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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/24 13:26:23」(JST)

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Protoporphyrins are tetrapyrroles containing the following side chains:

methyl (4)
propionic acid (2)
vinyl (2)

Protoporphyrin IX is a biochemical widely used as a carrier molecule for divalent cations. Together with iron (Fe 2+) the body of the heme- group of hemoglobin, myoglobin and many other heme-containing enzymes like cytochrome c and catalase are formed. Complexed with magnesium-ions (Mg 2+) the main part of the Chlorophylls are formed. Complexed with zinc-ions (Zn 2+) it forms Zinc protoporphyrin.

The number (e.g. IX) indicates the position of different side chains, but historically, as the nomenclature has grown, it has done so systematically only in parts.

Protoporphyrin IX as a direct precursor of heme is accumulated by patients of erythropoietic protoporphyria, which is one of the genetic disorders of the biosynthesis of the heme -pathway. It causes a severe photosensivity against visible light.

The sensitivity of protoporphyrin IX against light is also used as a therapy against different forms of cancer (photodynamic therapy, PDT).

Protoporphyrins are deposited in the shells of the eggs of some birds as a brown or red pigment, either as a ground colour or as spotting. This occurs in most passerine species, some ground-nesting non-passerines, such as waders, gulls, nightjars and sandgrouse, where it provides camouflage, and some parasitic cuckoos, which need to mimic their passerine hosts' eggs.

Protoporphyrins strengthen the egg shell, and are deposited where the shell is too thin as a result of calcium shortage. Spotting therefore tend to be heavier where the local soil is calcium-deficient, and in the eggs laid last in a clutch.

External links

Protoporphyrins at the US National Library of Medicine Medical Subject Headings (MeSH)
PubChem 4971 - protoporphyrin IX

This biochemistry article is a stub. You can help Wikipedia by expanding it.

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1. 骨髄性プロトポルフィリン症 erythropoietic protoporphyria
2. 成人における鉄欠乏性貧血の原因および診断 causes and diagnosis of iron deficiency anemia in the adult
3. ポルフィリン症：概要 porphyrias an overview
4. 晩発性皮膚ポルフィリン症および肝骨髄性ポルフィリン症 porphyria cutanea tarda and hepatoerythropoietic porphyria
5. 成人における鉛中毒 adult lead poisoning

English Journal

DHA suppresses Prevotella intermedia lipopolysaccharide-induced production of proinflammatory mediators in murine macrophages.

Choi EY1, Jin JY1, Choi JI2, Choi IS1, Kim SJ2.
The British journal of nutrition.Br J Nutr.2014 Apr 14;111(7):1221-30. doi: 10.1017/S0007114513003681. Epub 2013 Nov 19.
Several reports have indicated that dietary intake of DHA is associated with lower prevalence of periodontitis. In the present study, we investigated the effect of DHA on the production of proinflammatory mediators in murine macrophage-like RAW264.7 cells stimulated with lipopolysaccharide (LPS) iso
PMID 24252501

α-Tocopheryl succinate pre-treatment attenuates quinone toxicity in prostate cancer PC3 cells.

Bellezza I1, Grottelli S1, Gatticchi L1, Mierla AL1, Minelli A2.
Gene.Gene.2014 Apr 10;539(1):1-7. doi: 10.1016/j.gene.2014.02.009. Epub 2014 Feb 12.
α-Tocopheryl succinate is one of the most effective analogues of vitamin E for inhibiting cell proliferation and inducing cell death in a variety of cancerous cell lines while sparing normal cells or tissues. αTocopheryl succinate inhibits oxidative phosphorylation at the level of mitochondrial co
PMID 24530478

Antisense oligonucleotide-based therapy in human erythropoietic protoporphyria.

Oustric V1, Manceau H1, Ducamp S1, Soaid R1, Karim Z2, Schmitt C3, Mirmiran A1, Peoc'h K1, Grandchamp B4, Beaumont C2, Lyoumi S5, Moreau-Gaudry F6, Guyonnet-Dupérat V6, de Verneuil H6, Marie J7, Puy H8, Deybach JC9, Gouya L10.
American journal of human genetics.Am J Hum Genet.2014 Apr 3;94(4):611-7. doi: 10.1016/j.ajhg.2014.02.010. Epub 2014 Mar 27.
In 90% of people with erythropoietic protoporphyria (EPP), the disease results from the inheritance of a common hypomorphic FECH allele, encoding ferrochelatase, in trans to a private deleterious FECH mutation. The activity of the resulting FECH enzyme falls below the critical threshold of 35%, lead
PMID 24680888

Japanese Journal

Formation of meso, N-diphenylprotoporphyrin IX by an aerobic reaction of phenylhydrazine with oxyhemoglobins.

Nakanishi Akira,Kinuta Keiko,Abe Tadashi,Araki Kenta,Yoshida Yumi,Liang Shuang,Li Shun-Ai,Takei Kohji,Kinuta Masahiro
Acta Medica Okayama 57(5), 2003-10
… 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. …
NAID 120002311426