9,10-Diphenylanthracene as a matrix for MALDI-MS electron transfer secondary reactions

Journal of Mass Spectrometry

Volumn 47, Issue 8, 2012, Pages 995-1003

  Nazim Boutaghou, M ^a   Cole, Richard B ^a,b  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b Université Pierre et Marie Curie   (France)

Author keywords

9,10 diphenylanthracene; electron transfer; endothermic; MALDI; matrix; secondary reaction

Indexed keywords

9 ,10-DIPHENYLANTHRACENE; ELECTRON TRANSFER; ENDOTHERMIC; MALDI; SECONDARY REACTIONS;

CHARGE TRANSFER; ELECTRON TRANSITIONS; IONIZATION POTENTIAL; MATRIX ALGEBRA; PROTEINS;

FREE RADICAL REACTIONS;

9,10 DIPHENYLANTHRACENE; ANTHRACENE DERIVATIVE; CHLOROPHYLL; CHOLESTEROL; FULLERENE DERIVATIVE; MENAQUINONE; PORPHYRIN; PROTOPORPHYRIN ZINC; RETINOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; GAS; IONIZATION; LASER; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; THERMODYNAMICS;

EID: 84865206753     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3027     Document Type: Article

References (41)

1. M. Karas, D. Bachman, U. Bahr, F. Hillenkamp,. Matrix-assisted ultraviolet Laser desorption of non-volatile compounds. Int. J. Mass Spectrom. Ion Processes. 1987, 78, 53.
2. M. Karas, F. Hillenkamp,. Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons. Anal. Chem. 1988, 60, 2299.
3. K. Tanaka, H. Waki, Y. Ido, S. Akita, Y. Yoshida, T. Yoshida,. Protein and polymer analysis up to m/z 100,000 by laser ionization time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 1988, 2, 151.
4. R. C. Beavis, T. Chaudhary, B. T. Chait,. α-cyano-4-Hydroxycinnamic Acid as a Matrix for Matrix Assisted Laser-Desorption Mass Spectrometry. Org. Mass Spectrom. 1992, 27, 156.
5. R. C. Beavis, B. T. Chait,. Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins. Rapid Commun. Mass Spectrom. 1989, 3, 432.
6. K. Breuker, R. Knochenmuss, J. Zhang, A. Stortelder, R. Zenobi,., Thermodynamic Control of Final Ion Distribution in MALDI: In-Plume Proton Transfer Reactions,. Int. J. Mass Spectrom. 2003, 226, 211.
7. U. Bahr, A. Depee, M. Karas, F. Hillenkamp, U. Giessman,. Mass spectrometry of synthetic polymers by UV-matrix-assisted laser desorption/ionization. Anal. Chem. 1992, 64, 2866.
8. Y. Suzuki, M. Suzuki, E Ito, N. Goto-Inoue, K. Miseki, J. Lida, Y. Yamazaki, M. Yamada, A. Suzuki,. Convenient structural analysis of glycosphingolipids using MALDI-QIT-TOF mass spectrometry with increased laser power and cooling gas flow. J. Biochem. 2006, 139, 771.
9. S. Trimpin, D. E. Clemmer, C. N. McEwen,. Charge-remote fragmentation of lithiated fatty acids on a TOF-TOF instrument using matrix-ionization. J. Am. Soc. Mass Spectrom. 2007, 18, 1967.
10. R. Knochenmuss,. MALDI ionization mechanisms: an overview. In Electrospray and MALDI Mass Spectrometry: fundamentals, Instrumentation, Practicalities, and Biological Applications, R. B. Cole, (Ed). John Wiley & Sons: Hoboken, NJ, 2010, 149-184.
11. T.D. Mc Carley, R. L. Mc Carley, P. A. Limbach,. Electron-Transfer Ionization in Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry. Anal. Chem. 1998, 70, 4376.
12. S. F. Macha, T. D. Mc Carley, P. A. Limbach,. Influence of ionization energy on charge-transfer ionization in matrix-assisted laser desorption/ionization mass spectrometry. Anal. Chim. Acta 1999, 397, 235.
13. A. J. Hoteling, W. F. Nichols, D. J. Giesen, J. R. Lenhard, R. Knochenmuss,. Electron transfer reactions in MALDI: factors influencing matrix and analyte ion intensities. Eur. J. Mass Spectrom. 2006, 12, 345.
14. R. Knochenmuss, L. V. Zhigilei,. Molecular dynamics simulations of MALDI: laser fluence and pulse width dependence of plume characteristics and consequences for matrix and analyte ionization. J. Mass Spectrom. 2010, 45, 333.
15. A. V. Streletskii, I. N. Ioffe, S. G. Kotsiris, M. P. Barrow, T. Drewello, S. Strauss, O. V. Boltalina,. In-plume thermodynamics of the MALDI generation of fluorofullerene anions. J. Phys. Chem. A 2005, 109, 714.
16. J. De Winter, G. Deshayes, F. Boon, O. Coulembier, P. Dubois, P. Gerbaux,. MALDI-ToF analysis of polythiophene: use of trans-2-[3-(4-t-butyl- phenyl)-2-methyl- 2-propenylidene]malononitrile-DCTB-as matrix. J. Mass Spectrom. 2011, 46, 237.
17. D. Akasawa, L. C. Chen, K. Hiraoka,. Negative-mode MALDI mass spectrometry for the analysis of pigments using tetrathiafulvalene as a matrix. J. Mass Spectrom. 2008, 43, 1494.
18. J. J. Coon, J. E. P. Syka, J. C. Schwartz, J. Shabanowitz, D. F. Hunt,. Anion dependence in the partitioning between proton and electron transfer in ion/ion reactions. Int. J. Mass Spectrom. 2004, 236, 33.
19. J. M. Masnovi, E. A. Seddon, J. K. Kochi,. Electron transfer from anthracenes. Comparison of photoionization, charge-transfer excitation and electrochemical oxidation. Can. J. Chem. 1984, 62, 2552.
20. Y. Ling, C. Lifshitz,. Time-Dependent Mass Spectra and Breakdown Graphs. 19. Fluoranthene. J. Phys. Chem. 1995, 99, 11074.
21. J. W. Hager, S. C. Wallace,. Two-laser photoionization supersonic jet mass spectrometry of aromatic molecules. Anal. Chem. 1988, 60, 5.
22. V. Karbach, R. Knochenmuss,. Do single matrix molecules generate primary ions in ultraviolet matrix-assisted laser desorption/ionization. Rapid Commun. Mass Spectrom. 1998, 12, 968.
23. R. G. Brereton, M. B. Bazzaz, S. Santikam, D. H. Williams,. Positive and negative ion fast atom bombardment mass spectrometric studies of chlorophylls: Structure of 4-vinyl-4desethyl chlorophyll B. Tetrahedron Lett. 1983, 24, 5775.
24. R. P. Grese, R. L. Cerny, M. L. Gross, M. Senge,. Determination of structure and properties of modified chlorophylls by using fast atom bombardment combined with tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 1991, 1, 72.
25. J-C. Tabet, M. Jablonski, R. J. Cotter, J. E. Hunt,. Time-resolved laser desorption. III. The metastable decomposition of chlorophyll-a and some derivatives. Int. J. Mass Spectrom Ion Processes. 1985, 65, 105.
26. M. J. Dale, K. F. Costello, A. C. Jones, P. R. R. Langrige-Smith,. Investigation of Porphyrins and Metalloporphyrins Using Two-Step Laser Mass Spectrometry. J. Mass Spectrom. 1996, 31, 590.
27. N. Srinivisan, C. A. Haney, J. S. Lindsey, W. Zhang, B. T. Chait,. Investigation of MALDI-TOF mass spectrometry of diverse synthetic metalloporphyrins, phthalocyanines and multiporphyrin arrays. J. Porphyrins Phthalocyanines. 1999, 3, 283.
28. From NIST CHEM webbook:, Y. Nakato, T. Chiyoda, H. Tsubomura,. Experimental determination of ionization potentials of organic amines, β-carotene and chlorophyll a. Bull. Chem. Soc. Jpn. 1974, 47, 3001.
29. T. Wingerath, D. Kirsh, B. Spengler, W. Stahl,. Analysis of Cyclic and Acyclic Analogs of Retinol, Retinoic Acid and Retinal by Laser Desorption Ionization-, Matrix-Assisted Laser Desorption Ionization-Mass Spectrometry, and UV/Vis Spectroscopy. Anal. Biochem. 1999, 272, 232.
30. M. Hossain, P. A. Limbach,. A comparison of MALDI matrices. In Electrospray and MALDI Mass Spectrometry: fundamentals, Instrumentation, Practicalities, and Biological Applications, R. B. Cole, (Ed). John Wiley & Sons: Hoboken, NJ, 2010, 215-244.
31. M. Karas, U. Bahr, K. Strupat, F. Hillenkamp, A. Tsarbopoulos, B. Pramanik,. Matrix dependence of of metastable fragmentation of glycoproteins in MALDI TOF mass spectrometry. Anal. Chem. 1995, 67, 675.
32. A. Bernas, D. Grand, S. Hautecloque, T. Myasoedova,. On the ionization potential of chlorophyll and bacteriochlorophyll in aqueous environment. Chem. Phys. Letters. 1984, 104, 105.
33. H. Kashiwagi, F. Hirota, U. Nagashima, T. Takada,. Ab initio mo calculations on the chlorophyll-water system and estimation of the structure of the special pair. Int. J. Quant. Chem. 1986, 30, 311.
34. A. Pandey, S. N. Datta,. Theoretical Determination of Standard Oxidation and Reduction Potentials of Chlorophyll-a in Acetonitrile. J. Phys. Chem. B 2005, 109, 9066.
35. S. Katsumata, N. Ikehata,. HeI photoelectron spectroscopic study of vitamin A and its derivatives. J. Electron Spec. Rel. Phenom. 2000, 107, 139.
36. G. J. Smith,. Reaction of Retinol and Retinal with Singlet Oxygen. Photochem. Photobiol. 1983, 38, 119.
37. T. Guaratini, R. L. Vessecchi, F. C. Lavarda, P. Maia Campos, Z. Naal, P. J. Gates, N. P. Lopes,. New chemical evidence for the ability to generate radical molecular ions of polyenes from ESI and HR-MALDI mass spectrometry. Analyst 2004, 129, 1223.
38. G. Kinsel, R. Knochenmuss, P. Setz, C. M. Land, S. -K Goh, E. F. Archibong, J. H. Hardesty, D. Marynick,. Ionization energy reductions in small 2,5-dihydroxybenzoic acid-proline clusters. J. Mass Spectrom. 2002, 37, 1131.
39. H. Ehring, M. Karas, F. Hillenkamp,. Role of photoionization and photochemistry in ionization processes of organic molecules and relevance for matrix-assisted laser desorption/ionization mass spectrometry. Org. Mass Spectrom. 1992, 27, 427.
40. J. A. Zimmerman, J. R. Eyler, S. B. H. Bach, S. W. McElvany,. "Magic number" carbon clusters: Ionization potentials and selective reactivity. J. Chem. Phys. 1991, 94, 3556.
41. X. B. Wang, H. K. Woo, L. S. Wang,. Vibrational cooling in a cold ion trap: Vibrationally resolved photoelectron spectroscopy of cold C-60(-) anions. J. Chem. Phys. 2005, 123, 051106.