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857231 | C18:1 Cyclic LPA

1-O-(9Z-octadecenyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt)

C18:1 Cyclic LPA

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C18:1 Cyclic LPA

1-O-(9Z-octadecenyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt)

Cyclic phosphatidic acid (cPA) is a naturally occurring analog of the growth factor-like phospholipid mediator, lysophosphatidic acid (LPA). The sn-2 hydroxy group of CPA forms a 5-membered ring with the sn-3 phosphate. cPA affects numerous cellular functions, including anti-mitogenic regulation of the cell cycle1, induction of stress fiber formation2, inhibition of tumor cell invasion and metastasis3, and regulation of differentiation and survival of neuronal cells4. Interestingly, many of these cellular responses caused by cPA oppose those of LPA despite the activation of apparently overlapping receptor populations.
You can find additional information on cPA at the following link: LIPID MAPS Lipidomics Gateway
1. Murakami-Murofushi, K., Kaji, K., Kano, K., Fukuda, M., Shioda, M., and Murofushi, H. (1993) Inhibition of cell proliferation by a unique lysophosphatidic acid, PHYLPA, isolated from Physarum polycephalum: signaling events of antiproliferative action by PHYLPA. Cell Struct. Funct. 18:363–370.
2. Fischer, D.L., Liliom, K., Guo, H., Nusser, N., Virag, T., Murakami-Murofushi, K., Kobayashi, S., Erickson, J.P., Sun, G., Miller, D.D., and Tigyi, G. (1998) Naturally occurring analogs of lysophosphatidic acid elicit different cellular responses through selective activation of multiple receptor subtypes. Mol. Pharmacol. 54:979–988.
3. Mukai, M., Imamura, F., Ayaki, M., Shinkai, K., Iwasaki, T., Murakami-Murofushi, K., Murofushi, H., Kobayashi, S., Yamamoto, T., Nakamura, H., and Akedo, H. (1999) Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA). Int. J. Cancer 81:918–922.
4. Fujiwara, Y., Sebok, A., Meakin, S., Kobayashi, T., Murakami-Murofushi, K., and Tigyi, G. (2003) Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons. J. Neurochem. 87:1272–1283.
Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C21H44NO5P
Percent Composition
C 59.83%, H 10.52%, N 3.32%, O 18.98%, P 7.35%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
799268-69-2
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
421.552
Exact Mass
421.296
Synonyms
1-O-octadecenyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt)
AGP 18:1
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References

Kaji I, Roland JT, Watanabe M, Engevik AC, Goldstein AE, Hodges CA, Goldenring JR. Lysophosphatidic Acid Increases Maturation of Brush Borders and SGLT1 activity in MYO5B-deficient Mice, a Model of Microvillus Inclusion Disease. Gastroenterology. 2020 Jun 11:S0016-5085(20)34760-0. doi: 10.1053/j.gastro.2020.06.008. Epub ahead of print. PMID: 32534933.

 PubMed ID: 32534933

Fujiwara Y. Cyclic phosphatidic acid - a unique bioactive phospholipid. Biochim Biophys Acta. 2008 Sep;1781(9):519-24. doi: 10.1016/j.bbalip.2008.05.002. Epub 2008 May 23. PMID: 18554524; PMCID: PMC2572151.

 PubMed ID: 18554524

Murakami-Murofushi K, Kaji K, Kano K, Fukuda M, Shioda M, Murofushi H. Inhibition of cell proliferation by a unique lysophosphatidic acid, PHYLPA, isolated from Physarum polycephalum: signaling events of antiproliferative action by PHYLPA. Cell Struct Funct. 1993 Oct;18(5):363-70. doi: 10.1247/csf.18.363. PMID: 8168160.

 PubMed ID: 8168160

Fischer DJ, Liliom K, Guo Z, Nusser N, Virág T, Murakami-Murofushi K, Kobayashi S, Erickson JR, Sun G, Miller DD, Tigyi G. Naturally occurring analogs of lysophosphatidic acid elicit different cellular responses through selective activation of multiple receptor subtypes. Mol Pharmacol. 1998 Dec;54(6):979-88. doi: 10.1124/mol.54.6.979. PMID: 9855625.

 PubMed ID: 9855625

Mukai M, Imamura F, Ayaki M, Shinkai K, Iwasaki T, Murakami-Murofushi K, Murofushi H, Kobayashi S, Yamamoto T, Nakamura H, Akedo H. Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA). Int J Cancer. 1999 Jun 11;81(6):918-22. doi: 10.1002/(sici)1097-0215(19990611)81:6<918::aid-ijc13>3.0.co;2-e. PMID: 10362139.

 PubMed ID: 10362139

Fujiwara Y, Sebök A, Meakin S, Kobayashi T, Murakami-Murofushi K, Tigyi G. Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons. J Neurochem. 2003 Dec;87(5):1272-83. doi: 10.1046/j.1471-4159.2003.02106.x. PMID: 14622107.

 PubMed ID: 14622107
Certificates of Analysis

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