Glyoxalase I inhibitor - CAS 221174-33-0
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Not Intended for Therapeutic Use. For research use only.
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Glyoxalase I inhibitor is a potent Glyoxalase I inhibitor, candidate for anticancer agents.
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Glycine, L-γ-glutamyl-S-[[(4-bromophenyl)hydroxyamino]carbonyl]-L-cysteinyl-, diethyl ester, monohydrochloride (9CI)
1.Oxidative stress and glyoxalase I activity mediate dicarbonyl toxicity in MCF-7 mamma carcinoma cells and a tamoxifen resistant derivative.
Nass N1, Sel S2, Ignatov A3, Roessner A4, Kalinski T4. Biochim Biophys Acta. 2016 Jun;1860(6):1272-80. doi: 10.1016/j.bbagen.2016.03.006. Epub 2016 Mar 10.
BACKGROUND: Acquired tamoxifen resistance is a significant problem in estrogen receptor positive breast cancer. In a cellular model, tamoxifen resistance was associated with increased sensitivity towards toxic dicarbonyls and reduced free sulfhydryl group content. We here analyzed the role of oxidative stress and glyoxalase I activity on dicarbonyl resistance and the significance of glyoxalase I expression for survival.
2.Inhibition by active site directed covalent modification of human glyoxalase I.
Holewinski RJ1, Creighton DJ2. Bioorg Med Chem. 2014 Jul 1;22(13):3301-8. doi: 10.1016/j.bmc.2014.04.055. Epub 2014 May 6.
The glyoxalase pathway is responsible for conversion of cytotoxic methylglyoxal (MG) to d-lactate. MG toxicity arises from its ability to form advanced glycation end products (AGEs) on proteins, lipids and DNA. Studies have shown that inhibitors of glyoxalase I (GLO1), the first enzyme of this pathway, have chemotherapeutic effects both in vitro and in vivo, presumably by increasing intracellular MG concentrations leading to apoptosis and cell death. Here, we present the first molecular inhibitor, 4-bromoacetoxy-1-(S-glutathionyl)-acetoxy butane (4BAB), able to covalently bind to the free sulfhydryl group of Cys60 in the hydrophobic binding pocket adjacent to the enzyme active site and partially inactivate the enzyme. Our data suggests that partial inactivation of homodimeric GLO1 is due to the modification at only one of the enzymatic active sites. Although this molecule may have limited use pharmacologically, it may serve as an important template for the development of new GLO1 inhibitors that may combine this strategy with ones already reported for high affinity GLO1 inhibitors, potentially improving potency and specificity.
3.Novel bivalent inhibitors with sub-nanomolar affinities towards human glyoxalase I.
Sang Y1, Shi Q1, Mo M1, Ni C1, Li Z1, Liu B1, Deng Q1, Creighton DJ2, Zheng ZB3. Bioorg Med Chem Lett. 2015 Nov 1;25(21):4724-7. doi: 10.1016/j.bmcl.2015.08.055. Epub 2015 Aug 20.
The zinc metalloenzyme glyoxalase I (GlxI) catalyzes the glutathione-dependent inactivation of cytotoxic methylglyoxal. Two competitive bivalent GlxI inhibitors, polyBHG2-62 (Ki=1.0 nM) and polyBHG2-54 (Ki=0.3 nM), were synthesized based on the transition-state analog S-(N-bromophenyl-N-hydroxycarbamoyl) glutathione (BHG). The most effective inhibitor, polyBHG2-54, is the first subnanomolar inhibitor of GlxI, and is over 50-fold more potent than BHG itself.
4.Evaluation of potential flavonoid inhibitors of glyoxalase-I based on virtual screening and in vitro studies.
Yadav A1, Kumar R2, Sunkaria A1, Singhal N3, Kumar M2, Sandhir R1. J Biomol Struct Dyn. 2016 May;34(5):993-1007. doi: 10.1080/07391102.2015.1064830. Epub 2015 Jul 28.
Glyoxalase-I (GLO-I) is a component of the ubiquitous detoxification system involved in the conversion of methylglyoxal (MG) to d-lactate in the glycolytic pathway. MG toxicity arises from its ability to form advanced glycation end products. GLO-I has been reported to be frequently overexpressed in various types of cancer cells. In this study, we performed structure-based virtual screening of focused flavonoids commercial library to identify potential and specific inhibitors of GLO-I. The compounds were ranked based on Glide extra precision docking score and five hits (curcumin, quercetin, morin, naringin and silibinin) were selected on the basis of their interaction with active site amino acid residues of GLO-I. Mixed mode QM/MM calculation was performed on the top-scoring hit to ascertain the role of zinc ion in ligand binding. In addition, the identified hits were subjected to MM/GBSA binding energy prediction, ADME prediction and similarity studies.
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CAS 221174-33-0 Glyoxalase I inhibitor

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