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Sulfosuccinimidyl oleate sodium

(Synonyms: SSO) 目录号 : GC34817

Sulfosuccinimidyl oleate sodium是一种不可逆的CD36抑制剂。

Sulfosuccinimidyl oleate sodium Chemical Structure

Cas No.:1212012-37-7

规格 价格 库存 购买数量
10mM (in 1mL DMSO)
¥792.00
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5mg
¥720.00
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10mg
¥1,125.00
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25mg
¥2,160.00
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50mg
¥3,456.00
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Description

Sulfosuccinimidyl oleate sodium is an irreversible CD36 inhibitor [1]. Sulfosuccinimidyl oleate sodium blocks the binding of long-chain fatty acids to CD36 by covalently modifying the lysine residues of the CD36 receptor, thereby inhibiting the entry of fatty acids into cells [2]. Sulfosuccinimidyl oleate sodium is often used to study the CD36-mediated fatty acid uptake process [3].

In Chinese hamster ovary (CHO) cells, Sulfosuccinimidyl oleate sodium (100μM; 30min) treatment of these cells was effective in inhibiting the CD36-specific effects [4]. In BV2 cells, Sulfosuccinimidyl oleate sodium (20μM, 50μM; 2h) significantly reduced the lipopolysaccharide/interferon-γ-induced production of nitric oxide, interleukin-6 and tumor necrosis factor-α [5]. In in ARPE-19 cells, Sulfosuccinimidyl oleate sodium (50μM; 24h) inhibits 7KC-induced oxidative stress and cell death [6].

In High-fat diet (HFD) mice model, Sulfosuccinimidyl oleate sodium (50mg/kg; po; 8 weeks) reduces intestinal fatty acid absorption by reducing the inhibition of intestinal CD36 expression, followed by decreased TG and FFA levels, which attenuates HFD-induced fatty live [7]. In a mouse oral squamous cell carcinoma (OSCC) model, tumor growth was significantly delayed in OSCC mice treated with Sulfosuccinimidyl oleate sodium (20mg/kg; ip; 11d) [8].

References:
[1]. Drahota Z, Vrbacký M, Nůsková H, et al. Succinimidyl oleate, established inhibitor of CD36/FAT translocase inhibits complex III of mitochondrial respiratory chain. Biochemical and biophysical research communications. 2010 Jan 15; 391(3): 1348-1351.
[2]. Zhao J, Rui H, Yang M, et al. CD36‐mediated lipid accumulation and activation of NLRP3 inflammasome lead to podocyte injury in obesity‐related glomerulopathy. Mediators of Inflammation, 2019, 2019(1): 3172647.
[3]. Coort SL, Willems J, Coumans WA, et al. Sulfo-N-succinimidyl esters of long chain fatty acids specifically inhibit fatty acid translocase (FAT/CD36)-mediated cellular fatty acid uptake. Molecular and cellular biochemistry. 2002 Oct; 239: 213-219.
[4]. Kuda O, Pietka TA, Demianova Z, et al. 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. Journal of Biological Chemistry. 2013 May 31; 288(22): 15547-15555.
[5]. Dhungana H, Huuskonen MT, Jaronen M, et al. Sulfosuccinimidyl oleate sodium is neuroprotective and alleviates stroke-induced neuroinflammation. Journal of Neuroinflammation. 2017 Dec; 14: 1-3.
[6]. Nury T, Ghzaiel I, Hichami A, et al. Lipid droplets dependent or independent cytoprotective activities of unsaturated fatty acids, Lorenzo’s oil and sulfo-N-succinimidyl oleate on 7-ketocholesterol-induced oxidative stress, organelle dysfunction and cell death on 158N and ARPE-19 cells: Cell targets and benefits of sulfo-N-succinimidyl oleate. Current Research in Biotechnology. 2024 Jan 1; 7: 100195.
[7]. Ma Q, Wen L, Tian Y, et al. Sulfosuccinimidyl oleate ameliorates the high-fat diet-induced obesity syndrome by reducing intestinal and hepatic absorption. Frontiers in Pharmacology. 2023 May 26; 14: 1193006.
[8]. Takaichi M, Tachinami H, Takatsuka D, et al. Targeting CD36-mediated lipid metabolism by selective inhibitor-augmented antitumor immune responses in oral cancer. International Journal of Molecular Sciences. 2024 Aug 30; 25(17): 9438.

Sulfosuccinimidyl oleate sodium是一种不可逆的CD36抑制剂 [1]。Sulfosuccinimidyl oleate sodium通过共价修饰CD36受体的赖氨酸残基,阻断长链脂肪酸与CD36的结合,从而抑制脂肪酸进入细胞 [2]。Sulfosuccinimidyl oleate sodium常用于研究CD36介导的脂肪酸吸收过程 [3]

在中国仓鼠卵巢(CHO)细胞中,Sulfosuccinimidyl oleate sodium(100μM;30min)处理这些细胞可有效抑制CD36特异性作用 [4]。在BV2细胞中,Sulfosuccinimidyl oleate sodium(20μM、50μM;2h)显著降低脂多糖/干扰素-γ诱导的一氧化氮、白细胞介素-6和肿瘤坏死因子-α的产生 [5]。在ARPE-19细胞中,Sulfosuccinimidyl oleate sodium(50μM;24h)可抑制7KC诱导的氧化应激和细胞死亡 [6]

在高脂饮食(HFD)小鼠模型中,Sulfosuccinimidyl oleate sodium(50mg/kg;po;8周)通过降低肠道CD36表达的抑制来减少肠道脂肪酸的吸收,进而降低甘油三酸酯(TG)和游离脂肪酸(FFA)水平,从而减轻HFD诱导的脂肪肝 [7]。在小鼠口腔鳞状细胞癌(OSCC)模型中,用Sulfosuccinimidyl oleate sodium(20mg/kg;ip;11d)治疗的OSCC小鼠的肿瘤生长显著延缓 [8]

实验参考方法

Cell experiment [1]:

Cell lines

Chinese hamster ovary (CHO) cells

Preparation Method

CHO cells were grown to confluency in 100-mm dishes, washed three times with phosphate-buffered saline, and incubated with or without 100μM Sulfosuccinimidyl oleate sodium in PBS for 30min on ice. Sulfosuccinimidyl oleate sodium was freshly dissolved in DMSO and mixed with PBS just before application onto cells.

Reaction Conditions

100μM; 30min

Applications

Sulfosuccinimidyl oleate sodium treatment of these cells was effective in inhibiting the CD36-specific effects.
Animal experiment [2]:

Animal models

High-fat diet (HFD) mice model

Preparation Method

C57BL mice (20 ± 2g) were maintained at a controlled temperature (22℃ ± 1℃), humidity (50%), and light (12-h light/dark). A HFD consists of 20% carbohydrates, 35% protein, and 45% fat. The Sulfosuccinimidyl oleate sodium drug was fed at a dose of 50mg/kg. Blood glucose level was measured using equipment and glucose test strips.

Dosage form

50mg/kg; po; 8 weeks

Applications

Sulfosuccinimidyl oleate sodium reduces intestinal fatty acid absorption by reducing the inhibition of intestinal CD36 expression, followed by decreased TG and FFA levels, which attenuates HFD-induced fatty live.

References:
[1]. Kuda O, Pietka TA, Demianova Z, et al. 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. Journal of Biological Chemistry. 2013 May 31; 288(22): 15547-15555.
[2]. Ma Q, Wen L, Tian Y, et al. Sulfosuccinimidyl oleate ameliorates the high-fat diet-induced obesity syndrome by reducing intestinal and hepatic absorption. Frontiers in Pharmacology. 2023 May 26; 14: 1193006.

化学性质

Cas No. 1212012-37-7 SDF
别名 SSO
Canonical SMILES O=S(C(C1)C(N(OC(CCCCCCC/C=C\CCCCCCCC)=O)C1=O)=O)(O[Na])=O
分子式 C22H36NNaO7S 分子量 481.58
溶解度 25 mg/ml in DMF; 25 mg/ml DMSO 储存条件 -20°C, sealed storage, away from moisture
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1 mM 2.0765 mL 10.3825 mL 20.765 mL
5 mM 0.4153 mL 2.0765 mL 4.153 mL
10 mM 0.2076 mL 1.0382 mL 2.0765 mL
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