Dec;12(2):10624-10637. doi: 10.1080/21655979.2021.2000731. PMID: 34738502; PMCID: PMC8809977. 2. Corti A, Dominici S, Piaggi S, Belcastro E, Chiu M, Taurino G, Pacini S, Bussolati O, Pompella A. γ-Glutamyltransferase enzyme activity of cancer cells modulates L-γ-glutamyl-p-nitroanilide (GPNA) cytotoxicity. Sci Rep. 2019 Jan 29;9(1):891. doi: 10.1038/s41598-018-37385-x. PMID: 30696905; PMCID: PMC6351548.

In vitro protocol:

In vivo protocol:

TBD

1: Chiu M, Sabino C, Taurino G, Bianchi MG, Andreoli R, Giuliani N, Bussolati O. GPNA inhibits the sodium-independent transport system L for neutral amino acids. Amino Acids. 2017 Aug;49(8):1365-1372. doi: 10.1007/s00726-017-2436-z. Epub 2017 May 17. PubMed PMID: 28516268. 2: Dragulescu-Andrasi A, Zhou P, He G, Ly DH. Cell-permeable GPNA with appropriate backbone stereochemistry and spacing binds sequence-specifically to RNA. Chem Commun (Camb). 2005 Jan 14;(2):244-6. Epub 2004 Dec 2. PubMed PMID: 15724200. 3: Zhou P, Wang M, Du L, Fisher GW, Waggoner A, Ly DH. Novel binding and efficient cellular uptake of guanidine-based peptide nucleic acids (GPNA). J Am Chem Soc. 2003 Jun 11;125(23):6878-9. PubMed PMID: 12783535.