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L7260

Oleoyl-L-α-lysophosphatidic acid sodium salt

≥98%, solid

Sinónimos:

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

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Tamaño de envaseSKUDisponibilidadPrecio
1 mg
Comprobar disponibilidad del carrito
$99.800
5 mg
Comprobar disponibilidad del carrito
$347.000
25 mg
Comprobar disponibilidad del carrito
$1.400.000

Acerca de este artículo

Fórmula empírica (notación de Hill):
C21H41O7P · xNa+
Número CAS:
Peso molecular:
436.52 (free acid basis)
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:

$99.800


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Quality Level

assay

≥98%

form

solid

color

white

lipid type

phosphoglycerides

storage temp.

−20°C

SMILES string

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+;;

InChI key

CHJOEWDRTPWOCY-TTWKNDKESA-N

General description

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. Oleoyl-L-α-lysophosphatidic acid activates the receptor LPA4. In keratinocytes, oleoyl-L-α-lysophosphatidic acid promotes growth to some extent.

Application

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
  • in RH7777 cells for cyclic adenosine monophosphate (cAMP) accumulation assay and calcium mobilisation assay
  • in vitro luciferase assay and live-cell imaging

Biochem/physiol Actions

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.

Features and Benefits

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.

Preparation Note

Prepared by the action of phospholipase A on L-α-phosphatidic acid, dioleoyl.

Disclaimer

Hygroscopic, photosensitive

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Este artículo
P9511459620220411
assay

≥98%

assay

≥98%

assay

≥98% (TLC)

assay

>95% (TLC)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

15-25°C

form

solid

form

powder

form

solid

form

solid

color

white

color

-

color

white to off-white

color

white

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

lipid type

phosphoglycerides

lipid type

-

lipid type

-

lipid type

-


Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Artículos

Discover Bioactive Small Molecules for Lipid Signaling Research


TRPM7 controls mesenchymal features of breast cancer cells by tensional regulation of SOX4
Kuipers AJ, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1864(7), 2409-2419 (2018)
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
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



Número de artículo de comercio global

SKUGTIN
L7260-5MG04061833965429
L7260-1MG04061833965405
L7260-25MG04061833965412

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/418/501/product-dating-information-06-25-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.

      Helpful?

  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

      Helpful?

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