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12-oxo Leukotriene B4

Cayman Chemical Item Number 20140

12-keto LTB4; 12-oxo LTB4 (CAS 136696-10-1)

12-oxo Leukotriene B4 (CAS 136696-10-1)

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Description

Leukotriene B4 (LTB4) is a dihydroxy fatty acid derived from arachidonic acid through the 5-LO pathway. It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. 12-oxo LTB4 is an initial metabolite of LTB4 formed via the LTB4 12-hydroxydehydrogenase pathway.1,2,3 It is rapidly converted to 10,11-dihydro-12-oxo-LTB4, followed by reduction of the 12-oxo group to give 10,11-dihydro-LTB4.2 12-oxo-LTB4 (EC50 = 33 nM) is about 70-fold less potent than LTB4 (EC50 = 0.46 nM) at stimulating Ca2+ mobilization in human neutrophils.4 It is also significantly less potent than LTB4 at stimulating neutrophil migration with EC50 values of 170 and 2.7 nM for 12-oxo-LTB4 and LTB4, respectively.4

1 Yokomizo, T., Izumi, T., Takahashi, T., et al. Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase. J Biol Chem 268 18128-18135 (1993).

2 Wainwright, S.L., and Powell, W.S. Mechanism for the formation of dihydro metabolites of 12-hydroxyeicosanoids conversion of leukotriene B4 and 12-hydroxy-5,8,10,14-eicosatetraenoic acid to 12-oxo intermediates. J Biol Chem 266(31) 20899-20906 (1991).

3 Wheelan, P., Zirrolli, J.A., Morelli, J.G., et al. Metabolism of leukotriene B4 by cultural human keratinocytes. Formation of glutathione conjugates and dihydro metabolites. J Biol Chem 268 25439-25448 (1993).

4 Powell, W.S., Rokach, J., Khanapure, S.P., et al. Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther 276(2) 728-736 (1996).

Synonyms
  • 12-keto LTB4
  • 12-oxo LTB4
Formal Name 5S-​hydroxy-​12-​oxo-​6Z,​8E,​10E,​14Z-​eicosatetraenoic acid
CAS Number 136696-10-1
Molecular Formula C20H30O4
Formula Weight 334.4
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=C\CC(=O)​\C=C/C=C\C=C\[C@@H]​(O)​CCCC(=O)​O

Background Reading

Powell, W.S., Rokach, J., Khanapure, S.P., et al. Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther 276(2) 728-736 (1996).

Wheelan, P., Zirrolli, J.A., Morelli, J.G., et al. Metabolism of leukotriene B4 by cultural human keratinocytes. Formation of glutathione conjugates and dihydro metabolites. J Biol Chem 268 25439-25448 (1993).

Wainwright, S.L., and Powell, W.S. Mechanism for the formation of dihydro metabolites of 12-hydroxyeicosanoids conversion of leukotriene B4 and 12-hydroxy-5,8,10,14-eicosatetraenoic acid to 12-oxo intermediates. J Biol Chem 266(31) 20899-20906 (1991).

Yokomizo, T., Izumi, T., Takahashi, T., et al. Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase. J Biol Chem 268 18128-18135 (1993).

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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
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Cart Total $0.00

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Pricing updated 2012-05-26. 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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