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SML2148

Sigma-Aldrich

Sulfo-N-succinimidyl Oleate sodium

≥95% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C22H36NO7S· Na
Numéro CAS:
135661-44-8
Poids moléculaire :
481.58
Numéro CE :
801-756-1
Numéro MDL:
MFCD12547938
Code UNSPSC :
51111800
Nomenclature NACRES :
NA.77

Pureté

≥95% (HPLC)

Forme

powder

Conditions de stockage

desiccated
under inert gas

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear (warmed)

Température de stockage

−20°C

Chaîne SMILES 

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);

Clé InChI

IENDXPSKPJDQKO-UHFFFAOYSA-N

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

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
C M Harmon et al.
The Journal of membrane biology, 121(3), 261-268 (1991-05-01)
Sulfo-N-succinimidyl derivatives of the long-chain fatty acids, oleic and myristic, were synthesized and covalently reacted with isolated rat adipocytes. The plasma membrane proteins labeled by these compounds and the effect of labeling on the transport of long-chain fatty acids were
Structure-function of CD36 and importance of fatty acid signal transduction in fat metabolism
Pepino MY, et al.
Annual Review of Nutrition, 34, 281-303 (2014)
S Sini et al.
Molecular and cellular biochemistry, 427(1-2), 23-34 (2016-12-21)
Although high-density lipoprotein is atheroprotective, it can become dysfunctional in chronic inflammatory conditions and increase cardiovascular risk. We previously demonstrated that HDL from subjects with documented coronary artery disease is dysfunctional and is pro-oxidant/proinflammatory in macrophages. Here we examined the
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
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