Identification and structural characterization by LC-ESI-IONTRAP and LC-ESI-TOF of some metabolic conjugation products of homovanillic acid in urine of neuroblastoma patients

Journal of Mass Spectrometry

Volumn 47, Issue 7, 2012, Pages 816-824

  Scapolla, Carlo ^a   Cangemi, Giuliana ^b   Barco, Sebastiano ^b   Barbagallo, Laura ^b   Bugnone, Daniela ^b   Maffia, Angelo ^b   Melioli, Giovanni ^b   Profumo, Aldo ^c   Benatti, Umberto ^a   Damonte, Gianluca ^a  

^a UNIVERSITY OF GENOA   (Italy)

^b G GASLINI INSTITUTE   (Italy)

^c UNIVERSITY OF GENOA   (Italy)

Author keywords

ESI; homovanillic acid; HR MS; LC MS MS; neuroblastoma

Indexed keywords

ESI; HOMOVANILLIC ACID; HR-MS; LC-MS/MS; NEUROBLASTOMAS;

IONS; ISOMERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; ORGANIC POLYMERS; PHENOLS;

ENZYMATIC HYDROLYSIS;

BETA GLUCURONIDASE; GLUCURONIDE; HOMOVANILLIC ACID; PHENOL; VANILMANDELIC ACID;

ALKALINITY; ANALYZER; ARTICLE; CONJUGATION; ELECTRON SPIN RESONANCE; HUMAN; HYDROLYSIS; ION TRAP MASS SPECTROMETRY; ISOMER; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; TIME OF FLIGHT MASS SPECTROMETRY; URINALYSIS;

CHROMATOGRAPHY, LIQUID; HOMOVANILLIC ACID; HUMANS; IONS; MODELS, MOLECULAR; NEUROBLASTOMA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 84863897444     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3016     Document Type: Article

References (28)

1. J. R. Park, A. Eggert, H. Caron,. Neuroblastoma: biology, prognosis, and treatment. Hematol. Oncol. Clin. North Am. 2010, 24, 65.
2. D. J. Erdelyi, M. Elliott, B. Phillips,. Urine catecholamines in pediatrics. Arch. Dis. Child Educ. Pract. 2011, 96, 107.
3. Monsaingeon M, Perel Y, Simonnet G, Corcuff JB,. Comparative values of catecholamines and metabolites for the diagnosis of neuroblastoma. Eur. J. Pediatr. 2003, 162, 397.
4. M. Tsunoda,. Recent advances in methods for the analysis of catecholamines and their metabolites. Anal. Bioanal. Chem. 2006, 386, 506.
5. J. M. Zuetenhorst, C.M. Korse, J. M. G. Bonfrer, E. Peter, C. Lamers, B.G. Taal,. Daily cyclic changes in the urinary excretion of 5-hydroxyindoleacetic acid in patients with carcinoid tumors. Clin. Chem. 2004, 50, 1636.
6. A. Roux, D. Lison, C. Junot, J. F. Heilier,. Applications of liquid chromatography coupled to mass spectrometry-based metabolomics in clinical chemistry and toxicology: A review. Clin. Biochem. 2011, 44, 119.
7. W.J. Griffiths, Y. Wang,. Mass spectrometry: from proteomics to metabolomics and lipidomics. Chem. Soc. Rev. 2009, 38, 1882.
8. J. Gu, D. Zhong, X. Chen,. Analysis of O -glucuronide conjugates in urine by electrospray ion trap mass spectrometry. Fresenius J. Anal. Chem. 1999, 365, 553.
9. Q. Li, Y. Zhang, B. Wu, H. Qu,. Identification of indole alkaloids in Nauclea officinalis using high-performance liquid chromatography coupled with ion trap and time-of-flight mass spectrometry. Eur. J. Mass Spectrom. 2011, 17, 277.
10. Y. L. Song, R. Yan, W. H. Jing, H. Y. Zhao, Y.T. Wang,. Characterization of metabolism of (+)-praeruptorin B and (+)-praeruptorin E in human and rat liver microsomes by liquid chromatography coupled with ion trap mass spectrometry and time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2011, 25, 719.
11. M. Holčapek, L. KoláÅová, M. Nobilis,. High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of phase I and phase II drug metabolites. Anal. Bioanal. Chem. 2008, 391, 59.
12. H. Horai, M. Arita, S. Kanaya, Y. Nihei, T. Ikeda, K. Suwa,., Y. Ojima, K. Tanaka, S. Tanaka, K. Aoshima, Y. Oda, Y. Kakazu, M. Kusano, T. Tohge, F. Matsuda, Y. Sawada, M. Yokota Hirai, H. Nakanishi, K. Ikeda, N. Akimoto, T. Maoka, H. Takahashi, T. Ara, N. Sakurai, H. Suzuki, D. Shibata, S. Neumann, T. Iida, K. Tanaka, K. Funatsu, F. Matsuura, T. Soga, R. Taguchi, K. Saito, T. Nishioka,. MassBank: A public repository for sharing mass spectral data for life sciences. J. Mass Spectrom. 2010, 45, 703 (ID KO000815).
13. P. Uutela, R. Reinila, K. Harju, P. Piepponen, R. A. Ketola, R. Kostiainen,. Analysis of intact glucuronides and sulfates of serotonin, dopamine, and their phase I metabolites in rat brain microdialysates by liquid chromatography-tandem mass spectrometry. Anal. Chem. 2009, 81, 8417.
14. S. Bourcier, J. F. Benoist, F. Clerc, O. Rigal, M. Taghi, Y. Hoppilliard,. Detection of 28 neurotransmitters and related compounds in biological fluids by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20, 1405.
15. I. Ferrer, E. M. Thurman,. Measuring the Mass of an Electron by LC/TOF-MS: A Study of "Twin Ions". Anal. Chem. 2005, 77, 3394.
16. A. D. N. Vaz, W. W. Wang, A. J. Bessire, R. Sharma, A. E. Hagen,. A rapid and specific derivatization procedure to identify acyl-glucuronides by mass spectrometry. Rapid Commun. Mass Spec. 2010, 24, 2109.
17. R. Jaggi, R. S. Addison, A. R. King, B. D. Suthers, R. G. Dickinson,. Conjugation of desmethylnaproxen in the rat. A novel acyl glucuronide-sulfate diconjugate as a major biliary metabolite. Drug Metab. Dispos. 2002, 30, 161.
18. Z. Wen, M. N. Tallman, S. Y. Ali, P. C. Smith,. UDP- Glucuronosyltransferase 1A1 Is the Principal Enzyme Responsible for Etoposide Glucuronidation in Human Liver and Intestinal Microsomes: Structural Characterization of Phenolic and Alcoholic Glucuronides of Etoposide and Estimation of Enzyme Kinetics. Drug Metab. Dispos. 2007, 35, 371.
19. N. R. Niemeijer, T. K. Gerding, R. A. De Zeeuw,. Glucuronidation of labetalol at the two hydroxy positions by bovine liver microsomes. Isolation, purification, and structure elucidation of the glucuronides of labetalol. Drug Metab. Dispos. 1991, 19, 20.
20. C. Fenselau, L. P. Johnson,. Analysis of intact glucuronides by mass spectrometry and gas chromatography. Drug Metab. Dispos. 1980, 8, 274.
21. A. Aresta, T. Carbonara, F. Palmisano, C. G. Zambonin,. Profiling urinary metabolites of naproxen by liquid chromatography-electrospray mass spectrometry. J. Pharm. Biomed. Anal. 2006, 41, 1312.
22. K. Srinivasan, P. Nouri, O. Kavetskaia,. Challenges in the indirect quantitation of acyl-glucuronide metabolites of a cardiovascular drug from complex biological mixtures in the absence of reference standards. Biomed. Chromatogr. 2010, 24, 759.
23. A. Hermening, A. K. Grafe, G. Baktir, E. Mutschler, H. S. Langguth,. Gemfibrozil and its oxidative metabolites: quantification of aglycones, acyl glucuronides, and covalent adducts in samples from preclinical and clinical kinetic studies. J. Chromatogr. B 2000, 74, 129.
24. N. B. Cech, C. G. Enke,. Pratical implications of some recent studies in electrospray ionization fundamentals. Mass Spectr. Rev. 2001, 20, 362.
25. T. Manickum,. Simultaneous analysis of neuroendocrine tumor markers by HPLC-electrochemical detection. J. Chromatogr. B 2009, 877, 4140.
26. S. Parrota, P. C. Neuzereta, L. Denoroya,. A rapid and sensitive method for the analysis of brain monoamine neurotransmitters using ultra-fast liquid chromatography coupled to electrochemical detection. J. Chromatogr. B 2011, 879, 3871.
27. M. A. Saracino, G. Gerra, L. Somaini, M. Colombati, M. A. Raggi,. Chromatographic analysis of serotonin, 5-hydroxyindolacetic acid and homovanillic acid in dried blood spots and platelet poor and rich plasma samples. J. Chromatogr. A 2010, 1217, 4808.
28. I. AL Mulla, J. P. Lowry, P. A. Serra, R. D. O'Neill,. Development of a voltammetric technique for monitoring brain dopamine metabolism: compensation for interference caused by DOPAC electrogenerated during homovanillic acid detection. Analyst 2009, 134, 893.