A carbonyl capture approach for profiling oxidized metabolites in cell extracts

Metabolomics

Volumn 8, Issue 6, 2012, Pages 989-996

  Mattingly, Stephanie J ^a   Xu, Tao ^a   Nantz, Michael H ^a   Higashi, Richard M ^a   Fan, Teresa W M ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

ketoglutarate; Aldehyde; Cellular oxidation state; Ketone; Mass spectrometry; Metabolite profiling; Oxaloacetate; Pyruvate

Indexed keywords

CARBONYL DERIVATIVE; CELL EXTRACT; IODIDE; N [2 (AMINOOXY)ETHYL] N,N DIMETHYL 1 DODECYLAMMONIUM IODIDE; PYRUVIC ACID; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; CELL ASSAY; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); HUMAN; HUMAN CELL; HYDROPHOBICITY; ION CYCLOTRON RESONANCE MASS SPECTROMETRY; METABOLITE; MOLECULAR DYNAMICS; MOLECULAR WEIGHT; QUANTITATIVE ANALYSIS; SENSITIVITY ANALYSIS; SEPARATION TECHNIQUE;

EID: 84868347609     PISSN: 15733882     EISSN: 15733890     Source Type: Journal    
DOI: 10.1007/s11306-011-0395-z     Document Type: Article

References (27)

1. Barry, S. J., Carr, R. M., Lane, S. J., Leavens, W. J., Manning, C. O., Monté, S., et al. (2003). Use of S-pentafluorophenyl tris(2, 4, 6-trimethoxyphenyl)phosphonium acetate bromide and (4-hydrazino-4-oxobutyl) [tris(2, 4, 6-trimethoxyphenyl)phosphonium bromide for the derivatization of alcohols, aldehydes and ketones for detection by liquid chromatography/electrospray mass spectrometry. Rapid Communications in Mass Spectrometry, 17, 484-497.
2. Biswas, S., Huang, X., Badger, W. R., & Nantz, M. H. (2010). Nucleophilic cationization reagents. Tetrahedron Letters, 51, 1727-1729.
3. Eggink, M., Wijtmans, M., Kretschmer, A., Kool, J., Lingeman, H., Esch, I. J. P. d., et al. (2010). Targeted LC-MS derivatization for aldehydes and carboxylic acids with a new derivatization agent 4-APEBA. Analytical and Bioanalytical Chemistry, 397, 665-675.
4. Fan, T. W., Lane, A. N., Higashi, R. M., Farag, M. A., Gao, H., Bousamra, M., et al. (2009). Altered regulation of metabolic pathways in human lung cancer discerned by (13)C stable isotope-resolved metabolomics (SIRM). Molecular Cancer, 8, 41.
5. Fan, T., Lane, A., Higashi, R., & Yan, J. (2011). Stable isotope resolved metabolomics of lung cancer in a SCID mouse model. Metabolomics, 7, 257-269.
6. Fang, K., Pan, X., Huang, B., Liu, J., Wang, Y., & Gao, J. (2010). Simultaneous derivatization of hydroxyl and ketone groups for the analysis of steroid hormones by GC-MS. Chromatographia, 72, 949-956.
7. Griffiths, W. J., Hornshaw, M., Woffendin, G., Baker, S. F., Lockhart, A., Heidelberger, S., et al. (2008). Discovering oxysterols in plasma: A window on the metabolome. Journal of Proteome Research, 7, 3602-3612.
8. Griffiths, W. J., Koal, T., Wang, Y., Kohl, M., Enot, D. P., & Deigner, H. -P. (2010). Targeted metabolomics for biomarker discovery. Angewandte Chemie International Edition, 49, 5426-5446.
9. Grochowski, E., & Jurczak, J. (1976). A new synthesis of O-alkylhydroxylamines. Synthesis, 682-684.
10. Hong, H., & Wang, Y. (2007). Derivatization with girard reagent T combined with LC-MS/MS for the sensitive detection of 5-formyl-2′-deoxyuridine in cellular DNA. Analytical Chemistry, 79, 322-326.
11. Iglesias, J., Gallardo, J. M., & Medina, I. (2010). Determination of carbonyl compounds in fish species samples with solid-phase microextraction with on-fibre derivatization. Food Chemistry, 123, 771-778.
12. Johnson, D. W. (2007). A modified Girard derivatizing reagent for universal profiling and trace analysis of aldehydes and ketones by electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 21, 2926-2932.
13. Kalia, J., & Raines, R. T. (2008). Hydrolytic stability of hydrazones and oximes. Angewandte Chemie International Edition, 47, 7523-7526.
14. Lane, A. N., Fan, T. W. -M., & Higashi, R. M. (2008). Isotopomer-based metabolomic analysis by NMR and mass spectrometry. Biophysical Tools for Biologists, 84, 541-588.
15. Lane, A. N., Fan, T. W. -M., Xie, Z., Moseley, H. N. B., & Higashi, R. M. (2009). Isotopomer analysis of lipid biosynthesis by high resolution mass spectrometry and NMR. Analytica Chimica Acta, 651, 201-208.
16. Li, Z., Tang, Y., Liu, Y., & Li, Y. (1995). Salting effect in partially miscible systems of n-butanol-water and butanone-water. Fluid Phase Equilibria, 103, 143-153.
17. Lorkiewicz, P. K., Higashii, R. M., Lane, A. N., & Fan, T. W. -M. (2011). High information throughput analysis of nucleotides and their isotopically enriched isotopologues by direct-infusion FTICR-MS. Metabolomics.
18. Maboudou, P., Mathieu, D., Bachelet, H., Wiart, J. F., & Lhermitte, M. (2002). Detection of oxidative stress. Interest of GC-MS for malondialdehyde and formaldehyde monitoring. Biomedical Chromatography, 16, 199-202.
19. Negre-Salvayre, A., Auge, N., Ayala, V., Basaga, H., Boada, J., Brenke, R., et al. (2010). Pathological aspects of lipid peroxidation. Free Radical Research, 44, 1125-1171.
20. Noda, Y., Berlett, B. S., Stadtman, E. R., Aponte, A., Morgan, M., & Shen, R. -F. (2007). Identification of enzymes and regulatory proteins in Escheria coli that are oxidized under nitrogen, carbon, or phosphate starvation. Proceedings of National Academy of Sciences, 104, 18456-18460.
21. Psychogios, N., Hau,D. D., Peng, J., Guo, A. C., Mandal, R., & Bouatra, S. et al. (2011) The Human Serum Metabolome. PLoS ONE 6.
22. Rodriguez, E. C., Marcaurelle, L. A., & Bertozzi, C. R. (1998). Aminooxy-, hydrazide-, and thiosemicarbazide-functionalized saccharides: versatile reagents for glycoconjugate synthesis. The Journal of organic chemistry, 63, 7134-7135.
23. Ross, M. M., Kidwell, D. A., & Colton, R. J. (1985). Selective detection of aldehydes and ketones by derivatization/secondary ion mass spectrometry. International Journal of Mass Spectrometry and Ion Processes, 63, 141-148.
24. Sugaya, N., Sakurai, K., Nakagawa, T., Onda, N., Onodera, S., Morita, M., et al. (2004). Development of a headspace GC/MS analysis for carbonyl compounds (Aldehydes and Ketones) in household products after derivatization with o-(2, 3, 4, 5, 6-Pentafluorobenzyl)-hydroxylamine. Analytical Sciences, 20, 865-870.
25. Wheeler, O. H. (1968). The girard reagents. Journal of Chemical Education, 45, 435-437.
26. Wikoff, W. R., Anfora, A. T., Liu, J., Schultz, P. G., Lesley, S. A., Peters, E. C., et al. (2009). Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites. Proceedings of the National Academy of Sciences of the United States of America, 106, 3698-3703.
27. Zajdel, A., Wilczok, A., Slowinski, J., Orchel, J., & Mazurek, U. (2007). Aldehydic lipid peroxidation products in human brain astrocytomas. Journal of Neuro-Oncology, 84, 167-173.