Chemical and technical challenges in the analysis of central carbon metabolites by liquid-chromatography mass spectrometry

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 966, Issue , 2014, Pages 21-33

  Siegel, David ^a   Permentier, Hjalmar ^a   Reijngoud, Dirk Jan ^b   Bischoff, Rainer ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

Author keywords

Central carbon metabolism; Chemical degradation; Energy metabolism; Metal interaction

Indexed keywords

BIOMOLECULES; CARBON; DEGRADATION; LIQUID CHROMATOGRAPHY; LIQUIDS; MASS SPECTROMETRY; METABOLISM; METABOLITES;

ANALYTICAL APPROACH; CENTRAL CARBON METABOLISMS; CHEMICAL DEGRADATION; CHEMICAL INSTABILITY; ENERGY METABOLISM; METAL INTERACTIONS; TECHNICAL CHALLENGES; TRICARBOXYLIC ACID CYCLE;

CHEMICAL ANALYSIS;

ACETOACETIC ACID; CARBON; CARBOXYLIC ACID; COENZYME A; DIHYDROXYACETONE; GLYCERALDEHYDE; GUANOSINE TRIPHOSPHATE; METAL; NICOTINAMIDE ADENINE DINUCLEOTIDE; NUCLEOTIDE; OXALOACETIC ACID; OXOACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; THIOESTER; TRICARBOXYLIC ACID;

ARTICLE; CARBON METABOLISM; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CITRIC ACID CYCLE; DEGRADATION; ENERGY METABOLISM; GLYCOLYSIS; ISOMERIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; METABOLOMICS; OXIDATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; ANIMAL; CHEMISTRY; HUMAN; METABOLISM; PROCEDURES;

ANIMALS; CARBON; CHROMATOGRAPHY, LIQUID; HUMANS; MASS SPECTROMETRY; METABOLOMICS;

EID: 84904618330     PISSN: 15700232     EISSN: 1873376X     Source Type: Journal    
DOI: 10.1016/j.jchromb.2013.11.022     Document Type: Article

References (137)

1. Lanpher B., Brunetti-Pierri N., Lee B. Nat. Rev. Genet. 2006, 7:449-460.
2. Koide T., Pang W.L., Baliga N.S. Nat. Rev. Microbiol. 2009, 7:297-305.
3. Dang L., White D.W., Gross S., Bennett B.D., Bittinger M.A., Driggers E.M., Fantin V.R., Jang H.G., Jin S., Keenan M.C., Marks K.M., Prins R.M., Ward P.S., Yen K.E., Liau L.M., Rabinowitz J.D., Cantley L.C., Thompson C.B., Vander Heiden M.G., Su S.M. Nature 2009, 462:739-744.
4. Fendt S.-M., Bell E.L., Keibler M.A., Olenchock B.A., Mayers J.R., Wasylenko T.M., Vokes N.I., Guarente L., Heiden M.G.V., Stephanopoulos G. Nat. Commun. 2013, 4:2236.
5. Metallo C.M., Gameiro P.A., Bell E.L., Mattaini K.R., Yang J., Hiller K., Jewell C.M., Johnson Z.R., Irvine D.J., Guarente L., Kelleher J.K., Vander Heiden M.G., Iliopoulos O., Stephanopoulos G. Nature 2013, 481:380-384.
6. Mullen A.R., Wheaton W.W., Jin E.S., Chen P.-H., Sullivan L.B., Cheng T., Yang Y., Linehan W.M., Chandel N.S., DeBerardinis R.J. Nature 2012, 481:385-388.
7. Losman J.-A., Looper R.E., Koivunen P., Lee S., Schneider R.K., McMahon C., Cowley G.S., Root D.E., Ebert B.L., Kaelin W.G. Science 2013, 339:1621-1625.
8. Gieger C., Geistlinger L., Altmaier E., Hrabé de Angelis M., Kronenberg F., Meitinger T., Mewes H.-W., Wichmann H.-E., Weinberger K.M., Adamski J., Illig T., Suhre K. PLoS Genet. 2008, 4:e1000282.
9. Illig T., Gieger C., Zhai G., Römisch-Margl W., Wang-Sattler R., Prehn C., Altmaier E., Kastenmüller G., Kato B.S., Mewes H.-W., Meitinger T., de Angelis M.H., Kronenberg F., Soranzo N., Wichmann H.-E., Spector T.D., Adamski J., Suhre K. Nat. Genet. 2009, 42:137-141.
10. Suhre K., Gieger C. Nat. Rev. Genet. 2012, 13:759-769.
11. Yerges-Armstrong L.M., Ellero-Simatos S., Georgiades A., Zhu H., Lewis J.P., Horenstein R.B., Beitelshees A.L., Dane A., Reijmers T., Hankemeier T., Fiehn O., Shuldiner A.R., Kaddurah-Daouk R. Clin. Pharmacol. Ther. 2013.
12. Mishur R.J., Rea S.L. Mass Spectrom. Rev. 2012, 31:70-95.
13. Nicholson J.K., Wilson I.D., Lindon J.C. Pharmacogenomics 2011, 12:103-111.
14. Yin P., Peter A., Franken H., Zhao X., Neukamm S.S., Rosenbaum L., Lucio M., Zell A., Haring H.-U., Xu G., Lehmann R. Clin. Chem. 2013, 59:833-845.
15. Bernini P., Bertini I., Luchinat C., Nincheri P., Staderini S., Turano P. J. Biomol. NMR 2011, 49:231-243.
16. Shurubor Y., Matson W., Willett W., Hankinson S., Kristal B. BMC Clin. Pathol. 2007, 7:9.
17. Vuckovic D. Anal. Bioanal. Chem. 2012, 403:1523-1548.
18. Zacharias D.E., Murrayrust P., Preston R.M., Glusker J.P. Arch. Biochem. Biophys. 1983, 222:22-34.
19. Castro E.A. J. Sulfur Chem. 2007, 28:401-429.
20. Castro E.A. Chem. Rev. 1999, 99:3505-3524.
21. Blachnio-Zabielska A.U., Koutsari C., Jensen M.D. Rapid Commun. Mass Spectrom. 2011, 25:2223-2230.
22. Gao L., Chiou W., Tang H., Cheng X., Camp H.S., Burns D.J. J. Chromatogr. B 2007, 853:303-313.
23. Gilibili R.R., Kandaswamy M., Sharma K., Giri S., Rajagopal S., Mullangi R. Biomed. Chromatogr. 2011, 25:1352-1359.
24. Kasuya F., Oti Y., Tatsuki T., Igarashi K. Anal. Biochem. 2004, 325:196-205.
25. Liu G.S., Chen J.N., Che P., Ma Y.F. Anal. Chem. 2003, 75:78-82.
26. Magnes C., Suppan M., Pieber T.R., Moustafa T., Trauner M., Haemmerle G., Sinner F.M. Anal. Chem. 2008, 80:5736-5742.
27. Mauriala T., Herzig K.H., Heinonen M., Idziak J., Auriola S. J. Chromatogr. B 2004, 808:263-268.
28. Qualley A.V., Cooper B.R., Dudareva N. Anal. Biochem. 2012, 420:182-184.
29. Armando J.W., Boghigian B.A., Pfeifer B.A. Lett. Appl. Microbiol. 2012, 54:140-148.
30. Perera M.A.D.N., Choi S.-Y., Wurtele E.S., Nikolau B.J. J. Chromatogr. B 2009, 877:482-488.
31. Minkler P.E., Kerner J., Ingalls S.T., Hoppel C.L. Anal. Biochem. 2008, 376:275-276.
32. Reszko A.E., Kasumov T., Comte B., Pierce B.A., David F., Bederman I.R., Deutsch J., Des Rosiers C., Brunengraber H. Anal. Biochem. 2001, 298:69-75.
33. Norwood D.L., Bus C.A., Millington D.S. J. Chromatogr. 1990, 527:289-301.
34. Bracher P.J., Snyder P.W., Bohall B.R., Whitesides G.M. Origins Life Evol. Biosphere 2011, 41:399-412.
35. Tarbell D.S., Cameron D.P. J. Am. Chem. Soc. 1956, 78:2731-2735.
36. Hawkins P.J., Tarbell D.S. J. Am. Chem. Soc. 1953, 75:2982-2985.
37. Kopka J., Ohlrogge J.B., Jaworski J.G. Anal. Biochem. 1995, 224:51-60.
38. Tamvakopoulos C.S., Anderson V.E. Anal. Biochem. 1992, 200:381-387.
39. Siegel D. Analyst 2012, 137:5457-5482.
40. Hansen R.E., Winther J.R. Anal. Biochem. 2009, 394:147-158.
41. Schlüter H., Meissner M., van der Giet M., Tepel M., Bachmann J., Groß I., Nordhoff E., Karas M., Spieker C., Witzel H., Zidek W. Circ. Res. 1995, 76:675-680.
42. Van Laer K., Hamilton C.J., Messens J. Antioxid. Redox Signaling 2013, 18:1642-1653.
43. Bramanti E., Vecoli C., Neglia D., Pellegrini M.P., Raspi G., Barsacchi R. Clin. Chem. 2005, 51:1007-1013.
44. Mangino M.J., Zografakis J., Murphy M.K., Anderson C.B. J. Chromatogr. 1992, 577:157-162.
45. Palladino A.A., Chen J., Kallish S., Stanley C.A., Bennett M.J. Mol. Genet. Metab. 2012, 107:679-683.
46. Assary R.S., Curtiss L.A. J. Phys. Chem. A 2011, 115:8754-8760.
47. Nagorski R.W., Richard J.P. J. Am. Chem. Soc. 2001, 123:794-802.
48. Hall A., Knowles J.R. Biochemistry 1975, 14:4348-4352.
49. Lookhart G.L., Feather M.S. Carbohydr. Res. 1978, 60:259-265.
50. Adams C.J., Manley-Harris M., Molan P.C. Carbohydr. Res. 2009, 344:1050-1053.
51. Atrott J., Haberlau S., Henle T. Carbohydr. Res. 2012, 361:7-11.
52. Richard J.P. J. Am. Chem. Soc. 1984, 106:4926-4936.
53. Phillips S.A., Thornalley P.J. Eur. J. Biochem. 1993, 212:101-105.
54. Laffel L. Diabetes Metab. Res. Rev. 1999, 15:412-426.
55. Guthrie J.P. Bioorg. Chem. 2002, 30:32-52.
56. Wolfenden R., Lewis C.A., Yuan Y. J. Am. Chem. Soc. 2011, 133:5683-5685.
57. Lu S.B., Sun X.M., Shi C.O., Zhang Y.X. J. Chromatogr. A 2003, 1012:161-168.
58. Laplante A., Comte B., Desrosiers C. Anal. Biochem. 1995, 224:580-587.
59. Johnson S.L., Tuazon P.T. Biochemistry 1977, 16:1175-1183.
60. Miksic J.R., Brown P.R. Biochemistry 1978, 17:2234-2238.
61. Wu J.T., Wu L.H., Knight J.A. Clin. Chem. 1986, 32:314-319.
62. Gerhardt W., Kofoed B., Westlund L., Pavlu B. Scand. J. Clin. Lab. Invest. 1974, 139:1-51.
63. Gallati H. J. Clin. Chem. Clin. Biochem. 1976, 14:9-13.
64. Lowry O.H., Rock M.K., Passonneau J.V. J. Biol. Chem. 1961, 236:2756-&.
65. Rover L., Fernandes J.C.B., Neto G.D., Kubota L.T., Katekawa E., Serrano S.H.P. Anal. Biochem. 1998, 260:50-55.
66. Pogolotti A.L., Santi D.V. Anal. Biochem. 1982, 126:335-345.
67. Johnson R.W., Marschner T.M., Oppenheimer N.J. J. Am. Chem. Soc. 1988, 110:2257-2263.
68. Lazzarino G., Amorini A.M., Fazzina G., Vagnozzi R., Signoretti S., Donzelli S., Di Stasio E., Giardina B., Tavazzi B. Anal. Biochem. 2003, 322:51-59.
69. Sporty J.L., Kabir M.M., Turteltaub K.W., Ognibene T., Lin S.J., Bench G. J. Sep. Sci. 2008, 31:3202-3211.
70. Wagner T.C., Scott M.D. Anal. Biochem. 1994, 222:417-426.
71. Zerez C.R., Lee S.J., Tanaka K.R. Anal. Biochem. 1987, 164:367-373.
72. Umemura K., Kimura H. Anal. Biochem. 2005, 338:131-135.
73. Klaidman L.K., Leung A.C., Adams J.D. Anal. Biochem. 1995, 228:312-317.
74. Anderson R.M., Bitterman K.J., Wood J.G., Medvedik O., Cohen H., Lin S.S., Manchester J.K., Gordon J.I., Sinclair D.A. J. Biol. Chem. 2002, 277:18881-18890.
75. Ashrafi K., Lin S.S., Manchester J.K., Gordon J.I. Genes Dev. 2000, 14:1872-1885.
76. Lin S.J., Ford E., Haigis M., Liszt G., Guarente L. Genes Dev. 2004, 18:12-16.
77. Lin S.S., Manchester J.K., Gordon J.I. J. Biol. Chem. 2001, 276:36000-36007.
78. Smith J.S., Brachmann C.B., Celic I., Kenna M.A., Muhammad S., Starai V.J., Avalos J.L., Escalante-Semerena J.C., Grubmeyer C., Wolberger C., Boeke J.D. PNAS 2000, 97:6658-6663.
79. Micheli V., Simmonds H.A., Bari M., Pompucci G. Clin. Chim. Acta 1993, 220:1-17.
80. Ogasawara Y., Funakoshi M., Ishii K. Biol. Pharm. Bull. 2009, 32:1819-1823.
81. Caruso R., Campolo J., Dellanoce C., Mariele R., Parodi O., Accinni R. Anal. Biochem. 2004, 330:43-51.
82. Spiro T.G., Wa K., Zeydel M., Butow R.A. Biochemistry 1968, 7:859-&.
83. Sigel H., Amsler P.E. J. Am. Chem. Soc. 1976, 98:7390-7400.
84. Suzuki S., Higashiyama T., Nakahara A. Bioinorg. Chem. 1978, 8:277-289.
85. Buescher J.M., Moco S., Sauer U., Zamboni N. Anal. Chem. 2010, 82:4403-4412.
86. Coolen E.J.C.M., Arts I.C.W., Swennen E.L.R., Bast A., Stuart M.A.C., Dagnelie P.C. J. Chromatogr. B 2008, 864:43-51.
87. von Papen M., Gambaryan S., Schuetz C., Geiger J. Transfus. Med. Hemother. 2013, 40:109-116.
88. Buescher J.M., Czernik D., Ewald J.C., Sauer U., Zamboni N. Anal. Chem. 2009, 81:2135-2143.
89. Coulier L., Bas R., Jespersen S., Verheij E., van der Werf M.J., Hankemeier T. Anal. Chem. 2006, 78:6573-6582.
90. Kiefer P., Delmotte N.I., Vorholt J.A. Anal. Chem. 2010, 83:850-855.
91. Bennette N.B., Eng J.F., Dismukes G.C. Anal. Chem. 2011, 83:3808-3816.
92. Luo B., Groenke K., Takors R., Wandrey C., Oldiges M. J. Chromatogr. A 2007, 1147:153-164.
93. Kamphorst J.J., Fan J., Lu W.Y., White E., Rabinowitz J.D. Anal. Chem. 2011, 83:9114-9122.
94. Kiefer P., Delmotte N., Vorholt J.A. Anal. Chem. 2011, 83:850-855.
95. Lu W.Y., Clasquin M.F., Melamud E., Amador-Noguez D., Caudy A.A., Rabinowitz J.D. Anal. Chem. 2010, 82:3212-3221.
96. Antonio C., Larson T., Gilday A., Graham I., Bergstroem E., Thomas-Oates J. J. Chromatogr. A 2007, 1172:170-178.
97. Chaimbault P., Petritis K., Elfakir C., Dreux M. J. Chromatogr. A 2000, 870:245-254.
98. Koizumi K. J. Chromatogr. A 1996, 720:119-126.
99. Monser L. Chromatographia 2004, 59:455-459.
100. Okamoto T., Isozaki A., Nagashima H. J. Chromatogr. A 1998, 800:239-245.
101. Wang J., Lin T., Lai J., Cai Z., Yang M.S. J. Chromatogr. B 2009, 877:2019-2024.
102. Xia Y.Q., Jemal M., Zheng N.Y., Shen X.H. Rapid Commun. Mass Spectrom. 2006, 20:1831-1837.
103. Xing J.S., Apedo A., Tymiak A., Zhao N. Rapid Commun. Mass Spectrom. 2004, 18:1599-1606.
104. Pabst M., Grass J., Fischl R., Leonard R., Jin C., Hinterkorner G., Borth N., Altmann F. Anal. Chem. 2010, 82:9782-9788.
105. Alpert A.J. J. Chromatogr. 1990, 499:177-196.
106. Spagou K., Wilson I.D., Masson P., Theodoridis G., Raikos N., Coen M., Holmes E., Lindon J.C., Plumb R.S., Nicholson J.K., Want E.J. Anal. Chem. 2010, 83:382-390.
107. Zhang T., Creek D.J., Barrett M.P., Blackburn G., Watson D.G. Anal. Chem. 2012, 84:1994-2001.
108. Uehara T., Yokoi A., Aoshima K., Tanaka S., Kadowaki T., Tanaka M., Oda Y. Anal. Chem. 2009, 81:3836-3842.
109. Hemstrom P., Irgum K. J. Sep. Sci. 2006, 29:1784-1821.
110. Guo K., Li L. Anal. Chem. 2010, 82:8789-8793.
111. Lamos S.M., Shortreed M.R., Frey B.L., Belshaw P.J., Smith L.M. Anal. Chem. 2007, 79:5143-5149.
112. Deng P., Zhan Y., Chen X., Zhong D. Bioanalysis 2012, 4:49-69.
113. Yang W.C., Sedlak M., Regnier F.E., Mosier N., Ho N., Adamec J. Anal. Chem. 2008, 80:9508-9516.
114. Abello N., Geurink P.P., Toorn M.V., Oosterhout A.J., Lugtenburg J., Marel G.A., Kerstjens H.A., Postma D.S., Overkleeft H.S., Bischoff R. Anal. Chem. 2008, 80:9171-9180.
115. Boughton B.A., Callahan D.L., Silva C., Bowne J., Nahid A., Rupasinghe T., Tull D.L., McConville M.J., Bacic A., Roessner U. Anal. Chem. 2011, 83:7523-7530.
116. Siegel D., Permentier H., Bischoff R. J. Chromatogr. A 2013, 1294:87-97.
117. Xiao J.F., Zhou B., Ressom H.W. Trends Anal. Chem. 2012, 32:1-14.
118. Yuan M., Breitkopf S.B., Yang X., Asara J.M. Nat. Protoc. 2012, 7:872-881.
119. Avery M.J. Rapid Commun. Mass Spectrom. 2003, 17:197-201.
120. Sojo L.E., Lum G., Chee P. Analyst 2003, 128:51-54.
121. Liang H.R., Foltz R.L., Meng M., Bennett P. Rapid Commun. Mass Spectrom. 2003, 17:2815-2821.
122. Amad M.H., Cech N.B., Jackson G.S., Enke C.G. J. Mass Spectrom. 2000, 35:784-789.
123. Ghosh C., Shinde C.P., Chakraborty B.S. J. Chromatogr. B 2012, 893:193-200.
124. Schmidt A., Karas M., Dulcks T. J. Am. Soc. Mass Spectrom. 2003, 14:492-500.
125. Gangl E.T., Annan M., Spooner N., Vouros P. Anal. Chem. 2001, 73:5635-5644.
126. Staack R.F., Varesio E., Hopfgartner G. Rapid Commun. Mass Spectrom. 2005, 19:618-626.
127. Ejsing C.S., Sampaio J.L., Surendranath V., Duchoslav E., Ekroos K., Klemm R.W., Simons K., Shevchenko A. PNAS 2009, 106:2136-2141.
128. Schuhmann K., Almeida R., Baumert M., Herzog R., Bornstein S.R., Shevchenko A. J. Mass Spectrom. 2012, 47:96-104.
129. Beach D.G., Gabryelski W. Anal. Chem. 2013, 85:2127-2134.
130. Chen M.L., Cook K.D. Anal. Chem. 2007, 79:2031-2036.
131. Moolayil J.T., George M., Giblin D., Gross M.L. Int. J. Mass Spectrom. 2009, 283:222-228.
132. Plattner S., Erb R., Chervet J.-P., Oberacher H. Anal. Bioanal. Chem. 2012, 404:1571-1579.
133. Ibrahim H., Couderc F., Perio P., Collin F., Nepveu F. Rapid Commun. Mass Spectrom. 2012, 27:621-628.
134. Ma S.G., Chowdhury S.K., Alton K.B. Anal. Chem. 2005, 77:3676-3682.
135. Bagag A., Giuliani A., Laprevote O. Int. J. Mass Spectrom. 2007, 264:1-9.
136. March R.E., Stadey C.J. Rapid Commun. Mass Spectrom. 2005, 19:805-812.
137. Clowers B.H., Dwivedi P., Steiner W.E., Hill H.H., Bendiak B. J. Am. Soc. Mass Spectrom. 2005, 16:660-669.