The Action of Hypochlorous Acid on Polymeric Components of Cartilage

Schiller, Jürgen; Arnhold, Jürgen; Gründer, Wilfried; Arnold, Klaus

doi:10.1515/bchm3.1994.375.3.167

Cited by 47 publications

(30 citation statements)

References 21 publications

(10 reference statements)

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“…The high molecular weight of native hyaluronan in cartilage and the resulting considerable linewidth are further reasons that prevent its detection. In contrast, the lower molecular weight of chondroitin sulfate (about 50 kDa in comparison to about 800 kDa of the native hyaluronan) favors its detection (35).…”

Section: Establishing Working Conditionsmentioning

confidence: 95%

Cartilage Degradation by Stimulated Human Neutrophils: Elastase Is Mainly Responsible for Cartilage Damage

Hilbert

Schiller

Arnhold

et al. 2002

Bioorganic Chemistry

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Section: Establishing Working Conditionsmentioning

confidence: 95%

Cartilage Degradation by Stimulated Human Neutrophils: Elastase Is Mainly Responsible for Cartilage Damage

Hilbert

Schiller

Arnhold

et al. 2002

Bioorganic Chemistry

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“…Additionally, the molecular mechanism of the involved reactions has been studied using NMR spectroscopy (12,13). HOCl clearly damages N-acetylglucosamine as well as chondroitin sulfate and hyaluronic acid in vitro.…”

Section: Introductionmentioning

confidence: 99%

“…HOCl clearly damages N-acetylglucosamine as well as chondroitin sulfate and hyaluronic acid in vitro. Two different effects have been observed: a breakdown of large polymers, such as hyaluronic acid, into smaller oligomeric units, and a simultaneous reaction of HOCl with N-acetyl side groups of these carbohydrates to yield acetate as final product via a transient chlorinated product (12). Only in the presence of extremely high concentrations of hypochlorous acid are further oxidation products like formate detectable (13).…”

Section: Introductionmentioning

confidence: 99%

IR and NMR Studies on the Action of Hypochlorous Acid on Chondroitin Sulfate and Taurine

Servaty

Schiller

Binder

et al. 1998

Bioorganic Chemistry

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“…HOCl reacts with a variety of molecules, including amino acids, proteins, carbohydrates, nucleic acids, and lipids (7)(8)(9)(10)(11)(12). In the latter case, chlorohydrins are generated as the primary products when HOCl reacts with the double bonds in unsaturated phosphatidylcholines (12)(13)(14).…”

mentioning

confidence: 99%

Hypochlorous acid-mediated generation of glycerophosphocholine from unsaturated plasmalogen glycerophosphocholine lipids

Lessig

Schiller

Arnhold

et al. 2007

Journal of Lipid Research

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The myeloperoxidase-derived metabolite hypochlorous acid (HOCl) promotes the selective cleavage of plasmalogens into chloro fatty aldehydes and 1-lysophosphatidylcholine (LPC). The subsequent conversion of the initially generated LPC was investigated in plasmalogen samples in dependence on the fatty acid residue in the sn-2 position by matrix-assisted laser desorption and ionization time-of-flight mass spectrometry and 31 P NMR spectroscopy. Plasmalogens containing an oleic acid residue in the sn-2 position are converted by moderate amounts of HOCl primarily to 1-lyso-2-oleoyl-sn-glycero-3-phosphocholine and at increased HOCl concentrations to the corresponding chlorohydrin species. In contrast, plasmalogens containing highly unsaturated docosahexaenoic acid yield upon HOCl treatment 1-lyso-2-docosahexaenoyl-glycerophosphocholine and glycerophosphocholine. The formation of the latter product denotes a novel pathway for the action of HOCl on plasmalogens. Olefinic residues of fatty acyl residues of phospholipids are an important target for oxidative damage induced by reactive oxygen species (ROS) known to occur under various pathological conditions, including chronic inflammation, atherosclerosis, aging, and cancer. Some mammalian tissues and cells, such as erythrocytes, kidney, lung, testes, skeletal muscle, brain, heart, and particularly selected animal spermatozoa (e.g., from bull), contain considerable levels of plasmalogen glycerophosphocholine lipids (1). Plasmalogens also represent an important target for ROS (2) and are often considered antioxidants. Although the 1-alkenyl residues in plasmalogens (mainly plasmalogen glycerophosphocholine and glycerophosphoethanolamine) of mammalian cells are usually derived from saturated long-chain fatty aldehydes, the acyl residues are highly unsaturated (2). For instance, in spermatozoa from boar or bull, docosahexaenoic and docosapentaenoic acid residues do nearly occur exclusively (3). Accordingly, the oxidative attack of ROS may affect the vinyl-ether function as well as the olefinic residue in the fatty acid moiety (4). The presence of a vinyl-ether bond makes plasmalogens more susceptible to oxidative damages compared with their 1-acyl analogs (2). This has prompted the hypothesis that plasmalogens may act as ROS scavengers, protecting other phospholipids and lipoprotein particles from oxidative damage (2). Thus, plasmalogens seem to have an antioxidative effect toward many ROS (5).Hypochlorous acid (HOCl) is generated by polymorphonuclear leukocytes under the catalysis of the enzyme myeloperoxidase (MPO) (6). HOCl reacts with a variety of molecules, including amino acids, proteins, carbohydrates, nucleic acids, and lipids (7-12). In the latter case, chlorohydrins are generated as the primary products when HOCl reacts with the double bonds in unsaturated phosphatidylcholines (12)(13)(14). HOCl and the MPO-H 2 O 2 -Cl 2 system also induce the formation of 2-lysophosphatidylcholines (LPCs) in polyunsaturated phosphatidylcholines, as shown by matrixassisted...

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The Action of Hypochlorous Acid on Polymeric Components of Cartilage

Cited by 47 publications

References 21 publications

Cartilage Degradation by Stimulated Human Neutrophils: Elastase Is Mainly Responsible for Cartilage Damage

Cartilage Degradation by Stimulated Human Neutrophils: Elastase Is Mainly Responsible for Cartilage Damage

IR and NMR Studies on the Action of Hypochlorous Acid on Chondroitin Sulfate and Taurine

Hypochlorous acid-mediated generation of glycerophosphocholine from unsaturated plasmalogen glycerophosphocholine lipids

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