High-performance liquid chromatography/electrospray ionization tandem mass spectrometry of hydroxylated uroporphyrin and urochlorin derivatives formed by photochemical oxidation of uroporphyrinogen I

Biomedical Chromatography

Volumn 21, Issue 5, 2007, Pages 534-545

  Danton, Malcolm ^a   Lim, Chang Kee ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Cis and trans hydroxyurochlorins; Hydroxyuroporphyrins; Photochemical oxidation; Utoporphyrinogen

Indexed keywords

ELECTROSPRAY IONIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; MASS SPECTROMETRY; OXIDATION;

CHLORINS; CIS- AND TRANS-HYDROXYUROCHLORIN; ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY-ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; HYDROXYPROPIONIC ACID; HYDROXYUROPORPHYRIN; PHOTOCHEMICAL OXIDATION; SPECTRA'S; UTOPORPHYRINOGEN;

PORPHYRINS;

PORPHYRIN DERIVATIVE; UROPORPHYRIN; UROPORPHYRINOGEN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; OXIDATION; PHOTOCHEMISTRY; SENSITIVITY AND SPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; TANDEM MASS SPECTROMETRY;

EID: 34248561173     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.790     Document Type: Article

References (16)

1. Battersby AR, Fookes CJ, Matcham GW and McDonald E. Biosynthesis of the pigments of life: formation of the macrocycle. Nature 1980; 285(5759): 17-21.
2. Cantoni L, dal Fiume D, Rizzardini M and Ruggieri R. In vitro inhibitory effect on porphyrinogen carboxylyase of liver extracts from TCDD treated mice. Toxicology Letters 1984; 20: 211-217.
3. Danton M and Lim CK. Identification of monovinyl tripropionic acid porphyrins and metabolites from faeces of patients with hereditary coproporphyria by high-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2004; 18: 2309-2316.
4. Danton M and Lim CK. Porphyrin profiles in blood, urine and faeces by HPLC/electrospray ionization tandem mass spectrometry. Biomedical Chromatography 2006; 20: 612-621.
5. Elder GH. Porphyria cutanea tarda and related disorders. In: The Porphyrin Handbook. Medical Aspects of Porphyrins, Vol. 14, Kadish KM, Smith KM and Guilard R (eds). Academic Press: San Diego, CA, 2003; 67-92.
6. Francis JE and Smith AG. Oxidation of uroporphyrinogens by hydroxyl radicals. Evidence for nonporphyrin products as potential inhibitors uroporphyrinogen decarboxylase. FEBBS Letters 1988; 233: 311-314.
7. Guo R, Rideout JM, Chai W, Lawson AM and Lim CK. Identification of peroxacetic acid uroporphyrin I in the urine of patients with congenital erythropoietic porphyria by liquid chromatography and mass spectrometry. Biomedical Chromatography 1991; 5: 53-56.
8. Guo R, Lim CK and De Matteis F. Peroxylated and hydroxylated uroporphyrins: a study of their production in vitro in enzymic and chemical model systems. Biomedical Chromatography 1996; 10: 213-220.
9. Lim CK, Razzaque MA, Luo J and Farmer PB. Isolation and characterization of protoporphyrin glycoconjugates from rat Harderian gland by HPLC, capillary electrophoresis and HPLC/electrospray ionization MS. Biochemical Journal 2000; 347: 757-761.
10. Lim CK, Danton M, Clothier B and Smith AG. Dihydroxy-, hydroxyspirolactone- and dihydroxyspirolactone-urochlorins induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in liver of mice. Chemical Research in Toxicology 2006; 19: 1660-1667.
11. Lin W and Timkovich R. Oxygenated tetrapyrroles produced from porphyrinogens. Bioorganic Chemistry 1994; 22: 72-94.
12. Luo J and Lim CK. Isolation and characterization of new porphyrin metabolites in human porphyria cutanea tarda and in rats treated with hexachlorobenzene by HPTLC, HPLC and liquid secondary ion mass spectrometry. Biomedical Chromatography 1995; 9: 113-122.
13. Shoolingin-Jordan PM. Porphobilinogen deaminase and uroporphyrinogen III synthase: structure, molecular biology, and mechanism. Journal of Bioenergetics and Biomembranes 1995; 27: 181-195.
14. Smith AG and Francis JE. Chemically-induced formation of an inhibitor of hepatic uroporphyrinogen decarboxylase in inbred mice with iron overload. Biochemical Journal 1987; 246: 221-226.
15. Smith AG, Clothier B, Robinson S, Scullion MJ, Carthew P, Edwards R, Luo J, Lim CK and Toledano M. Interaction between iron metabolism and 2,3,7,8-tetrachlorobibenzo-p-dioxin in mice with variants of Ahr gene: a hepatic oxidation mechanism. Molecular Pharmacology 1998; 53: 52-61.
16. Warren MJ and Scott AI. Tetrapyrrole assembly and modification into ligands of biologically functioning cofactors. Trends in Biochemical Sciences 1990; 15: 486-491.