Literature DB >> 19716306

Substrate specificity effects of lipoxygenase products and inhibitors on soybean lipoxygenase-1.

Aaron T Wecksler1, Natalie K Garcia, Theodore R Holman.   

Abstract

Recently, it has been shown that lipoxygenase (LO) products affect the substrate specificity of human 15-LO. In the current paper, we demonstrate that soybean LO-1 (sLO-1) is not affected by its own products, however, inhibitors which bind the allosteric site, oleyl sulfate (OS) and palmitoleyl sulfate (PS), not only lower catalytic activity, but also change the substrate specificity, by increasing the arachidonic acid (AA)/linoleic acid (LA) ratio to 4.8 and 4.0, respectively. The fact that LO inhibitors can lower activity and also change the LO product ratio is a new concept in lipoxygenase inhibition, where the goal is to not only reduce the catalytic activity but also alter substrate selectivity towards a physiologically beneficial product.

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Year:  2009        PMID: 19716306      PMCID: PMC2737062          DOI: 10.1016/j.bmc.2009.08.005

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  27 in total

Review 1.  Mammalian lipoxygenases: molecular structures and functions.

Authors:  S Yamamoto
Journal:  Biochim Biophys Acta       Date:  1992-10-30

2.  15-lipoxygenase-1 metabolites down-regulate peroxisome proliferator-activated receptor gamma via the MAPK signaling pathway.

Authors:  L C Hsi; L Wilson; J Nixon; T E Eling
Journal:  J Biol Chem       Date:  2001-07-10       Impact factor: 5.157

3.  Stopped-flow kinetic investigations of the activation of soybean lipoxygenase-1 and the influence of inhibitors on the allosteric site.

Authors:  Viola C Ruddat; Stephanie Whitman; Theodore R Holman; Claude F Bernasconi
Journal:  Biochemistry       Date:  2003-04-15       Impact factor: 3.162

Review 4.  Plant and fungal lipoxygenases.

Authors:  Ernst H Oliw
Journal:  Prostaglandins Other Lipid Mediat       Date:  2002-08       Impact factor: 3.072

Review 5.  Lipoxygenase modulation to reverse carcinogenesis.

Authors:  I Shureiqi; S M Lippman
Journal:  Cancer Res       Date:  2001-09-01       Impact factor: 12.701

6.  Alterations in lipoxygenase and cyclooxygenase-2 catalytic activity and mRNA expression in prostate carcinoma.

Authors:  S B Shappell; S Manning; W E Boeglin; Y F Guan; R L Roberts; L Davis; S J Olson; G S Jack; C S Coffey; T M Wheeler; M D Breyer; A R Brash
Journal:  Neoplasia       Date:  2001 Jul-Aug       Impact factor: 5.715

7.  Nonapoptotic cell death associated with S-phase arrest of prostate cancer cells via the peroxisome proliferator-activated receptor gamma ligand, 15-deoxy-delta12,14-prostaglandin J2.

Authors:  R Butler; S H Mitchell; D J Tindall; C Y Young
Journal:  Cell Growth Differ       Date:  2000-01

8.  Inhibition studies of soybean and human 15-lipoxygenases with long-chain alkenyl sulfate substrates.

Authors:  R Mogul; T R Holman
Journal:  Biochemistry       Date:  2001-04-10       Impact factor: 3.162

Review 9.  Role of eicosanoids in prostate cancer progression.

Authors:  D Nie; M Che; D Grignon; K Tang; K V Honn
Journal:  Cancer Metastasis Rev       Date:  2001       Impact factor: 9.264

10.  Opposing effects of 15-lipoxygenase-1 and -2 metabolites on MAPK signaling in prostate. Alteration in peroxisome proliferator-activated receptor gamma.

Authors:  Linda C Hsi; Leigh C Wilson; Thomas E Eling
Journal:  J Biol Chem       Date:  2002-08-19       Impact factor: 5.157

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  5 in total

1.  Biosynthesis of the Maresin Intermediate, 13S,14S-Epoxy-DHA, by Human 15-Lipoxygenase and 12-Lipoxygenase and Its Regulation through Negative Allosteric Modulators.

Authors:  Cody Freedman; Adrianne Tran; Benjamin E Tourdot; Chakrapani Kalyanaraman; Steve Perry; Michael Holinstat; Matthew P Jacobson; Theodore R Holman
Journal:  Biochemistry       Date:  2020-05-07       Impact factor: 3.162

Review 2.  Mammalian lipoxygenases and their biological relevance.

Authors:  Hartmut Kuhn; Swathi Banthiya; Klaus van Leyen
Journal:  Biochim Biophys Acta       Date:  2014-10-12

3.  Hydrogen-deuterium exchange reveals long-range dynamical allostery in soybean lipoxygenase.

Authors:  Adam R Offenbacher; Anthony T Iavarone; Judith P Klinman
Journal:  J Biol Chem       Date:  2017-11-30       Impact factor: 5.157

Review 4.  Development of multitarget agents possessing soluble epoxide hydrolase inhibitory activity.

Authors:  Kerstin Hiesinger; Karen M Wagner; Bruce D Hammock; Ewgenij Proschak; Sung Hee Hwang
Journal:  Prostaglandins Other Lipid Mediat       Date:  2018-12-26       Impact factor: 3.072

Review 5.  Fatty Acid Allosteric Regulation of C-H Activation in Plant and Animal Lipoxygenases.

Authors:  Adam R Offenbacher; Theodore R Holman
Journal:  Molecules       Date:  2020-07-24       Impact factor: 4.411

  5 in total

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