Document Detail


Interaction of exogenous hypochlorite or hypochlorite produced by myeloperoxidase + H2O2 + Cl- system with unsaturated phosphatidylcholines.
MedLine Citation:
PMID:  12223088     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The interaction between unsaturated phosphatidylcholines and either exogenous or endogenous (produced by the enzyme system involving myeloperoxidase (MPO), H2O2, and Cl-) hypochlorite was studied in multilayer liposomes containing oleic, linoleic, and arachidonic acid residues using MALDI-TOF mass spectrometry. At pH 7.4, hypochlorite reacts with the double bond of the oleic acid residue in 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine producing oleic acid chlorohydrin as the main product. Minor amounts of glycols and epoxides were also detected. The main products of the reaction of hypochlorite with 1-stearoyl-2-linoleyl-sn-glycero-3-phosphocholine were mono- and di-chlorohydrins of linoleic acid. The signals of monoglycol, epoxide, and glycol- or epoxide-containing monochlorohydrin derivatives were also present in the mass spectrum. The main products of the reaction of hypochlorite with 1-stearoyl-2-arachidonyl-sn-glycero-3-phosphocholine were lysophosphatidylcholine (1-stearoyl-sn-glycero-3-phosphocholine) and mono-, di-, and trichlorohydrin. Monoglycol and its derivatives containing one or two chlorohydrin groups were also detected. Along with those, carbonyl compounds (aldehyde and acid) formed as a result of double bond breakage in fifth position of arachidonate were detected. Monochlorohydrin was also found when liposomes comprising 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine were incubated in the presence of enzymatic mixture, MPO + H2O2 + Cl-, at pH 6.0. In the absence of the enzyme or either of its substrates (H2O2 or Cl-) or in the presence of the MPO inhibitor (sodium azide) or hypochlorite scavengers (taurine or methionine), monochlorohydrin formation was not observed. These data confirm the suggestion that just the hypochlorite generated in MPO-catalysis provides for chlorohydrin formation. Thus, the use of MALDI-TOF mass spectrometry has shown, along with chlorohydrins, glycols and epoxides as the products of hypochlorite interaction with unsaturated phosphatidylcholines at physiological pH. It was first determined that hypochlorite breaks double bonds in polyunsaturated phosphatidylcholine and also causes lysophosphatidylcholine formation.
Authors:
O M Panasenko; A N Osipov; J Schiller; J Arnhold
Related Documents :
489538 - Phosphorylation of atp citrate lyase in response to glucagon.
6715338 - Phospholipase a1 acting on phosphatidic acid in porcine platelet membranes.
6466678 - The dynamics of lipid motion in sarcoplasmic reticulum membranes determined by steady-s...
3178828 - A lecithin:retinol acyltransferase activity in human and rat liver.
7339868 - An electrophoretic fraction of urinary glycosaminoglycans reflecting connective tissue ...
8396608 - Comparison of cd271 (adapalene) and all-trans retinoic acid in human skin: dissociation...
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biochemistry. Biokhimii͡a     Volume:  67     ISSN:  0006-2979     ISO Abbreviation:  Biochemistry Mosc.     Publication Date:  2002 Aug 
Date Detail:
Created Date:  2002-09-11     Completed Date:  2003-08-25     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0376536     Medline TA:  Biochemistry (Mosc)     Country:  United States    
Other Details:
Languages:  eng     Pagination:  889-900     Citation Subset:  IM    
Affiliation:
Research Institute of Physico-Chemical Medicine, Moscow, 119828 Russia. oleg-panasenko@newmail.ru
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Chlorides / metabolism*
Fatty Acids, Unsaturated / chemistry,  metabolism
Hydrogen Peroxide / metabolism*
Hypochlorous Acid / metabolism*
Molecular Structure
Peroxidase / metabolism*
Phosphatidylcholines / chemistry*,  metabolism*
Phosphorylcholine / analogs & derivatives,  metabolism
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Chemical
Reg. No./Substance:
0/Chlorides; 0/Fatty Acids, Unsaturated; 0/Phosphatidylcholines; 107-73-3/Phosphorylcholine; 18892-74-5/1-stearoyl-2-arachidonylphosphatidylcholine; 6753-56-6/1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine; 7722-84-1/Hydrogen Peroxide; 7790-92-3/Hypochlorous Acid; EC 1.11.1.7/Peroxidase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Peroxyl radical is produced upon the interaction of hypochlorite with tert-butyl hydroperoxide.
Next Document:  Effects of oxygen on the dark recombination between photoreduced secondary quinone and oxidized bact...