ArticleThe Biochemical journal2005
Oxidation of heparan sulphate by hypochlorite: role of N-chloro derivatives and dichloramine-dependent fragmentation.
Article in The Biochemical journal, 2005. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 57 citations in OpenAlex.
- Modification of extracellular matrix proteins by oxidants and electrophiles.Biochemical Society transactions · 2024Review
- Mass spectrometric investigations of the action of hypochlorous acid on monomeric and oligomeric components of glycosaminoglycans.Biochemistry and biophysics reports · 2023Article
- Hypochlorous Acid Chemistry in Mammalian Cells-Influence on Infection and Role in Various Pathologies.International journal of molecular sciences · 2022Review
- The Nrf2 transcription factor: A multifaceted regulator of the extracellular matrix.Matrix biology plus · 2021Review
- Binding of the human antioxidation protein αRedox biology · 2021Article
- Article
- Cell-free Biochemical Fluorometric Enzymatic Assay for High-throughput Measurement of Lipid Peroxidation in High Density Lipoprotein.Journal of visualized experiments : JoVE · 2017Article
- Oxidative release of natural glycans for functional glycomics.Nature methods · 2016Article
- Preparation and characterization of heparin hexasaccharide library with N-unsubstituted glucosamine residues.Glycoconjugate journal · 2015Article
- The mechanisms and physiological relevance of glycocalyx degradation in hepatic ischemia/reperfusion injury.Antioxidants & redox signaling · 2014Review
- Heparan sulfate containing unsubstituted glucosamine residues: biosynthesis and heparanase-inhibitory activity.The Journal of biological chemistry · 2014Article
- Polymorphonuclear neutrophils and instability of the atherosclerotic plaque: a causative role?Inflammation research : official journal of the European Histamine Research Society ... [et al.] · 2013Review
- Molecular functions of syndecan-1 in disease.Matrix biology : journal of the International Society for Matrix Biology · 2012Review
- Preparation of heparin/heparan sulfate oligosaccharides with internal N-unsubstituted glucosamine residues for functional studies.Glycoconjugate journal · 2011Article
- Oxidative stress, extracellular matrix targets, and idiopathic pulmonary fibrosis.Free radical biology & medicine · 2010Review
- Peroxynitrite modifies the structure and function of the extracellular matrix proteoglycan perlecan by reaction with both the protein core and the heparan sulfate chains.Free radical biology & medicine · 2010Article
- Myeloperoxidase-derived oxidants selectively disrupt the protein core of the heparan sulfate proteoglycan perlecan.Matrix biology : journal of the International Society for Matrix Biology · 2010Article
- Organ-specific heparan sulfate structural phenotypes.The Journal of biological chemistry · 2009Article
- Degradation of extracellular matrix and its components by hypobromous acid.The Biochemical journal · 2007Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Activated phagocytes release the haem enzyme MPO (myeloperoxidase) and produce superoxide radicals and H2O2 via an oxidative burst. MPO uses H2O2 and Cl- to form HOCl, the physiological mixture of hypochlorous acid and its anion present at pH 7.4. As MPO binds to glycosaminoglycans, oxidation of extracellular matrix and cell surfaces by HOCl may be localized to these materials. However, the reactions of HOCl with glycosaminoglycans are poorly characterized. The GlcNAc (N-acetylglucosamine), GlcNSO3 (glucosamine-N-sulphate) and GlcNH2 [(N-unsubstituted) glucosamine] residues of heparan sulphate are potential targets for HOCl. It is shown here that HOCl reacts with each of these residues to generate N-chloro derivatives, and the absolute rate constants for these reactions have been determined. Reaction at GlcNH2 residues yields chloramines and, subsequently, dichloramines with markedly slower rates, k2 approximately 3.1x10(5) and 9 M(-1) x s(-1) (at 37 degrees C) respectively. Reaction at GlcNSO3 and GlcNAc residues yields N-chlorosulphonamides and chloramides with k2 approximately 0.05 and 0.01 M(-1) x s(-1) (at 37 degrees C) respectively. The corresponding monosaccharides display a similar pattern of reactivity. Decay of the polymer-derived chloramines, N-chlorosulphonamides and chloramides is slow at 37 degrees C and does not result in major structural changes. In contrast, dichloramine decay is rapid at 37 degrees C and results in fragmentation of the polymer backbone. Computational modelling of the reaction of HOCl with heparan sulphate proteoglycans (glypican-1 and perlecan) predicts that the GlcNH2 residues of heparan sulphate are major sites of attack. These results suggest that HOCl may be an important mediator of damage to glycosaminoglycans and proteoglycans at inflammatory foci.
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