SML2148

Sulfo-N-succinimidyl Oleate sodium

Name: Sulfo-N-succinimidyl Oleate sodium
Brand: SIGMA

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

Synonym(s):

(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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About This Item

Empirical Formula (Hill Notation):

C₂₂H₃₆NO₇S· Na

CAS Number:

135661-44-8

Molecular Weight:

481.58

NACRES:

NA.77

UNSPSC Code:

51111800

EC Number:

801-756-1

MDL number:

MFCD12547938

Product Name

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

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

SMILES string

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

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

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.

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Sulfo-N-succinimidyl oleate (SSO) inhibits fatty acid uptake and signaling for intracellular calcium via binding CD36 lysine 164: SSO also inhibits oxidized low density lipoprotein uptake by macrophages.

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

Sulfo-N-succinimidyl esters of long chain fatty acids specifically inhibit fatty acid translocase (FAT/CD36)-mediated cellular fatty acid uptake.

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

A new leptin-mediated mechanism for stimulating fatty acid oxidation: a pivotal role for sarcolemmal FAT/CD36.

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

Metformin prevents glucotoxicity by alleviating oxidative and ER stress-induced CD36 expression in pancreatic beta cells.

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

Potentiation of Ecstasy-induced hyperthermia and FAT/CD36 expression in chronically exercised animals.

Sandra L Hrometz et al.

Temperature (Austin, Tex.), 3(4), 557-566 (2017-01-17)

Fatal hyperthermia as a result of 3,4-methylenedioxymethamphetamine (MDMA) use involves non-esterified free fatty acids (NEFA) and the activation of mitochondrial uncoupling proteins (UCP). NEFA gain access into skeletal muscle via specific transport proteins, including fatty acid translocase (FAT/CD36). FAT/CD36 expression

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