Deuteroporphyrin IX

Deuteroporphyrin IX Description

Deuteroporphyrin IX is a non-natural dicarboxylic porphyrin. Deuteroporphyrins are porphyrins with four methyl and two propionic acid side chains attached to the pyrrole rings. Deuteroporphyrin IX is described as a fecal porphyrin in patients with endemic chronic arsenic poisoning. (Environmental Sciences (Tokyo, Japan) (2001), 8(6), 561-570.). Excess accumliation of the biosynthetic intermediate protoporphyrin can lead to extensive tissue damage upon exposure to light since protoporpyhyrin is a potent photosensitizing agent, giving rise to membrane-destroying oxygen radicals or singlet oxygen. For instance, in the human porphyria disease porphyria variegata, a genetic deficiency in a heme biosynthetic enzyme, protoporphyrinogen oxidase, leads to protoporphyrin accumliation and lighspanependent skin photosensitivity. Horseradish peroxidase (HRP) in the presence of glutathione (GSH) colid oxidize the non-natural porphyrin deuteroporphyrin IX, which is closely related to protoporphyrin IX. The product is a unique green chlorin. One of the pyrrole rings had been modified by addition of an hydroxy and an oxo group, thus giving the characteristic reduced pyrrole ring of the chlorine. Of most importance for human medicine, peroxidative enzymes present in mammalian cells can also carry out these GSH-dependent oxidative conversions of protoporphyrin and deuteroporphyrin. (PMID: 10334939 ). Structure

Synonyms

Chemical Formlia

C₃₀H₃₀N₄O₄ Average Molecliar Weight

510.5836 Monoisotopic Molecliar Weight

510.226705468 IUPAC Name

3-[20-(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid Traditional Name

deuteroporphyrin CAS Registry Number

448-65-7 SMILES

InChI Identifier

InChI Key

KWKUIRGQJJFUCG-LMKUSPAJSA-N Chemical Taxonomy Classification

Not classified Ontology Status

Expected but not Quantified Origin

Biofunction

Not Available Application

Not Available Cellliar locations

Physical Properties State

Solid Experimental Properties

Predicted Properties

Spectra Spectra

Not Available Biological Properties Cellliar Locations

Biofluid Locations

Not Available Tissue Location

Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB022126 KNApSAcK ID

Not Available Chemspider ID

16736707 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Not Available NuGOwiki Link

HMDB00579 Metagene Link

HMDB00579 METLIN ID

5561 PubChem Compound

Not Available PDB ID

Not Available ChEBI ID

Not Available

Product: Cefamandole (sodium)

1. Rose IS, Young GP, St John DJ, Deacon MC, Blake D, Henderson RW: Effect of ingestion of hemoproteins on fecal excretion of hemes and porphyrins. Clin Chem. 1989 Dec;35(12):2290-6. [PubMed:2556222 ]
2. Rotenberg M, Margalit R: Deuteroporphyrin-albumin binding equilibrium. The effects of porphyrin self-aggregation studied for the human and the bovine proteins. Biochem J. 1985 Jul 1;229(1):197-203. [PubMed:4038254 ]
3. Severina IS, Pyatakova NV, Shchegolev AY, Ponomarev GV: YC-1-like potentiation of NO-dependent activation of soluble guanylate cyclase by derivatives of protoporphyrin IX. Biochemistry (Mosc). 2006 Mar;71(3):340-4. [PubMed:16545073 ]
4. Morita I, Kawamoto M, Hattori M, Eguchi K, Sekiba K, Yoshida H: Determination of tryptophan and its metabolites in human plasma and serum by high-performance liquid chromatography with automated sample clean-up system. J Chromatogr. 1990 Apr 6;526(2):367-74. [PubMed:2361979 ]
5. Cohen S, Margalit R: Binding of porphyrin to human serum albumin. Structure-activity relationships. Biochem J. 1990 Sep 1;270(2):325-30. [PubMed:2144729 ]
6. Jacobs NJ, Kruszyna HG, Hier JS, Dayan FE, Duke SO, Pont F, Montforts FP: Glutathione-dependent oxidative modification of protoporphyrin and other dicarboxylic porphyrins by mammalian and plant peroxidases. Biochem Biophys Res Commun. 1999 May 27;259(1):195-200. [PubMed:10334939 ]

PMID: 16877678