基于8-羟基久洛尼定的荧光探针用于谷胱甘肽的特异性检测研究
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摘要
还原型谷胱甘肽(GSH)是一种由三个氨基酸组成的小分子肽,是细胞与组织内重要的活性分子,与多种生理和病理功能相关.以8-羟基久洛尼定为骨架,设计、合成了一例基于香豆素荧光团的GSH荧光探针,利用8-羟基久洛尼定的刚性平面结构增强荧光母体的平面性,以实现荧光波长的红移.光谱分析表明该荧光探针对GSH具有较高的特异性,对GSH呈现典型的比率型响应特征,在516nm处的荧光强度逐渐减弱,561nm处荧光强度逐渐增强.同时,荧光强度与GSH浓度呈现较好的线性关系,表明该探针可以实现GSH的定量检测.
Reduced glutathione(GSH)is a small molecule peptide consisting of three amino acids,which is an important active molecule in cells and tissues,associated with a variety of physiological and pathological functions.In this paper,a GSH fluorescent probe based on coumarin fluorophore was designed and synthesized by using 8-hydroxyjulolidine skeleton.The planarity of the fluorophore was enhanced by the rigid planar structure of 8-hydroxyjulolidine,which achieves a red shift of the fluorescence wavelength.The spectral analysis indicates that the fluorescence probe has a high specific response to GSH.The gradual decrease of the fluorescence at 516 nm and increase at 561 nm reveal a typical ratiometric response to GSH.Meanwhile,the good linear relation between the fluorescent intensity and concentration of GSH indicates that the probe can be used for quantitative detection of GSH.
Reduced glutathione(GSH)is a small molecule peptide consisting of three amino acids,which is an important active molecule in cells and tissues,associated with a variety of physiological and pathological functions.In this paper,a GSH fluorescent probe based on coumarin fluorophore was designed and synthesized by using 8-hydroxyjulolidine skeleton.The planarity of the fluorophore was enhanced by the rigid planar structure of 8-hydroxyjulolidine,which achieves a red shift of the fluorescence wavelength.The spectral analysis indicates that the fluorescence probe has a high specific response to GSH.The gradual decrease of the fluorescence at 516 nm and increase at 561 nm reveal a typical ratiometric response to GSH.Meanwhile,the good linear relation between the fluorescent intensity and concentration of GSH indicates that the probe can be used for quantitative detection of GSH.
引文
[1]Anderson M E.Glutathione:An overview of biosynthesis and modulation[J].Chemico-Biological Interactions,1998,111-112:1-14.
[2]Townsend D M,Tew K D,Tapiero H.The importance of glutathione in human disease[J].Biomedicine&Pharmacotherapy,2003,57(3-4):145-155.
[3]钟华,张慧,许海平.谷胱甘肽的测定方法进展[J].氨基酸和生物资源,2014,36(1):23-26.
[4]吕向菲,李婷,霍霄楠,等.罗丹明类小分子荧光探针对水中Hg~(2+)检测的比较研究[J].陕西科技大学学报(自然科学版),2015,33(5):34-39.
[5]Niu L Y,Chen Y Z,Zheng H R,et al.Design strategies of fluorescent probes for selective detection among biothiols[J].Chemical Society Reviews,2015,44(17):6 143-6 160.
[6]Lavis L D,Raines R T.Bright ideas for chemical biology[J].ACS Chemical Biology,2008,3(3):142-155.
[7]朱勍,和思扬,窦言东.荧光探针技术在谷胱甘肽检测中的应用[J].发酵科技通讯,2016,45(3):170-174.
[8]王媛,陈潇潇,刘学良,等.选择性检测谷胱甘肽的荧光探针[J].影像科学与光化学,2017,35(4):536-545.
[9]杨润洁,唐尧,朱维平.用于检测细胞内谷胱甘肽的比率型荧光探针[J].高等学校化学学报,2016,37(4):643-647.
[10]Niu L Y,Guan Y S,Chen Y Z,et al.Bodipy-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine[J].Journal of the American Chemical Society,2012,134(46):18 928-18 931.
[11]Xu C,Li H,Yin B.A colorimetric and ratiometric fluorescent probe for selective detection and cellular imaging of glutathione[J].Biosensors&Bioelectronics,2015,72:275-281.
[12]Liu J,Sun Y Q,Huo Y,et al.Simultaneous fluorescence sensing of cys and GSH from different emission channels[J].Journal of the American Chemical Society,2014,136(2):574-577.
[13]Liu S,Wang W H,Dang Y L,et al.Rational design and efficient synthesis of a fluorescent-labeled jasmonate[J].Tetrahedron Letters,2012,53(32):4 235-4 239.
[14]Chen J,Liu W,Zhou B,et al.Coumarin and rhodaminefused deep red fluorescent dyes:Synthesis,photophysical properties,and bioimaging in vitro[J].The Journal of Organic Chemistry,2013,78(12):6 121-6 130.
[15]Zhang P,Liu W,Niu G,et al.Coumarin-based boron complexes with aggregation-induced emission[J].The Journal of Organic Chemistry,2017,82(7):3 456-3 462.
[2]Townsend D M,Tew K D,Tapiero H.The importance of glutathione in human disease[J].Biomedicine&Pharmacotherapy,2003,57(3-4):145-155.
[3]钟华,张慧,许海平.谷胱甘肽的测定方法进展[J].氨基酸和生物资源,2014,36(1):23-26.
[4]吕向菲,李婷,霍霄楠,等.罗丹明类小分子荧光探针对水中Hg~(2+)检测的比较研究[J].陕西科技大学学报(自然科学版),2015,33(5):34-39.
[5]Niu L Y,Chen Y Z,Zheng H R,et al.Design strategies of fluorescent probes for selective detection among biothiols[J].Chemical Society Reviews,2015,44(17):6 143-6 160.
[6]Lavis L D,Raines R T.Bright ideas for chemical biology[J].ACS Chemical Biology,2008,3(3):142-155.
[7]朱勍,和思扬,窦言东.荧光探针技术在谷胱甘肽检测中的应用[J].发酵科技通讯,2016,45(3):170-174.
[8]王媛,陈潇潇,刘学良,等.选择性检测谷胱甘肽的荧光探针[J].影像科学与光化学,2017,35(4):536-545.
[9]杨润洁,唐尧,朱维平.用于检测细胞内谷胱甘肽的比率型荧光探针[J].高等学校化学学报,2016,37(4):643-647.
[10]Niu L Y,Guan Y S,Chen Y Z,et al.Bodipy-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine[J].Journal of the American Chemical Society,2012,134(46):18 928-18 931.
[11]Xu C,Li H,Yin B.A colorimetric and ratiometric fluorescent probe for selective detection and cellular imaging of glutathione[J].Biosensors&Bioelectronics,2015,72:275-281.
[12]Liu J,Sun Y Q,Huo Y,et al.Simultaneous fluorescence sensing of cys and GSH from different emission channels[J].Journal of the American Chemical Society,2014,136(2):574-577.
[13]Liu S,Wang W H,Dang Y L,et al.Rational design and efficient synthesis of a fluorescent-labeled jasmonate[J].Tetrahedron Letters,2012,53(32):4 235-4 239.
[14]Chen J,Liu W,Zhou B,et al.Coumarin and rhodaminefused deep red fluorescent dyes:Synthesis,photophysical properties,and bioimaging in vitro[J].The Journal of Organic Chemistry,2013,78(12):6 121-6 130.
[15]Zhang P,Liu W,Niu G,et al.Coumarin-based boron complexes with aggregation-induced emission[J].The Journal of Organic Chemistry,2017,82(7):3 456-3 462.