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Merck

SML2148

Sulfo-N-succinimidyl Oleate sodium

≥95% (HPLC), fatty acid translocase inhibitor, powder

Sinónimos:

(Z)-1-(oleoyloxy)-2,5-dioxopyrrolidine-3-sulfonic acid, sodium salt, (Z)-2,5-Dioxo-1-[(1-oxo-9-octadecenyl)oxy]-3-pyrrolidinesulfonic acid, sodium salt, 2,5-Dioxo-1-[[(9Z)-1-oxo-9-octadecenyl]oxy]-3-pyrrolidinesulfonic acid, sodium salt, SSO sodium salt, Sulfosuccinimidyl oleate sodium

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Fórmula empírica (notación de Hill):
C22H36NO7S· Na
Número CAS:
135661-44-8
Peso molecular:
481.58
NACRES:
NA.77
UNSPSC Code:
51111800
EC Number:
801-756-1
MDL number:
MFCD12547938
Assay:
≥95% (HPLC)
Form:
powder
Storage condition:
desiccated

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Nombre del producto

Sulfo-N-succinimidyl Oleate sodium, ≥95% (HPLC)

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

CCCCCCCC/C=C\CCCCCCCC(ON1C(C(CC1=O)S([O-])(=O)=O)=O)=O.[Na+]

InChI

1S/C22H37NO7S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(25)30-23-20(24)18-19(22(23)26)31(27,28)29;/h9-10,19H,2-8,11-18H2,1H3,(H,27,28,29);

InChI key

IENDXPSKPJDQKO-UHFFFAOYSA-N

Categorías relacionadas

Application

Sulfo-N-succinimidyl Oleate sodium has been used as a cluster of differentiation 36 (CD36) blocker in Raw264.7 cells and bone marrow-derived macrophages. It has also been used as an irreversible inhibitor of CD36 in acute myeloid leukemia (AML) to monitor CD36 induced apoptosis.

Biochem/physiol Actions

Covalently modifies fatty acid translocase (CD36/FAT) Lys164 and irreversibly inhibits CD36-dependent FA uptake in vitro and in vivo.
Sulfo-N-succinimidyl oleate (SSO; Sulfosuccinimidyl oleate) inhibits fatty acid translocase (CD36/FAT)-mediated signaling as well as long-chain fatty acid (LCFA) and oxidized low density lipoproteins (oxLDL) uptake in an irreversible manner via covalent modification of CD36 Lys164 within its FA- and oxLDL-binding domain. SSO is employed both in cultures (5-500 μM) and in animals in vivo (40 mg/kg i.p.) for studying CD36-mediated cellular and physiological functions.
SSO is an inhibitor of the respiratory chain happening in mitochondria. SSO targets the lysine 164 residue of the fatty acid binding site, observed in CD36 (cluster of differentiation 36), a scavenger receptor.

Clase de almacenamiento

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000521985
0000521985
0000256370
0000126382
0000126382

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Jun Sung Moon et al.
Journal of diabetes and its complications, 31(1), 21-30 (2016-09-25)
Cluster determinant 36 (CD36), a fatty acid transporter, was reported to have a pivotal role in glucotoxicity-induced beta cell dysfunction. However, little is known about how glucotoxicity influences CD36 expression, and it is unknown whether this action can be counteracted
Ondrej Kuda et al.
The Journal of biological chemistry, 288(22), 15547-15555 (2013-04-23)
FAT/CD36 is a multifunctional glycoprotein that facilitates long-chain fatty acid (FA) uptake by cardiomyocytes and adipocytes and uptake of oxidized low density lipoproteins (oxLDL) by macrophages. CD36 also mediates FA-induced signaling to increase intracellular calcium in various cell types. The
Susan L M Coort et al.
Molecular and cellular biochemistry, 239(1-2), 213-219 (2002-12-14)
Sulfo-N-succinimidyl esters of LCFAs are a powerful tool to investigate the functional significance of plasmalemmal proteins in the LCFA uptake process. This notion is based on the following observations. First, sulfo-N-succinimidyl oleate (SSO) was found to inhibit the bulk of
Chemical Reagents for Protein Modification, 559-559 (2014)
Iman Momken et al.
The Biochemical journal, 474(1), 149-162 (2016-11-09)
Leptin stimulates fatty acid oxidation in muscle and heart; but, the mechanism by which these tissues provide additional intracellular fatty acids for their oxidation remains unknown. We examined, in isolated muscle and cardiac myocytes, whether leptin, via AMP-activated protein kinase
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