A LTB4 metabolite
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20-hydroxy Leukotriene B4

Item No. 20190

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,12R,20-trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid
CAS Number
79516-82-8
Synonyms
  • 20-hydroxy LTB4
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥97%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 1 mg/ml
λmax
270 nm
SMILES
OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1
InChi Key
PTJFJXLGRSTECQ-PSPARDEHSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $186

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    50 µg

    $354

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    100 µg

    $669

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    Product Description

    20-hydroxy LTB4 is a metabolite of LTB4 in human neutrophils. In human leukocytes, LTB4 is inactivated by the enzyme LTB4 20-hydroxylase. 20-hydroxy LTB4 is not only much less active (~5%) compared to LTB4 in causing degranulation of PMNL,1 but actually inhibits LTB4-induced degranulation of human neutrophils (Ki = 13.3 nM).2 However, 20-hydroxy LTB4 is as active as LTB4 in contracting parenchymal strips from guinea pig lung.3 20-hydroxy LTB4 retains considerable ligand binding affinity at the BLT2 receptor,4,5 but does not appear to function as an agonist.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Feinmark, S.J., Lindgren, J.Å., Claesson, H.E., et al. Stimulation of human leukocyte degranulation by leukotriene B4 and its ω-oxidized metabolites. FEBS Lett. 136, 141-144 (1981).

    2. Falcone, R.C., and Aharony, D. Modulation of ligand binding to leukotriene B4 receptors on guinea pig lung membranes by sulfhydryl modifying reagents. J. Pharmacol. Exp. Ther. 255, 565-571 (1990).

    3. Hansson, G., Lindgren, J.Å., Dahlén, S.E., et al. Identification and biological activity of novel w -oxidized metabolites of leukotriene B4 from human leukocytes. FEBS Lett. 130(1), 107-112 (1981).

    4. Wang, S., Gustafson, E., Pang, L., et al. A novel hepatointestinal leukotriene B4 receptor. The Journal of Biological Chemisty 275(52), 40686-40694 (2000).

    5. Yokomizo, T., Kato, K., Hagiya, H., et al. Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2. The Journal of Biological Chemisty 276(15), 12454-12459 (2001).

    6. Kamohara, M., Takasaki, J., Matsumoto, M., et al. Molecular cloning and characterization of another leukotriene B4 receptor. The Journal of Biological Chemisty 275(35), 27000-27004 (2000).

    Product Citations

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. The FASEB Journal 35(6), e21666 (2021).

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Brouwers, H., Jónasdóttir, H.S., Kuipers, M.E., et al. Anti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).