Key Documents

View All Documentation

D1692

GW4869

Name: GW4869
Brand: SIGMA

≥90% (NMR), powder, N-SMase inhibitor

Synonym(s):

N,N′-Bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-3,3′-p-phenylene-bis-acrylamide dihydrochloride

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₃₀H₂₈N₆O₂· 2HCl

CAS Number:

6823-69-4

Molecular Weight:

577.50

UNSPSC Code:

41121800

PubChem Substance ID:

24724460

NACRES:

NA.77

Assay:

≥90% (NMR)

Form:

powder

Quality level:

100

Storage condition:

desiccated, protect from light

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Product Name

GW4869, ≥90% (NMR)

Quality Level

100

assay

≥90% (NMR)

form

powder

storage condition

desiccated, protect from light

color

light yellow to yellow

mp

>300 °C

solubility

DMSO: 0.2 mg/mL

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

Cl.Cl.O=C(Nc1ccc(cc1)C2=NCCN2)\C=C/c3ccc(\C=C/C(=O)Nc4ccc(cc4)C5=NCCN5)cc3

InChI

1S/C30H28N6O2.2ClH/c37-27(35-25-11-7-23(8-12-25)29-31-17-18-32-29)15-5-21-1-2-22(4-3-21)6-16-28(38)36-26-13-9-24(10-14-26)30-33-19-20-34-30;;/h1-16H,17-20H2,(H,31,32)(H,33,34)(H,35,37)(H,36,38);2*1H/b15-5-,16-6-;;

InChI key

NSFKAZDTKIKLKT-LOLTXFFGSA-N

Description

General description

GW4869 is a commonly used pharmacological agent, which inhibits exosome generation. It blocks ceramide-mediated inward budding of multivesicular bodies (MVBs) and the release of mature exosomes from MVBs. GW4869 exhibits cytotoxicity to phosphatidylserine-expressing myeloma cells. It inhibits the secretion of IFN (interferon)-α by plasmacytoid dendritic cells (pDCs).

Application

GW4869 has been used:

as an inhibitor of neutral sphingomyelinase and exosome biogenesis
to analyse the effects of arsenic trioxide (ATO) treatment for hepatoma carcinoma HCCLM3 cells on ceramide production
to determine the contributions of p75 neurotrophin receptor (p75^NTR) and tropomyosin receptor kinase A (TrkA)- coupled pathways to nerve growth factor (NGF)-induced thermal hypersensitivity in rats

Biochem/physiol Actions

A cell-permeable, potent, specific, non-competitive inhibitor of N-SMase (neutral sphingomyelinase)

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Integrins and heparan sulfate proteoglycans on hepatic stellate cells (HSC) are novel receptors for HSC-derived exosomes.

Li Chen et al.

FEBS letters, 590(23), 4263-4274 (2016-10-25)

Exosomes mediate intercellular microRNA delivery between hepatic stellate cells (HSC), the principal fibrosis-producing cells in the liver. The purpose of this study was to identify receptors on HSC for HSC-derived exosomes, which bind to HSC rather than to hepatocytes. Our

Zika virus propagation and release in human fetal astrocytes can be suppressed by neutral sphingomyelinase-2 inhibitor GW4869.

Yunlong Huang et al.

Cell discovery, 4, 19-19 (2018-05-01)

Zika virus (ZIKV) is a neurotrophic flavivirus that is capable of infecting humans, leading to brain abnormalities during fetal development. The ZIKV infectivity in neural target cells remains poorly understood. Here, we found that ZIKV specifically infected glial fibrillary acidic

Sphingolipid-mediated inflammatory signaling leading to autophagy inhibition converts erythropoiesis to myelopoiesis in human hematopoietic stem/progenitor cells.

Marion Orsini et al.

Cell death and differentiation, 26(9), 1796-1812 (2018-12-14)

Elevated levels of the pro-inflammatory cytokine tumor necrosis factor-α (TNFα) inhibit erythropoiesis and cause anemia in patients with cancer and chronic inflammatory diseases. TNFα is also a potent activator of the sphingomyelinase (SMase)/ceramide pathway leading to ceramide synthesis and regulating

View All Related Papers