Fluorescence enhancement for alkaloids by anions: Spectroscopic and electrochemical characterizations

被引:8
作者
Chung, Yu-Ling [2 ]
Hong, Ruey-Ding [2 ]
Wu, Hsiao Wen [2 ]
Hung, Wei-Hsiu [1 ]
Lai, Lee-Jene [1 ]
Wang, Chong Mou [2 ]
机构
[1] Natl Synchrotron Res Ctr, Hsinchu, Taiwan
[2] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan
关键词
alkaloid; palmatine; berberine; anion; fluoride; fluorescence enhancement;
D O I
10.1016/j.jelechem.2007.07.003
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Alkaloids such as palmatine and berberine are potential phototoxins, but they exhibit low quantum yields for fluorescence (Phi(F)). We found that fluoride and hydroxide ions are promising promoters that enhance their values of Phi(F) in aprotic and aqueous solutions. For example, an increase of Phi(F) by a factor of 10(2) was observed when palmatine incorporated 40 equiv TBAF in dimethyl sulfoxide (DMSO). The cause of the enhancement in Phi(F) was shown to be the interaction of fluoride and hydroxide ions with the quaternary nitrogen atoms contained in the target alkaloid. The effect of substitution of fluoride with other anions such as Cl-, Br-, I-, PF6-, and ClO4- is insignificant. In aqueous media, the efficacy of fluoride and hydroxide ions was greatly reduced. Nevertheless, introducing DNA helped restore the effectiveness of fluoride in enhancing the value of Phi(F) of alkaloids. (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:85 / 89
页数:5
相关论文
共 17 条
[1]  
Bentley K.W., 1998, ISOQUINOLINE ALKALOI, P219
[2]   Characterization of the direct electron transfer and bioelectrocatalysis of horseradish peroxidase in DNA film at pyrolytic graphite electrode [J].
Chen, XH ;
Ruan, CM ;
Kong, JL ;
Deng, JQ .
ANALYTICA CHIMICA ACTA, 2000, 412 (1-2) :89-98
[3]   Light and singlet oxygen in plant defense against pathogens: Phototoxic phenalenone phytoalexins [J].
Flors, Cristina ;
Nonell, Santi .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (05) :293-300
[4]  
FOOTE CS, 1995, ACTIVE OXYGEN CHEM, pCH4
[5]  
Gatto B, 1996, CANCER RES, V56, P2795
[6]   The mechanism of guanine specific photooxidation in the presence of berberine and palmatine: Activation of photosensitized singlet oxygen generation through DNA-binding interaction [J].
Hirakawa, K ;
Kawanishi, S ;
Hirano, T .
CHEMICAL RESEARCH IN TOXICOLOGY, 2005, 18 (10) :1545-1552
[7]   Bacteria lacking a multidrug pump: A sensitive tool for drug discovery [J].
Hsieh, PC ;
Siegel, SA ;
Rogers, B ;
Davis, D ;
Lewis, K .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (12) :6602-6606
[8]   DNA and its associated processes as targets for cancer therapy [J].
Hurley, LH .
NATURE REVIEWS CANCER, 2002, 2 (03) :188-200
[9]   Intercalation of oganic dye molecules into double-stranded DNA. Part 2: The annelated quinolizinium ion as a structural motif in DNA intercalators [J].
Ihmels, H ;
Faulhaber, K ;
Vedaldi, D ;
Dall'Acqua, F ;
Viola, G .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2005, 81 (05) :1107-1115
[10]   Photochemistry and photocytotoxicity of alkaloids from goldenseal (Hydrastis canadensis L.).: 2.: Palmatine, hydrastine, canadine, and hydrastinine [J].
Inbaraj, J. J. ;
Kukielczak, B. M. ;
Bilski, P. ;
He, Y. -Y. ;
Sik, R. H. ;
Chignell, C. F. .
CHEMICAL RESEARCH IN TOXICOLOGY, 2006, 19 (06) :739-744