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KEAP1 and done? Targeting the NRF2 pathway with sulforaphane

Dinkova-Kostova, Albena T., Fahey, Jed W., Kostov, Rumen V., Kensler, Thomas W.·2017·Trends in Food Science & Technology
DOI 10.1016/j.tifs.2017.02.002PMC PMC5725197
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Fig. 1 The myrosinase reaction and the interconversion of sulforaphane and erucin. The glucosinolates glucoraphanin and glucoerucin are hydrolyzed by β-thioglucosidases (myrosinases) to give unstable aglycones and liberate glucose. Depending on the reaction conditions, a variety of reactive products can be formed, the most common of which are the isothiocyanates (sulforaphane and erucin) and their corresponding nitriles. In mammals, glucoraphanin is also taken up from the gut to the liver where it is interconverted to its reduced analog, glucoerucin, as is sulforaphane to erucin. R1 = 4-(methylsulfinyl)butane; R2 = 4-(methylthio)butane.
Fig. 1 The myrosinase reaction and the interconversion of sulforaphane and erucin. The glucosinolates glucoraphanin and glucoerucin are hydrolyzed by β-thioglucosidases (myrosinases) to give unstable aglycones and liberate glucose. Depending on the reaction conditions, a variety of reactive products can be formed, the most common of which are the isothiocyanates (sulforaphane and erucin) and their corresponding nitriles. In mammals, glucoraphanin is also taken up from the gut to the liver where it is interconverted to its reduced analog, glucoerucin, as is sulforaphane to erucin. R1 = 4-(methylsulfinyl)butane; R2 = 4-(methylthio)butane.CC BY · PubMed Central
Fig. 2 Metabolism of isothiocyanates in mammalian cells. The central carbon of the isothiocyanate (—NCS) group is electrophilic and reacts readily with sulfur-, nitrogen-, and oxygen-centered nucleophiles. The most common reaction in mammalian cells is conjugation with sulfhydryl groups, such as the sulfhydryl group of cysteine in proteins and glutathione. The reaction with glutathione is catalyzed by glutathione S-transferases (GSTs), and the resulting product is cleaved sequentially by γ-glutamyl-transpeptidase (γ-GT), cysteinyl-glycinease (GCase), and N-acetyltransferase (NAT) to give the N-acetylcysteine conjugate (mercapturic acid). The conjugates are collectively known as dithiocarbamates.
Fig. 2 Metabolism of isothiocyanates in mammalian cells. The central carbon of the isothiocyanate (—NCS) group is electrophilic and reacts readily with sulfur-, nitrogen-, and oxygen-centered nucleophiles. The most common reaction in mammalian cells is conjugation with sulfhydryl groups, such as the sulfhydryl group of cysteine in proteins and glutathione. The reaction with glutathione is catalyzed by glutathione S-transferases (GSTs), and the resulting product is cleaved sequentially by γ-glutamyl-transpeptidase (γ-GT), cysteinyl-glycinease (GCase), and N-acetyltransferase (NAT) to give the N-acetylcysteine conjugate (mercapturic acid). The conjugates are collectively known as dithiocarbamates.CC BY · PubMed Central
Fig. 3 The cyclical model of KEAP1-mediated degradation of NRF2. (A) At homeostatic conditions, de novo synthesized NRF2 binds sequentially to the Kelch domains of the KEAP1 dimer, first through its high affinity “ETGE” binding motif followed by the low affinity “DLG” binding motif. Fully bound NRF2 is ubiquitinated and degraded through the proteasome. Free KEAP1 is regenerated. (B) Sulforaphane blocks the cycle by chemically modifying cysteine sensor(s) of KEAP1 and disabling its substrate adaptor function. Consequently, NRF2 is not degraded, KEAP1 is not regenerated, de novo synthesized NRF2 accumulates and, as a heterodimer with a small Maf transcription factor (sMaf), initiates transcription of target genes.
Fig. 3 The cyclical model of KEAP1-mediated degradation of NRF2. (A) At homeostatic conditions, de novo synthesized NRF2 binds sequentially to the Kelch domains of the KEAP1 dimer, first through its high affinity “ETGE” binding motif followed by the low affinity “DLG” binding motif. Fully bound NRF2 is ubiquitinated and degraded through the proteasome. Free KEAP1 is regenerated. (B) Sulforaphane blocks the cycle by chemically modifying cysteine sensor(s) of KEAP1 and disabling its substrate adaptor function. Consequently, NRF2 is not degraded, KEAP1 is not regenerated, de novo synthesized NRF2 accumulates and, as a heterodimer with a small Maf transcription factor (sMaf), initiates transcription of target genes.CC BY · PubMed Central

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Metadata

Authors
Dinkova-Kostova, A. T., Fahey, J. W., Kostov, R. V., & Kensler, T. W.
Venue
Trends in Food Science & Technology
Publisher
Elsevier BV
Published
2017-11
Volume
69
Pages
257-269
ISSN
0924-2244
DOI
10.1016/j.tifs.2017.02.002
PMC
PMC5725197
Cited by
273
References
10
Language
en
Licence

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