CN110655510B - 一种靶向脂滴的亚硫酸盐比率荧光探针及其应用 - Google Patents

一种靶向脂滴的亚硫酸盐比率荧光探针及其应用 Download PDF

Info

Publication number
CN110655510B
CN110655510B CN201910867007.6A CN201910867007A CN110655510B CN 110655510 B CN110655510 B CN 110655510B CN 201910867007 A CN201910867007 A CN 201910867007A CN 110655510 B CN110655510 B CN 110655510B
Authority
CN
China
Prior art keywords
sulfite
fluorescent probe
probe
ratio
fluorescence
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201910867007.6A
Other languages
English (en)
Other versions
CN110655510A (zh
Inventor
赵宝祥
苗俊英
王伟
韩贤菁
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shandong University
Original Assignee
Shandong University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shandong University filed Critical Shandong University
Priority to CN201910867007.6A priority Critical patent/CN110655510B/zh
Publication of CN110655510A publication Critical patent/CN110655510A/zh
Application granted granted Critical
Publication of CN110655510B publication Critical patent/CN110655510B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/645—Specially adapted constructive features of fluorimeters
    • G01N21/6456—Spatial resolved fluorescence measurements; Imaging
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

本发明公开了一种基于荧光共振能量转移相应机理的靶向脂滴的亚硫酸盐比率荧光探针，是以香豆素荧光团为能量供体、共轭咔唑衍生物为能量受体，通过哌嗪烷基链连接构成；其化学结构式如式(I)所示。本发明的探针可以选择性地与亚硫酸盐HSO3 ‑/SO3 2‑作用，随着亚硫酸盐浓度的增加，其荧光发射强度在470nm处逐渐增强，在627nm处逐渐减弱；二者比值(I460/I627)与亚硫酸盐浓度在一定范围内呈线性关系。实现了细胞内的比率成像，并且该比率荧光探针对脂滴有着很好的靶向性，有望在工业生产和临床医学中发挥作用，具有广阔的应用前景。

Description

一种靶向脂滴的亚硫酸盐比率荧光探针及其应用
技术领域
本发明涉及一种比率荧光探针及其应用，尤其涉及一种基于荧光共振能量转移(FRET)机理的靶向脂滴的亚硫酸盐比率荧光探针及其应用；属于有机小分子荧光探针领域。
背景技术
二氧化硫作为大气污染物一旦被人体过量摄入，会引发一系列的疾病例如神经系统紊乱，心血管疾病，甚至诱发癌症。另一方面人体的细胞质和一些细胞器会在相关酶的催化下将一些含有硫原子的氨基酸分解并释放二氧化硫。二氧化硫还可以在体内作为一种气态生物信号参与一些新陈代谢过程，例如降低血压和调节血管壁张力。因此为了研究体内二氧化硫衍生物的生理、病理作用，发展生物体内二氧化硫衍生物成像技术、实时检测细胞内二氧化硫衍生物的时空与浓度分布具有重要的医学价值。
荧光探针作为一个生物工具去检测二氧化硫衍生物具有特异性、高敏性及快速响应等优点，因此该领域中有很多科研工作者积极参与并做出了许多贡献[Q.Zhang et al,Sens.Actuators B,2015,211,377；J.C.Xu et al,Biosens.Bioelectron,2016,77,725]；在检测抗干扰方面，比率荧光探针比单发射荧光探针有着更好的性能。[L.Yuan et al,Acc.Chem.Res.,2013,46,1462]。基于FRET的比率荧光探针一般是由一个能量供体荧光团和一个受体荧光团通过一个柔性链链接构成。当用能量供体荧光团的最佳激发光去照射探针时，供体的能量会沿着柔性链将能量传给受体荧光团，进而探针发射受体的荧光。同时受体也作为亚硫酸盐的检测基团，当受体和亚硫酸盐作用后，其共轭结构被阻断，不能够再吸收供体的能量，进而探针发射供体荧光团的荧光。因此随着亚硫酸盐的浓度变化，探针能量供体的荧光和能量受体的荧光强度也随之变化。基于此，可以根据两荧光的荧光强度的比值和已知标样的亚硫酸盐浓度做出一条滴定曲线，并在一定浓度范围内算出其工作曲线。进而为制备FRET类型的比率型荧光探针奠定基础。经检索，有关基于FRET机理的靶向脂滴的亚硫酸盐比率荧光探针及其应用的专利鲜见报道。
发明内容
针对现有技术的不足，本发明要解决的问题是提供一种基于荧光共振能量转移(FRET)机理的靶向脂滴的亚硫酸盐比率荧光探针及其应用。
本发明所述基于荧光共振能量转移机理的靶向脂滴的亚硫酸盐比率荧光探针，该比率荧光探针以香豆素荧光团为能量供体、共轭咔唑衍生物为能量受体，通过哌嗪烷基链连接构成；其特征在于：所述比率型荧光探针化学结构式如式(I)所示：
Figure BDA0002201554590000021
上述基于荧光共振能量转移机理的靶向脂滴的亚硫酸盐比率荧光探针的制备方法，步骤是：(E)-2-(3-氰基-5,5-二甲基-4-(2-(9-(3-(哌嗪-1-基)丙基)-9H-咔唑-3-基)乙烯基)呋喃2(5H)-亚基)丙二腈与7-(二乙氨基)-2-氧代-2H-色烯-3-碳酰氯共溶于无水二氯甲烷，向体系加入三乙基胺，室温反应，减压蒸馏除去反应溶剂，粗产品经柱层析纯化得到所述靶向脂滴的亚硫酸盐比率型荧光探针。
本发明所述基于荧光共振能量转移机理的靶向脂滴的亚硫酸盐比率荧光探针在检测含亚硫酸盐样品中的应用。
其中：所述含亚硫酸盐样品优选是含亚硫酸盐的溶液或培养的细胞
本发明所述的基于FRET机理的亚硫酸盐比率荧光探针在无亚硫酸盐条件下，能量供体被激发光激发后将其能量通过哌嗪烷基链传递给能量受体，导致能量受体发射荧光；在亚硫酸盐存在下，能量受体荧光团中的共轭双键与亚硫酸氢根发生加成(见式(Ⅱ)和图1)，大共轭体系遭受破坏，从而能量受体无法吸收能量，能量供体发射荧光。亚硫酸盐的浓度不同，上述两个发射波长的荧光强度也随之变化，据此关系实现最终达到比率检测亚硫酸盐的浓度的效果。
Figure BDA0002201554590000022
具体的：配制上述亚硫酸盐比率荧光探针的乙醇与磷酸盐(0.01M)缓冲液(v/v＝1：1，pH＝7)的溶液，分别加入定量的F-,Br-,S2-,SO4 2-,ClO-,H2PO4 -,HS-,SO3 2-,SCN-,S2O3 2-,Co2+,Pb2+,K+,Al3+,Ca2+,Fe3+,Fe2+,GSH,Cys。摇匀放置15分钟，对上述溶液进行荧光测试，结果表明本发明的上述比率荧光探针主要对亚硫酸盐有明显识别响应，见图2。
本发明所述的比率荧光探针伴随着亚硫酸盐浓度的增加，470nm处荧光强度逐渐增强，627nm处荧光强度逐渐减弱；二者荧光强度值的比值随着亚硫酸盐浓度的增加呈比例增加，并在一定浓度范围内呈线性关系。所以该探针能在一定浓度范围内定量检测亚硫酸盐浓度，见图3。
在加入上述比率荧光探针的HepG2活细胞中，A组为对照组，只加探针；B组实验组，加入探针后同时用GSH和Na2S2O3处理；C组实验组加入探针后只加GSH；D组实验组加入探针后加入GSH、Na2S2O3和TNBS；细胞染色情况分别用荧光显微镜观察。可以看出A组细胞蓝色通道荧光较弱，红色通道荧光较强；B组蓝色通道荧光比A组明显增强，红色通道荧光比A组明显减弱；其红色通道荧光与蓝色通道荧光强度统计值的比值变化非常明显。C组、D组与对照组无明显差异，见图4。
在细胞中作为一种亚细胞器存在的脂滴与很多的生理活动密切相关，例如蛋白质的降解，细胞膜的生成和维护等。在共定位实验中发现本发明的比率荧光探针对脂滴的特异性共定位系数高达0.92，说明本发明的探针对脂滴呈现出了很好的靶向性，见图5。
综上，本发明所述的比率荧光探针不仅可以定量检测低浓度硫酸盐，而且能够用于细胞内的比率成像和脂滴的靶向；因此该靶向脂滴的亚硫酸盐比率荧光探针有望在工业生产和临床医学中发挥作用，具有广阔的应用前景。
附图说明
图1为本发明所述靶向脂滴的亚硫酸盐比率荧光探针与亚硫酸盐生成产物的高分辨质谱。
图2为本发明所述靶向脂滴的亚硫酸盐比率荧光探针对各种离子的响应荧光发射谱图。
其中：a图为荧光光谱；b图为探针对各种被分析物的荧光响应柱状图，1～21分别为1.只加探针；2.F-；3.Br-；4.S2-；5.SO4 2-；6.ClO-；7.H2PO4 -；8.HS-；9.SCN-；10.S2O3 2-；11.Co2 +；12.Pb2+；13.K+；14.Al3+；15.Ca2+；16.Fe3+；17.Fe2+,18.GSH；19.Cys；20.SO3 2-；21.HSO3 -。
图3为本发明所述靶向脂滴的亚硫酸盐比率荧光探针在470nm与627nm处的荧光强度变化，及其比值与亚硫酸盐浓度间的线性关系图。
图4为本发明所述靶向脂滴的亚硫酸盐比率荧光探针在HepG2细胞内荧光显微成像图及比值对比图。
其中：A组：细胞用该比率亚硫酸盐荧光探针(1μM)溶液孵化1小时；B组：细胞用该比率亚硫酸盐荧光探针(1μM)溶液孵化1小时，进一步用GSH和Na2S2O3处理0.5h，最后收集蓝色和红色通道成像。C组：该比率亚硫酸盐荧光探针(1μM)溶液孵化1小时，进一步用GSH处理0.5h，最后收集蓝色和红色通道成像；D组：细胞用该比率亚硫酸盐荧光探针(1μM)溶液孵化1小时，进一步用GSH、Na2S2O3和TNBS分别处理0.5h，最后收集蓝色和红色通道成像。
图5为本发明所述靶向脂滴的亚硫酸盐比率荧光探针对脂滴特异性荧光显微成像图。
其中，a组为HepG2细胞用本发明的探针处理后的成像；b组为HepG2细胞用脂滴定位染料H34477处理后的成像；c组为a与b的合并；d为共定位系数。
具体实施方式
下面结合具体实施例对本发明内容进行详细说明。如下所述例子仅是本发明的较佳实施方式而已，并非对本发明作任何形式上的限制，凡是依据本发明的技术实质对实施方式所做的任何简单修改，等同变化与修饰，均属于本发明技术方案的范围内。
本发明使用的细胞、试剂或实验器材均为市售产品。
实施例1
(E)-2-(3-氰基-5,5-二甲基-4-(2-(9-(3-(哌嗪-1-基)丙基)-9H-咔唑-3-基)乙烯基)呋喃2(5H)-亚基)丙二腈(300mg,0.6mmol)和7-(二乙氨基)-2-氧代-2H-色烯-3-碳酰氯(167.8mg,0.6mmol)溶于30mL无水二氯甲烷，向体系加入三乙基胺(60mg,0.6mmol)。室温反应3小时。减压蒸馏除去反应溶剂，粗产品经柱层析(DCM:MeOH＝50:1)纯化得到固体306.1mg。产率：68％。
结构确认谱图数据，1H NMR(300MHz,DMSO-d6):δ(ppm)8.80(s,1H),8.27(d,J＝7.8Hz,1H),8.19(d,J＝16.2Hz,1H),8.08(d,J＝8.7Hz,1H),7.94(s,1H),7.80(d,J＝8.4Hz,1H),7.73(d,J＝8.1Hz,1H),7.47-7.57(m,2H),7.24-7.34(m,2H),6.73(d,J＝9Hz,1H),6.54(s,1H),4.53(s,2H),3.54(s,2H),3.45(d,J＝6.9Hz,4H),3.31(s,2H),2.24(s,6H),1.99(s,2H),1.84(s,5H),1.23(s,8H).13C NMR(75MHz,DMSO-d6):177.80,176.26,164.35,158.81,157.02,151.67,150.38,143.91,143.49,141.29,130.50,128.11,127.20,126.03,124.25,123.53,122.73,121.29,120.75,116.65,113.49,112.65,112.34,111.87,111.04,110.80,109.82,107.59,99.43,96.80,96.41,63.52,44.62,41.98,30.26,29.11,25.90,23.51,23.06,14.44,12.76,11.48.MS:m/z计算值[C45H43N7O4+H]+:746.3377,发现值：746.3190。
上述亚硫酸盐比率荧光探针的制备，如下式所示：
Figure BDA0002201554590000041
实施例2
向装有5μM该比率探针的10ml容量瓶中，加入乙醇与磷酸盐(0.01M)缓冲液(v/v＝1：1，pH＝7)的溶液10ml,用微量进样器分别加入20当量的:空白,F-；Br-；S2-；SO4 2-；ClO-；H2PO4 -；HS-；SCN-；S2O3 2-；Co2+；Pb2+；K+；Al3+；Ca2+；Fe3+；Fe2+；GSH；Cys；SO3 2-；HSO3 -,摇匀作用15min后进行荧光测试。
结果表明，该探针主要对亚硫酸盐SO3 2-及HSO3 -有较好的响应和选择性。见图2。
实施例3
向装有5μM该比率探针的10ml容量瓶中，加入乙醇与磷酸盐(0.01M)缓冲液(v/v＝1：1，pH＝7)的溶液10ml,用微量进样器分别加入不同浓度的NaHSO3，摇匀作用15min后进行荧光测试。
结果表明，470nm处荧光强度与627nm处荧光强度的比值相对NaHSO3浓度在一定范围内呈线性关系。见图3。
实施例4
细胞内荧光成像测试：
HepG2细胞转移到小的玻璃瓶中孵化24h后，A组用该比率探针(1μM)溶液孵化1小时，然后PBS洗涤三次；B组用该比率探针(1μM)溶液孵化1小时，然后PBS洗涤三次，用GSH(500μM)和Na2S2O3(250μM)处理0.5h；C组用该比率探针(1μM)溶液孵化1小时，然后PBS洗涤三次，只用GSH(500μM处理0.5h；D组用该比率探针(1μM)溶液孵化1小时，然后PBS洗涤三次，用GSH(500μM)、Na2S2O3(250μM)和TNBS(10mM)处理0.5h；进行共聚焦细胞成像检测。计算蓝色通道荧光与红色通道荧光强度统计值的比值。
所用激发波长为405nm，蓝色通道收集波长为450-555nm，红色通道收集波长为560-700nm。见图4。
实施例5
探针靶向定位测试：
将HepG2细胞用探针(2μM)培养半小时后，用脂滴定位试剂(H34477，0.1μM)继续培养30分钟，PBS洗涤三次，然后进行共聚焦成像。
所用激发波长为405nm，蓝色通道收集波长为450-550nm，红色通道收集波长为640-700nm，见图5；图中，a组为HepG2细胞用本发明的探针处理后的成像；b组为HepG2细胞用脂滴定位染料H34477处理后的成像；c组为a与b的合并；d为共定位系数。

Claims (2)

1.一种基于荧光共振能量转移相应机理的靶向脂滴的亚硫酸盐比率荧光探针，该比率荧光探针以香豆素荧光团为能量供体、共轭咔唑衍生物为能量受体，通过哌嗪烷基链连接构成；其特征在于：所述比率型荧光探针化学结构式如式(I)所示：
Figure FDA0003326077710000011
2.权利要求1所述基于荧光共振能量转移相应机理的靶向脂滴的亚硫酸盐比率荧光探针的制备方法，步骤是：(E)-2-(3-氰基-5,5-二甲基-4-(2-(9-(3-(哌嗪-1-基)丙基)-9H-咔唑-3-基)乙烯基)呋喃2(5H)-亚基)丙二腈与7-(二乙氨基)-2-氧代-2H-色烯-3-碳酰氯共溶于无水二氯甲烷，向体系加入三乙基胺，室温反应，减压蒸馏除去反应溶剂，粗产品经柱层析纯化得到所述靶向脂滴的亚硫酸盐比率型荧光探针。
CN201910867007.6A 2019-09-12 2019-09-12 一种靶向脂滴的亚硫酸盐比率荧光探针及其应用 Active CN110655510B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910867007.6A CN110655510B (zh) 2019-09-12 2019-09-12 一种靶向脂滴的亚硫酸盐比率荧光探针及其应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910867007.6A CN110655510B (zh) 2019-09-12 2019-09-12 一种靶向脂滴的亚硫酸盐比率荧光探针及其应用

Publications (2)

Publication Number Publication Date
CN110655510A CN110655510A (zh) 2020-01-07
CN110655510B true CN110655510B (zh) 2021-12-10

Family

ID=69037128

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910867007.6A Active CN110655510B (zh) 2019-09-12 2019-09-12 一种靶向脂滴的亚硫酸盐比率荧光探针及其应用

Country Status (1)

Country Link
CN (1) CN110655510B (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111171008B (zh) * 2020-01-10 2021-12-14 山东大学 一种检测靶向脂滴的so2衍生物的增效性比率荧光探针及其应用
CN112321570A (zh) * 2020-10-27 2021-02-05 四川大学华西医院 一种专一性标记脂滴的2,5-（杂）芳基取代咪唑类荧光探针及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104946248A (zh) * 2015-07-09 2015-09-30 山东大学 一种水溶性亚硫酸氢根比率荧光探针及其应用
CN108129428A (zh) * 2018-01-09 2018-06-08 山东大学 一种检测亚硫酸氢根的比率荧光探针及其应用
CN108623575A (zh) * 2017-03-21 2018-10-09 泰山医学院 一种简单而有效的检测亚硫酸盐的荧光探针
CN108997289A (zh) * 2018-09-25 2018-12-14 山东大学 一种靶向脂滴的次氯酸比率荧光探针及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104946248A (zh) * 2015-07-09 2015-09-30 山东大学 一种水溶性亚硫酸氢根比率荧光探针及其应用
CN108623575A (zh) * 2017-03-21 2018-10-09 泰山医学院 一种简单而有效的检测亚硫酸盐的荧光探针
CN108129428A (zh) * 2018-01-09 2018-06-08 山东大学 一种检测亚硫酸氢根的比率荧光探针及其应用
CN108997289A (zh) * 2018-09-25 2018-12-14 山东大学 一种靶向脂滴的次氯酸比率荧光探针及其应用

Also Published As

Publication number Publication date
CN110655510A (zh) 2020-01-07

Similar Documents

Publication Publication Date Title
US8153827B2 (en) Reagents for biomolecular labeling, detection and quantification employing Raman spectroscopy
Li et al. Chromogenic and fluorogenic chemosensors for hydrogen sulfide: review of detection mechanisms since the year 2009
Feng et al. A readily available colorimetric and near-infrared fluorescent turn-on probe for detection of carbon monoxide in living cells and animals
Palanisamy et al. A water soluble and fast response fluorescent turn-on copper complex probe for H2S detection in zebra fish
Zhao et al. A near-infrared and two-photon ratiometric fluorescent probe with a large Stokes shift for sulfur dioxide derivatives detection and its applications in vitro and in vivo
Peng et al. A novel fluorescent probe for selective detection of hydrogen sulfide in living cells
CN110590753B (zh) 一种靶向线粒体的近红外so2衍生物比率荧光探针及其应用
CN108844931B (zh) Lzq荧光探针在同时检测so2衍生物和hsa中的应用
Gong et al. A novel two-photon fluorescent probe with long-wavelength emission for monitoring HClO in living cells and tissues
Yang et al. BODIPY-based fluorescent probe for cysteine detection and its applications in food analysis, test strips and biological imaging
CN112745287B (zh) 一种荧光探针hm及其制备方法和应用
Zhu et al. A novel highly sensitive fluorescent probe for bioimaging biothiols and its applications in distinguishing cancer cells from normal cells
CN110655510B (zh) 一种靶向脂滴的亚硫酸盐比率荧光探针及其应用
CN108997289B (zh) 一种靶向脂滴的次氯酸比率荧光探针及其应用
Wu et al. A simple ratiometric fluorescent sensor selectively compatible of different combinations of characteristic groups for identification of glutathione, cysteine and homocysteine
Sun et al. Construction of a water-soluble fluorescent probe for copper (II) ion detection in live cells and food products
CN107286173B (zh) Rhodol类衍生物及其制备方法和应用
KR101584606B1 (ko) 이광자 형광 프로브, 이의 제조방법 및 이를 이용한 pH 이미지화 방법
Chen et al. A coumarin-based fluorescent probe with 4-phenylselenium as the active site for multi-channel discrimination of biothiols
Pei et al. Novel benzotriazole-based probes for the selective detection of Cu (II)
CN112694471B (zh) 一种苯并吲哚盐-吩噻嗪衍生物及其制备和应用
CN106518855A (zh) 一种以半川菁及黄酮醇为荧光团的二氧化硫衍生物比例荧光探针及其应用
CN111778014A (zh) β-半乳糖苷酶近红外荧光探针及其制备方法和用途
CN110894201B (zh) 一种用于线粒体过氧化氢、蛋白和核酸同时超分辨成像的单分子荧光探针及其制备和应用
CN109796966B (zh) 一种次氯酸比率荧光探针及其应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant