SML2148

Sulfo-N-succinimidyl Oleate sodium

≥95% (HPLC)

• 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
• Empirical Formula (Hill Notation): C₂₂H₃₆NO₇S· Na
• CAS Number: 135661-44-8
• Molecular Weight: 481.58
• EC Number: 801-756-1
• MDL number: MFCD12547938
• UNSPSC Code: 51111800
• NACRES: NA.77

Properties

• assay: ≥95% (HPLC)
• form: powder
• storage condition: desiccated; under inert gas
• 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

Description

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

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable