Site-Specific Chemoproteomic Profiling of Targets of Glyoxal

References

• Vistoli G , DeMaddis D, CipakA, ZarkovicN, CariniM, AldiniG. Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): an overview of their mechanisms of formation. Free Radic. Res.47(Suppl. 1), 3–27 (2013).
   PubMed Web of Science ®Google Scholar
• Wang Y , HoCT. Flavour chemistry of methylglyoxal and glyoxal. Chem. Soc. Rev.41(11), 4140–4149 (2012).
   PubMed Web of Science ®Google Scholar
• Semchyshyn HM . Reactive carbonyl species in vivo: generation and dual biological effects. Scientific World Journal2014, 417842 (2014).
   Google Scholar
• Thornalley PJ . Protein and nucleotide damage by glyoxal and methylglyoxal in physiological systems--role in ageing and disease. Drug Metabol. Drug Interact.23(1–2), 125–150 (2008).
   PubMedGoogle Scholar
• Glomb MA , PfahlerC. Amides are novel protein modifications formed by physiological sugars. J. Biol. Chem.276(45), 41638–41647 (2001).
   PubMed Web of Science ®Google Scholar
• Haddad M , PerrotteM, LandriS, LepageA, FulopT, RamassamyC. Circulating and extracellular vesicles levels of N-(1-carboxymethyl)-L-lysine (CML) differentiate early to moderate Alzheimer's disease. J. Alzheimers Dis.69(3), 751–762 (2019).
   PubMed Web of Science ®Google Scholar
• Girones X , GuimeraA, Cruz-SanchezCZet al. N epsilon-carboxymethyllysine in brain aging, diabetes mellitus, and Alzheimer's disease. Free Radic. Biol. Med.36(10), 1241–1247 (2004).
   PubMed Web of Science ®Google Scholar
• Ajith TA , VinodkumarP. Advanced glycation end products: association with the pathogenesis of diseases and the current therapeutic advances. Curr. Clin. Pharmacol.11(2), 118–127 (2016).
   PubMedGoogle Scholar
• Tong J , LiuN. Effect of advanced glycosylation end products on activity of protein kinase C in human peripheral blood mononuclear cells. Chin. Med. J. (Engl.)113(12), 1068–1070 (2000).
   PubMed Web of Science ®Google Scholar
• Ahmed N , ArgirovOK, MinhasHS, CordeiroCA, ThornalleyPJ. Assay of advanced glycation endproducts (AGEs): surveying AGEs by chromatographic assay with derivatization by 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and application to nepsilon-carboxymethyl-lysine- and nepsilon-(1-carboxyethyl)lysine-modified albumin. Biochem. J.364, 1–14 (2002).
   PubMed Web of Science ®Google Scholar
• Chen HJ , ChenYC, HsiaoCF, ChenPF. Mass spectrometric analysis of glyoxal and methylglyoxal-induced modifications in human hemoglobin from poorly controlled Type 2 diabetes mellitus patients. Chem. Res. Toxicol.28(12), 2377–2389 (2015).
   PubMed Web of Science ®Google Scholar
• Gorisse L , PietrementC, VuibletVet al. Protein carbamylation is a hallmark of aging. Proc. Natl Acad. Sci. USA113(5), 1191–1196 (2016).
   PubMed Web of Science ®Google Scholar
• Wendel U , PerssonN, RisingerCet al. A novel monoclonal antibody targeting carboxymethyllysine, an advanced glycation end product in atherosclerosis and pancreatic cancer. PLoS ONE13(2), e0191872 (2018).
   PubMed Web of Science ®Google Scholar
• Koito W , ArakiT, HoriuchiS, NagaiR. Conventional antibody against nepsilon-(carboxymethyl)lysine (CML) shows cross-reaction to nepsilon-(carboxyethyl)lysine (CEL): immunochemical quantification of CML with a specific antibody. J. Biochem.136(6), 831–837 (2004).
   PubMed Web of Science ®Google Scholar
• Klaus A , BaldenspergerT, FiedlerR, GirndtM, GlombMA. Influence of transketolase-catalyzed reactions on the formation of glycolaldehyde and glyoxal specific posttranslational modifications under physiological conditions. J. Agric. Food Chem.66(6), 1498–1508 (2018).
   PubMed Web of Science ®Google Scholar
• Codreanu SG , ZhangB, SobeckiSM, BillheimerDD, LieblerDC. Global analysis of protein damage by the lipid electrophile 4-hydroxy-2-nonenal. Mol. Cell. Proteomics8(4), 670–680 (2009).
   PubMed Web of Science ®Google Scholar
• Chen Y , CongY, QuanBet al. Chemoproteomic profiling of targets of lipid-derived electrophiles by bioorthogonal aminooxy probe. Redox Biol.12, 712–718 (2017).
   PubMed Web of Science ®Google Scholar
• Chavez J , WuJ, HanB, ChungWG, MaierCS. New role for an old probe: affinity labeling of oxylipid protein conjugates by N’-aminooxymethylcarbonylhydrazino d-biotin. Anal. Chem.78(19), 6847–6854 (2006).
   PubMed Web of Science ®Google Scholar
• Yuan W , ZhangY, XiongYet al. Highly selective and large scale mass spectrometric analysis of 4-hydroxynonenal modification via fluorous derivatization and fluorous solid-phase extraction. Anal. Chem.89(5), 3093–3100 (2017).
   PubMed Web of Science ®Google Scholar
• Zhang S , FangC, YuanWet al. Selective identification and site-specific quantification of 4-hydroxy-2-nonenal-modified proteins. Anal. Chem.91(8), 5235–5243 (2019).
   PubMed Web of Science ®Google Scholar
• Chen Y , LiuY, LanTet al. Quantitative profiling of protein carbonylations in ferroptosis by an aniline-derived probe. J. Am. Chem. Soc.140(13), 4712–4720 (2018).
   PubMed Web of Science ®Google Scholar
• Chen Y , LiuY, HouX, YeZ, WangC. Quantitative and site-specific chemoproteomic profiling of targets of acrolein. Chem. Res. Toxicol.32(3), 467–473 (2019).
   PubMed Web of Science ®Google Scholar
• Weerapana E , SpeersAE, CravattBF. Tandem orthogonal proteolysis-activity-based protein profiling (TOP-ABPP) – a general method for mapping sites of probe modification in proteomes. Nat. Protoc.2(6), 1414–1425 (2007).
   PubMed Web of Science ®Google Scholar
• Richarme G , MihoubM, DairouJ, BuiLC, LegerT, LamouriA. Parkinsonism-associated protein DJ-1/Park7 is a major protein deglycase that repairs methylglyoxal- and glyoxal-glycated cysteine, arginine, and lysine residues. J. Biol. Chem.290(3), 1885–1897 (2015).
   PubMed Web of Science ®Google Scholar
• O’Shea JP , ChouMF, QuaderSA, RyanJK, ChurchGM, SchwartzD. pLogo: a probabilistic approach to visualizing sequence motifs. Nat. Methods10(12), 1211–1212 (2013).
   PubMed Web of Science ®Google Scholar
• Wetzels S , WoutersK, MiyataTet al. Advanced glycation endproducts are increased in the animal model of multiple sclerosis but cannot be reduced by pyridoxamine treatment or glyoxalase 1 overexpression. Int. J. Mol. Sci.19(5), 1311–1322 (2018).
   PubMed Web of Science ®Google Scholar
• Sharma N , RaoSP, KalivendiSV. The deglycase activity of DJ-1 mitigates alpha-synuclein glycation and aggregation in dopaminergic cells: Role of oxidative stress mediated downregulation of DJ-1 in Parkinson's disease. Free Radic. Biol. Med.135, 28–37 (2019).
   PubMed Web of Science ®Google Scholar
• Nass N , IgnatovA, AndreasL, WeissenbornC, KalinskiT, SelS. Accumulation of the advanced glycation end product carboxymethyl lysine in breast cancer is positively associated with estrogen receptor expression and unfavorable prognosis in estrogen receptor-negative cases. Histochem. Cell Biol.147(5), 625–634 (2017).
   PubMed Web of Science ®Google Scholar
• Hacker SM , BackusKM, LazearMR, ForliS, CorreiaBE, CravattBF. Global profiling of lysine reactivity and ligandability in the human proteome. Nat. Chem.9(12), 1181–1190 (2017).
   PubMed Web of Science ®Google Scholar
• Ahmad S , AkhterF, ShahabUet al. Do all roads lead to the Rome? The glycation perspective! Semin. Cancer Biol. 49, 9–19 (2018).
   PubMed Web of Science ®Google Scholar
• Parvez S , FuY, LiJet al. Substoichiometric hydroxynonenylation of a single protein recapitulates whole-cell-stimulated antioxidant response. J. Am. Chem. Soc.137(1), 10–13 (2015).
   PubMed Web of Science ®Google Scholar
• Lin HY , HaegeleJA, DisareMT, LinQ, AyeY. A generalizable platform for interrogating target- and signal-specific consequences of electrophilic modifications in redox-dependent cell signaling. J. Am. Chem. Soc.137(19), 6232–6244 (2015).
   PubMed Web of Science ®Google Scholar
• Rexach JE , RogersCJ, YuSH, TaoJ, SunYE, Hsieh-WilsonLC. Quantification of O-glycosylation stoichiometry and dynamics using resolvable mass tags. Nat. Chem. Biol.6(9), 645–651 (2010).
   PubMed Web of Science ®Google Scholar
• Percher A , RamakrishnanS, ThinonE, YuanX, YountJS, HangHC. Mass-tag labeling reveals site-specific and endogenous levels of protein S-fatty acylation. Proc. Natl Acad. Sci. USA113(16), 4302–4307 (2016).
   PubMed Web of Science ®Google Scholar