D1692

Sigma-Aldrich

GW4869

≥90% (NMR)

Synonyme(s):
N,N′-Bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-3,3′-p-phenylene-bis-acrylamide dihydrochloride
Empirical Formula (Hill Notation):
C30H28N6O2 · 2HCl
Numéro CAS:
Poids moléculaire:
577.50
ID de substance PubChem:
NACRES:
NA.77

Niveau de qualité

100

Essai/Dosage

≥90% (NMR)

Forme

powder

Conditions de stockage

desiccated
protect from light

Couleur

light yellow to yellow

Pf

>300 °C

Solubilité

DMSO: 0.2 mg/mL

Auteur

GlaxoSmithKline

Temp. de stockage

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 générale

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 (p75NTR) and tropomyosin receptor kinase A (TrkA)- coupled pathways to nerve growth factor (NGF)-induced thermal hypersensitivity in rats

Conditionnement

5, 25 mg in glass bottle

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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

storage_class_code

13 - Non Combustible Solids

WGK Allemagne

WGK 3

Flash Point(F)

Not applicable

Point d'éclair C

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificat d'analyse

Certificat d'origine

E L Kavanagh et al.
Oncogenesis, 6(10), e388-e388 (2017-10-11)
Triple negative breast cancer (TNBC) is an aggressive subtype with relatively poor clinical outcomes and limited treatment options. Chemotherapy, while killing cancer cells, can result in the generation of highly chemoresistant therapeutic induced senescent (TIS) cells that potentially form stem...
Arsenic trioxide inhibits HCCLM3 cells invasion through de novo ceramide synthesis and sphingomyelinase-induced ceramide production
Zhang S, et al
Medical Oncology (Northwood, London, England), 29(3), 2251-2260 (2012)
Laura Hui-Ru Tan et al.
Molecular neurobiology, 55(7), 5741-5756 (2017-10-19)
Sphingomyelinases are a family of enzymes that hydrolyze sphingomyelin to generate phosphocholine and ceramide. The brain distribution and function of neutral sphingomyelinase 2 (nSMase2) were elucidated in this study. nSMase2 mRNA expression was greatest in the striatum, followed by the...
Blockade of exosome generation with GW4869 dampens the sepsis-induced inflammation and cardiac dysfunction
Essandoh K, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1852(11), 2362-2371 (2015)
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...
Contenu apparenté
Discover Bioactive Small Molecules for Lipid Signaling Research
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