Hydrogen-transfer reactions from phenols to TEMPO prefluorescent probes in micellar systems

被引:42
作者
Aliaga, Carolina [1 ]
Juarez-Ruiz, Juan M. [2 ]
Scaiano, J. C. [2 ]
Aspee, Alexis [1 ]
机构
[1] Univ Santiago Chile, Fac Quim & Biol, Santiago, Chile
[2] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/ol800446c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A nitroxide prefluorescent probe has been used to evaluate local reactivity of antioxidants in micellar systems. An apparent rate constant that directly reflects the relevance of antioxidant hydrophobicity on the reaction toward nitroxide radicals has been defined. Dramatic increases in this parameter for quercetin are shown on moving from methanol to micellar media: 90 and 230 fold enhancements for SDS and Triton X100 micelles, respectively. This is a clear consequence of the favorable partition of reactants in the micelles.
引用
收藏
页码:2147 / 2150
页数:4
相关论文
共 28 条
[1]   Comparison of the free radical scavenger activities of quercetin and rutin - An experimental and theoretical study [J].
Aliaga, C ;
Lissi, EA .
CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (12) :1668-1673
[2]   A new method to study antioxidant capability:: Hydrogen transfer from phenols to a prefluorescent nitroxide [J].
Aliaga, C ;
Aspée, A ;
Scaiano, JC .
ORGANIC LETTERS, 2003, 5 (22) :4145-4148
[3]   Free radical reactions in poly(methyl methacrylate) films monitored using a prefluorescent quinoline-TEMPO sensor [J].
Aspée, A ;
García, O ;
Maretti, L ;
Sastre, R ;
Scaiano, JC .
MACROMOLECULES, 2003, 36 (10) :3550-3556
[4]   Transient enol isomers of dibenzoylmethane and avobenzone as efficient hydrogen donors toward a nitroxide pre-fluorescent probe [J].
Aspee, Alexis ;
Allaga, Carolina ;
Scaiano, J. C. .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2007, 83 (03) :481-485
[5]   KINETICS OF NITROXIDE RADICAL TRAPPING .1. SOLVENT EFFECTS [J].
BECKWITH, ALJ ;
BOWRY, VW ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :4983-4992
[6]   The first example of an azaphenalene profluoreseent nitroxide [J].
Blinco, James P. ;
McMurtrie, John C. ;
Bottle, Steven E. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (28) :4638-4641
[7]   CHEMICALLY MEDIATED FLUORESCENCE YIELD SWITCHING IN NITROXIDE FLUOROPHORE ADDUCTS - OPTICAL SENSORS OF RADICAL REDOX REACTIONS [J].
BLOUGH, NV ;
SIMPSON, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1915-1917
[8]  
BURTON GW, 1986, ACCOUNTS CHEM RES, V19, P194, DOI 10.1021/ar00127a001
[9]   AUTOXIDATION OF BIOLOGICAL MOLECULES .4. MAXIMIZING THE ANTIOXIDANT ACTIVITY OF PHENOLS [J].
BURTON, GW ;
DOBA, T ;
GABE, EJ ;
HUGHES, L ;
LEE, FL ;
PRASAD, L ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7053-7065
[10]   AUTOXIDATION OF BIOLOGICAL MOLECULES .1. THE ANTIOXIDANT ACTIVITY OF VITAMIN-E AND RELATED CHAIN-BREAKING PHENOLIC ANTIOXIDANTS INVITRO [J].
BURTON, GW ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (21) :6472-6477