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Merck

437720

Lipoxin A4

≥95% (HPLC), NK cell activity inhibitor, liquid

Synonym(s):

Lipoxin A4, LXA4, 5(S),6(R),15(S)-Trihydroxyeicosa-7- trans-9- trans-11- cis-13- trans-tetraenoic Acid, LXA4, 5(S),6(R),15(S)-Trihydroxyeicosa-7-trans-9-trans-11-cis-13-trans-tetraenoic Acid

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About This Item

Empirical Formula (Hill Notation):
C20H32O5
CAS Number:
89663-86-5
Molecular Weight:
352.47
UNSPSC Code:
12352211
NACRES:
NA.77
MDL number:
MFCD00065845

Key Documents

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Product Name

Lipoxin A4, Lipoxin A4, CAS 89663-86-5, is a potent inhibitor of cytotoxic activity of human natural killer cells. Shown to be as potent as LTB4 in stimulating human neutrophils to generate superoxides.

SMILES string

O[C@H]([C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCCC)CCCC(=O)O

InChI

1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1

InChI key

IXAQOQZEOGMIQS-SSQFXEBMSA-N

assay

≥95% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

solubility

ethanol: soluble

shipped in

wet ice

storage temp.

−70°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: no
Primary Target
Potent inhibitor of cytotoxic activity of human natural killer cells
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Flammable (J)

General description

Caution! Product contains volatile liquid. Keep product cold at all times.
Potent inhibitor of cytotoxic activity of human natural killer cells; shown to be as potent as LTB4 in stimulating human neutrophils to generate superoxides. Involved in contractile responses and acts as a potent activator of human protein kinase C. Stimulates rapid lipid remodeling and pertussis-sensitive release of arachidonic acid in polymorphonuclear leukocytes. Stimulates MAP kinases via activation of G protein-coupled receptors.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
McMahon, B., et al. 2000. J. Biol. Chem. 275, 27566.
Soyombo, O., et al. 1994. Allergy 49, 230.
Flore, S., et al. 1992. J. Biol. Chem.267, 16168.
Badr, K.F., et al. 1989. Proc. Natl. Acad. Sci. USA86, 3438.

Physical form

In Ethanol.

Preparation Note

Following initial thaw, aliquot and freeze (-70°C).

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 2

Certificates of Analysis (COA)

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K F Badr et al.
Proceedings of the National Academy of Sciences of the United States of America, 86(9), 3438-3442 (1989-05-01)
Lipoxin A4 (LXA4) was competitive with [3H]leukotriene D4 (LTD4) for specific binding to cultured rat glomerular mesangial cells. Half-maximal inhibition was obtained with 100 nM LXA4, compared with 10 nM for unlabeled LTD4. At 10 and 50 nM LXA4 induced
B McMahon et al.
The Journal of biological chemistry, 275(36), 27566-27575 (2000-06-28)
The lipoxygenase-derived eicosanoids leukotrienes and lipoxins are well defined regulators of hemeodynamics and leukocyte recruitment in inflammatory conditions. Here, we describe a novel bioaction of lipoxin A(4) (LXA(4)), namely inhibition of leukotriene D(4) (LTD(4))-induced human renal mesangial cell proliferation, and
O Soyombo et al.
Allergy, 49(4), 230-234 (1994-04-01)
Lipoxins are trihydroxytetraene metabolites derived through a double lipoxygenation of arachidonic acid. Lipoxin A4 (LXA4) was prepared by total chemical synthesis, and its capacity to modulate eosinophil migration has been evaluated. LXA4 is a weak and partial chemotactic agent; at
S Fiore et al.
The Journal of biological chemistry, 267(23), 16168-16176 (1992-08-15)
Lipoxin A4 stimulates rapid lipid remodeling and a pertussis toxin-sensitive release of arachidonic acid in polymorphonuclear leukocytes (PMN) (Nigam, S., Fiore, S., Luscinskas, F.W., and Serhan, C.N. (1990) J. Cell. Physiol. 143, 512-523) and has been shown to inhibit leukocyte

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