一种检测水合肼荧光探针的合成与应用
|
摘要
基于香豆素类染料,设计合成了一种具有较高选择性和灵敏度,可在生理条件(pH 7.4)下检测水合肼的荧光探针,同时利用核磁共振和高分辨质谱对探针的分子结构进行了表征。基于水合肼进攻探针分子结构中的4-丁酸酯,生成酚氧负离子,同时发生分子内环化反应后生成具有强烈荧光的亚胺香豆素,实现了探针分子对水合肼的检测。光谱学研究表明,当向探针溶液加入水合肼(0~100μmol/L)后,探针溶液在绿色光谱区域(502 nm)呈现一个显著的荧光增强响应(增强至55倍)。并且,探针可以检测相对较低浓度的水合肼,检出限为1.7×10~(-7)mol/L。此外,相对于其他阴离子和亲核试剂,探针对水合肼的识别显示出较高的选择性和灵敏度。探针成功实现了细胞内水合肼的荧光成像,证明其在细胞成像中具有潜在的应用能力。
A fluorescent probe with high selectivity and sensitivity was synthesized for hydrazine determination in physioligical condition( pH 7. 4) based on coumarin dyes. Structure of the probe was characterized by nuclear magnetic resonnce and high resolution mass spectrometry. A strong fluorescence imine coumarin was generated by using hydrazine attacking 4-butyrate to release phenolic oxygen anion and produce molecular inner reaction. With the addition of hydrazine( 0-100 μmol/L),the fluorescence intensity of the probe displayed a remarked enhancement( 55 fold) in green spectral region( 502 nm). The probe could be used to detect low concentration of hydrazine,with a detection limit of 1. 7 × 10~(-7)mol/L. Compared with the other anions and nuclear reagents,this probe showed higher selectivity and sensitivity to recognize hydrazine. More importantly,the probe was successfully implemented to detect hydrazine in living cells,which proved that the hydrazine fluorescent probe has a potential capability in cell imaging.
A fluorescent probe with high selectivity and sensitivity was synthesized for hydrazine determination in physioligical condition( pH 7. 4) based on coumarin dyes. Structure of the probe was characterized by nuclear magnetic resonnce and high resolution mass spectrometry. A strong fluorescence imine coumarin was generated by using hydrazine attacking 4-butyrate to release phenolic oxygen anion and produce molecular inner reaction. With the addition of hydrazine( 0-100 μmol/L),the fluorescence intensity of the probe displayed a remarked enhancement( 55 fold) in green spectral region( 502 nm). The probe could be used to detect low concentration of hydrazine,with a detection limit of 1. 7 × 10~(-7)mol/L. Compared with the other anions and nuclear reagents,this probe showed higher selectivity and sensitivity to recognize hydrazine. More importantly,the probe was successfully implemented to detect hydrazine in living cells,which proved that the hydrazine fluorescent probe has a potential capability in cell imaging.
引文
[1]Garrod S,Bollard M E,Nicholls A W,Connor S C,Gonnelly J,Nicholson J K,Holmes E.Chem.Res.Toxicol.,2005,18:115-122.
[2]Chen S,Hou P,Wang J,Liu L,Zhang Q.Spectrochim.Acta A,2017,173:170-174.
[3]Liu B,Liu Q,Shah M,Wang J F,Zhang G,Pang Y.Sens.Actuators B,2014,202:194-200.
[4]Batchelor-Mc Auley C,Banks C E,Simm A O,Jones T G J,Compton R G.Analyst,2006,131:106-110.
[5]Elder D P,Snodin D,Teasdale A.J.Pharm.Biomed.Anal.,2011,54:900-910.
[6]Qu D Y,Chen J L,Di B.Anal.Methods,2014,6:4705-4709.
[7]Chen S,Wang J,Hou P,Liu L,Wang X.J.Instrum.Anal.(陈颂,王静,侯鹏,刘磊,王鑫.分析测试学报),2016,25(8):1046-1049.
[8]Yuan X Y,Wang T L,Guan T T,Wang J L,Huang H W,Yi S J,Tang C R,Zeng Y L.J.Instrum.Anal.(元晓云,王天伦,关婷婷,王金龙,黄昊文,易守军,唐春然,曾云龙.分析测试学报),2015,34(4):463-467.
[9]Xiao L L,Tu J,Sun S Q,Pei Z C,Pei Y X,Pang Y,Xu Y Q.RSC Adv.,2014,4:41807-41811.
[10]Zhou J,Shi R Y,Liu J X,Wang R,Xu Y F,Qian X H.Org.Biomol.Chem.,2015,13:5344-5348.
[11]Yu S L,Wang S X,Yu H Z,Feng Y,Zhang S T,Zhu M Z,Yin H,Meng X M.Sens.Actuators B,2015,220:1338-1345.
[12]Reja S I,Gupta N,Bhalla V,Kaur D,Arora S,Kumar M.Sens.Actuators B,2016,222:923-929.
[13]Cui L,Ji C F,Peng Z X,Zhong L,Zhou C H,Yan L L,Qu S,Zhang S P,Huang C S,Qian X H,Xu Y F.Anal.Chem.,2014,86:4611-4617.
[14]Xiao Y H,Xi G,Zhao X X,Zhou S,Zhou Z Q,Zhao B X.J.Fluoresc.,2015,25:1023-1029.
[15]Zhou D Y,Wang Y Y,Jia J,Yu W Z,Qu B F,Li X,Sun X.Chem.Commun.,2015,51:10656-10659.
[16]Lee D N,Kim G J,Kim H J.Tetrahedron Lett.,2009,50(33):4766-4768.
[2]Chen S,Hou P,Wang J,Liu L,Zhang Q.Spectrochim.Acta A,2017,173:170-174.
[3]Liu B,Liu Q,Shah M,Wang J F,Zhang G,Pang Y.Sens.Actuators B,2014,202:194-200.
[4]Batchelor-Mc Auley C,Banks C E,Simm A O,Jones T G J,Compton R G.Analyst,2006,131:106-110.
[5]Elder D P,Snodin D,Teasdale A.J.Pharm.Biomed.Anal.,2011,54:900-910.
[6]Qu D Y,Chen J L,Di B.Anal.Methods,2014,6:4705-4709.
[7]Chen S,Wang J,Hou P,Liu L,Wang X.J.Instrum.Anal.(陈颂,王静,侯鹏,刘磊,王鑫.分析测试学报),2016,25(8):1046-1049.
[8]Yuan X Y,Wang T L,Guan T T,Wang J L,Huang H W,Yi S J,Tang C R,Zeng Y L.J.Instrum.Anal.(元晓云,王天伦,关婷婷,王金龙,黄昊文,易守军,唐春然,曾云龙.分析测试学报),2015,34(4):463-467.
[9]Xiao L L,Tu J,Sun S Q,Pei Z C,Pei Y X,Pang Y,Xu Y Q.RSC Adv.,2014,4:41807-41811.
[10]Zhou J,Shi R Y,Liu J X,Wang R,Xu Y F,Qian X H.Org.Biomol.Chem.,2015,13:5344-5348.
[11]Yu S L,Wang S X,Yu H Z,Feng Y,Zhang S T,Zhu M Z,Yin H,Meng X M.Sens.Actuators B,2015,220:1338-1345.
[12]Reja S I,Gupta N,Bhalla V,Kaur D,Arora S,Kumar M.Sens.Actuators B,2016,222:923-929.
[13]Cui L,Ji C F,Peng Z X,Zhong L,Zhou C H,Yan L L,Qu S,Zhang S P,Huang C S,Qian X H,Xu Y F.Anal.Chem.,2014,86:4611-4617.
[14]Xiao Y H,Xi G,Zhao X X,Zhou S,Zhou Z Q,Zhao B X.J.Fluoresc.,2015,25:1023-1029.
[15]Zhou D Y,Wang Y Y,Jia J,Yu W Z,Qu B F,Li X,Sun X.Chem.Commun.,2015,51:10656-10659.
[16]Lee D N,Kim G J,Kim H J.Tetrahedron Lett.,2009,50(33):4766-4768.