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Eicosanoid


DATA No : XPR3111 INFORMANT : Takao Shimizu

NAME : 5S-hydroxy-12-keto-[6Z, 8E, 10E, 14Z]-eicosatetraenoic acid

COMMON NAME: 12-oxo-Leukotriene B4
SYMBOL: 12-oxo-LTB4
FORMULA: C20H30O4 MOL.WT (average) : 334.450


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BIOLOGICAL ACTIVITY
Increase in intracellular calcium in human leukocytes probably through BLT (LTB4 receptor). The IC 50 value is 100 times higher than that of LTB4.
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:Soluble in ethanol, methanol, ethyl acetate, acetonitril
SPECTRAL DATA
UV SPECTRA:UV maxima 316 nm, Absorbance at 320 nm is 41000/M

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA
12-oxo-LTB4 is eluted at 7.8 min on RP-HPLC system as follows: Solvent:acetonitril/water/acetic acid, 50:50:0.01 (v/v/v), 0.01 % (w/v) Na2EDTA, pH 5.6 with ammonia Flow: 1 ml/min, isocratic Column: Cosmosil 5C18-AR (4.6 x 150 mm, Nacalai tesque, Tokyo) (Ref. 3111)
SOURCE
This metabolite is derived from LTB4 by LTB4 12-hydroxydehydrogenase. LTB4 12-hydroxydehydrogenase is expressed most abunduntly in liver and kidney.
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION
LTB4 12-hydroxydehydrogenase cDNA is cloned from various animals. The accession numbers in DDBJ/EMBL/Genbank are shown in ( ). Pig (D49386) (Ref. 3112) (Ref. 3113) Human (D49387) (Ref. 3112) Rat (U66322) (Ref. 3114)
NOTE

REFERENCES
[3111]
AUTHOR:Yokomizo, T.,Izumi, T., Takahashi, T., Kasama, T., Kobayashi, Y., Sato, F., Taketani, Y., Shimizu, T.
TITLE:Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12- hydroxydehydrogenase. PubMed ID:8394361
JOURNAL:J. Biol. Chem.
VOL:268 PAGE : 18128 -18135 (1993)
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[3112]
AUTHOR:Yokomizo,T., Ogawa,Y., Uozumi,N., Kume,K., Izumi,T. , Shimizu,T.
TITLE:cDNA cloning, expression, and mutagenesis study of leukotriene B4 12-hydroxydehydrogenase. PubMed ID:8576264
JOURNAL:J. Biol. Chem.
VOL:271 PAGE : 2844 -2850 (1996)
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[3113]
AUTHOR:Ensor, C. M., Zhang, H., and Tai, H. H.
TITLE:Purification, cDNA cloning and expression of 15-oxoprostaglandin 13-reductase from pig lung PubMed ID:9461497
JOURNAL:Biochem J.
VOL:330 (Pt 1) PAGE : 103-108 (1998)
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[3114]
AUTHOR:Primiano, T., Gastel, J. A., Kensler, T. W., and Sutter, T. R.
TITLE:Isolation of cDNAs representing dithiolethione-responsive genes PubMed ID:8968041
JOURNAL:Carcinogenesis.
VOL:17 PAGE : 2297-2303 (1996)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.