Artículo

El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

A group of nitrogen heterocyclic aromatic compounds used, among others, as UV-MALDI matrices was studied. By using spectroscopic, luminescence and photoacoustic techniques, as well as time resolved phosphorescence for singlet oxygen production determination, the behaviour of 9-aminoacridine (9AA), 3-aminoquinoline (3AQ), 2-(2-aminoethylamino)-5-nitropyridine (AAN) and 3,4-dihydro-7-methoxy-1-methyl-9H-pyrido[3,4-b] indole (harmaline, HLA) in acetonitrile solutions is described. The results show that for these compounds radiationless processes that release prompt heat to the media are a quite important deactivation mechanism. © The Royal Society of Chemistry and Owner Societies 2012.

Registro:

Documento: Artículo
Título:Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution
Autor:Petroselli, G.; Erra-Balsells, R.; Gara, P.D.; Bilmes, G.M.
Filiación:Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 3, Buenos Aires, 1428, Argentina
Centro de Investigaciones Ópticas-CIOp (CONICET-CIC), Universidad Nacional de La Plata, Casilla de Correo 3, Gonnet, 1897, Argentina
Palabras clave:2 (2 aminoethylamino) 5 nitropyridine; 2-(2-aminoethylamino)-5-nitropyridine; acetonitrile; acetonitrile derivative; aminoacridine; aminoquinoline derivative; harmaline; heterocyclic compound; nitrogen; pyridine derivative; singlet oxygen; article; chemistry; mass spectrometry; photoacoustics; solution and solubility; ultraviolet spectrophotometry; Acetonitriles; Aminacrine; Aminoquinolines; Harmaline; Heterocyclic Compounds; Nitrogen; Photoacoustic Techniques; Pyridines; Singlet Oxygen; Solutions; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Spectrophotometry, Ultraviolet
Año:2012
Volumen:11
Número:6
Página de inicio:1062
Página de fin:1068
DOI: http://dx.doi.org/10.1039/c2pp05388h
Título revista:Photochemical and Photobiological Sciences
Título revista abreviado:Photochem. Photobiol. Sci.
ISSN:1474905X
CODEN:PPSHC
CAS:acetonitrile, 75-05-8; aminoacridine, 134-50-9, 27254-80-4, 90-45-9; harmaline, 304-21-2; nitrogen, 7727-37-9; 2-(2-aminoethylamino)-5-nitropyridine; Acetonitriles; Aminacrine, 90-45-9; Aminoquinolines; Harmaline, 304-21-2; Heterocyclic Compounds; Nitrogen, 7727-37-9; Pyridines; Singlet Oxygen, 17778-80-2; Solutions; acetonitrile, 75-05-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v11_n6_p1062_Petroselli

Referencias:

  • Karas, M., Hillenkamp, F., Laser desorption ionization of proteins with molecular masses exceeding 10 000 Daltons (1987) Anal. Chem., 60, pp. 2299-2301
  • Tanaka, K., Waki, H., Ido, Y., Akita, S., Yoshida, Y., Yoshida, T., Protein and polymer analyses up to m/z 100 000 by laser ionization time-of-flight mass spectrometry (1988) Rapid Commun. Mass Spectrom., 2, pp. 151-153
  • Hillenkamp, F., Karas, M., The MALDI process and methods (2007) MALDI MS. A Practical Guide to Instrumentation, Methods and Applications, pp. 1-28. , ed. F. Hillenkamp and J. Peter-Katalinic, Wiley-VCH Verlag GmbH & Co. KGaA, Winheim, ch. 1
  • Hossain, M., Limbach, P.A., A comparison of MALDI matrices (2010) Electrospray and MALDI Mass Spectrometry, Fundamentals, Instrumentation, Practicalities, and Biological Applications, pp. 215-261. , ed. R. B. Cole, John Wiley and Sons, New Jersey, ch. 7
  • Urban, P.L., Amantonico, A., Zenobi, R., Lab-on-a-plate: Extending the functionality of MALDI-MS and LDI-MS targets (2011) Mass Spectrom. Rev., 30, pp. 435-478
  • Ehring, H., Karas, M., Hillenkamp, F., Role of photoionization and photochemistry in ionization processes of organic molecules and relevance for MALDI-MS (1992) Org. Mass Spectrom., 27, pp. 472-480
  • Ehring, H., Sundqvist, B.U.R., Studies of the MALDI process by luminescence spectroscopy (1995) J. Mass Spectrom., 30, pp. 1303-1310
  • Knochenmuss, R.J., A quantitative model of ultraviolet matrix-assisted laser desorption-ionization (2002) J. Mass Spectrom., 37, pp. 867-877
  • Karas, M., Glückmann, M., Schäfer, J., Ionization in matrix-assisted laser desorption-ionization: Singly charged molecular ions are the lucky survivors (2000) J. Mass Spectrom., 35, pp. 1-12
  • Zenobi, R., Knochenmuss, R., Ion formation in MALDI mass spectrometry (1998) Mass Spectrom. Rev., 17, pp. 337-366
  • Knochenmuss, R., Ion formation mechanism in UV-MALDI (2006) Analyst, 131, pp. 966-986
  • Johnson, R.E., Models for matrix-assisted desorption by a laser-pulse (1994) Int. J. Mass Spectrom. Ion Processes, 139, pp. 25-38
  • Mowry, C.D., Johnston, M.V., Simultaneous detection of ions and neutrals produced by matrix-assisted laser desorption (1993) Rapid Commun. Mass Spectrom., 7, pp. 569-575
  • Zhang, J., Zenobi, R., Matrix-dependent cationization in MALDI mass spectrometry (2004) J. Mass Spectrom., 39, pp. 808-816
  • Burton, R.D., Watson, C.H., Eyler, J.R., Lang, G.L., Powell, D.H., Avery, M.Y., Proton affinities of eight matrices used for matrix-assisted laser desorption-ionization (1997) Rapid Commun. Mass Spectrom., 11, pp. 443-446
  • Knochenmuss, R., MALDI ionization mechanisms: An overview (2010) Electrospray and MALDI Mass Spectrometry, Fundamentals, Instrumentation, Practicalities, and Biological Applications, pp. 149-183. , ed. R. B. Cole, John Wiley and Sons, New Jersey, ch. 5
  • Turro, N.J., (1978) Modern Molecular Photochemistry, , The Benjamin/Cummings Publishing Co., Inc., Menlo Park, California
  • Ludemann, H.-C., Redmond, R.W., Hillenkamp, F., Singlet-singlet annihilation in ultraviolet matrix-assisted laser desorption-ionization studied by fluorescence spectroscopy (2002) Rapid Commun. Mass Spectrom., 16, pp. 1287-1294
  • Hakansson, K., Klassen, J.S., Ion activation methods for tandem mass spectrometry (2010) Electrospray and MALDI Mass Spectrometry, Fundamentals, Instrumentation, Practicalities, and Biological Applications, pp. 571-630. , ed. R. B. Cole, John Wiley and Sons, New Jersey, ch. 16
  • Afonso, C., Cole, R.B., Tabet, J.C., Dissociation of even-electron ions (2010) Electrospray and MALDI Mass Spectrometry, Fundamentals, Instrumentation, Practicalities, and Biological Applications, pp. 631-682. , ed. R. B. Cole, John Wiley and Sons, New Jersey, ch. 17
  • Gross, J.H., (2004) Mass Spectrometry, pp. 223-330. , Springer-Verlag, Berlin, Heidelberg, ch. 6
  • Mesaros, M., Tarzi, O.I., Erra-Balsells, R., Bilmes, G.M., The photophysics of some UV-MALDI matrices studied by using spectroscopic, photoacoustic and luminescence techniques (2006) Chem. Phys. Lett., 426, pp. 334-340
  • Lorkiewicks, P., Yappert, M.C., 2-(2-Aminoethylamino)-5-nitropyridine as a basic matrix for negative-mode matrix-assisted laser desorption/ ionization analysis of phospholipids (2009) J. Mass Spectrom., 44, pp. 137-143
  • Guo, Z., He, L., A binary matrix for background suppression in MALDI-MS of small molecules (2007) Anal. Bioanal. Chem., 387, pp. 1939-1944
  • Dannenberger, D., Süß, R., Teuber, K., Fuchs, B., Nuernberg, K., Schiller, J., The intact muscle lipid composition of bulls: An investigation by MALDI-TOF and 31PNMR (2010) Chem. Phys. Lipids, 163, pp. 157-164
  • Harvey, D.J., Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates and glycoconjugates (2003) Int. J. Mass Spectrom., 226, pp. 1-35
  • Nonami, H., Fukui, S., Erra-Balsells, R., β-Carboline alkaloids as matrices for matrix-assisted ultraviolet laser desorption time of flight mass spectrometry of proteins and sulfated oligosaccharides: A comparative study using phenylcarbonyl compounds, carbazoles and classical matrices (1997) J. Mass Spectrom., 32, pp. 287-296
  • Nonami, H., Tanaka, K., Fukuyama, Y., Erra-Balsells, R., β-Carboline alkaloids as matrices for UV-matrix-assisted laser desorption/ionization time-of-flight mass spectrometry in positive and negative ion modes. Analysis of proteins of high molecular mass, and of cyclic and acyclic oligosaccharides (1998) Rapid Commun. Mass Spectrom., 12, pp. 285-296
  • Panda, D., Datta, A., The role of the ring nitrogen and the amino group in the solvent dependence of the excited-state dynamics of 3-aminoquinoline (2006) J. Chem. Phys., 125, pp. 054513/1-054513/9
  • Panda, D., Ghosh, D., Datta, A., Acid-base behaviour of 3-aminoquinoline in its ground and exited states (2009) J. Photochem. Photobiol., A, 207, pp. 254-259
  • Murza, A., Sánchez-Cortés, S., García-Ramos, J.V., Fluorescence and surface-enhanced Raman study of 9-aminoacridine in relation to its aggregation and excimer emission in aqueous solution and on silver surface (1998) Biospectroscopy, 4, pp. 327-339
  • Biondic, M.C., Erra-Balsells, R., Photochemical reactions of harmaline. Part 1. Electronic spectra (1992) J. Chem. Soc., Perkin Trans., 2, pp. 1049-1058
  • Biondic, M.C., Erra-Balsells, R., Photochemical reaction of dihydro β-carbolines. Part 3. Some kinetic aspects (1993) An. Asoc. Quim. Argent., 81, pp. 403-414
  • Biondic, M.C., Erra-Balsells, R., Photochemical behavior of β-carbolines. Part 4. Acid-base equilibria in the ground and excited states in organic media (1997) J. Chem. Soc., Perkin Trans., 2, pp. 1323-1328
  • Krishnamurthy, M., Dogra, S.K., Phototautomerism of harmaline and harmalol in the excited singlet state (1986) Photochem. Photobiol., 44, pp. 574-577
  • Krishnamurthy, M., Dogra, S.K., Prototropic equilibria of some harmala alkaloids in acid solution: Proton-induced fluorescence quenching of the monocations of harmaline and harmalol (1986) J. Chem. Soc., Perkin Trans., 2, pp. 1247-1251
  • Balón, M., Hidalgo, J., Guardado, P., Muñoz, M.A., Carmona, M.C., Acid-base and spectral properties of β-carbolines. Part 2. Dehydro and fully aromatic β-carbolines (1993) J. Chem. Soc., Perkin Trans., 2, pp. 99-104
  • Tomás Vert, F., Zabala Sánchez, I., Olba Torrent, A., Acidity constants of harmaline and harmalol in the ground and excited singlet states (1984) J. Photochem., 26, pp. 285-294
  • Olba Torrent, A., Tomas Vert, F., Zabala Sanchez, I., Medina Casamayor, P., Fluorescence, phosphorescence and basicity in the first excited triplet of 2-methylharmine and harmaline (1987) J. Photochem., 37, pp. 109-116
  • Pardo, A., Reyman, D., Poyato, J.M.L., Medina, F., Some β-carboline derivatives as fluorescence standars (1992) J. Lumin., 51, pp. 269-274
  • Yamagaki, T., Suzuki, H., Tachibana, K., Solid-phase fluorescence and ionization efficiency in negative-ion matrix-assisted laser desorption/ionization of neutral oligosaccharides: Interaction between beta-carboline matrix and ammonium salt (2007) J. Am. Soc. Mass Spectrom., 18, pp. 714-723
  • Terazima, M., Azumi, T., A time-resolved photoacoustic method with pulsed laser excitation in the condensed phase: The relation between signal intensity and decay rate constant (1990) Bull. Chem. Soc. Jpn., 63, pp. 741-745
  • Martí, C., Jürgens, O., Cuenca, O., Casals, M., Nonell, S., Aromatic ketones as standards for singlet molecular oxygen O2 (1Δg) photosensitization. Time-resolved photoacoustic and NIR emission studies (1996) J. Photochem. Photobiol., A, 97, pp. 11-18
  • Braslavsky, S.E., Heibel, G.E., Time-resolved photothermal and photoacoustic methods applied to photoinduced processes in solution (1992) Chem. Rev., 92, pp. 1381-1410
  • Tarzi, O.I., Erra-Balsells, R., Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O-(8-bromo-nor-harmane) and other bromo-β-carbolines (2005) J. Photochem. Photobiol., B, 80, pp. 29-45
  • Tarzi, O.I., Erra-Balsells, R., Effect of chlorine on the photochemistry and acid-base properties of β-carbolines alkaloids (2006) J. Photochem. Photobiol., B, 82, pp. 79-93
  • Cabrerizo, F.M., Arnbjerg, J., Denofrio, M.P., Erra-Balsells, R., Ogilby, P.R., Fluorescence quenching by oxygen: "Debunking" a classic rule (2010) ChemPhysChem, 11, pp. 796-798
  • Eaton, D.F., Luminiscence spectroscopy (1989) Handbook of Organic Photochemistry, 1, pp. 233-236. , ed. J. C. Scaiano, CRC Press, Boca Raton, FL
  • Meech, S.R., Phillips, D., Photophysics of some common fluorescence standards (1983) J. Photochem., 23, pp. 193-217
  • Mesaros, M., Bonesi, S.M., Ponce, M.A., Erra-Balsells, R., Bilmes, G.M., The photophysics of nitrocarbazoles studied by using photoacoutic and luminescence techniques (2003) Photochem. Photobiol. Sci., 2, pp. 808-816
  • Van Haver, Ph., Viaene, L., Van Der Auweraer, M., De Schryver, F.C., References for laser-induced opto-acoustic spectroscopy using UV excitation (1990) J. Photochem. Photobiol., A, 63, pp. 265-277
  • Schmidt, R., Tanielian, C., Dunsbach, R., Wolff, C., Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O2 (1Δg) sensitization (1994) J. Photochem. Photobiol., A, 79, pp. 11-17

Citas:

---------- APA ----------
Petroselli, G., Erra-Balsells, R., Gara, P.D. & Bilmes, G.M. (2012) . Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution. Photochemical and Photobiological Sciences, 11(6), 1062-1068.
http://dx.doi.org/10.1039/c2pp05388h
---------- CHICAGO ----------
Petroselli, G., Erra-Balsells, R., Gara, P.D., Bilmes, G.M. "Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution" . Photochemical and Photobiological Sciences 11, no. 6 (2012) : 1062-1068.
http://dx.doi.org/10.1039/c2pp05388h
---------- MLA ----------
Petroselli, G., Erra-Balsells, R., Gara, P.D., Bilmes, G.M. "Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution" . Photochemical and Photobiological Sciences, vol. 11, no. 6, 2012, pp. 1062-1068.
http://dx.doi.org/10.1039/c2pp05388h
---------- VANCOUVER ----------
Petroselli, G., Erra-Balsells, R., Gara, P.D., Bilmes, G.M. Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution. Photochem. Photobiol. Sci. 2012;11(6):1062-1068.
http://dx.doi.org/10.1039/c2pp05388h