One- and Two-Photon Excitation of β-Carbolines in Aqueous Solution: pH-Dependent Spectroscopy, Photochemistry, and Photophysics

被引:60
作者
Micaela Gonzalez, M. [2 ]
Arnbjerg, Jacob [1 ]
Paula Denofrio, M. [3 ]
Erra-Balsells, Rosa [2 ]
Ogilby, Peter R. [1 ]
Cabrerizo, Franco M. [2 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Oxygen Microscopy & Imaging, DK-8000 Aarhus, Denmark
[2] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, CIHIDECAR CONICET, RA-1428 Buenos Aires, DF, Argentina
[3] Univ Nacl La Plata, Fac Ciencias Exactas, Dept Quim, INIFTA CONICET CIC, RA-1900 La Plata, Argentina
基金
新加坡国家研究基金会;
关键词
SINGLET OXYGEN; MOLECULAR-OXYGEN; ACID-BASE; RESONANCE ENHANCEMENT; FLUORESCENCE-SPECTRA; INDUCED MUTAGENESIS; ELECTRONIC-SPECTRA; AROMATIC KETONES; PROTON-TRANSFER; CROSS-SECTIONS;
D O I
10.1021/jp902105x
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
beta-Carboline (beta C) alkaloids are present in a wide range of biological systems and play a variety of significant photodependent roles. In this work, a study of the aqueous solution-phase photochemistry, photophysics, and spectroscopy of three important beta Cs [norharmane (nHo), harmane (Ho), and harmine (Ha)] and two beta C derivatives [N-methylnorharmane (N-Me-nHo) and N-methylharmane (N-Me-Ho)] upon one- and two-photon excitation is presented. The results obtained depend significantly on pH, the ambient oxygen concentration, and the beta C substituent and provide unique insight into a variety of fundamental photophysical phenomena. The data reported herein should not only help to understand the roles played by beta C alkaloids in biological systems but should also help in the development of methods by which the photoinduced behavior of these important compounds can be controlled.
引用
收藏
页码:6648 / 6656
页数:9
相关论文
共 72 条
[1]   High-speed extraction and HPLC fingerprinting of medicinal plants -: II.: Application to harman alkaloids of genus Passiflora [J].
Abourashed, EA ;
Vanderplank, J ;
Khan, IA .
PHARMACEUTICAL BIOLOGY, 2003, 41 (02) :100-106
[2]   Design of organic molecules with large two-photon absorption cross sections [J].
Albota, M ;
Beljonne, D ;
Brédas, JL ;
Ehrlich, JE ;
Fu, JY ;
Heikal, AA ;
Hess, SE ;
Kogej, T ;
Levin, MD ;
Marder, SR ;
McCord-Maughon, D ;
Perry, JW ;
Röckel, H ;
Rumi, M ;
Subramaniam, C ;
Webb, WW ;
Wu, XL ;
Xu, C .
SCIENCE, 1998, 281 (5383) :1653-1656
[3]  
ALLAIN CC, 1974, CLIN CHEM, V20, P470
[4]  
[Anonymous], SPIE P
[5]  
Arnbjerg J, 2007, J PHYS CHEM A, V111, P5756, DOI [10.1021/jp071197l, 10.1021/jp0711971]
[6]   Two-photon absorption in tetraphenylporphycenes:: Are porphycenes better candidates than porphyrins for providing optimal optical properties for two-photon photodynamic therapy? [J].
Arnbjerg, Jacob ;
Jimenez-Banzo, Ana ;
Paterson, Martin J. ;
Nonell, Santi ;
Borrell, Jose I. ;
Christiansen, Ove ;
Ogilby, Peter R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :5188-5199
[7]   Two-photon photosensitized production of singlet oxygen: Optical and optoacoustic characterization of absolute two-photon absorption cross sections for standard sensitizers in different solvents [J].
Arnbjerg, Jacob ;
Johnsen, Mette ;
Frederiksen, Peter K. ;
Braslavsky, Silvia E. ;
Ogilby, Peter R. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (23) :7375-7385
[8]   RETRACTED: Exudation of fluorescent β-carbolines from Oxalis tuberosa L. roots (Retracted article. See vol. 71, pg. 123, 2010) [J].
Baisa, HP ;
Park, SW ;
Stermitz, FR ;
Halligan, KM ;
Vivanco, JM .
PHYTOCHEMISTRY, 2002, 61 (05) :539-543
[9]   Hydrogen-bonding interactions between harmane and pyridine in the ground and lowest excited singlet states [J].
Balon, M ;
Munoz, MA ;
Guardado, P ;
Carmona, C .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1996, 64 (03) :531-536
[10]   Spectral and photophysical properties of the δ-carboline anhydrobase (N1-methyl-5H-pyrido[3,2-b]indole) [J].
Balón, M ;
Carmona, C ;
Muñoz, MA .
CHEMICAL PHYSICS, 2004, 302 (1-3) :13-20