Tandem mass spectrometry in the study of fatty acids, bile acids, and steroids

Mass Spectrometry Reviews

Volumn 22, Issue 2, 2003, Pages

  Griffiths, William J ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Bile acids; Charge remote fragmentation; Derivatization; Fatty acids; Liquid chromatography mass spectrometry; Reaction mechanism; Steroids; Tandem mass spectrometry

Indexed keywords

ALCOHOLS; ALDEHYDES; ESTERIFICATION; FATTY ACIDS; LIPIDS;

RING FRAGMENTATION;

MASS SPECTROMETRY;

ALDEHYDE; BILE ACID; FATTY ACID; FATTY ALCOHOL; GLUCURONIDE; LIPID; PHOSPHOLIPID; STEROID; SULFATE; TRIACYLGLYCEROL;

ANIMAL; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; HUMAN; MASS SPECTROMETRY; METHODOLOGY; PHYSICAL CHEMISTRY; REVIEW;

ALDEHYDES; ANIMALS; BILE ACIDS AND SALTS; CHEMISTRY, PHYSICAL; FATTY ACIDS; FATTY ALCOHOLS; GLUCURONIDES; HUMANS; LIPIDS; MASS SPECTROMETRY; PHOSPHOLIPIDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STEROIDS; SULFATES; TRIGLYCERIDES;

EID: 85046983127     PISSN: 02777037     EISSN: None     Source Type: Journal    
DOI: 10.1002/mas.10046     Document Type: Review

References (197)

1. Abian J, Oosterkamp AJ, Gelpi E. 1999. Comparison of conventional, narrow bore and capillary liquid chromatography/mass spectrometry for electrospray ionization mass spectrometry: Practical considerations. J Mass Spectrom 34:244-254.
2. Adams J. 1987. Proceedings of the 35th ASMS conference on mass spectrometry and allied topics, p 227-228.
3. Adams J. 1990. Charge-remote fragmentations: Analytical applications and fundamental studies. Mass Spectrom Rev 9: 141-186.
4. Adams J, Gross ML. 1988. Structural determination of modified fatty acids by collisional activation of cationized molecules. Org Mass Spectrom 23:307-316.
5. Al-Saad KA, Zabrouskov V, Siems WF, Knowles NR, Hannan RM, Hill HH. 2003. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of lipids: lonization and prompt fragmentation patterns. Rapid Commun Mass Spectrom 17:87-96.
6. 1. J Lipid Res 42:1571-1577.
7. Amster IJ. 1996. Fourier transform mass spectrometry. J Mass Spectrom 31:1325-1337.
8. Amy JW, Baitinger WE, Cooks RG. 1990. Building mass spectrometers and a philosophy of research. J Am Soc Mass Spectrom 1:119-128.
9. Antignac J-P, Le Bizec B, Monteau F, Poulain F, André F. 2000. Collision induced dissociation of corticosteroids in electrospray tandem mass spectrometry and development of a screening method by high performance liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 14:33-39.
10. Asbury GR, Al-Saad K, Siems WF, Hannan RM, Hill HH. 1999. Analysis of triacylglycerols and whole oils by matrix-assisted laser desorption/ionization time of flight mass spectrometry. J Am Soc Mass Spectrom 10:983-991.
11. Axelson M, Sjövall J. 1979. Strong non-polar cation exchangers for the separation of steroids in mixed Chromatographic systems. J Chromatogr 186:725-732.
12. Ballatore AM, Beckner CF, Caprioli RM, Hoffman NE, Liehr JG. 1983. Synthesis and spectroscopic analysis of modified bile salts. Steroids 41:197-206.
13. -] anions from negative ion chemical ionization of fatty acid methyl esters. Org Mass Spectrom 21:485-488.
14. Barber M, Bordoli RS, Sedgwick RD, Tyler AN. 1981. Fast atom bombardment of solids (FAB): A new ion source for mass spectrometry. J Chem Soc Chem Commun 325-327.
15. Barber M, Bordoli RS, Elliott GJ, Sedgwick RN, Tyler AN. 1982. Fast atom bombardment mass spectrometry. Anal Chem 54:645A-657A.
16. Baronti C, Curini R, D'Ascenzo G, Di Corcia A, Gentili A, Samperi R. 2000. Monitoring natural and synthetic estrogens at activated sludge sewage treatment plants in a receiving river water. Environ Sci Technol 34:5059-5066.
17. Bateman RH, Green MR, Scott G, Clayton E. 1995. A combined magnetic sector-time-of-flight mass spectrometer for structural determination studies by tandem mass spectrometry. Rapid Commun Mass Spectrom 9:1227-1233.
18. Beynon JH. 1960. Mass speclrometry and its Applications to Organic Chemistry. Amsterdam: Elsevier.
19. Blau K, King GS. 1977. Handbook of derivatives for chromatography. London: Heyden & Sons.
20. Bootsma AH, Overmars H, van Rooij A, van Lint AE, Wander RJ, van Gennip AH, Vreken P. 1999. Rapid analysis of conjugated bile acids in plasma using eleclrospray tandem mass spectrometry: Application for selective screening of peroxisomal disorders. J Inher Metab Dis 22:307-310.
21. Borts DJ, Bowers LD. 2000. Direct measurement of urinary testosterone and epitestosterone conjugates using high-performance liquid chromatography/tandem mass spectrometry. J Mass Spectrom 35:50-61.
22. Bowers LD, Sanaullah. 1996. Direct measurement of steroid sulphate and glucuronide conjugates with high-performance liquid chromatography-mass spectrometry. J Chromatogr B 687:61-68.
23. 7) chemotactic for human granulocytes. J Biol Chem 275:29931-29934.
24. Bryant DK, Orlando R. 1991. Location of unsaturated positions in phosphatidylcholines by consecutive-reaction monitoring. Rapid Commun Mass Spectrom 5:124-127.
25. Bryant DK, Orlando RC, Fenselau C, Sowder RC, Henderson LE. 1991. Four-sector tandem mass spectrometric analysis of complex mixtures of phosphatidylcholines present in a human immunodeficiency virus preparation. Anal Chem 63:1110-1114.
26. Bryant MS, Korfmacher WA, Nardo CL, Lapiguera AP, Lin C-C, Langevin CN, Oglesby TD. 1995. Determination of be-clomethasone dipropionate and three metabolites in human, dog and rat plasma via HPLC-APCI/MS/MS. Proceedings of the 43rd ASMS conference on mass spectrometry and allied topics. May 21-26, Atlanta Ga. p 334.
27. Budavari S, O'Neil MJ. 1996. The Merck Index: An encyclopaedia of chemicals, drugs, and biologicals. Boca Raton, Fl: CRC Press.
28. Caprioli RM. 1990. Continuous-flow fast atom bombardment mass spectrometry. Chichester: John Wiley & Sons.
29. Carson R. 1962. Silent spring. Boston: Houghton Mifflin.
30. Chang Y-S, Watson JT. 1992. Charge-remote fragmentation during FAB-CAD-B/E linked-scan mass spectrometry of aminoethyl-triphenylphosphonium derivatives of fatty acids. J Am Soc Mass Spectrom 3:769-775.
31. Chatman K, Hollenbeck T, Hagey L, Vallee M, Purdy R, Weiss F, Siuzdak G. 1999. Nanoelectrospray mass spectrometry and precursor ion monitoring for quantitative steroid analysis and attomole sensitivity. Anal Chem 71:2358-2363.
32. Cheng C, Gross ML, Pittenauer E. 1998. Complete structural elucidation of triacylglycerols by tandem sector mass spectrometry. Anal Chem 70:4417-4426.
33. Cheng C, Pittenauer E, Gross ML. 1998. Charge-remote fragmentations are energy-dependent processes. J Am Soc Mass Spectrom 9:840-844.
34. Cheng C, Gross ML. 2000. Application and mechanisms of charge-remote fragmentation. Mass Spectrom Rev 19:398-420.
35. Claeys M, Van den Heuvel H. 1994. Radical processes in remote charge fragmentations of lithium cationized long-chain alkenyl and alkadienyl salicylic acids. Biol Mass Spectrom 23:20-26.
36. Claeys M, Nizigiyimana L, Van den Heuvel H, Derrick PJ. 1996. Mechanistic aspects of charge remote fragmentation in saturated and mono-unsaturated fatty acid derivatives. Evidence for homolytic cleavage. Rapid Commun Mass Spectrom 10:770-774.
37. Claeys M, Nizigimana L, Van den Heuvel H, Vedemikova I, Haemers A. 1998. Charge-remote and charge-proximate fragmentation processes in alkali-cationized fatty acid esters upon high-energy collisional activation. A new mechanistic proposal. J. Mass Spectrom 33:631-643.
38. Clayton PT. 2001. Application of mass spectrometry in the study of inborn errors of metabolism. J Inherit Metab Dis 24:139-150.
39. Cole MJ, Enke CG. 1991. Direct determination of phospholipid structure in microorganisms by fast atom bombardment triple quadrupole mass spectrometry. Anal Chem 63:1032-1038.
40. Cooks RG, Beynon JH, Caprioli RM, Lester GR. 1973. Meta-stable Ions. Amsterdam: Elsevier.
41. Crockett JS, Gross ML, Christie WW, Holman RT. 1990. Collisional activation of a series of homoconjugated octa-decadienoic acids with fast atom bombardment and tandem mass spectrometry. J Am Soc Mass Spectrom 1:183-191.
42. Croley TR, Hughes RJ, Koenig BG, Metcalfe CD, March RE. 2000. Mass spectrometry applied to the analysis of estrogens in the environment. Rapid Commun Mass Spectrom 14: 1087-1093.
43. de Hoffmann E. 1996. Tandem mass spectrometry: A primer. J Mass Spectrom 31:129-137.
44. Deterding LJ, Curtis JF, Tomer KB. 1992. Tandem mass spectrometric identification of eicosanoids: Leukotrienes and hydroxyeicosatetraenoic acids. Biol Mass Spectrom 21:597-609.
45. Dharmasiri KAN, Huang Z-H, Watson JT. 1993. Derivatives for detection of anabolic ketosteroids by positive electrospray mass spectrometry. Proceedings of the 41st ASMS conference on mass spectrometry and allied topics. May 31June 4, San Francisco CA. p 541a.
46. Dusza JP, Joseph JP, Bernstein S. 1968. Steroid conjugates IV. The preparation of steroid sulfates with triethylamine-sulfur trioxide. Steroids 12:49-61.
47. Eckers C, East PB, Haskins NJ. 1991. The use of negative ion thermospray liquid chromatography/tandem mass spectrometry for the determination of bile acids and their glycine conjugates. Biol Mass Spectrom 20:731-739.
48. Eckers C, New AP, East PB, Haskins NJ. 1990. The use of tandem mass spectrometry for the differentiation of bile acid isomers and for the identification of bile acids in biological extracts. Rapid Commun Mass Spectrom 4:449-453.
49. Ekroos K, Chernushevich IV, Simons K, Shevchenko A. 2002. Quantitative profiling of phospholipids by multiple precursor ion scanning on a hybrid quadrupole time-of-flight mass spectrometer. Anal Chem 74:941-949.
50. Emmett MR, Caprioli RM. 1994. Micro-electrospray mass spectrometry: Ultra-high sensitivity analysis of peptides and proteins. J Am Soc Mass Spectrom 5:605-613.
51. Ferguson PL, Iden CR, McElroy AE, Brownawell BJ. 2001. Determination of steroid estrogens in wastewater by immunoaffinity extraction coupled with HPLC-electrospray-MS. Anal Chem 73:3890-3895.
52. Gale DC, Smith RD. 1993. Small volume and low flow-rate electrospray ionization mass spectrometry of aqueous samples. Rapid Commun Mass spectrom 7:1017-1021.
53. Gaskell SJ. 1988. Evaluation of the quantitative analysis of a steroid sulphate using fast atom bombardment and tandem mass spectrometry. Biomed Environ Mass Spectrom 15:99-104.
54. Gaskell SJ, Brownsey BG, Brooks PW, Green BN. 1983. Fast atom bombardment mass spectrometry of steroid sulphates: Qualitative and quantitative analysis. Biomed Mass Spectrom 10:215-219.
55. Gohlke RS. 1959. Time-of-flight mass spectrometry and gasliquid partition chromatography. Anal Chem 31:535-541.
56. Cower DB, Mallet AI, Watkins WJ, Wallace LM, Calame J-P. 1997. Capillary gas chromatography with chemical ionization negative ion mass spectrometry in the identification of odorous steroids formed in metabolic studies of the sulphates of androsterone, DHA and 5α-androst-16-en-3β-ol with human axillary bacterial isolates. J Steroid Biochem Mol Biol 63:81-89.
57. Griffiths WJ, Egestad B, Sjövall J. 1991a. Differentiation of taurochenodeoxycholate from taurodeoxycholate by collision-induced dissociation of pseudomolecular anions generated by fast atom bombardment. Rapid Commun Mass Spectrom 5:196-197.
58. Griffiths WJ, Egestad B, Sjövall J. 1991b. Charge-remote fragmentation of taurine-conjugated bile acids. Rapid Commun Mass Spectrom 5:391-394.
59. Griffiths WJ, Zhang J, Sjövall J. 1993. Charge-remote fragmentation of bile acids derivatized with amino-sulphonic acids. Rapid Commun Mass Spectrom 7:235-240.
60. Griffiths WJ, Yang Y, Zhang J, Lindgren JÅ, Sjövall J. 1995. A comparison of high- and low-energy CID of derivatised lipids. Proceedings of the 43rd ASMS conference on mass spectrometry and allied topics. May 21-26, Atlanta Georgia, p 1160.
61. Griffiths WJ, Brown A, Reimendal R, Yang Y, Zhang J, Sjövall J. 1996a. A comparison of fast atom bombardment and electrospray as methods of ionization in the study of sulphated- and sulphonated-lipids by tandem mass spectrometry. Rapid Commun Mass Spectrom 10:1169-1174.
62. Griffiths WJ, Yang Y, Lindgren JÅ, Sjövall J. 1996b. Charge remote fragmentation of fatty acid anions in 400 eV collisions with xenon atoms. Rapid Commun Mass Spectrom 10:21-28.
63. Griffiths WJ, Yang Y, Sjövall J, Lindgren JÅ. 1996c. Electrospray/collision-induced dissociation mass spectrometry of mono-, di- and tri-hydroxylated lipoxygenase products, including leukotrienes of the B-series and lipoxins. Rapid Commun Mass Spectrom 10:183-196.
64. Griffiths WJ, Yang Y, Sjövall J, Lindgren JÅ. 1996d. Electrospray tandem mass spectrometry of cysteinyl leukotrienes. Rapid Commun Mass Spectrom 10:1054-1070.
65. Griffiths WJ, Hjertman M, Lundsjö A, Wejde J, Sjövall J, Larsson O. 1996e. Analysis of dolichols and polyprenols and their derivatives by electron impact, fast atom bombardment and electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 10:663-675.
66. Griffiths WJ, Liu S, Yang Y, Purdy RH, Sjövall J. 1999. Nanoelectrospray tandem mass spectrometry for the analysis of neurosteroid sulphates. Rapid Commun Mass Spectrom 13: 1595-1610.
67. Griffiths WJ, Jonsson AP, Liu S, Rai DK, Wang Y. 2001. Electrospray and tandem mass spectrometry in biochemistry. Biochem J 355:545-561.
68. Griffiths WJ, Liu S, Alvelius G, Sjövall J. 2002. Derivatives revisited: Analysis of neutral steroids by ESMS. Proceedings of the 50th ASMS conference on mass spectrometry and allied topics. June 2-6, Orlando Fl. WODam 11:55.
69. Griffiths WJ, Liu S, Alvelius G, Sjövall J. 2003. Derivatisation for the characterisation of neutral steroids by electrospray and MALDI tandem mass spectrometry: The Girard P derivative. Rapid Commun Mass Spectrom 17:924-935.
70. Gross ML. 1992. Charge-remote fragmentations: Method, mechanism and applications. Int J Mass Spectrom Ion Processes 118(119):137-165.
71. Gross ML, Hu P. 1994. Ion chemistry for structure elucidation of biomolecules. In: Matsuo T, Caprioli RM, Gross ML, Seyama Y, editors. Biological Mass Spectrometry. Chichester: John Wiley and Sons, p 255-272.
72. Guilhaus M, Selby D, Mlynski V. 2000. Orthogonal acceleration time-of-flight mass spectrometry. Mass Spectrom Rev 19: 65-107.
73. 2 formed by isolated rat hepatocytes. Arch Biochim Biophys 340:317-330.
74. - ions occur via a collision decomposition of adduct anions. J Mass Spectrom 30:1772-1773.
75. Harvey DJ. 1982. Picolinyl esters as derivatives for the structural determination of long chain branched and unsaturated fatty acids. Biomed Mass Spectrom 9:33-38.
76. Harvey DJ. 1984. Picolinyl derivatives for the structural determination of fatty acids by mass spectrometry: Applications to polyenoic acids, di-acids and related compounds. Biomed Mass Spectrom 11:340-347.
77. Harvey DJ. 1992. Mass spectrometry of picolinyl and other nitrogen-containing derivatives of lipids. In: Christie WW, editor. Advances in lipid methodology - one. Ayr: The Oily Press, p 19-80.
78. Harvey DJ. 1995. Matrix-assisted laser desorption/ionization mass spectrometry of phospholipids. J Mass Spectrom 30: 1333-1346.
79. Harvey DJ, Bateman RH, Bordoli RS, Tyldesley R. 2002. Ionisation and fragmentation of complex glycans with a quadrupole time-of-flight mass spectrometer fitted with a matrix-assisted laser desorption/ionisation ion source. Rapid Commun Mass Spectrom 14:2135-2142.
80. Hermansson K, Jansson PE, Loew P, Dallner G, Swiezewska E, Chojnacki T. 1992. Analysis of long chain polyisoprenoids by fast atom bombardment mass spectrometry. Biol Mass Spectrom 21:548-553.
81. Hevko JM, Murphy RC. 2001. Electrospray ionization and tandem mass spectrometry of cysteinyl eicosanoids: Leukotriene C4 and FOG7. J Am Soc Mass Spectrom 12:763-771.
82. Hoiberg CP, Mumma RO, Weber WW. 1969. Preparation of sulphate esters. The synthesis of steroid sulphates by a dicyclohexylcarbodiimide-mediated sulphation. Steroids 14:67-74.
83. Horning EC. 1970. Gas phase analytical methods for the study of steroid hormones and their metabolites. In: Eik-Nes KB, Horning EC, editors. Gas phase chromatography of steroids. New York: Springer-Verlag, p 1-71.
84. Hsu FF, Bohrer A, Turk J. 1998. Formation of lithium adducts of glycerolphosphocholine lipid facilitates their identification by electrospray ionization tandem mass spectrometry. J Am Soc Mass Spectrom 9:516-526.
85. Hsu F-F, Turk J. 1999a. Distinction among isomeric unsaturaled fatty acids as lithium adducts by electrospray ionisation mass spectrometry using low energy collisional activated dissociation on a triple stage quadrupole instrument. J Am Soc Mass Spectrom 10:600-612.
86. Hsu FF, Turk J. 1999b. Structural characterization of triacylglycerols as lithium adducts by electrospray ionization mass spectrometry using low-energy collisionally activated dissociation on a triple stage quadrupole instrument. J Am Soc Mass Spectrom 10:587-599.
87. Hsu F-F, Turk J. 2000a. Charge-remote and charge-driven fragmentation processes in diacyl glycerolphospoethanolamine upon low-energy collisional activation: A mechanistic proposal. J Am Soc Mass Spectrom 11:892-899.
88. Hsu F-F, Turk J. 2000b. Charge-driven fragmentation processes in diacyl glycerophosphatidic acids upon low-energy collisional activation. A mechanistic proposal. J Am Soc Mass Spectrom 11:797-803.
89. Hsu F-F, Turk J. 2000c. Characterization of phosphatidylinositol, phosphatidylinositol-4-phosphate, and phospatidylinositol-4,5-bisphosphate by electrospray ionization tandem mass spectrometry: A mechanistic study. J Am Soc Mass Spectrom 11:986-999.
90. Hunnam V, Harvey DJ, Priestman DA, Bateman RH, Bordoli RS, Tyldesley R. 2001. Ionization and fragmentation of neutral and acidic glycosphingolipids with a Q-TOF mass spectrometer fitted with a Maldi ion source. J Am Soc Mass Spectrom 12:1220-1225.
91. Hunt DF, Stafford GC, Crow FW, Russell JW. 1976. Pulsed positive negative ion chemical ionization mass spectrometry. Anal Chem 48:2098-2105.
92. Jennings KR. 1968. Collision-induced decomposition of aromatic molecular ions. Int J Mass Spectrom Ion Phys 1:227-235.
93. Jensen NJ, Tomer KB, Gross ML. 1985. Gas phase ion decomposition occurring remote to a charge site. J Am Chem Soc 107:1863-1868.
94. Jensen NJ, Tomer KB, Gross ML. 1988. Fast atom bombardment and tandem mass spectrometry of phosphatidylserine and phosphatidylcholine. Lipids 21:580-588.
95. Jensen NJ, Gross ML. 1988. A comparison of mass spectrometry methods for structural determination and analysis of phospholipids. Mass Spectrum Rev 7:41-69.
96. Johnson DW. 1999. Dimethylaminoethyl esters for trace, rapid analysis of fatty acids by electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 13:2388-2393.
97. Johnson DW. 2000. Alkyldimethylaminoethyl ester iodides for improved analysis of fatty acids by electrospray tandem mass spectrometry. Rapid Commun Mass spectrom 14: 2019-2024.
98. Johnson DW, ten Brink HJ, Jakobs C. 2001a. A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res 42:1699-1705.
99. 27 bile acids in plasma and blood samples by tandem mass spectrometry. J Lipid Res 42:9-16.
100. Kaltashov I A, Doroshenko V, Cotter RJ, Takayama K, Qureshi N. 1997. Confirmation of the structure of lipid A derived from the lipopolysaccharide of Rhodobacter sphaeroides by a combination of MALDI, LSIMS, and tandem mass spectrometry. Anal Chem 69:2317-2322.
101. Karas M, Bachmann D, Bahr U, Hillenkamp F. 1987. Matrix-assisted ultraviolet laser desorption of non-volatile compounds. Int J Mass Spectrom Ion Proc 78:53-68.
102. 2-isoprostanes-containing phospholipids. J Lipid Res 34: 1229-1235.
103. Kerwin JL, Wiens AM, Ericsson LH. 1996. Identification of fatty acids by electrospray mass spectrometry and tandem mass spectrometry. J Mass Spectrom 31:184-192.
104. Kingston EE, Beynon JH, Newton RP, Liehr JG. 1985. The differentiation of isomeric biological compounds using collision-induced dissociation of ions generated by fast atom bombardment. Biomed Mass Spectrom 12:525-534.
105. Kuuranne T, Vahermo M, Leinenen A, Kostiainen R. 2000. Electrospray and atmospheric pressure ionization tandem mass spectrometric behaviour of eight anabolic steroid glucuronides. J Am Soc Mass Spectrom 11:722-730.
106. Laganà A, Bacaloni A, Fago G, Marino A. 2000. Trace analysis of estrogenic chemicals in sewage effluent using liquid chromatography combined with tandem mass spectrometry. Rapid Commun Mass Spectrom 14:401-407.
107. Lawson JA, Rokach J, Fitzgerald GA. 1999. Isoprostanes: Formation, analysis and use as indicies of lipid peroxidation in vivo. J Biol Chem 274:24441-24444.
108. 2α-VI, in human urine. J Biol Chem 273:29295-29301.
109. Leinonen A, Kuuranne T, Kostiainen R. 2002. Liquid chromatography/mass spectrometry in anabolic steroid analysis optimization and comparison of three ionization techniques: Electrospray ionisation, atmospheric pressure chemical ionization and atmospheric pressure photoionization. J Mass Spectrom 37:693-698.
110. Lemonde HA, Johnson AW, Clayton PT. 1999. The identification of unusual bile acid metabolites by tandem mass spectrometry: Use of low-energy collision-induced dissociation to produce informative spectra. Rapid Commun Mass Spectrom 13:1159-1164.
111. LePage G, Major H, Preece S. 1996. The identification and characterisation of bile acids by LC/electrospray/MS/MS. Proceedings of the 44th ASMS conference on mass spectrometry and allied topics. May 7-12, Portland Oregon, p 601.
112. LePage G, Yousef I, Sanchez G, Shushan B, Sakuma T. 1995. LC/ Ion Spray/MS/MS analysis of bile acids. Proceedings of the 43rd ASMS conference on mass spectrometry and allied topics. May 21-26, Atlanta Georgia, p 545.
113. Libert R, Hermans D, Draye J.-P, Van Hoof F, Sokal E, de Hoffmann E. 1991. Bile acids and conjugates identified in metabolic disorders by fast atom bombardment and tandem mass spectrometry. Clin Chem 37:2102-2110.
114. Liehr JG, Kingston EE, Beynon JH. 1985. Collision-induced dissociation-mass analyzed ion kinetic energy (CID-MIKE) analysis of ions generated by fast atom bombardment of isomeric bile salts. Biomed Mass Spectrom 12:95-99.
115. Liu S, Sjövall J, Griffiths WJ. 2000. Analysis of oxosteroids by nano-electrospray mass spectrometry of their oximes. Rapid Commun Mass Spectrom 14:390-400.
116. MacPherson JC, Pavlovich JG, Jacobs RS. 1996. Biosynthesis of arachidonic acid metabolites in Limulus polyphemus amebocytes: Analysis by liquid chromatography-electrospray ionization mass spectrometry. Biochim Biophys Acta 1303:127-136.
117. March J. 1977. Advanced organic chemistry: Reactions, mechanisms, and structure. 2nd edition. Tokyo: McGraw-Hill Kogakusha.
118. March RE, Todd JFJ. 1995. Practical aspects of ion trap mass spectrometry. Boca Raton: CRC Press. Vols. I-III.
119. Margalit A, Duffin KL, Isakson PC. 1996. Rapid quantitation of a large scope of eicosanoids in two models of inflammation: Development of an electrospray and tandem mass spectrometry method and application to biological studies. Anal Biochem 235:73-81.
120. Marschall H-U, Griffiths WJ, Zhang J, Wietholtz H, Matern H, Matern S, Sjövall J. 1994a. Position of conjugation of bile acids with glucose and N-acetylglucosamine in vitro. J Lipid Res 35:1599-1610.
121. Marschall H-U, Griffiths WJ, Götze U, Zhang J, Wietholtz H, Busch N, Sjövall J, Matern S. 1994b. The major metabolites of ursodeoxycholic acid in human urine are conjugated with N-acetylglucosamine. Hepatalogy 20:845-853.
122. Mata de Urquiza A, Liu S, Sjöberg M, Zetterström R, Griffiths WJ, Sjövall J, Perlmann T. 2000. Docosahaxaenoic acid, a ligand for the retinoid X receptor in mouse brain. Science 290:2140-2144.
123. McLafferty FW. 1983. Tandem mass spectrometry. New York: John Wiley & Sons.
124. Meng LJ, Griffiths WJ, Sjövall J. 1996. The identification of novel steroid N-acetylglucosaminides in the urine of pregnant women. J Steroid Biochem Mol Biol 58:585-598.
125. Meng LJ, Griffiths WJ, Nazer H, Yang Y, Sjövall J. 1997. High levels of (24S)-24-hydroxycholesterol 3-sulfate 24-glucuronide in the serum and urine of children with severe cholestatic liver disease. J Lipid Res 38:926-934.
126. Metzger K, Rehberger PA, Erben G, Lehmann WD. 1995. Identification and quantification of lipid sulphate esters by electrospray ionization MS/MS techniques: Cholesterol sulphate. Anal Chem 67:4178-4183.
127. Mills KA, Mushlaq I, Johnson AW, Whitfield PD, Clayton PT. 1998. A method for the quantitation of conjugated bile acids in dried blood spots using electrospray ionization mass spectrometry. Pediatr Res 43:361-368.
128. 2-isoprostanes using gas chromatograophy-mass spectrometry. Anal Biochem 268:117-125.
129. Morris HR, Paxton T, Dell A, Langhorne J, Berg M, Bordoli RS, Hoyes J, Bateman RH. 1996. High sensitivity collisionally-activated decomposition tandem mass spectrometry on a novel quadrupole/orthogonal-acceleration time-of-flight mass spectrometer. Rapid Commun Mass Spectrom 10: 889-896.
130. Murphy RC. 1993. Mass spectrometry of lipids. In: Snyder F, editor. Handbook of lipid research. Volume 7. New York: Plenum, p 213-243.
131. Murphy RC. 1995. Lipid mediators, leukotrienes and mass spectrometry. J Mass Spectrom 30:5-16.
132. Murphy RC, Fiedler J, Hevko J. 2001. Analysis of nonvolatile lipids by mass spectrometry. Chem Rev 101:479-526.
133. Murphy RC, Harrison KA. 1994. Fast atom bombardment mass spectrometry of phospholipds. Mass Spectrom Rev 13:57-75.
134. Murphy RC, Harrison KA. 1996. Isoeicosanoids: Mass spectrometry of free radical oxidation products derived from aracidonyl phospholipids. In: Burlingame AL, Carr SA, editors. Mass spectrometry in biological sciences. New Jersey: Humana Press Inc. p 451-475.
135. Murphy RC, Zirrolli JA. 1994. Lipid mediators, eicosanoids and fatty acids. In: Matsuo T, Caprioli RM, Gross ML, Seyma Y, editors. Biological mass spectrometry present and future. Chichester: John Wiley & Sons, p 463-479.
136. Murray S, Rendell NB, Taylor GW. 1996. Microbore high-performance liquid chromalography-electrospray ionisation mass spectrometry of steroid sulphates. J Chromatogr A 738:191-199.
137. Mushtaq I, Logan S, Morris M, Johnson AW, Wade AM, Kelly D, Clayton PT. 1999. Screening of newborn infants for cholestatic hepatobiliary disease with tandem mass spectrometry. Br Med J 319:471-477.
138. Nakamura T, Takazawa T, Maruyama-Ohkai Y, Nagaki H, Kinoshita T. 1993. Location of double bonds in unsaturated fatty alchols by microderivatization and liquid secondary ion tandem mass spectrometry. Anal Chem 65:837-840.
139. Nieves E, Tang X-J, Cohen P, Pollard J. 1994. Investigation of testicular steroidogenesis in osteopetrotic mice by electrospray ionization tandem mass spectrometry. Proceedings of the 42nd ASMS conference on mass spectrometry and allied topics. May 29-June 3, Chicago IL. p 161.
140. Nizigimana L, Rajan PK, Haemers A, Claeys M, Derrick PJ. 1997. Mechanistic aspects of high-energy collision-induced dissociation proximate to the charge in saturated fatty acid esters cationized with lithium. Evidence for hydrogen radical removal. Rapid Commun Mass Spectrom 11:1808-1812.
141. O'Brien-Coker IC, Perkins G, Mallet AI. 2001. Aldehyde analysis by high performance liquid chromatography/ tandem mass spectrometry. Rapid Commun Mass Spectrom 15:920-928.
142. Pelizzi N, Catinella S, Barboso S, Zanol M. 2002. Different electrospray tandem mass spectrometric approaches for rapid characterization of phospholipid classes of Curosurf, a natural surfactant. Rapid Commun Mass Spectrom 16: 2215-2220.
143. Perwaiz S, Tuchweber B, Mignault D, Gilat T, Yousef IM. 2001. Determination of bile acids in biological fluids by liquid chromatography-electrospray tandem mass spectrometry. J Lipid Res 42:114-119.
144. Petković M, Schiller J, Müller M, Benard S, Reichl S, Arnold K, Arnhold J. 2001. Detection of individual phospholipids in lipid mixtures by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry: Phosphatidylcholine prevents the detection of further species. Anal Biochem 289:202-216.
145. Purdom CE, Hardiman PA, Bye VJ, Eno NC, Tyler CR, Sumpter JP. 1994. Estrogenic effects of effluents from sewage treatment works. Chem Ecol 8:275-285.
146. Quirke JM, Hsu Y-L, Van Berkel GJ. 2000. Ferrocene-based electroactive deivatizing reagents for the rapid selective screening of alcohols and phenols in natural product mixtures using electrospray-tandem mass spectrometry. J Nat Prod 63:230-237.
147. Raftery MJ, Thorne GC, Orkiszewski RS, Gaskell SJ. 1990. Preparation and tandem mass spectrometric analysis of deuterium-labeled cysteine-containing leukotrienes. Biomed Environ Mass Spectrom 19:465-474.
148. Roda A, Gioacchini AM, Cerrè C, Baraldini M. 1995. High performance liquid chromatographic-eleclrospray mass spectrometric analysis of bile acids in biological fluids. J Chromatogr 665:281-294.
149. Roepstorff P, Fohl man J. 1984. Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed Mass Spectrom 11:601.
150. Routledge EJ, Sheahan D, Desbrow C, Sumpter JP, Waldock M. 1998. Identification of estrogenic chemicals in STW effluent. 2. In vivo response in trout and roach. Environ Sci Technol 32:1559-1565.
151. Rule G, Henion J. 1999. High-throughput sample preparation and analysis using 96-well membrane solid-phase extraction and liquid chromatography-tandem mass spectrometry for the determination of steroids in human urine. J Am Soc Mass Spectrom 10:1322-1327.
152. Ryhage R. 1993. The mass spectrometry laboratory at the Karolinska Institute 1944-1987. Mass Spectrom Rev 12:1-49.
153. Sakuma T, Sanchez G, Burton L, Shushan B. 1996. LC/Ionspray/MS/MS analysis of bile acids. Proceedings of the 44th ASMS conference on mass spectrometry and allied topics. May 7-12, Portland Oregon. p 1292.
154. 4 in human urine. J Am Soc Mass Spectrom 2:314-321.
155. Sandhoff R, Brügger B, Jeckel D, Lehmann WD, Wieland FT. 1999. Determination of cholesterol at the low picomole level by nano-electrospray ionization mass spectrometry. J Lipid Res 40:126-132.
156. Schorno KS, Winslow LD. 1995. Application of ionspray MS/ MS quantification of beclomethasone dipropionate. Proceedings of the 43rd ASMS conference on mass spectrometry and allied topics. May 21-26, Atlanta Ga. p 662.
157. Setchell KDR, Schwarz M, O'Connell NC, Lund EG, Davis DL, Lathe R, Thompson HR, Tyson RW, Sokol RJ, Russell DW. 1998. Identification of a new inborn error in bile acid synthesis: Mutation of the oxysterol 7α-hydroxylase gene causes severe neonatal liver disease. J Clin Invest 102:1690-1703.
158. Shackleton CH, Merdinck J, Lawson AM. 1990. Steroid and bile acid analysis. In: McEwen CN, Larsen BS, editors. Mass spectrometry of biological materials. New York: Marcel Dekker Inc. p 297-377.
159. Shackleton CHL, ChuangH, Kirn J, de la TorreX, Segura J. 1997. Electrospray mass spectrometry of testosterone esters: Potential for use in doping control. Steroids 62:523-529.
160. Shimada K, Mukai Y, Yago K. 1998. Studies on neurosteroids. VII. Characterization of pregnenolone, its sulfate and dehydroepiandrosterone in rat brain using liquid chromatography/mass spectrometry. J Liq Chrom Rel Technol 21: 765-775.
161. Shimada K, Mukai Y. 1998. Studies on neurosteroids VII. Determination of pregnenolone and its 3-stearate in rat brains using high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. J Chromatogr B 714:153-160.
162. Singh G, Gutierrez A, Xu K, Blair IA. 2000. Liquid chromatography/electron capture atmospheric pressure chemical ionization/mass spectrometry: Analysis of pentafluorobenzyl derivatives of biomolecules and drugs in the attomole range. Anal Chem 72:3007-3013.
163. Sjövall J, Axelson M. 1982. Newer approaches to the isolation,
164. SjÖvall J, Vihko R. 1968. Analysis of solvolyzable steroids in human plasma by combined gas chromatography - mass spectrometry. Acta Endocrinol 57:247-260.
165. Stroobant V, de Hoffmann E, Libert R, Van Hoof F. 1995. Fast-atom bombardment mass spectrometry and low energy collision-induced tandem mass spectrometry of tauroconjugated bile acid anions. J Am Soc Mass Spectrom 6:588-596.
166. Taguchi R, Hayakawa J, Takeuchi Y, Ishida M. 2000. Two-dimensional analysis if phospholipids by capillary liquid chromatography/electrospray ionization mass spectrometry. J Mass Spectrom 35:953-966.
167. Takach EJ, Wang R, Zhu Q, Hsieh F, Campbell JM, Vestal ML. 2002. Drug characterization and metabolite identification using MALDI-TOF/TOF for accurate mass MS/MS analysis. Proceedings of the 50th ASMS conference on mass spectrometry and allied topics. June 2-6, Orlando FL. ThPN 295.
168. Tomer KB, Crow FW, Gross ML. 1983. Location of double bond position in unsaturated fatty acids by negative ion MS/MS. J Am Chem Soc 105:5487-5488.
169. Tomer KB, Gross ML. 1988. Fast atom bombardment and tandem mass spectrometry for structural determination: Remote charge site fragmentation of steroid conjugates and bile salts. Biomed Environ Mass Spectrom 15:89-98.
170. Tomer KB, Jensen NJ, Gross ML, Whitney J. 1986. Fast atom bombardment combined with tandem mass spectrometry for determination of bile salts and their conjugates. Biomed Environ Mass Spectrom 13:265-272.
171. Tsikas D. 1998. Application of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to asses in vivo synthesis of prostaglandins, thromboxane, leukotrienes, isoprostanes and related compounds in human. J Chromatogr 717:201-245.
172. Tyler AN, Clayton E, Green BN. 1996. Exact mass measurements of polar organic molecules at low resolution using electrospray ionization and a quadrupole mass spectrometer. Anal Chem 68:3561-3569.
173. Van Berkel GJ, Quirke JME, Tigani RA, Dilley AS, Covey TR. 1998. Derivatization for electrospray ionization mass spectrometry. 3. Electrochemically ionizable derivatives. Anal Chem 70:1544-1554.
174. Vetter W, Meister W, Oesterhelt G. 1998. 2-Alkylimidazoline derivative to control fatty acid fragmentation upon electron impact and electrospray ionization. J Mass Spectrom 33: 461-472.
175. Warrack BM, DiDonato GC. 1993. Ion spray liquid chromatography/mass spectrometric characterization of bile acids. Biol Mass Spectrom 22:101-111.
176. Watson D, Taylor GW, Murray S. 1985. Thermospray liquid chromatography negative ion mass spectrometry of steroid sulphate conjugates. Biomed Mass Spectrom 12:610-615.
177. 2-isoprostane regioisomers formed in vivo in the rat. Free Radical Biol Med 23:943-954.
178. Weidolf LOG, Lee ED, Henion JD. 1988. Determination of boldenone sulfoconjugate and related steroid sulfates in equine urine by high-performance liquid chromatography/tandem mass spectrometry. Biomed Environ Mass Spectrom 15:283-289.
179. Wheelan P, Zirrolli JA, Murphy RC. 1993. Low energy fast atom bombardment tandem mass spectrometry of monohydroxy substituted unsaturated fatty acids. Biol Mass Spectrom 22:465-473.
180. 4-derived metabolites. J Am Soc Mass Spectrom 7:129-139.
181. Wheelan P, Zirrolli JA, Murphy RC. 1996b. Electrospray ionizalion and low energy tandem mass spectrometry of polyhydroxy unsaturated fatty acids. J Am Soc Mass Spectrom 7:140-149.
182. Wheeler OH. 1968. The Girard reagents. J Chem Edu 45:435-437.
183. Whitney J, Lewis S, Straub KM, Thaler MM, Burlingame AL. 1981. Analysis of conjugated bile salts in human duodenal bile using fast atom bombardment and field desorption mass spectrometry. Koenshu-Iyo Masu Kenkyukai 6:33-44.
184. Williams TM, Kind AJ, Houghton E, Hill DW. 1999. Electrospray collision induced dissociation of testosterone and testosterone hydroxy analogs. J Mass Spectrom 34:206-216.
185. Wilm MS, Mann M. 1994, Electrospray and Taylor-cone theory: Dole's beam of macromolecules at last? Int J Mass Spectrom Ion Processes 136:167-180.
186. Wong T, Shackleton CHL, Covey TR, Ellis G. 1992. Identification of the steroids in neonatal plasma that interfere with 17α-hydroxyprogesterone radioimmuoassays. Clin Chem 38:1830-1837.
187. Wood KV, Sun Y, Elkin RG. 1991. Differentiation of isomeric conjugated bile acids using positive-ion B/E linked scans. Anal Chem 63:247-250.
188. 4 in human urine by liquid chromatography coupled with ionspray tandem mass spectrometry. J Mass Spectrom 31: 987-993.
189. Wysocki VH, Ross MM. 1991. Charge-remote fragmentation of gas-phase ions: Mechanistic and energetic considerations in the dissociation of long-chain functionalized alkanes and alkenes. Int J Mass Spectrom Ion Processes 104:179-211.
190. Yamashita M, Fenn JB. 1984a. Electrospray ion source. Another variation on the free-jet theme. J Phys Chem 88:4451-4459.
191. Yamashita M, Fenn JB. 1984b. Negative ion production with the electrospray ion source. J Phys Chem 88:4671-4675.
192. Yang Y, Griffiths WJ, Lindgren JÅ, Sjövall J. 1995. Liquid chromatography/mass spectrometry with collision induced dissociation of arachidonic acid metabolites derivatized with aminobenzenesulphonic acid. Rapid Commun Mass Spectrom 9:289-299.
193. Yang Y, Griffiths WJ, Nazer H, Sjövall J. 1997. Analysis of bile acids and bile alcohols in urine by capillary column liquid chromatography-mass spectrometry using fast atom bombardment or electrospray ionisation and collision induced dissociation. Biomed Chromatogr 11:240-255.
194. Yergey AL, Coorssen JR, Backlund PS, Blank PS, Humphrey GA, Zimmerberg J, Campbell JM, Vestal ML. 2002. De novo sequencing of peptides using MALDI/TOF-TOF. J Am Soc Mass Spectrom 13:784-791.
195. Yost RA, Enke CG. 1978. Selected ion fragmentation with a tandem quadrupole mass spectrometer. J Am Chem Soc 100:2274-2275.
196. Zhang J, Griffiths WJ, Bergman T, Sjövall J. 1993. Derivatization of bile acids with taurine for analysis by fast atom bombardment mass spectrometry with collision-induced fragmentation. J Lipid Res 11:1895-1900.
197. Zirrolli J.A., Davoli E., Bettazzoli L., Gross M.L, Murphy R.C. 1990. Fast atom bombardment and collision-induced dissociation of prostaglandins and thromboxanes: Some examples of charge remote fragmentation. J Am Soc Mass Spectrom 1:325-335.