“关-开”型近红外荧光探针用于铁离子和黑茶抗氧化活性测定
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摘要
以4-甲基喹啉与二醛缩合剂反应得到新型喹啉基花菁类衍生物Cy Q,用~1H NMR、HRMS-ESI确证其结构。Cy Q与半胱氨酸(Cys)通过卤素-巯基亲核取代和重排反应得到Cy Q-Cys,而铁离子(Fe~(3+))可诱导Cy Q-Cys荧光信号明显增强,且荧光信号的变化与Fe~(3+)浓度在40～300μmol/L范围内呈现良好的线性关系,线性回归方程为y=1.0619x+0.01355(R~2=0.9910),检出限为10.4μmol/L(S/N=3)。同时,利用黑茶金花可还原Fe~(3+)的性质,采用Fe~(3+)介导的"关-开"策略,建立了黑茶抗氧化活性的荧光分析方法。
A novel quinoline-based cyanine derivative of CyQ was facilely synthesized by the condensation reaction of 4-methyl quinoline and dialdehyde,and its structure was characterized by ~1H NMR and HRMSESI. Then, the target compound CyQ-cysteine( Cys) was obtained by halogen-mercapto nucleophilic substation reaction and then rearrangement reaction between CyQ and Cys. The results showed that ferric ion( Fe~(3+)) could efficiently cause the fluorescence enhancement of CyQ-Cys,and the fluorescence intensity was linear with the Fe~(3+)concentration in the range of 40-300 mmol/L with a regression equation of y = 1.0619 x +0.01355( R2= 0.9910) and a detection limit of 10.4 μmol/L( S/N = 3). In addition,by virtue of the excellent reductive properties of dark teas towards Fe~(3+),a NIR fluorescent method for assaying antioxidant capacity of dark teas was constructed by Fe~(3+)-mediated off-on strategy.
A novel quinoline-based cyanine derivative of CyQ was facilely synthesized by the condensation reaction of 4-methyl quinoline and dialdehyde,and its structure was characterized by ~1H NMR and HRMSESI. Then, the target compound CyQ-cysteine( Cys) was obtained by halogen-mercapto nucleophilic substation reaction and then rearrangement reaction between CyQ and Cys. The results showed that ferric ion( Fe~(3+)) could efficiently cause the fluorescence enhancement of CyQ-Cys,and the fluorescence intensity was linear with the Fe~(3+)concentration in the range of 40-300 mmol/L with a regression equation of y = 1.0619 x +0.01355( R2= 0.9910) and a detection limit of 10.4 μmol/L( S/N = 3). In addition,by virtue of the excellent reductive properties of dark teas towards Fe~(3+),a NIR fluorescent method for assaying antioxidant capacity of dark teas was constructed by Fe~(3+)-mediated off-on strategy.
引文
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5 Sandro A,Martina U M. J. Alzheimers Dis.,2009,16(4):879-895
6 WANG Ruo,JIANG Guang-Qi. Chinese J. Inorg. Chem.,2017,33(5):881-889王若,江光奇.无机化学学报,2017,33(5):881-889
7 Narayanaswamy N,Govindaraju T. Sens. Actuators B,2012,161:304-310
8 Oh J W,Kim T H,Yoo S W. Sens. Actuators B,2013,177:813-817
9 Calds L,Brum D M,Paula C. Talanta,2013,110:21-27
10 YU Li-Hua,LIU Yong-Sheng,CHEN Xue-Yuan. Chin. J. Lumin.,2018,39(1):27-49于莉华,刘永升,陈学元.发光学报,2018,39(1):27-49
11 Gupta S C,Kim J H,Prasad S,Aggarwal B B. Cancer Matast. Rev.,2010,29(3):405-434
12 Qiu L,Zhu C,Chen H,Hu M,He W,Guo Z. Chem. Commun.,2014,50(35):4631-4634
13 Lai T,Zheng E,Chen L,Wang X,Kong L,You C,Ruan Y,Weng X. Nanoscale,2013,5(17):8015-8021
14 Kaya N E,Yuksel F,zpinar G A,Bulut M,Durmus M. Sens. Actuators B,2014,194:377-388
15 MENG Wen-Fei,YANG Mei-Pan,CHENG Zhao,LI Shao-Ni,YANG Bing-Qin. Chinese J. Org. Chem.,2014,34:398-402孟文斐,杨美盼,成昭,李少妮,杨秉勤.有机化学,2014,34:398-402
16 Kumar R,Gahlyan P,Yadav N,Bhandari M,Kakkar R,Dalela M,Prasad A K. Dye Pigments,2017,147:420-428
17 Chen Z,Lu D,Zhang G,Yang J,Dong C,Shuang S. Sens. Actuators B,2014,202:631-637
18 Liu Z,Sun Y,Huo Y,Zhang H,Wang L,Zhang P,Song D,Shi Y,Guo W. Dyes Pigments,2014,105:7-11
19 Hu Y,Wang J,Long L,Xiao X. J. Lumin.,2016,31(1):16-21
20 Kanwar J,Taskeen M,Mohammad I,Huo C,Chan T H,Dou Q P. Front. Biosci.(Elite Ed),2012,4:111-131
21 Macedo J A,Battestin V,Ribeiro M L,Macsdo G A. Food Chem.,2011,126(2):491-497
22 Dávalos A,Gómez-Cordovés C,BartoloméB. J. Agric. Food Chem.,2004,52(1):48-54
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24 FENG Yuan-Jiao,YANG Xiao-Ming,ZHU Shan-Shan,LIAO Hong-Bo,LIU Han-Ru. Sci. China Chem.,2015,45(1):90-97冯媛娇,杨晓明,朱姗姗,廖洪波,刘汉儒.中国科学:化学,2015,45(1):90-97
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26 Niu L Y,Guan Y S,Chen Y Z,Wu L Z,Tung C H,Yang Q Z. J. Am. Chem. Soc.,2012,134(46):18928-18932
27 Tang B,Liu X,Xu K,Huang H,Yang G,An L. Chem. Commun.,2007,36:3726-3728
28 LIU Chang-Hui,LI Yin-Hui,QI Feng-Pei,LONG Li-Ping,YANG Rong-Hua. Sci. China Chem.,2017,47(8):1015-1021刘长辉,李银辉,齐风佩,龙立平,杨荣华.中国科学:化学,2017,47(8):1015-1021
29 Xu C,Li H,Yin B. Biosens. Bioelectron.,2015,72:275-281
30 Wang F,Guo Z,Li X,Li X,Zhao C. Chem. Eur. J.,2014,20:11471-11478