Lysophosphatidic acid
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| Names | |
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| Systematic IUPAC name
(2R)-2-hydroxy-3-{[(9Z)-octadec-9-enoyl]oxy}propyl dihydrogen phosphate | |
| Other names
LPA
1-acyl-sn-glycerol 3-phosphate | |
| Identifiers | |
3D model (
JSmol ) |
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| ChEMBL | |
| ChemSpider | |
ECHA InfoCard
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100.040.631 |
| EC Number |
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IUPHAR/BPS |
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| MeSH | lysophosphatidic+acid |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C21H41O7P | |
| Molar mass | 436.52 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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A lysophosphatidic acid (LPA) is a phospholipid derivative that can act as a signaling molecule.[1][2][3][4]
Function
LPA acts as a potent
Clinical significance
Because of its ability to stimulate cell proliferation, aberrant LPA-signaling has been linked to cancer in numerous ways. Dysregulation of autotaxin or the LPA receptors can lead to hyperproliferation, which may contribute to oncogenesis and metastasis.[5]
LPA may be the cause of pruritus (itching) in individuals with cholestatic (impaired bile flow) diseases.
GTPase activation
Downstream of LPA receptor activation, the small GTPase
Metabolism
There are a number of potential routes to its biosynthesis, but the most well-characterized is by the action of a lysophospholipase D called autotaxin, which removes the choline group from lysophosphatidylcholine.
Lysophosphatidic acids are also intermediates in the synthesis of phosphatidic acids.
See also
References
Further reading
- Kremer, Andreas E.; Martens, Job J.W.W.; Kulik, Wim; Ruëff, Franziska; Kuiper, Edith M.M.; Van Buuren, Henk R.; Van Erpecum, Karel J.; Kondrackiene, Jurate; et al. (2010). "Lysophosphatidic Acid is a Potential Mediator of Cholestatic Pruritus". Gastroenterology. 139 (3): 1008–18, 1018.e1. PMID 20546739.
- Moolenaar, Wouter H. (1995). "Lysophosphatidic Acid, a Multifunctional Phospholipid Messenger". The Journal of Biological Chemistry. 270 (22): 12949–52. PMID 7768880.
- Mills, Gordon B.; Moolenaar, Wouter H. (2003). "The emerging role of lysophosphatidic acid in cancer". Nature Reviews Cancer. 3 (8): 582–91. S2CID 29079135.
- Panupinthu, N; Lee, H Y; Mills, G B (2010). "Lysophosphatidic acid production and action: Critical new players in breast cancer initiation and progression". British Journal of Cancer. 102 (6): 941–6. PMID 20234370.
- Park, S Y; Jeong, K J; Panupinthu, N; Yu, S; Lee, J; Han, J W; Kim, J M; Lee, J-S; et al. (2010). "Lysophosphatidic acid augments human hepatocellular carcinoma cell invasion through LPA1 receptor and MMP-9 expression". Oncogene. 30 (11): 1351–9. PMID 21102517.
- Yakubu, M A; Liliom, K; Tigyi, G J; Leffler, C W (1997). "Role of lysophosphatidic acid in endothelin-1-and hematoma-induced alteration of cerebral microcirculation". 273 (2): R703–R709. )
- Tigyi, G J; Hong, L; Yakubu, M; Parfenova, H; Shibata, M; Leffler, C W (1995). "Lysophosphatidic acid alters cerebrovascular reactivity in piglets". 268 (5): H2048–H2055. )