Analysis of urinary porphyrins by high performance liquid chromatography-electrospray ionization mass spectrometry

Journal of Liquid Chromatography and Related Technologies

Volumn 34, Issue 15, 2011, Pages 1578-1593

  Li, Jinhua ^a,b   Cai, Zongwei ^b   Xu, Shoufang ^a,d   Liao, Chunyang ^a   Song, Xingliang ^c   Chen, Lingxin ^a  

^a YANTAI INSTITUTE OF COASTAL ZONE RESEARCH   (China)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^c LINYI UNIVERSITY   (China)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

electrospray ionization; high performance liquid chromatography; human urine; mass spectrometry; porphyrins; solid phase extraction

Indexed keywords

ELECTROSPRAY IONIZATION MASS SPECTROMETRY; HPLC-ESI MS; HUMAN URINE; IONIZATION MASS SPECTROMETRY; LIMITS OF DETECTION; LIVER DISEASE; MESOPORPHYRIN; SIMULTANEOUS SEPARATION; SOLID-PHASE EXTRACTION; URINE SAMPLE;

BODY FLUIDS; CHROMATOGRAPHY; DIAGNOSIS; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; IONIZATION; LIQUIDS; MASS SPECTROMETRY; PORPHYRINS;

ELECTROSPRAY IONIZATION;

COPROPORPHYRIN; HEPTACARBOXYLIC ACID PORPHYRIN; HEXACARBOXYLIC ACID PORPHYRIN; MESOPORPHYRIN; PENTACARBOXYLIC ACID PORPHYRIN; PORPHYRIN; UNCLASSIFIED DRUG; UROPORPHYRIN;

ADULT; ARTICLE; CLINICAL ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIMIT OF DETECTION; LIVER DISEASE; MALE; URINALYSIS; URINARY EXCRETION; URINE LEVEL;

EID: 80052721346     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826076.2011.575981     Document Type: Article

References (48)

1. Porra, R. J. Recent Progress in Porphyrin and Chlorophyll Biosynthesis. Phorochem. Phorobiol. 1997, 65, 492-516.
2. Biiesaga, M.; Pyrzynska, K.; Trojanowicz, M. Porphyrins in Analytical Chemistry. A review. Talanta 2000, 51, 209-224.
3. Avilov, I. V.; Zenkevich, E. I.; Sagun, E. I.; Shulga, A. M.; Filatov, I. V. The Influence of Electronic and Structural Factors on the Photoinduced Electron Transfer in Sterically Strained Meso- Nitrophenyl-Substituted Porphyrins. Opt. and Spect. 2003, 95, 696-706.
4. Alimelli, A.; Pennazza, G.; Santonico, M.; Paolesse, R.; Filippini, D.; Damico, A.; Lundstrom, I.; Di, N. C. Fish Freshness Detection by a Computer Screen Photoassisted Based Gas Sensor Array. Anal. Chim. Acta 2007, 582, 320-328.
5. Weinberger, R.; Sapp, E. Capillary Electrophoresis of Urinary Porphyrins with Absorbance and Fluorescence Detection. J. Chromatogr. 1990, 516, 271-285.
6. Doss, M. O. Porphyrinurias and Occupational Disease. In Mechanisms of Chemical-Induced Porphyrinopathies; Silbergeld, E.; Fowler, B., Eds.; Annals of the New York Academy of Sciences Press: New York, 1987, pp. 204-218.
7. Leikin, J. B.; Davis, A.; Klodd, D. A. Selected Topics Related to Occupational Exposures. Part IV. Occupational Liver Disease. Dis. Mon. 2000, 46, 295-310.
8. Pingree, S. D.; Simmonds, P. L.; Rummel, K. T.; Woods, J. S. Quantitative Evaluation of Urinary Porphyrins as a Measure of Kidney Mercury and Mercury Body Burden During Prolonged Methlmercury Exposure in Rats. Toxicol. Sci. 2001, 61, 234-240.
9. Nataf, R.; Skorupka, C.; Amet, L. Porphyrinuria in Childhood Autistic Disorder: Implications for Environmental Toxicity. Toxicol. Appl. Pharmacol. 2006, 214, 99-108.
10. Doss, M. O.; Kuhnel, A.; Gross, U. Alcohol and Porphyrin Metabolism. Alcohol. Alcohol. 2000, 35, 109-125.
11. Sugisaki, K.; Usui, T.; Nishiyama, N.; Jang, W. D.; Yanagi, Y.; Yamagami, S.; Amano, S.; Kataoka, K. Photodynamic Therapy for Corneal Neovascularization Using Polymeric Micelles Encapsulating Dendrimer Porphyrins. Invest. Ophthalmol. Vis. Sci. 2008, 49, 894-899.
12. Haeubl, M.; Reith, L. M.; Gruber, B.; Karner, U.; Mueller, N.; Knoer, G. DNA Interactions and Photocatalytic Strand Cleavage by Artificial Nucleases Based on Water-soluble Gold(III) Porphyrins. JBIC J. Biol. Inorg. Chem. 2009, 14, 1037-1052.
13. Jurow, M.; Schuckman, A. E.; Batteas, J. D.; Drain, C. M. Porphyrins as Molecular Electronic Components of Functional Devices. Coordin. Chem. Rev. 2010, 254, 2297-2310.
14. Zhu, X. J.; Fu, S. T.; Wong, W. K.; Guo, J. P.; Wong, W. Y. A Near-Infrared-Fluorescent Chemodosimeter for Mercuric Ion Based on an Expanded Porphyrin. Angew. Chem. Int. Ed. 2006, 45, 3150-3154.
15. Boyle, N. M.; Rochford, J.; Pryce, M. T. Thienyl-Appended Porphyrins: Synthesis, Photophysical and Electrochemical Properties, and their Applications. Coordin. Chem. Rev. 2010, 254, 77-102.
16. Walter, M. G.; Rudine, A. B.; Wamser, C. C. Porphyrins and Phthalocyanines in Solar Photovoltaic Cells. J. Porphyr. Phthalocya. 2010, 14, 759-792.
17. Conradie, M. M.; Conradie, J.; Ghosh, A. Capturing the Spin State Diversity of Iron(III)-aryl Porphyrins OLYP is Better than TPSSh. J. Inorg. Biochem. 2011, 105, 84-91.
18. Schaming, D.; Farha, R.; Xu, H. L.; Goldmann, M.; Ruhlmann, L. Formation and Photocatalytic Properties of Nanocomposite Films Containing Both Tetracobalt Dawson-Derived Sandwich Polyanions and Tetracationic Porphyrins. Langmuir 2011, 27, 132-143.
19. Askevold, R. Routine Analysis of Porphyrines in Urine. Scand. J. Clin. Lab. Invest. 1951, 3, 318-319.
20. With, T. K. Quantitative and Fractional Porphyrin Analysis in Urine. Clin. Biochem. 1968, 2, 97-104.
21. Yu, Z. Q.; Sheng, G. Y.; Piu, J. M.; Peng, P. A. Determination of Porphyrin Carbon Isotopic Composition Using Gas Chromatography-Isotope Ratio Monitoring Mass Spectrometry. J. Chromatogr. A 2000, 903, 183-191.
22. Fang, Q.; Du, M.; Huie, C. W. On-Line Incorporation of Cloud Point Extraction to Flow Injection Analysis. Anal. Chem. 2001, 73, 3502-3505.
23. Nowakowska, J. Use of HPTLC with Non-aqueous Binary Mobile Phases for Determination of Selected Porphyrins. J. Planar. Chromatogr. 2004, 17, 388-390.
24. Hift, R. J.; Davidson, B. P.; Hooft, C.; Meissner, D. M.; Meissner, P. N. Plasma Fluorescence Scanning and Fecal Porphyrin Analysis for the Diagnosis of Variegate Porphyria: Precise Determination of Sensitivity and Specificity with Detection of Protoporphyrinogen Oxidase Mutations as a Reference Standard. Clin. Chem. 2004, 50, 915-923.
25. Johnson, P. M.; Perkins, S. L.; Kennedy, S. W. A High-Speed Liquid-Chromatographic Method for Measuring Urinary Porphyrins. Clin. Chem. 1988, 34, 103-105.
26. Tronin, A.; Strzalka, J.; Chen, X.; Dutton, P. L.; Blasie, J. K. Determination of the Porphyrin Orientation Distribution in Langmuir Monolayers by Polarized Epifluorescence. Langmuir 2000, 16, 9878-9886.
27. Bu, W.; Myers, N.; McCarty, J. D.; Neill, S. T. O.; Hollar, S.; Stetson, P. L.; Sved, D. W. Simultaneous Determination of Six Urinary Porphyrins Using Liquid Chromatography-Tandem Mass Spectrometry. J. Chromatogr. B 2003, 783, 411-423.
28. Li, Q.; Huie, C. W. Coupling of Acetonitrile Deproteinization and Salting-out Extraction with Acetonitrile Stacking for Biological Sample Clean-up and the Enrichment of Hydrophobic Compounds (Porphyrins) in Capillary Electrophoresis. Electrophoresis 2006, 27, 4219-4229.
29. Li, J. H.; Cai, Z. W. Stacking and Separation of Urinary Porphyrins in Capillary Electrophoresis: Optimization of Concentration Efficiency and Resolution. Talanta 2008, 77, 331-339.
30. Lim, C. K. Porphyrins: Liquid Chromatography. In Encyclopaedia of Separation Science; Cooke, M., Poole, C. F., Eds.; Academic Press: London, 2000, Vol. III.
31. Matveeva, E. G.; Savitsky, A. P.; Gomez-Hens, A. Determination of Corproporphyrin in Urine by Using Stopped-Flow Fluoroimmunoassay. Anal. Chim. Acta 1998, 361, 27-32.
32. Rivaro, P.; Frache, R. Determination of Trace Amounts of Vanadyl Porphyrin in Marine Mussel Tissues by High-Performance Liquid Chromatography with Both Ultraviolet/Visible and Inductively Coupled Plasma Atomic Emission Spectrometric Detection. Analyst 1997, 122, 1069-1072.
33. Gu, G.; Lim, C. K. Preparation and Separation of Hydroxy Derivatives of Uroporphyrinogen I by High-Performance Liquid Chromatography with Electrochemical Detection. J. Chromatogr. A 1996, 722, 245-248.
34. Kachadourian, R.; Menzeleev, R.; Agha, B.; Bocckino, S. B.; Day, B. J. High-Performance Liquid Chromatography with Spectrophotometric and Electrochemical Detection of a Series of Manganese( III) Cationic Porphyrins. J. Chromatogr. B-Biomed. Sci. Appl. 2002, 767, 61-67.
35. Magi, E.; Ianni, C.; Rivaro, P.; Frache, R. Determination of Porphyrins and Metalloporphyrins Using Liquid Chromatography-Diode Array Detection and Mass Spectrometry. J. Chromatogr. A 2001, 905, 141-149.
36. Macours, P.; Cotton, F. Improvement in HPLC Separation of Porphyrin Isomers and Application to Biochemical Diagnosis of Porphyrias. Clin. Chem. Lab. Med. 2006, 44, 1433-1440.
37. Melanson, J. E.; Lucy, C. A. Enhanced Detection of Porphyrins by Capillary Electrophoresis-Laser Induced Fluorescence. Electrophoresis 2002, 23, 1689-1694.
38. Bozek, P.; Hutta, M.; Hrivnakova, B. Rapid Analysis of Porphyrins at Low ng=l and μg=l Levels in Human Urine by a Gradient Liquid Chromatography Method Using Octadecylsilica Monolithic Columns. J. Chromatogr. A 2005, 1084, 24-32.
39. Canada, F. C.; Sanchez, A. B.; Taverna, M.; Prognon, P.; Maillard, P.; Grierson, D. S.; Kasselouri, A. Simple Sensitive and Simultaneous High-Performance Liquid Chromatography Method of Glucoconjugated and Non-glucoconjugated Porphyrins and Chlorins Using Near Infra-Red Fluorescence Detection. J. Chromatogr. B 2005, 821, 166-172.
40. Ausio, X.; Grimalt, J. O.; Ozalla, D.; Herrero, C. On-Line LC-MS Analysis of Urinary Porphyrins. Anal. Chem. 2000, 72, 4874-4877.
41. Danton, M.; Lim, C. K. 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 Commun. Mass Spectrom. 2004, 18, 2309-2316.
42. Qian, K. N.; Mennito, A. S.; Edwards, K. E.; Ferrughelli, D. T. Observation of Vanadyl Porphyrins and Sulfurcontaining Vanadyl Porphyrins in a Petroleum Asphaltene by Atmospheric Pressure Photonionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. Rapid Commun. Mass Spectrom. 2008, 22, 2153-2160.
43. Danton, M.; Lim, C. K. Porphyrin Profiles in Blood, Urine and Faeces by HPLC/Electrospray Ionization Tandem Mass Spectrometry. Biomed. Chromatogr. 2006, 20, 612-621.
44. Li, J. H.; Chan, W.; Cai, Z. W. On-line Capillary Electrophoresis- Electrospray Ionization Mass Spectrometry Analysis of Urinary Porphyrins. Electrophoresis 2009, 30, 1790-1797.
45. Lingeman, H.; Hoekstra-Oussoren, S. J. F. Particle-Loaded Membranes for Sample Concentration and=or Cleanup in Bioanalysis. J. Chromatogr. B 1997, 689, 221-237.
46. Zuijderhoudt, F. M. J.; Koehorst, S. G. A.; Kluitenberg, W. E.; Dorresteijn-de Bok, J. On Accuracy and Precision of a HPLC Method for Measurement of Urine Porphyrin Concentrations. Clin. Chem. Lab. Med. 2000, 38, 227-230.
47. Parnas, M. L.; Frank, E. L. Development and Validation of an HPLC Method for the Separation of Porphyrin Isomers in Urine. Clin. Chem. 2009, 55, A212-A213.
48. Respaud, R.; Benz-de Bretagne, I.; Blasco, H.; Hulot, J. S.; Lechat, P.; Le Guellec, C. Quantification of Coproporphyrin Isomers I and III in Urine by HPLC and Determination of their Ratio for Investigations of Multidrug Resistance Protein 2 (MRP2) Function in Humans. J. Chromatogr. B 2009, 877, 3893-3898.