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

12-epi Leukotriene B4

Cayman Chemical Item Number 20135

12-epi LTB4 (CAS 83709-73-3)

12-epi Leukotriene B4 (CAS 83709-73-3)

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Description

Leukotriene B4 (LTB4) compounds are produced by both enzymatic and non-enzymatic processes. The products of enzymatic origin, via Leukotriene A4 (LTA4) hydrolase, are stereospecifically 12(R). Non-enzymatic hydrolysis products are 50:50 mixtures at C-12, but are almost exclusively trans at C-6. Thus, the non-enzymatic hydrolysis product of LTA4 is 6-trans-12-epi LTB4. 12-epi LTB4 is an isomer which would not be expected to occur in either non-enzymatic hydrolysis products, or in the enzymatic products of LTA4 hydrolase.1 Compared to LTB4, 12-epi LTB4 has significantly reduced activity for the LTB4 receptor on human neutrophils (IC50 of 7.5 mM),2 and on guinea pig lung membranes with a (Ki of 4.7 mM).3 12-epi LTB4 is an weak agonist at both the recombinant human BLT1 and BLT2 receptors, requiring approximately 10 mM for full activation of the receptor.4

1 Sala, A., Bolla, M., Zarini, S., et al. Release of leukotriene A4 versus leukotriene B4 from human polymorphonuclear leukocytes. J Biol Chem 271 17944-17948 (1996).

2 Jackson, R.H., Morrissey, M.M., Sills, M.A., et al. Comparison of antagonist and agonist binding to the leukotriene B4 receptor on intact human polymorphonuclear neutrophils (PMN). J Pharmacol Exp Ther 262(1) 80-89 (1992).

3 Cristol, J.P., Provençal, B., Borgeat, P., et al. Characterization of leukotriene B4 binding sites on guinea pig lung macrophages. J Pharmacol Exp Ther 247(3) 1199-1203 (1988).

4 Yokomizo, T., Kato, K., Hagiya, H., et al. Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2. J Biol Chem 276(15) 12454-12459 (2001).

Synonyms
  • 12-epi LTB4
Formal Name 5S,​12S-​dihydroxy-​6Z,​8E,​10E,​14Z-​eicosatetraenoic acid
CAS Number 83709-73-3
Molecular Formula C20H32O4
Formula Weight 336.5
Formulation A solution in ethanol
Purity >97%
λmax 270 nm
ε 50
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C[C@H]​(O)​/C=C/C=C/C=C\[C@@H]​(O)​CCCC(O)​=O

Background Reading

Sala, A., Bolla, M., Zarini, S., et al. Release of leukotriene A4 versus leukotriene B4 from human polymorphonuclear leukocytes. J Biol Chem 271 17944-17948 (1996).

Yokomizo, T., Kato, K., Hagiya, H., et al. Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2. J Biol Chem 276(15) 12454-12459 (2001).

Cristol, J.P., Provençal, B., Borgeat, P., et al. Characterization of leukotriene B4 binding sites on guinea pig lung macrophages. J Pharmacol Exp Ther 247(3) 1199-1203 (1988).

Jackson, R.H., Morrissey, M.M., Sills, M.A., et al. Comparison of antagonist and agonist binding to the leukotriene B4 receptor on intact human polymorphonuclear neutrophils (PMN). J Pharmacol Exp Ther 262(1) 80-89 (1992).

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12-epi Leukotriene B4 is available in the following screening library:

Size Price Quantity Subtotal
25 µg $134.00 $0.00
50 µg $255.00 $0.00
100 µg $482.00 $0.00
500 µg $2,144.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-02-12. 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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