5(S),6(R)-Lipoxin A4-d5

5(S),6(R)-Lipoxin A₄-d₅ Exclusive

Cayman Chemical Item Number 10007737

5(S),6(R)-LXA₄-d₅; 5(S),6(R),15(S)-TriHETE-d₅

Description

5(S),6(R)-Lipoxin A₄-d₅ (5(S),6(R)-LXA₄-d₅) contains five deuterium atoms at the 19, 19’, 20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of 5(S),6(R)-LXA₄ by GC- or LC-mass spectrometry (MS). 5(S),6(R)-Lipoxin A₄ is a trihydroxy fatty acid containing a conjugated tetraene, produced by the metabolism of 15-HETE or 15-HpETE with human leukocytes.¹ 5(S),6(R)-Lipoxin A₄ is equipotent to leukotriene B₄ (LTB₄) in inducing superoxide generation in human neutrophils at 0.1 µM.² 5(S),6(R)-Lipoxin A₄ is associated with several other biological functions including leukocyte activation, chemotaxis effects, natural killer cell inhibition, and monocyte migration and adhesion.^2,3,4

1 Serhan, C.N., Nicolaou, K.C., Webber, S.E., et al. Lipoxin A. Stereochemistry and biosynthesis. J Biol Chem 261 16340-16345 (1986).

2 Serhan, C.N., Hamberg, M., and Samuelsson, B. Lipoxins: Novel series of biologically active compounds formed from arachidonic acid in human leukocytes. Proc Natl Acad Sci USA 81 5335-5339 (1984).

3 Ramstedt, U., Serhan, C.N., Nicolaou, K.C., et al. Lipoxin A-induced inhibition of human natural killer cell cytotoxicity: Studies on stereospecificity of inhibition and mode of action. J Immunol 138 266-270 (1987).

4 Maddox, J.F., and Serhan, C.N. Lipoxin A₄ and B₄ are potent stimuli for human monocyte migration and adhesion: Selective inactivation by dehydrogenation and reduction. J Exp Med 183 137-146 (1996).

Synonyms

5(S),6(R)-LXA4-d5
5(S),6(R),15(S)-TriHETE-d5

Formal Name

5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid-19,19,20,20,20-d5

Molecular Formula

C₂₀H₂₇D₅O₅

Formula Weight

357.5

Formulation

A solution in ethanol

Purity

≥99% deuterated forms (d1-d5)

λ_max

302 nm

Stability

1 year

Storage

-80°C

Shipping

Dry ice in continental US; may vary elsewhere

SMILES

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

Background Reading

Maddox, J.F., and Serhan, C.N. Lipoxin A₄ and B₄ are potent stimuli for human monocyte migration and adhesion: Selective inactivation by dehydrogenation and reduction. J Exp Med 183 137-146 (1996).

Serhan, C.N., Nicolaou, K.C., Webber, S.E., et al. Lipoxin A. Stereochemistry and biosynthesis. J Biol Chem 261 16340-16345 (1986).

Ramstedt, U., Serhan, C.N., Nicolaou, K.C., et al. Lipoxin A-induced inhibition of human natural killer cell cytotoxicity: Studies on stereospecificity of inhibition and mode of action. J Immunol 138 266-270 (1987).

Serhan, C.N., Hamberg, M., and Samuelsson, B. Lipoxins: Novel series of biologically active compounds formed from arachidonic acid in human leukocytes. Proc Natl Acad Sci USA 81 5335-5339 (1984).

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10 µg 
$157.00

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25 µg 
$373.00

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50 µg 
$707.00

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100 µg 
$1,256.00

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5(S),6(R)-Lipoxin A₄-d₅ Exclusive