The reactivity of various free radicals with hyaluronic acid: steady-state and pulse radiolysis studies

Myint, Pe; Deeble, David J.; Beaumont, Paul C.; Blake, Susan M.; Phillips, Glyn O.

doi:10.1016/0304-4165(87)90109-7

Cited by 80 publications

(31 citation statements)

References 17 publications

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“…In such systems it is the hydroxyl radical which is the main H-abstracting entity. The hydroxyl radicals react with hyaluronan with a rate constant k 2 = 0.9 x 10 9 mol -1 dm 3 s -1 , whereas H atoms rate is a lower order of magnitude k 2 = 7 x 10 7 mol -1 dm 3 s -1 (Myint et al, 1987). Figure 11 shows the various hydrolysis, rearrangement, and fragmentation reactions during aqueous radiolysis of cellobiose to gives possible chain break (Sonntag, 1987 Fei et al, 2000;Liu et al, 2002b;Wach et al, 2003a;) (Fei et al, 2000;Liu et al, 2002b;Wach et al, 2001;Wach et al, 2003a;) Hydroxy ethyl cellulose (Fei et al, 2000;Wach et al, 2003a) (Fei et al, 2000;Wach et al, 2001) chitin, chitosan & derivatives (Ershov et al, 1993;Ershov, 1998;Jarry et al, 2001;Jarry et al, 2002;) (Wasikiewicz et al, 2005) Cellulose & derivatives (Ershov, 1998;Nakamura et al, 1985;Phillips, 1961;Phillips, 1963;Wach et al, 2002) (Phillips & Moody, 1959;Wach et al, 2002) Starch and derivatives (Ershov, 1998;Nagasawa et al, 2004;Phillips, 1961;Zhai et al, 2003) D-glucose (Phillips, 1963;Schiller et al, 1998) (Sharpatyi, 2003) Hyaluronan & hyaluronic acid (Al-Assaf et al, 1995;Al-Assaf et al, 2006a;…”

Section: Aqueous State Radiationmentioning

confidence: 99%

Hydrogels: Methods of Preparation, Characterisation and Applications

Gulrez¹,

Al-Assaf²,

Phillips³

2011

Progress in Molecular and Environmental Bioengineering - From Analysis and Modeling to Technology Applications

256

178

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Section: Aqueous State Radiationmentioning

confidence: 99%

Hydrogels: Methods of Preparation, Characterisation and Applications

Gulrez¹,

Al-Assaf²,

Phillips³

2011

Progress in Molecular and Environmental Bioengineering - From Analysis and Modeling to Technology Applications

256

178

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“…[24] ) and also likely to be unselective in their sites of attack with abstraction possible at 11 C-H bonds in HA . In contrast , the moderately strong oxidizing agent , the bromide radical ion, reacts at similar rates to the carbonate radical in the current study, and was found only to abstract hydrogen at C-1 of 2-deoxy-D-ribose , in a uniquely sitespecific reaction [61].…”

Section: Oxidation By Carbonate Radicalsmentioning

confidence: 99%

“…OH), the hydrated electron, (eaq ) and the hydrogen atom (H . ) with HA [24]. In a more recent study, this was extended to reactions of the dichloride radical anion (Cl 2 .-), the dibromide radical anion (Br 2 .-), the carbonate radical (CO 3 .-) and the azide radical ( N 3 . )…”

Section: Introductionmentioning

confidence: 99%

One-electron oxidation and reduction of glycosaminoglycan chloramides: A kinetic study

Sibanda

Parsons

Houée-Levin⊥

et al. 2013

Free Radical Biology and Medicine

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Hypochlorous acid and its acid-base counterpart, hypochlorite ions, produced in inflammatory conditions, may produce chloramides of glycosaminoglycans, the latter being significant components of the extracellular matrix (ECM). This may occur through the binding of myeloperoxidase directly to the glycosaminoglycans.The N-Cl group in the chloramides is a potential selective target for both reducing and oxidising radicals, leading possibly to more efficient and damaging fragmentation of these biopolymers relative to the parent glycosaminoglycans. In this study,the fast reaction techniques of pulse radiolysis and nanosecond laser flash photolysis have been used to generate both oxidizing and reducing radicals to react with the chloramides of hyaluronan (HACl) and heparin (HepCl).The strong reducing formate radicals and hydrated electrons were found to react rapidly with both HACl and HepCl with rate constants of (1-1.7) x 10 8 M -1 s -1 and (0.7-1.2) x 10 8 M -1 s -1 for formate radicals and 2.2 x 10 9 M -1 s and 7.2 x 10 8 M -1 s -1 for hydrated electrons, respectively. The spectral characteristics of the products of these reactions were identical and were consistent with initial attack at the N-Cl groups, followed by elimination of chloride ions to produce nitrogencentred radicals, which re-arrange subsequently and rapidly to produce C-2 radicals on the glucosamine moiety supporting an earlier EPR study by Rees et 3 This is the first study therefore to conclusively demonstrate that reducing radicals react rapidly with glycosaminoglycan chloramides in a site-specific attack at the N-Cl groups, probably to produce a 100 % efficient biopolymer fragmentation process. Although less reactive, carbonate radicals, which may be produced in vivo via reactions of peroxynitrite with serum levels of carbon dioxide ,also appear to react in a highly site-specific manner at the N-Cl group. It is not yet known if such site-specific attacks by this important in vivo species lead to a more efficient fragmentation of the biopolymers than would be expected for attack by the stronger oxidising species, the hydroxyl radical. It is clear however that the N-Cl group formed in inflammatory conditions in the extracellular matrix does present a more likely target for both reactive oxygen species and for reducing species than the N-H groups in the parent glycosaminoglycans. Graphical abstract4

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“…In this early study, the rate constant for the reaction of hydroxyl radicals with heparin was found to be 2.2 9 10 8 M -1 s -1 (Balazs et al 1968). A similar pulse radiolysis study on hyaluronan yielded a value of 7 9 10 8 M -1 s -1 (Myint et al 1987). Pulse radiolysis was again used to measure the kinetic reactivities of several radicals with hyaluronan (Al-Assaf et al 2006).…”

Section: Pulse Radiolysis and Laser Flash Photolysismentioning

confidence: 98%

“…Although convenient and simple to use, measurements of the efficiency of degradation by a particular oxidant were not calculated. However, in 1987, Myint et al (1987) used the Mark-Houwink equation to calculate molecular weight changes of hyaluronan solutions and so were able to calculate the concentration of HA chain breaks. The MarkHouwink equation relates intrinsic viscosity to average molecular weight as follows:…”

Section: Viscoelastic Studies Of the Free Radical Degradation Of Hyalmentioning

confidence: 99%

Free radical studies of components of the extracellular matrix: contributions to protection of biomolecules and biomaterials from sterilising doses of ionising radiation

Parsons

2017

Cell Tissue Bank

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The purpose of the current review is show how the principles and techniques of radiation chemistry have enabled the direct reactions of free radicals with biomolecules and biomaterials to be investigated at the molecular level. In particular, the review focusses on the free radical-induced fragmentation of glycosaminoglycans. Glycosaminoglycans are large linear polysaccharides consisting of repeating disaccharide units and are important components of the extracellular matrix (ECM) either in free form (hyaluronan) or as a component of proteoglycans. Oxidative damage of the extracellular matrix components by either enzymatic or non-enzymatic pathways may have implications for the initiation and progression of a range of human diseases. These include arthritis, kidney disease, cardiovascular disease, lung disease, periodontal disease and chronic inflammation. Oxidative damage to hyaluronan by reactive oxidative species and thus the potential mechanism of damage to the ECM and its role in human pathologies is reviewed with particular focus on damage initiated by potential in vivo free radicals such as superoxide, carbonate and hydroxyl radicals. Such knowledge has also allowed radiation protecting systems to be developed so that sterilising doses of radiation can be delivered to sensitive biomolecules such as proteins and glycosaminoglycans, and also to sensitive biomaterials such as tissue allografts.

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The reactivity of various free radicals with hyaluronic acid: steady-state and pulse radiolysis studies

Cited by 80 publications

References 17 publications

Hydrogels: Methods of Preparation, Characterisation and Applications

Hydrogels: Methods of Preparation, Characterisation and Applications

One-electron oxidation and reduction of glycosaminoglycan chloramides: A kinetic study

Free radical studies of components of the extracellular matrix: contributions to protection of biomolecules and biomaterials from sterilising doses of ionising radiation

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