| Disappearance of plasmalogens from membranes of animal cells subjected to photosensitized oxidation. | |
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MedLine Citation:
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PMID: 3403548 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Chinese hamster ovary cells (CHO-K1) photosensitized with 12-(1'-pyrene)dodecanoic acid (P12) are killed when exposed to long wavelength ultraviolet (UV) light (greater than 300 nm). Mutants deficient in plasmalogen biosynthesis are hypersensitive to this treatment. We now demonstrate that plasmenylethanolamine is rapidly and preferentially destroyed when CHO-K1 cells, photosensitized either with P12 or merocyanine 540, are irradiated with light of the appropriate wavelength. Using [2-14C]ethanolamine, [1-14C]hexadecanol, or [U-14C]hexadecanol to follow the turnover of plasmenylethanolamine, we show that 2-monoacylglycerophosphoethanolamine, formic acid, and pentadecanal are formed during P12/UV treatment of CHO-K1 cells, but not of mutant cells deficient in plasmalogen synthesis. The decomposition of plasmenylethanolamine is O2-dependent, is enhanced in D2O, and is reduced in the presence of sodium azide. The process may be explained, in part, by the cycloaddition of singlet oxygen to the vinyl ether linkage of plasmenylethanolamine, generating a dioxetane intermediate that would be expected to decompose under physiological conditions to the observed products. An additional possibility is the formation of an allylic hydroperoxide at the 1'-carbon of the alkyl moiety by an "ene" reaction of singlet oxygen, or by radical-mediated oxidation, followed by metabolism or chemical decomposition of the hydroperoxide. Given the P12/UV hypersensitivity of plasmalogen-deficient mutants, we suggest that plasmalogens might protect animal cell membranes from singlet oxygen and/or radical-initiated oxidation by functioning as scavengers and decomposing to products that can be reutilized. |
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Authors:
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O H Morand; R A Zoeller; C R Raetz |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: The Journal of biological chemistry Volume: 263 ISSN: 0021-9258 ISO Abbreviation: J. Biol. Chem. Publication Date: 1988 Aug |
Date Detail:
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Created Date: 1988-09-16 Completed Date: 1988-09-16 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 2985121R Medline TA: J Biol Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 11597-606 Citation Subset: IM |
Affiliation:
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Department of Biochemistry, College of Agricultural and Life Sciences, University of Wisconsin, Madison 53706. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Chromatography, High Pressure Liquid Cricetinae Cricetulus Membranes / metabolism Oxidation-Reduction Plasmalogens / metabolism* Radiation-Sensitizing Agents / metabolism* |
| Grant Support | |
ID/Acronym/Agency:
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DK 21722/DK/NIDDK NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Plasmalogens; 0/Radiation-Sensitizing Agents; 0/phosphatidal ethanolamines |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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