A literature search has found articles where in vitro cultured cells were treated with this product for up to 24 hours. Conducting a literature search may provide further guidance on long-term treatment.
D1692
GW4869
≥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
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Product Name
GW4869, ≥90% (NMR)
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
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
Quality Level
Related Categories
1 of 4
This Item | G5172 | D8946 | SML1832 |
|---|---|---|---|
| form powder | form powder | form powder | form powder |
| assay ≥90% (NMR) | assay ≥97% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) |
| Quality Level 100 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| storage temp. 2-8°C | storage temp. 2-8°C | storage temp. 2-8°C | storage temp. 2-8°C |
| solubility DMSO: 0.2 mg/mL | solubility DMSO: 10 mg/mL, clear | solubility DMSO: 5 mg/mL, clear (warmed) | solubility DMSO: 10 mg/mL, clear |
| storage condition desiccated, protect from light | storage condition desiccated | storage condition desiccated | storage condition - |
Application
GW4869 has been used:
- as an inhibitor of neutral sphingomyelinase and exosome biogenesis[1][2][3]
- to analyse the effects of arsenic trioxide (ATO) treatment for hepatoma carcinoma HCCLM3 cells on ceramide production[4]
- 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[5]
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.
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.[6] GW4869 exhibits cytotoxicity to phosphatidylserine-expressing myeloma cells.[7] It inhibits the secretion of IFN (interferon)-α by plasmacytoid dendritic cells (pDCs).[8]
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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
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)
Hasna Ahyayauch et al.
Scientific reports, 8(1), 7456-7456 (2018-05-12)
The mechanisms of Pb(II) toxicity have been studied in human red blood cells using confocal microscopy, immunolabeling, fluorescence-activated cell sorting and atomic force microscopy. The process follows a sequence of events, starting with calcium entry, followed by potassium release, morphological
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
Articles
Discover Bioactive Small Molecules for Lipid Signaling Research
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Can in vitro cultured cells be treated longterm with GW4869? (for example 10 days treatment)
1 answer-
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After resuspending 5 mg GW4869 from Millipore D1692 in DMSO, should it still be stored at 4°C?
1 answer-
GW4869 has a maximum solubility of 0.2 mg/mL in DMSO. It is hygroscopic and light-sensitive, so solutions of GW4869 should be stored as single-use aliquots. When stored at -20 degrees C, stock solutions should be stable for at least 3 months.
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