15(R)-Lipoxin A4 (CAS 171030-11-8) | Cayman Chemical
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15(R)-Lipoxin A4

Item № 90415
CAS № 171030-11-8
Purity ≥95%
product image
                (CAS 171030-11-8)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     25 µg $165.00 0.00
     50 µg $314.00 0.00
     100 µg $594.00 0.00
     250 µg $1,320.00 0.00

Pricing updated 2018-05-26. Prices are subject to change without notice.

Description
Synonyms
  • AT-Lipoxin A4
  • 15-epi Lipoxin A4
  • 15(R)-LXA4

Lipid-derived lipoxins are produced at the site of vascular and mucosal inflammation where they down-regulate polymorphonuclear leukocyte recruitment and function. 15(R)-Lipoxin A4 (15(R)-LXA4) is derived from the aspirin-triggered formation of 15(R)-HETE (Item No. 34710) from arachidonic acid (Item No. 90010).1,2 15(R)-LXA4 inhibits LTB4-induced chemotaxis, adherence, and transmigration of neutrophils with twice the potency of LXA4 (Item No. 90410) demonstrating activity in the nM range.2,3 The anti-inflammatory effects of aspirin may be ascribed in part to the ability of 15(R)-LXA4 to regulate leukocyte function.4 15(R)-LXA4 is reported to promote resolution of inflammation in LPS-treated stromal cells derived from intermediate-stage diseased supraspinatus tendons as evidenced by increased expression of the STAT-6 pathway target genes, ALOX15 and CD206.5

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Technical Information
Formal Name
5(S),6(R),15(R)-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid
CAS Number
171030-11-8
Synonyms
  • AT-Lipoxin A4
  • 15-epi Lipoxin A4
  • 15(R)-LXA4
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥95%
Formulation
A solution in ethanol
λmax
302 nm
SMILES
CCCCC[C@@H](O)\C=C/C=C/C=C\C=C/[C@@H](O)C(O)CCCC(=O)O
InChI Code
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+/m1/s1
InChI Key
IXAQOQZEOGMIQS-JEWNPAEBSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
Stability
≥ 1 year
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References & Product Citations
Product Description References

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. Molecular Medicine 2, 583-596 (1996).

2. Clària, J., and Serhan, C.N. Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. Proceedings of the National Academy of Sciences of the United States of America 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. Journal of Immunology 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. Proceedings of the National Academy of Sciences of the United States of America 101(42), 15178-15183 (2004).

5. Dakin, S.G., Martinez, F.O., Yapp, C., et al. Inflammation activation and resolution in human tendon disease. Sci.Transl.Med. 7(311), (2015).

Product Citations

Tibrewal, S., Ivanir, Y., Sarkar, J., et al. Hyperosmolar stress induces neutrophil extracellular trap formation: implications for dry eye disease. Invest. Opthalmol. Vis. Sci. 55(12), 7961-7969 (2014).

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