437720
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.
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:
Molecular Weight:
352.47
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥95% (HPLC)
form
liquid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
solubility
ethanol: soluble
shipped in
wet ice
storage temp.
−70°C
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
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 enhancer of human protein kinase C. Stimulates the rapid lipid remodeling and pertussis-sensitive release of arachidonic acid in polymorphonuclear leukocytes.
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.
Biochem/physiol Actions
Cell permeable: no
Primary Target
Potent inhibitor of cytotoxic activity of human natural killer cells
Potent inhibitor of cytotoxic activity of human natural killer cells
Product does not compete with ATP.
Reversible: no
Warning
Toxicity: Flammable (J)
Physical form
In Ethanol.
Reconstitution
Following initial thaw, aliquot and freeze (-70°C).
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.
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.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
Storage Class Code
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
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
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
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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