Novel fragmentation pathways of anionic adducts of steroids formed by electrospray anion attachment involving regioselective attachment, regiospecific decompositions, charge-induced pathways, and ion-dipole complex intermediates

Journal of the American Society for Mass Spectrometry

Volumn 23, Issue 9, 2012, Pages 1558-1568

  Rannulu, Nalaka S ^a   Cole, Richard B ^a,b  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b Université Pierre et Marie Curie   (France)

Author keywords

Anion attachment; Charge induced decomposition; Electrospray; Ion dipole complex; Ion neutral complex; Mass spectrometry; Regioselective; Regiospecific; Steroids

Indexed keywords

ELECTROSPRAYS; ION-DIPOLE COMPLEXES; ION-NEUTRAL COMPLEX; REGIO-SELECTIVE; REGIOSPECIFIC; STEROIDS;

CHLORINE COMPOUNDS; DECOMPOSITION; DEUTERIUM; FLUORINE; FUNCTIONAL GROUPS; LIPIDS; MASS SPECTROMETRY; REGIOSELECTIVITY; SULFONATION; VOLATILE FATTY ACIDS;

NEGATIVE IONS;

BICARBONATE; PREGNENOLONE; STEROID;

ARTICLE; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; COMPLEX FORMATION; DECOMPOSITION; ELECTROSPRAY; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; ION DIPOLE COMPLEX; NEGATIVE ION ELECTROSPRAY; PROTON TRANSPORT; STATIC ELECTRICITY; STRUCTURE ANALYSIS;

ACETATES; ANIONS; BICARBONATES; ESTRADIOL; ISOMERISM; MODELS, MOLECULAR; PREGNENOLONE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84865736199     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-012-0422-y     Document Type: Article

References (61)

1. Rachel, L.G., Snape, W.M., Colin, E., Sephton, M.A.: Conjugated steroids: Analytical approaches and applications. Anal. Bioanal. Chem. 393(2), 453-458 (2009) (Pubitemid 50307417)
2. Buko, V.U.: Non-structural lipids and their derivatives as antioxidants. Curr. Top. Biophys. 24(2), 29-34 (2000)
3. Aumais, J.P., Lee, H.S., DeGannes, C., Horsford, J., White, J.H.: Function of directly repeated half-sites as response elements for steroid hormone receptors. J. Biol. Chem. 271(21), 12568-12577 (1996) (Pubitemid 26160931)
4. Pulkkinen, M., Hamalainen, M.M.: Myometrial estrogen and progesterone receptor binding in pregnancy: Inhibition by the detergent action by phospholipids. J. Steroid Biochem. Mol. Biol. 52(3), 287-294 (1995)
5. Baulieu, E.E.: Neurosteroids: A new function in the brain. Biol. Cell 71 (1/2), 3-10 (1991)
6. Galigniana, M.D.: Functional regulation of corticosteroid receptors by phosphorylation and redox potential. Curr. Top. Steroid Res. 3, 1-22 (2000)
7. Wendler, A., Wehling, M.: Translational research on rapid steroid actions. Steroids 75(8-9), 619-623 (2010)
8. Scarf, A.M., Ittner, L.M., Kassiou, M.: The translocator protein (18 kDa): Central nervous system disease and drug design. J. Med. Chem. 52(3), 581-592 (2009)
9. Thevis, M., Schanzer, W.: Mass spectrometry in sports drug testing: Structure characterization and analytical assays. Mass Spectrom. Rev. 26, 79-107 (2007) (Pubitemid 46051814)
10. Segura, J., Ventura, R., Marcos, J., Gutierrez-Gallego, R.: In: Bogusz, M.J. (ed.) Handbook of Analytical Separations. Forensic Sci, vol. 6, p. 699. Elsevier Science, Amsterdam (2008)
11. Zacharia, L.C., Dubey, R.K., Jackson, E.K.: A gas chromatography/ mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma. Steroids 69(4), 255-261 (2004) (Pubitemid 38748721)
12. Bowden, A.J., Colosi, C.D., Stutts, W.L., Mora-Montero, D.C., Garrett, T.J., Yost, R.A.: Enhanced analysis of steroids by gas chromatography/ mass spectrometry using microwave-accelerated derivatization. Anal. Chem. 81, 6725-6734 (2009)
13. Petrovic, M., Eljarrat, E., López de Alda, M.J., Barcelo, D.: Recent advances in the mass spectrometric analysis related to endocrine disrupting compounds in aquatic environmental samples. J. Chromatogr. A 974, 23-51 (2002)
14. Hernando, M.D., Mezcua, M., Gomez, M.J., Malato, O., Aguera, A., Fernandez-Alba, A.R.: Comparative study of analytical methods involving gas chromatography-mass spectrometry after derivatization and gas chromatography-tandem mass spectrometry for the determination of selected endocrine disrupting compounds in wastewaters. J. Chromatogr. A 1047, 129-135 (2004) (Pubitemid 39092920)
15. Ternes, T.A., Anderson, H., Gilberg, D., Bonerz, M.: Determination of estrogens in sludge and sediments by liquid extraction and GC/MS/MS. Anal. Chem. 74, 3498-3504 (2002) (Pubitemid 34764959)
16. Wang, Y., Hornshaw, M., Alvelius, G., Bodin, K., Liu, S., Sjoevall, J., Griffiths, W.J.: Matrix-assisted laser desorption/ionization high-energy collision-induced dissociation of steroids: Analysis of oxysterols in rat brain. Anal. Chem. 78(1), 164-173 (2006) (Pubitemid 43050151)
17. Guo, T., Chan, M., Soldin, S.: Steroid profiles using liquid chromatography-tandem mass spectrometry with atmospheric pressure photoionization source. J. Arch. Pathol. Lab. Med. 128, 469-475 (2004) (Pubitemid 38451141)
18. Shimada, K., Mitamura, K., Higashi, T.: Gas chromatography and highperformance liquid chromatography of natural steroids. J. Chromatogr. A 935, 141-172 (2001) (Pubitemid 33044645)
19. Ho, E.N.M., Leung, D.K.K., Wan, T.S.M., Yu, N.H.: Comprehensive screening of anabolic steroids, corticosteroids, and acidic drugs in horse urine by solid-phase extraction and liquid chromatography-mass spectrometry. J. Chromatogr. A 1120, 38-53 (2006) (Pubitemid 43866772)
20. Griffiths, W.J., Wang, Y., Alvelius, G., Liu, S., Bodin, K., Sjovall, J.: Analysis of oxysterols by electrospray tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 17, 341-362 (2006) (Pubitemid 43290194)
21. Hommerson, P., Khan, A.M., De Jong, G.J., Somsen, G.W.: Comparison of electrospray ionization and atmospheric pressure photoionization for coupling of micellar electrokinetic chromatography with ion trap mass spectrometry. J. Chromatogr. A 1204, 197-203 (2008)
22. Li, X., David, C.S.: Analysis of steroidal estrogens as pyridine-3-sulfonyl derivatives by liquid chromatography electrospray tandem mass spectrometry. Anal. Biochem. 375, 105-114 (2008)
23. Lin, Y.H., Chen, C.Y., Wang, G.S.: Analysis of steroid estrogens in water using liquid chromatography/tandem mass spectrometry with chemical derivatizations. Rapid Commun. Mass Spectrom. 21, 1973-1983 (2007)
24. El-Aneed, A., Banoub, J., Koen-Alonso, M., Boullanger, P., Lafont, D.: Establishment of mass spectrometric fingerprints of novel synthetic cholesteryl neoglycolipids: The presence of a unique C-glycoside species during electrospray ionization and during collision-induced dissociation tandem mass spectrometry. J. Am. Soc.Mass Spectrom. 18, 294-310 (2007) (Pubitemid 46150103)
25. Spfeifer, U.T., Spiteler, M.: APCI-MS/MS: A powerful tool for the analysis of bound residues resulting from the interaction of pesticides with DOM and humic substances. Environ. Sci. Technol. 34, 3514-3520 (2000)
26. Khan, M.A., Wang, Y., Heidelberger, S., Alvelius, G., Liu, S., Sjovall, J., Griffiths, W.J.: Analysis of derivatized steroids by matrix-assisted laser desorption/ionization and post-source decay mass spectrometry. Steroids 71(1), 42-53 (2006) (Pubitemid 41743827)
27. Galesio, M., Rial-Otero, R., Capelo-Martinez, J.L.: Comparative study of matrices for their use in the rapid screening of anabolic steroids by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 23, 1783-1791 (2009)
28. Brombacher, S., Owen, S.J., Volmer, D.A.: Automated coupling of capillary-HPLC to matrix-assisted laser desorption/ionization mass spectrometry for the analysis of small molecules utilizing a reactive matrix. Anal. Bioanal. Chem. 376(6), 773-779 (2003) (Pubitemid 40877939)
29. Summers, R.H., Herold, D.A., Seely, B.L.: Hormonal and genetic analysis of a patient with congenital adrenal hyperplasia. Clin. Chem. 42, 1483-1487 (1996) (Pubitemid 26300250)
30. Kuuranne, T., Vahermo, M., Leinonen, A., Kostiainen, R.: Electrospray and atmospheric pressure chemical ionization tandem mass spectrometric behavior of eight anabolic steroid glucuronides. J. Am. Soc. Mass Spectrom. 11, 722-730 (2000) (Pubitemid 34521228)
31. Liu, S., Sjovall, J., Griffiths, W.J.: Analysis of oxosteroids by nanoelectrospray mass spectrometry of their oximes. Rapid Commun. Mass Spectrom. 14, 390-400 (2000) (Pubitemid 30152986)
32. Griffiths, W.J.: Tandem mass spectrometry in the study of fatty acids, bile acids, and steroids. Mass Spectrom. Rev. 22, 81-152 (2003)
33. Guan, F., Soma, L.R., Luo, Y., Uboh, C.E., Peterman, S.: Collisioninduced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry. J. Am. Soc. Mass. Spectrom. 17 (4), 477-489 (2006)
34. Thevis, M., Schaenzer, W.: Mass spectrometric analysis of androstan-17β-ol-3-one and androstadiene-17β-ol-3-one isomers. J. Am. Soc. Mass. Spectrom. 16(10), 1660-1669 (2005) (Pubitemid 41345158)
35. Catlin, D.H., Sekera, M.H., Ahrens, B.D., Starcevic, B., Chang, Y.C., Hatton, C.K.: Tetrahydrogestrinone: Discovery, synthesis, and detection in urine. Rapid Commun. Mass Spectrom. 18, 1245-1249 (2004) (Pubitemid 38843145)
36. Ferguson, P.L., Iden, C.R., McElroy, A.E., Brownawell, B.J.: Determination of steroid estrogens in wastewater by immunoaffinity extraction coupled with HPLC-electrospray-MS. Anal. Chem. 73, 3890-3895 (2001) (Pubitemid 32896161)
37. Mazzarino, M., Botre, F.: A fast liquid chromatographic/mass spectrometric screening method for the simultaneous detection of synthetic glucocorticoids, some stimulants, anti-estrogen drugs, and synthetic anabolic steroids. Rapid Commun. Mass Spectrom. 20, 3465-3476 (2006) (Pubitemid 44763947)
38. Higashi, T., Takayama, N., Shimada, K.: Enzymic conversion of 3-hydroxy-5-ene-steroids and their sulfates to 3-oxo-4-ene-steroids for increasing sensitivity in LC-APCI-MS. J. Pharm. Biomed. Anal. 39, 718-723 (2005) (Pubitemid 41196088)
39. Pozo, O.J., Van Eenoo, P., Deventer, K., Delbeke, F.T.: Ionization of anabolic steroids by adduct formation in liquid chromatography electrospray mass spectrometry. J. Mass Spectrom. 42, 497-516 (2007) (Pubitemid 46649086)
40. Antignac, J.P., Le Bizec, B., Monteau, F., Poulain, F., Andre, F.: 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 (2000) (Pubitemid 30033790)
41. Pozo, O.J., Ventura, R., Monfort, N., Segura, J., Delbeke, F.T.: Evaluation of different scan methods for the urinary detection of corticosteroid metabolites by liquid chromatography tandem mass spectrometry. J. Mass Spectrom. 44, 929-944 (2009)
42. Tolgyesi, A., Sharmab, V.K., Kovacsicsa, L., Feketec, J.: Quantification of corticosteroids in bovine urine using selective solid phase extraction and reversed-phase liquid chromatography /tandem mass spectrometry. J. Chromatogr. B 878, 1471-1479 (2010)
43. Cole, R.B., Zhu, J.: Chloride Anion Attachment in Negative Ion Electrospray Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom. 13, 607-611 (1999) (Pubitemid 29160412)
44. Zhu, J., Cole, R.B.: Formation and decompositions of chloride adduct ions, [M+Cl], in negative ion electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 11, 932-941 (2000) (Pubitemid 34546663)
45. Zhu, J., Cole, R.B.: Ranking of gas-phase acidities and chloride affinities of monosaccharides and linkage specificity in collisioninduced decompositions of negative ion electrospray-generated chloride adducts of oligosaccharides. J. Am. Soc. Mass Spectrom. 12, 1193-1204 (2001) (Pubitemid 34552647)
46. Cai, Y., Cole, R.B.: Stabilization of anionic adducts in negative ion electrospray mass spectrometry. Anal. Chem. 74, 985-991 (2002) (Pubitemid 34203020)
47. Cai, Y., Concha, M.C., Murray, J.S., Cole, R.B.: Evaluation of the role of multiple hydrogen bonding in offering stability to negative ion adducts in electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 13, 1360-1369 (2002) (Pubitemid 36873818)
48. Cai, Y., Jiang, Y., Cole, R.B.: Anionic adducts of oligosaccharides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal. Chem. 75, 1638-1644 (2003) (Pubitemid 36512602)
49. Jiang, Y., Cole, R.B.: Oligosaccharide analysis using anion attachment in negative mode electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 16, 60-70 (2005) (Pubitemid 40093801)
50. Guan, B., Cole, R.B.: Differentiation of both linkage position and anomeric configuration in underivatized glucopyranosyl disaccharides by anion attachment with post-source decay in matrix-assisted laser desorption/ionization linear field reflectron time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 21, 3165-3168 (2007) (Pubitemid 47401456)
51. Guan, B., Cole, R.B.: MALDI linear-field reflectron TOF post-source decay analysis of underivatized oligosaccharides: Determination of glycosidic linkages and anomeric configurations using anion attachment. J. Am. Soc. Mass Spectrom. 19, 1119-1131 (2008)
52. Cole, R.B., Rannulu, N.S.: Regioselective anion attachment leading to regiospecific decompositions of bifunctional steroids in negative ion electrospray tandem mass spectrometry. Rapid Commun. Mass Spectrom. 25, 558-562 (2011)
53. Thevis, M., Makarov, A.A., Horning, S., Schanzer, W.: Mass spectrometry of stanozolol and its analogues using electrospray ionization and collision-induced dissociation with quadrupole-linear ion trap and linear ion trap-Orbitrap hybrid mass analyzers. Rapid Commun. Mass Spectrom. 19, 3369-3378 (2005) (Pubitemid 41682068)
54. Mallard, W.G.: Linstrom, P.J., Eds., NIST Chemistry WebBook, NIST Standard Reference Database Number 69; National Institute of Standards and Technology; Gaithersburg,MD. Available at: Http://webbook.nist.gov. Accessed 2011
55. Breuker, K., Knochenmuss, R., Zenobi, R.: Gas-phase basicities of deprotonated matrix-assisted laser desorption/ionization matrix molecules. Int. J. Mass Spectrom. 184, 25-38 (1999)
56. Blondel, C., Cacciani, P., Delsart, C., Trainham, R.: High-resolution determination of the electron affinity of fluorine and bromine using crossed ion and laser beams. Phys. Rev. A 40, 3698-3701 (1989)
57. Squires, R.R.: Gas-phase thermochemical properties of the bicarbonate and bisulfite ions. Int. J. Mass Spectrom. Ion Process. 117, 565-600 (1992)
58. Silwal, I.K.C., Rasaiah, J.C., Szulejko, J.E., Solouki, T.: Proton transfer reactions of halogenated compounds: Using gas chromatography/Fourier transform ion cyclotron resonance mass spectrometry (GC/FT-ICR MS) and ab initio calculations. Int. J. Mass Spectrom. 293, 1-11 (2010)
59. Jobst, K.J., Hasan, S.A., Terlouw, J.K.: Does the ion-molecule reaction between HC≡CH·+ and HCN lead to CH2=CH-C≡N·+? A computational and experimental study of the reverse process. Chem. Phys. Lett. 450, 243-247 (2008)
60. Longevialle, P.: Ion-neutral complexes in the unimolecular reactivity of organic cations in the gas phase. Mass Spectrom. Rev. 11, 157-192 (1992)
61. McLafferty, F., Turecek, F.: Interpretation of Mass Spectra, 4th edn, p. 131. University Science Books, Mill Valley, CA (1993)