Glutathione-Dependent Oxidative Modification of Protoporphyrin and Other Dicarboxylic Porphyrins by Mammalian and Plant Peroxidases
| Autor: | F. Pont, Franz-Peter Montforts, J.S.L. Hier, Stephen O. Duke, Nicholas J. Jacobs, H.G. Kruszyna, Franck E. Dayan |
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| Rok vydání: | 1999 |
| Předmět: |
Porphyrins
Biophysics Polysorbates Protoporphyrins Biochemistry chemistry.chemical_compound polycyclic compounds Animals Organic chemistry Lactoperoxidase Molecular Biology Heme Horseradish Peroxidase Plant Proteins Molecular Structure biology Cell Biology Glutathione Ascorbic acid Combinatorial chemistry Porphyrin Peroxidases chemistry Spectrophotometry Chlorin biology.protein Cattle Protoporphyrin Deuteroporphyrins Peroxidase |
| Zdroj: | Biochemical and Biophysical Research Communications. 259:195-200 |
| ISSN: | 0006-291X |
| DOI: | 10.1006/bbrc.1999.0749 |
| Popis: | Protoporphyrin, an intermediate in heme and chlorophyll biosynthesis, can accumulate in human and plant tissues under certain pathological conditions and is a photosensitizer used in cancer phototherapy. We previously showed that protoporphyrin and the related non-natural dicarboxylic porphyrin deuteroporphyrin are rapidly oxidized by horseradish peroxidase in the presence of some thiols, especially glutathione. This study reports that bovine lactoperoxidase, but not leucocyte myeloperoxidase, can also catalyze this reaction and that Tween and ascorbic acid are inhibitors. Exogenous hydrogen peroxide is not required and cannot replace glutathione. Deuteroporphyrin was oxidized to a unique green chlorin product with two oxygen functions added directly to the characteristic reduced pyrrole ring of the chlorin. Spectroscopic and chromatographic results suggest that protoporphyrin was oxidized not to a green chlorin, but to a much more polar red porphyrin modified by oxidative addition to the two vinyl side chains. Two related nonnatural dicarboxylic porphyrins, with ethyl or hydroxyethyl instead of vinyl side chains, are not substrates or products for this enzymatic conversion. |
| Databáze: | OpenAIRE |
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