GW-4869 HCl
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MedKoo CAT#: 555211

CAS#: 6823-69-4 (HCl)

Description: GW-4869 is a cell-permeable, non-competitive inhibitor of neutral sphingomyelinases (IC50 = 1 μM). It inhibits TNF-α-mediated sphingomyelin hydrolysis (100% inhibition at 20 μM). GW4869 is cytotoxic to high phosphatidylserine-expressing myeloma cells. Blockade of exosome generation with GW4869 dampens the sepsis-induced inflammation and cardiac dysfunction.


Price and Availability

Size
Price

100mg
USD 1450
1g
USD 3450
Size
Price

200mg
USD 1950
2g
USD 5450
Size
Price

500mg
USD 2750
5g
USD 9650

GW-4869 HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 555211
Name: GW-4869 HCl
CAS#: 6823-69-4 (HCl)
Chemical Formula: C30H30Cl2N6O2
Exact Mass:
Molecular Weight: 577.51
Elemental Analysis: C, 62.39; H, 5.24; Cl, 12.28; N, 14.55; O, 5.54


Related CAS #: 6823-69-4 (HCl)   475570-61-7 (free base)    

Synonym: GW4869; GW-4869; GW 4869; GW554869A; GW-554869A; GW 554869A; GW69A; GW-69A; GW 69A; GW-4869 HCl

IUPAC/Chemical Name: (2E,2'E)-3,3'-(1,4-phenylene)bis(N-(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)acrylamide) dihydrochloride

InChi Key: NSFKAZDTKIKLKT-CLEIDKRQSA-N

InChi Code: 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+;;

SMILES Code: O=C(/C=C/C1=CC=C(C=C1)/C=C/C(NC2=CC=C(C=C2)C3=NCCN3)=O)NC4=CC=C(C=C4)C5=NCCN5.[H]Cl.[H]Cl


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

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2: Lee HY, Chen CK, Ho CM, Lee SS, Chang CY, Chen KJ, Jou YS. EIF3C-enhanced exosome secretion promotes angiogenesis and tumorigenesis of human hepatocellular carcinoma. Oncotarget. 2018 Jan 11;9(17):13193-13205. doi: 10.18632/oncotarget.24149. eCollection 2018 Mar 2. PubMed PMID: 29568350; PubMed Central PMCID: PMC5862571.

3: Yang L, Niu F, Yao H, Liao K, Chen X, Kook Y, Ma R, Hu G, Buch S. Exosomal miR-9 Released from HIV Tat Stimulated Astrocytes Mediates Microglial Migration. J Neuroimmune Pharmacol. 2018 Mar 1. doi: 10.1007/s11481-018-9779-4. [Epub ahead of print] PubMed PMID: 29497921.

4: Panigrahi GK, Praharaj PP, Peak TC, Long J, Singh R, Rhim JS, Elmageed ZYA, Deep G. Hypoxia-induced exosome secretion promotes survival of African-American and Caucasian prostate cancer cells. Sci Rep. 2018 Mar 1;8(1):3853. doi: 10.1038/s41598-018-22068-4. PubMed PMID: 29497081; PubMed Central PMCID: PMC5832762.

5: Sobue A, Ito N, Nagai T, Shan W, Hada K, Nakajima A, Murakami Y, Mouri A, Yamamoto Y, Nabeshima T, Saito K, Yamada K. Astroglial major histocompatibility complex class I following immune activation leads to behavioral and neuropathological changes. Glia. 2018 May;66(5):1034-1052. doi: 10.1002/glia.23299. Epub 2018 Jan 30. PubMed PMID: 29380419.

6: Won JH, Kim SK, Shin IC, Ha HC, Jang JM, Back MJ, Kim DK. Dopamine transporter trafficking is regulated by neutral sphingomyelinase 2/ceramide kinase. Cell Signal. 2018 Apr;44:171-187. doi: 10.1016/j.cellsig.2018.01.006. Epub 2018 Jan 9. PubMed PMID: 29329781.

7: Zhou W, Woodson M, Neupane B, Bai F, Sherman MB, Choi KH, Neelakanta G, Sultana H. Exosomes serve as novel modes of tick-borne flavivirus transmission from arthropod to human cells and facilitates dissemination of viral RNA and proteins to the vertebrate neuronal cells. PLoS Pathog. 2018 Jan 4;14(1):e1006764. doi: 10.1371/journal.ppat.1006764. eCollection 2018 Jan. PubMed PMID: 29300779; PubMed Central PMCID: PMC5754134.

8: Menck K, Sönmezer C, Worst TS, Schulz M, Dihazi GH, Streit F, Erdmann G, Kling S, Boutros M, Binder C, Gross JC. Neutral sphingomyelinases control extracellular vesicles budding from the plasma membrane. J Extracell Vesicles. 2017 Sep 26;6(1):1378056. doi: 10.1080/20013078.2017.1378056. eCollection 2017. PubMed PMID: 29184623; PubMed Central PMCID: PMC5699186.

9: Zhang YZ, Liu F, Song CG, Cao XL, Zhang YF, Wu HN, Guo CJ, Li YQ, Zheng QJ, Zheng MH, Han H. Exosomes derived from human umbilical vein endothelial cells promote neural stem cell expansion while maintain their stemness in culture. Biochem Biophys Res Commun. 2018 Jan 1;495(1):892-898. doi: 10.1016/j.bbrc.2017.11.092. Epub 2017 Nov 15. PubMed PMID: 29154990.

10: Chen L, Chen R, Kemper S, Brigstock DR. Pathways of production and delivery of hepatocyte exosomes. J Cell Commun Signal. 2018 Mar;12(1):343-357. doi: 10.1007/s12079-017-0421-7. Epub 2017 Oct 23. PubMed PMID: 29063370; PubMed Central PMCID: PMC5842184.

11: Tan LH, Tan AJ, Ng YY, Chua JJ, Chew WS, Muralidharan S, Torta F, Dutta B, Sze SK, Herr DR, Ong WY. Enriched Expression of Neutral Sphingomyelinase 2 in the Striatum is Essential for Regulation of Lipid Raft Content and Motor Coordination. Mol Neurobiol. 2017 Oct 17. doi: 10.1007/s12035-017-0784-z. [Epub ahead of print] PubMed PMID: 29043558.

12: Niu Z, Pang RTK, Liu W, Li Q, Cheng R, Yeung WSB. Polymer-based precipitation preserves biological activities of extracellular vesicles from an endometrial cell line. PLoS One. 2017 Oct 12;12(10):e0186534. doi: 10.1371/journal.pone.0186534. eCollection 2017. PubMed PMID: 29023592; PubMed Central PMCID: PMC5638560.

13: Kavanagh EL, Lindsay S, Halasz M, Gubbins LC, Weiner-Gorzel K, Guang MHZ, McGoldrick A, Collins E, Henry M, Blanco-Fernández A, Gorman PO, Fitzpatrick P, Higgins MJ, Dowling P, McCann A. Protein and chemotherapy profiling of extracellular vesicles harvested from therapeutic induced senescent triple negative breast cancer cells. Oncogenesis. 2017 Oct 9;6(10):e388. doi: 10.1038/oncsis.2017.82. PubMed PMID: 28991260; PubMed Central PMCID: PMC5668881.

14: Tavakoli Dargani Z, Singla R, Johnson T, Kukreja R, Singla DK. Exosomes derived from embryonic stem cells inhibit doxorubicin and inflammation-induced pyroptosis in muscle cells. Can J Physiol Pharmacol. 2018 Mar;96(3):304-307. doi: 10.1139/cjpp-2017-0340. Epub 2017 Sep 19. PubMed PMID: 28926719.

15: Liu T, Chen G, Sun D, Lei M, Li Y, Zhou C, Li X, Xue W, Wang H, Liu C, Xu J. Exosomes containing miR-21 transfer the characteristic of cisplatin resistance by targeting PTEN and PDCD4 in oral squamous cell carcinoma. Acta Biochim Biophys Sin (Shanghai). 2017 Sep 1;49(9):808-816. doi: 10.1093/abbs/gmx078. PubMed PMID: 28910982.

16: Gon Y, Maruoka S, Inoue T, Kuroda K, Yamagishi K, Kozu Y, Shikano S, Soda K, Lötvall J, Hashimoto S. Selective release of miRNAs via extracellular vesicles is associated with house-dust mite allergen-induced airway inflammation. Clin Exp Allergy. 2017 Dec;47(12):1586-1598. doi: 10.1111/cea.13016. PubMed PMID: 28859242.

17: Cheng Q, Li X, Wang Y, Dong M, Zhan FH, Liu J. The ceramide pathway is involved in the survival, apoptosis and exosome functions of human multiple myeloma cells in vitro. Acta Pharmacol Sin. 2018 Apr;39(4):561-568. doi: 10.1038/aps.2017.118. Epub 2017 Aug 31. PubMed PMID: 28858294.

18: Trajkovic K, Jeong H, Krainc D. Mutant Huntingtin Is Secreted via a Late Endosomal/Lysosomal Unconventional Secretory Pathway. J Neurosci. 2017 Sep 13;37(37):9000-9012. doi: 10.1523/JNEUROSCI.0118-17.2017. Epub 2017 Aug 16. PubMed PMID: 28821645; PubMed Central PMCID: PMC5597981.

19: Cao YL, Zhuang T, Xing BH, Li N, Li Q. Exosomal DNMT1 mediates cisplatin resistance in ovarian cancer. Cell Biochem Funct. 2017 Aug;35(6):296-303. doi: 10.1002/cbf.3276. Epub 2017 Aug 8. PubMed PMID: 28791708.

20: Jung AL, Herkt CE, Schulz C, Bolte K, Seidel K, Scheller N, Sittka-Stark A, Bertrams W, Schmeck B. Legionella pneumophila infection activates bystander cells differentially by bacterial and host cell vesicles. Sci Rep. 2017 Jul 24;7(1):6301. doi: 10.1038/s41598-017-06443-1. PubMed PMID: 28740179; PubMed Central PMCID: PMC5524687.