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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

5(S),6(R),15(R)-Lipoxin A4

Cayman Chemical Item Number 90415

5(S),6(R),15(R)-LXA4; AT-Lipoxin A4; 15-epi Lipoxin A4 (CAS 171030-11-8)

5(S),6(R),15(R)-Lipoxin A4 (CAS 171030-11-8)

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Description

Lipid-derived lipoxins are produced at the site of vascular and mucosal inflammation where they down-regulate polymorphonuclear leukocyte recruitment and function. 5(S),6(R),15(R)-Lipoxin A4 (5(S),6(R),15(R)-LXA4) is derived from the aspirin-triggered formation of 15(R)-HETE from arachidonic acid.1,2 5(S),6(R),15(R)-LXA4 inhibits LTB4-induced chemotaxis, adherence, and transmigration of neutrophils with twice the potency of LXA4 demonstrating activity in the nM range.3,2 The anti-inflammatory effects of aspirin may be ascribed in part to the ability of 5(S),6(R),15(R)-LXA4 to regulate leukocyte function.4

1 Clària, J., Lee, M.H., and Serhan, C.N. Aspirin-triggered lipoxins (15-epi-LX) are generated by the human lung adenocarcinoma cell line (A549)-neutrophil interactions and are potent inhibitors of cell proliferation. Mol Med 2 583-596 (1996).

2 Clària, J., and Serhan, C.N. Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. Proc Natl Acad Sci USA 92 9475-9479 (1995).

3 Fierro, I.M., Colgan, S.P., Bernasconi, G., et al. Lipoxin A4 and aspirin-triggered 15-epi-lipoxin A4 inhibit human neutrophil migration: Comparisons between synthetic 15 epimers in chemotaxis and transmigration with microvessel endothelial cells and epithelial cells. J Immunol 170 2688-2694 (2003).

4 Chiang, N., Bermudez, E.A., Ridker, P.M., et al. Aspirin triggers antiinflammatory 15-epi-lipoxin A4 and inhibits thromboxane in a randomized human trial. Proc Natl Acad Sci USA 101(42) 15178-15183 (2004).

Synonyms
  • 5(S),6(R),15(R)-LXA4
  • AT-Lipoxin A4
  • 15-epi Lipoxin A4
Formal Name 5(S),​6(R),​15(R)-​trihydroxy-​7E,​9E,​11Z,​13E-​eicosatetraenoic acid
CAS Number 171030-11-8
Molecular Formula C20H32O5
Formula Weight 352.5
Formulation A solution in ethanol
Purity ≥95%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC[C@@H]​(O)​\C=C/C=C/C=C\C=C/[C@@H]​(O)​C(O)​CCCC(=O)​O

Background Reading

Chiang, N., Bermudez, E.A., Ridker, P.M., et al. Aspirin triggers antiinflammatory 15-epi-lipoxin A4 and inhibits thromboxane in a randomized human trial. Proc Natl Acad Sci USA 101(42) 15178-15183 (2004).

Fierro, I.M., Colgan, S.P., Bernasconi, G., et al. Lipoxin A4 and aspirin-triggered 15-epi-lipoxin A4 inhibit human neutrophil migration: Comparisons between synthetic 15 epimers in chemotaxis and transmigration with microvessel endothelial cells and epithelial cells. J Immunol 170 2688-2694 (2003).

Clària, J., and Serhan, C.N. Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. Proc Natl Acad Sci USA 92 9475-9479 (1995).

Clària, J., Lee, M.H., and Serhan, C.N. Aspirin-triggered lipoxins (15-epi-LX) are generated by the human lung adenocarcinoma cell line (A549)-neutrophil interactions and are potent inhibitors of cell proliferation. Mol Med 2 583-596 (1996).

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Size Price Quantity Subtotal
25 µg $157.00 $0.00
50 µg $298.00 $0.00
100 µg $565.00 $0.00
250 µg $1,256.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-08. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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