65446-08-4
Chemical Structure
1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA
Synonym(s): 1-Arachidonoyl-sn-glycerol 3-phosphate; 1-Arachidonoyl LPA;LPA (20:4)
- CAS No.: 65446-08-4
- Formula:C23H39O7P
- Molecular Weight:458.53
InChIKey: XBFQFMCUPHZKTI-NZRYSPDRSA-N
SMILES: O=P(O)(O)OC[C@H](O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
Biological Activity: 1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA is a phospholipid containing arachidonic acid at the sn-1 position. It is a precursor to 1-arachidonoyl glycerol (1-Monoarachidin; HY-130567)[1]. 1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA binds to the LPA2/EDG4 receptor with an EC50 value of approximately 10 nM[2]. It prevents TNF-α and IL-6 secretion in wild-type but not Lpa2-/- dendritic cells stimulated by LPS[3]. It also decreases differentiation of HT-29 human colon carcinoma cells to goblet cells in the presence of sodium butyrate[4].
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1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA | 1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA is a phospholipid containing arachidonic acid at the sn-1 position. It is a precursor to 1-arachidonoyl glycerol (1-Monoarachidin; HY-130567). 1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA binds to the LPA2/EDG4 receptor with an EC50 value of approximately 10 nM. It prevents TNF-α and IL-6 secretion in wild-type but not Lpa2-/- dendritic cells stimulated by LPS. It also decreases differentiation of HT-29 human colon carcinoma cells to goblet cells in the presence of sodium butyrate. | |||||||||||||||||||||
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References
- [1]. Nakane, S., Oka, S., Arai, S., et al. 2-Arachidonoyl-sn-glycero-3-phosphate, an arachidonic acid-containing lysophosphatidic acid: occurrence and rapid enzymatic conversion to 2-arachidonoyl-sn-glycerol, a cannabinoid receptor ligand, in rat brain. Arch. Biochem. Biophys. 402(1), 51-58 (2002). [Content Brief]
- [2]. Bandoh, K., Aoki, J., Taira, A., et al. Lysophosphatidic acid (LPA) receptors of the EDG family are differentially activated by LPA species. Structure-activity relationship of cloned LPA receptors. FEBS Lett. 478(1-2), 159-165 (2000). [Content Brief]
- [3]. Emo, J., Meednu, N., Chapman, T.J., et al. Lpa2 is a negative regulator of both dendritic cell activation and murine models of allergic lung inflammation. J. Immunol. 188(8), 3784-3790 (2012). [Content Brief]
- [4]. Hidaka, M., Nishihara, M., and Tokumura, A. Three lysophosphatidic acids with a distinct long chain moiety differently affect cell differentiation of human colon epithelial cells to goblet cells. Life Sci. 197, 73-79 (2018). [Content Brief]
