Home>>Lipids>> Endocannabinoid/Endocannabinoid-like>>N-Oleoyl-L-Serine

N-Oleoyl-L-Serine

目录号 : GC44445

An endogenous lipid with bone anabolic activity

N-Oleoyl-L-Serine Chemical Structure

Cas No.:107743-37-3

规格 价格 库存 购买数量
1mg
¥240.00
现货
5mg
¥1,079.00
现货
10mg
¥1,918.00
现货
50mg
¥8,395.00
现货

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Sample solution is provided at 25 µL, 10mM.

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产品描述

Bone mass and shape is continuously remodeled by the concerted and balanced action of osteoblasts (bone forming cells) and osteoclasts (bone-resorbing cells). The endocannabinoid system plays an essential role in the maintenance of normal bone mass via signaling through the CB2 receptor. N-Oleoyl-L-serine is an endogenous lipid that has been reported to stimulate bone formation and to inhibit bone resorption.

Chemical Properties

Cas No. 107743-37-3 SDF
Canonical SMILES CCCCCCCC/C=C\CCCCCCCC(N[C@H](C(O)=O)CO)=O
分子式 C21H39NO4 分子量 369.5
溶解度 DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 30 mg/ml,Ethanol:PBS pH 7.2 (1:1): 0.5 mg/ml 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.7064 mL 13.5318 mL 27.0636 mL
5 mM 0.5413 mL 2.7064 mL 5.4127 mL
10 mM 0.2706 mL 1.3532 mL 2.7064 mL
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Research Update

Oleoyl serine, an endogenous N-acyl amide, modulates bone remodeling and mass

Proc Natl Acad Sci U S A 2010 Oct 12;107(41):17710-5.PMID:20876113DOI:PMC2955099

Bone mass is determined by a continuous remodeling process, whereby the mineralized matrix is being removed by osteoclasts and subsequently replaced with newly formed bone tissue produced by osteoblasts. Here we report the presence of endogenous amides of long-chain fatty acids with amino acids or with ethanolamine (N-acyl amides) in mouse bone. Of these compounds, N-Oleoyl-L-Serine (OS) had the highest activity in an osteoblast proliferation assay. In these cells, OS triggers a Gi-protein-coupled receptor and Erk1/2. It also mitigates osteoclast number by promoting osteoclast apoptosis through the inhibition of Erk1/2 phosphorylation and receptor activator of nuclear-κB ligand (RANKL) expression in bone marrow stromal cells and osteoblasts. In intact mice, OS moderately increases bone volume density mainly by inhibiting bone resorption. However, in a mouse ovariectomy (OVX) model for osteoporosis, OS effectively rescues bone loss by increasing bone formation and markedly restraining bone resorption. The differential effect of exogenous OS in the OVX vs. intact animals is apparently a result of an OVX-induced decrease in skeletal OS levels. These data show that OS is a previously unexplored lipid regulator of bone remodeling. It represents a lead to antiosteoporotic drug discovery, advantageous to currently available therapies, which are essentially either proformative or antiresorptive.