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Merck

L7260

Sigma-Aldrich

Oleoyl-L-α-lysophosphatidic acid sodium salt

≥98%, solid

Synonim(y):

1-Oleoyl-sn-glycerol 3-phosphate sodium salt, 3-sn-Lysophosphatidic acid, 1-oleoyl sodium salt, LPA sodium salt

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1 MG
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5 MG
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25 MG
3410,00 zł

480,00 zł


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1 MG
480,00 zł
5 MG
821,00 zł
25 MG
3410,00 zł

About This Item

Wzór empiryczny (zapis Hilla):
C21H41O7P · xNa+
Numer CAS:
Masa cząsteczkowa:
436.52 (free acid basis)
Numer MDL:
Kod UNSPSC:
12352211
Identyfikator substancji w PubChem:
NACRES:
NA.77

480,00 zł


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Próba

≥98%

Formularz

solid

kolor

white

typ lipidu

phosphoglycerides

temp. przechowywania

−20°C

ciąg SMILES

O[C@](COP([O-])(O)=O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O.[Na+]

InChI

1S/C21H41O7P.Na.H/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26;;/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26);;/b10-9+;;

Klucz InChI

CHJOEWDRTPWOCY-TTWKNDKESA-N

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Opis ogólny

Lysophosphatidic acid (LPA) is an essential metabolite for membrane biosynthesis. LPA interacts with the G protein-coupled receptors (GPCRs), called the LPA receptor and mediates signaling.[1] Oleoyl-L-α-lysophosphatidic acid activates the receptor LPA4.[2] In keratinocytes, oleoyl-L-α-lysophosphatidic acid promotes growth to some extent.[3]

Zastosowanie

Oleoyl-L-α-lysophosphatidic acid sodium salt has been used:
  • for the activation of Ras homolog gene family, member A (RhoA) and expression of claudin-1 in human breast cancer epithelial cell line[4]
  • in RH7777 cells for cyclic adenosine monophosphate (cAMP) accumulation assay and calcium mobilisation assay[5]
  • in vitro luciferase assay and live-cell imaging[6]

Działania biochem./fizjol.

Endogenous agonist for LPA1 and LPA2 receptors. LPA does not induce angiogenesis, but has effects on endothelial cell physiology that are similar to those of sphingosine 1-phosphate. Induces cell migration of cancer and non-cancer cells.

Cechy i korzyści

This compound is featured on the Lysophospholipid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Przestroga

Hygroscopic, photosensitive

Uwaga dotycząca przygotowania

Prepared by the action of phospholipase A on L-α-phosphatidic acid, dioleoyl.
Ta strona może zawierać tekst przetłumaczony maszynowo.

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

Eyeshields, Gloves, type N95 (US)


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Certyfikaty analizy (CoA)

Lot/Batch Number

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Masz już ten produkt?

Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

Identification of compounds acting as negative allosteric modulators of the LPA 1 receptor
Ellery J, et al.
European Journal of Pharmacology (2018)
Tracee Scalise Panetti
Biochimica et biophysica acta, 1582(1-3), 190-196 (2002-06-19)
This review discusses multiple effects of sphingosine 1-phosphate (S1P) and lysophosphatidic acid (LPA) on endothelial cells and proposes that S1P and LPA are important regulators of the vascular system. Two physiologic sources of S1P and LPA are platelets and lipoproteins.
A Gohla et al.
The Journal of biological chemistry, 273(8), 4653-4659 (1998-03-21)
Lysophosphatidic acid (LPA) utilizes a G-protein-coupled receptor to activate the small GTP-binding protein Rho and to induce rapid remodeling of the actin cytoskeleton. We studied the signal transduction from LPA receptors to Rho activation. Analysis of the G-protein-coupling pattern of
F N van Leeuwen et al.
Biochemical Society transactions, 31(Pt 6), 1209-1212 (2003-12-04)
LPA (lysophosphatidic acid), the simplest of al glycerophospholipids, is a potent inducer of cell proliferation, migration and survival. It does so by activating its cognate G-protein-coupled receptors, four of which have been identified. LPA receptors couple to at least three
T Nishizaki et al.
Brain research. Molecular brain research, 50(1-2), 121-126 (1997-12-24)
The effect of lysophosphatidic acid (lysoPA) on acetylcholine (ACh)-evoked currents was examined using normal and mutant Torpedo nicotinic ACh receptors expressed in Xenopus oocytes. LysoPA enhanced ACh-evoked currents in a washing time- and dose-dependent manner at concentrations of 0.1-3 microM

Produkty

Discover Bioactive Small Molecules for Lipid Signaling Research

Questions

1–4 of 4 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. What substance can be used to dissolve this product?

    1 answer
    1. Water is typically not an ideal solvent for lipids. The choice of solvent depends on the intended application. A mixture of chloroform, methanol, and acetic acid at a ratio of 95:5:5, could be considered. Ideally, consulting the scientific literature would be necessary to determine if a specific solvent is used for the intended application.

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  4. Is this version of the compound cell culture grade?

    1 answer
    1. This product is not cell culture grade. Unfortunately, there is not a LPA sodium salt offered that is cell culture suitable. The suitability for this product in cell culture would have to be determined by the end-user. See below the links to the product datasheet, a sample Certificate of Analysis, and Peer Reviewed Papers, respectively:

      Datasheet
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/296/848/l7260pis.pdf

      Sample COA
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/L7260-BULKSLCM6356.pdf

      Peer Reivewed Papers
      https://www.sigmaaldrich.com/search/l7260?focus=papers&page=1&perpage=30&sort=relevance&term=l7260&type=citation_search

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