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Protoporphyrins

About: Protoporphyrins is a research topic. Over the lifetime, 145 publications have been published within this topic receiving 3486 citations.


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Journal ArticleDOI
TL;DR: It is suggested that the formation of phenyl radicals and the replacement of heme with Phenyl-substituted protoporphyrins cause the destabilization of hemoglobins to induce Heinz bodies and hemolytic anemia with phenylhydrazine.
Abstract: Administration of phenylhydrazine to rabbits resulted in the denaturation of hemoglobins in erythrocytes, causing the formation of intracellular precipitates known as Heinz bodies, severe hemolytic anemia, and reticulocytosis To elucidate the molecular mechanism of the destabilization, we allowed human oxyhemoglobins to react aerobically with phenylhydrazine After treatment with acetic acid/HCl and H2SO4/methanol, the chloroform extract contained blue-green pigments of major products accompanied by different minor products Each product was isolated by column chromatography By fast-atom-bombardment mass spectrometry (FAB-MS) and proton nuclear magnetic resonance (1H-NMR) spectrometry, dimethyl esters of N-phenylprotoporphyrin IX and meso, N-diphenylprotoporphyrin IX were determined Other major products also were determined to be dimethyl esters of triphenyl-and tetraphenyl-substituted protoporphyrins by FAB-MS The formation of meso, N-diphenylprotoporphyrin indicated that the addition of a phenyl radical to the meso-carbon atom of the protoporphyrin ring occurred Triphenyl and tetraphenyl adducts also indicated the formation of phenyl radicals in the aerobic reaction of phenylhydrazine with oxyhemoglobins From these results, we suggest that the formation of phenyl radicals and the replacement of heme with phenyl-substituted protoporphyrins cause the destabilization of hemoglobins to induce Heinz bodies and hemolytic anemia with phenylhydrazine

6 citations

Journal Article
Frank M1, Doss Mo

6 citations

Journal ArticleDOI
TL;DR: From the first trimester of pregnancy, symptoms of light sensitivity improved or disappeared completely in all seven pregnancies in women with EPP and the largest decrease in erythrocyte PpIX was calculated as the decrease from the last measured value before pregnancy to the lowest measured value during pregnancy.
Abstract: DEAR EDITOR, Erythropoietic protoporphyria (EPP) is a rare genetic disorder characterized by reduced activity of the ferrochelatase enzyme (FECH), which converts protoporphyrin IX (PpIX) into haem. This results in PpIX accumulation in erythrocytes both in a free form and bound to zinc. In the present paper we investigate only the free form as it can be transferred to plasma and tissue including the skin, where it generates painful skin reactions upon exposure to sunlight. A reduction in photosensitivity during pregnancies of women with EPP has been reported, attributed to measured lower erythrocyte PpIX concentrations. This is surprising because the erythrocyte PpIX increases in healthy women during pregnancy. Only seven cases of erythrocyte PpIX in both nongestational and gestational periods in patients with EPP have previously been published. To support the knowledge about erythrocyte PpIX during pregnancy we report levels during seven new pregnancies of patients with EPP and compare these findings with their data accumulated over nongestational periods. The patients were four women (age 31–43 years) with a biochemically confirmed diagnosis of EPP who attended routine clinical and biochemical follow-ups at the Department of Dermatology of Bispebjerg Hospital from 2002 to 2014. In total the women were pregnant seven times and had seven clinically healthy babies without mutated FECH alleles. Moreover, we report erythrocyte PpIX in 20 pregnant healthy women and in 15 healthy nonpregnant women. The healthy women (age 26–43 years) donated blood samples in the period 2011–2015 at the Department of Dermatology, Bispebjerg Hospital. Blood samples were analysed for erythrocyte PpIX at the Department of Clinical Biochemistry, Viborg Regional Hospital. PpIX was extracted by high-performance liquid chromatography and was subsequently quantified fluorometrically by comparison with the internal PpIX standard. Independent samples were analysed with the Mann–Whitney test and paired samples with the Wilcoxon signed-rank test in IBM SPSS statistics version 22.0.0 (IBM, Armonk, NY, U.S.A.). The small number of pregnancies in patients with EPP did not allow an exact assessment of the variation in response to pregnancy within an individual woman vs. between women. We have assumed homogeneity in variance and have included each pregnancy as an independent event. P-values < 0 05 were considered significant. From the first trimester of pregnancy, symptoms of light sensitivity improved or disappeared completely in all seven pregnancies in women with EPP. The erythrocyte PpIX decreased in all seven pregnancies and we calculated the largest decrease in each pregnancy as the decrease from the last measured value before pregnancy to the lowest measured value during pregnancy. The largest decrease in erythrocyte PpIX ranged from 19% to 66% with a median of 53%, and the decrease was significant (P = 0 016). The last measured value before pregnancy was in all cases close to the overall mean in the nongestational period (Table 1). There was no difference in the concentration before and after pregnancy

6 citations

Journal ArticleDOI
TL;DR: In this paper, total syntheses of hemins with permutations of the propionic side-chains in the C and D rings (compared with protoporphyrin-IX) are described.

6 citations

Journal ArticleDOI
TL;DR: In this paper, it was shown that the relative position of the two acetyl groups influences the absorption pattern of the visible spectrum more precisely than was previously appreciated, and it is possible to recognize the 1,4, 2,3 and 2,4 relative distribution of the acetyl group by an examination of the electronic spectrum.
Abstract: A range of isomeric diacetyldeuteroporphyrins has been synthesized by the oxidative cyclization of appropriately substituted bilenes-b, and the electronic and n.m.r. spectra of these porphyrins have been studied. As a result it has been shown that the relative position of the two acetyl groups influences the absorption pattern of the visible spectrum more precisely than was previously appreciated. In consequence, it is possible to recognize the 1,4, 2,3 and 2,4 relative distribution of the acetyl groups by an examination of the electronic spectrum. In addition, it is clear that the acetyl groups present in this series of porphyrins affect the chemical shift of all the methine protons and not only the one which is directly adjacent to the carbonyl function.

6 citations

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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20212
20191
20181
20173
20162
20152