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1-Oleoyl Lysophosphatidic Acid

(Synonyms: 1-Oleoyl LPA, Oleoyl-sn-3-Glycerophosphate) 目录号 : GC42011

A potent LPA receptor agonist

1-Oleoyl Lysophosphatidic Acid Chemical Structure

Cas No.:65528-98-5

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1mg
¥361.00
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5mg
¥1,442.00
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10mg
¥2,350.00
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25mg
¥4,960.00
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产品描述

1-Oleoyl lysophosphatidic acid is a species of lysophosphatidic acid (LPA) containing oleic acid at the sn-1 position. Phosphatidic acid is produced either directly through the action of phospholipase D (PLD) or through a two step process involving liberation of diacylglycerol (DAG) by phospholipase C (PLC) followed by phosphorylation of DAG by diglycerol kinase.[1] Hydrolysis of the fatty acid at the sn-2 position by phospholipase A2 (PLA2) yields bioactive LPA. LPA binds to one of five different G protein linked receptors to mediate a variety of biological responses including cell proliferation, smooth muscle contraction, platelet aggregation, neurite retraction, and cell motility.[2],[1] 1-Oleoyl lysophosphatidic acid is the most potent of the LPA analogs for calcium mobilization in A431 cells and for growth stimulation of a variety of cell lines.[3],[4]

1-油酰溶血磷脂酸是一种溶血磷脂酸 (LPA),在 sn-1 位置含有油酸。磷脂酸是通过磷脂酶 D (PLD) 的作用直接产生的,或者是通过磷脂酶 C (PLC) 释放二酰甘油 (DAG) 然后通过双甘油激酶对 DAG 进行磷酸化的两步过程产生的。 [1]磷脂酶 A2 (PLA2) 水解 sn-2 位的脂肪酸产生具有生物活性的 LPA。 LPA 与五种不同的 G 蛋白连接受体之一结合,介导多种生物反应,包括细胞增殖、平滑肌收缩、血小板聚集、神经突收缩和细胞运动。[2]、[1] 1-油酰溶血磷脂酸是LPA 类似物中最有效的 A431 细胞钙动员和多种细胞系的生长刺激。[3],[4]

Reference:
[1]. Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends in Cell Biology 4, 213-219 (1994).
[2]. Noguchi, K., Ishii, S., and Shimizu, T. Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family. The Journal of Biological Chemisty 278(28), 25600-25606 (2003).
[3]. Jalink, K., Hengeveld, T., Mulder, S., et al. Lysophosphatidic acid-induced Ca2+ mobilization in human A4431 cells: Structure-activity analysis. Biochemistry Journal 307, 609-616 (1995).
[4]. van Corven, E.J., van Rijswijk, A., Jalink, K., et al. Mitogenic action of lysophosphatidic acid and phosphatidic acid on fibroblasts. Dependence on acyl-chain length and inhibition by suramin. Biochemistry Journal 281, 163-169 (1992).

Chemical Properties

Cas No. 65528-98-5 SDF
别名 1-Oleoyl LPA, Oleoyl-sn-3-Glycerophosphate
化学名 1-O-9Z-octadecenoyl-sn-glyceryl-3-phosphoric acid
Canonical SMILES CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O
分子式 C21H41O7P 分子量 436.5
溶解度 DMF: 2 mg/ml; DMSO: 2.5 mg/ml; Ethanol: 25 mg/ml; PBS (pH 7.2): 3 mg/ml 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.291 mL 11.4548 mL 22.9095 mL
5 mM 0.4582 mL 2.291 mL 4.5819 mL
10 mM 0.2291 mL 1.1455 mL 2.291 mL
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Research Update

1-Oleoyl Lysophosphatidic Acid: a new mediator of emotional behavior in rats

PLoS One 2014 Jan 7;9(1):e85348.PMID:24409327DOI:10.1371/journal.pone.0085348.

The role of lysophosphatidic acid (LPA) in the control of emotional behavior remains to be determined. We analyzed the effects of the central administration of 1-oleoyl-LPA (LPA 18∶1) in rats tested for food consumption and anxiety-like and depression-like behaviors. For this purpose, the elevated plus-maze, open field, Y maze, forced swimming and food intake tests were performed. In addition, c-Fos expression in the dorsal periaqueductal gray matter (DPAG) was also determined. The results revealed that the administration of LPA 18∶1 reduced the time in the open arms of the elevated plus-maze and induced hypolocomotion in the open field, suggesting an anxiogenic-like phenotype. Interestingly, these effects were present following LPA 18∶1 infusion under conditions of novelty but not under habituation conditions. In the forced swimming test, the administration of LPA 18∶1 dose-dependently increased depression-like behavior, as evaluated according to immobility time. LPA treatment induced no effects on feeding. However, the immunohistochemical analysis revealed that LPA 18∶1 increased c-Fos expression in the DPAG. The abundant expression of the LPA1 receptor, one of the main targets for LPA 18∶1, was detected in this brain area, which participates in the control of emotional behavior, using immunocytochemistry. These findings indicate that LPA is a relevant transmitter potentially involved in normal and pathological emotional responses, including anxiety and depression.