一种基于联萘衍生物荧光探针的合成及其对精氨酸的识别

doi:10.11944/j.issn.1000-0518.2018.01.170317

摘要/Abstract

摘要：

构建了一种基于(R)-2,2'-二羟基-[1,1'-联萘]-3-醛的荧光探针。通过核磁共振波谱仪(NMR)以及质谱(MS)等技术手段对其结构进行了表征。结果表明,该荧光探针能够灵敏、高选择性地检测精氨酸,并显示出颜色和强烈的荧光变化双重响应。相应的荧光增强比值与精氨酸的浓度(0~30 μmol/L)呈现良好的线性关系,相关系数R²为0.9914,检测限低至1.3 μmol/L。此外,精氨酸的加入还促使该探针结构中的联萘酚手性结构发生偏转。

关键词: 联萘酚, 荧光探针, 精氨酸, 手性

Abstract:

A kind of fluorescence probe based on (R)-2,2'-dihydroxy-[1,1'-binaphthalene]-3-carboxaldehyde was constructed. The structure was characterized by hydrogen/carbon nuclear magnetic resonance spectroscopy(¹H NMR, ¹³C NMR) and mass spectrometry(MS). The results show that the fluorescent probe can detect arginine in a sensitive and highly selective manner with a double response of color and intense fluorescence. The corresponding fluorescence enhancement ratio is in good linear relation with the concentration of arginine(0~30 μmol/L), the correlation coefficient R² is 0.9914 and the lowest detection limit is 1.3 μmol/L. In addition, the addition of arginine also caused the chiral structure of the probe to deflect, and the changes of binaphthol derivative axial chiral were verified by the changes of the circular dichromatic spectrum.

Key words: binaphthol, fluorescence probe, arginine, chirality

刘传涛, 肖婷, 王芳, 陈小强. 一种基于联萘衍生物荧光探针的合成及其对精氨酸的识别[J]. 应用化学, 2018, 35(1): 40-45.

LIU Chuantao, XIAO Ting, WANG Fang, CHEN Xiaoqiang. Synthesis of Binol-based Fluorescence Probe and Recognition of Arginine[J]. Chinese Journal of Applied Chemistry, 2018, 35(1): 40-45.

参考文献

[1]	Gong D Y,Tian Y J,Yang C D,et al.A Fluorescence Enhancement Probe Based on BODIPY for the Discrimination of Cysteine from Homocysteine and Glutathione[J]. Biosens Bioelectron,2016,85:178-183.
[2]	Liu G T,Liu D,Han X,et al.A Hemicyanine-Based Colorimetric and Ratiometric Fluorescent Probe for Selective Detection of Cysteine and Bioimaging in Living Cell[J]. Talanta,2017,170:406-412.
[3]	Cheng D X,Zhu H Y. Determination of L-Arginine Content in Radix isatidis by a Composite Fluorescent Probe of Pd(Ⅱ)[J]. J Food Drug Anal,2014,22(4):537-541.
[4]	Shahida P S D,Affrose A,Pitchumani K. Plumbagin as Colorimetric and Ratiometric Sensor for Arginine[J]. Sens Actuators B:Chem,2015,221:521-527.
[5]	Shang X F,Li J,Guo K R,et al.Development and Cytotoxicity of Schiff Base Derivative as a Fluorescence Probe for the Detection of L-Arginine[J]. J Mol Struct,2017,1134:369-373.
[6]	Shang X F,Luo L M,Ren K,et al.Synthesis and Cytotoxicity of Azo Nano-Materials as New Biosensors for L-Arginine Determination[J]. Mater Sci Eng C,2015,51:279-286.
[7]	Yu M M,Du W W,Li H,et al.Near-infrared Ratiometric Fluorescent Detection of Arginine in Lysosome with a New Hemicyanine Derivative[J]. Biosens Bioelectron,2017,92:385-389.
[8]	Lu X H,Wang W,Dong Q,et al.A Multi-Functional Probe to Discriminate Lys, Arg, His, Cys, Hcy and GSH from Common Amino Acids[J]. Chem Commun,2015,51(8):1498-501.
[9]	YANG Tingting,GUO Zhiqian,SHAO Andong,et al.A Turn-on Fluorescent Probe for Cysteine Based on Benzopyran[J]. Chinese J Appl Chem,2016,33(4):397-405(in Chinese). 杨婷婷,郭志前,邵安东,等. 基于苯并吡喃腈的激活型半胱氨酸荧光探针[J]. 应用化学,2016,33(4):397-405
[10]	Wang F,Nandhakumar R,HU Y,et al.BINO(L)-based Chiral Receptors as Fluorescent and Colorimetric Chemosensors for Amino Acids[J]. J Org Chem,2013,78(22):11571-11576.
[11]	Wang F,Nandhakumar R,Moon J H,et al.Ratiometric Fluorescent Chemosensor for Silver Ion at Physiological pH[J]. Inorg Chem,2011,50(6):2240-2245.
[12]	Chen X Q,Nam S W,KIM G H,et al.A Near-Infrared Fluorescent Sensor for Detection of Cyanide in Aqueous Solution and Its Application for Bioimaging[J]. Chem Commun,2010,46(47):8953-8955.
[13]	Liu C T,Xiao T,Wang Y C,et al.Rhodamine Based Turn-on Fluorescent Sensor for Hg2+ and Its Application of Microfluidic System and Bioimaging[J]. Tetrahedron,2017,73(34):5189-5193.
[14]	Wanderley M M,Wang C,Wu C D,et al.A Chiral Porous Metal-organic Framework for Highly Sensitive and Enantioselective Fluorescence Sensing of Amino Alcohols[J]. J Am Chem Soc,2012,134(22):9050-9053.
[15]	CHEN Xiuying,GUO Lin,ZHENG Changge,et al.Synthesis and Spectral Properities of Benzothiazole Cyanine Dyes for Nucleic Acid Fluorescence Probe[J]. Chinese J Appl Chem,2012,29(8):892-897(in Chinese). 陈秀英,郭琳,郑昌戈. 苯并噻唑类核酸分子荧光探针的合成及光谱性质[J]. 应用化学,2012,29(8):892-897.
[16]	Alexey S,Monica P,Aaron J R,et al.Anode Catalysts for Direct Hydrazine Fuel Cells:From Laboratory Test to an Electric Vehicle[J]. Angew Chem Int Ed,2014,53:10336-10339
[17]	Wang H L,Zhou G D,Mao C,et al.A Fluorescent Sensor Bearing Nitroolefin Moiety for the Detection of Thiols and Its Biological Imaging[J]. Dyes Pigm,2013,96(1):232-236.
[18]	Zhou M,Smith A M,Das A K,et al.Self-assembled Peptide-Based Hydrogels as Scaffolds for Anchorage-dependent Cells[J]. Biomaterials,2009,30(13):2523-2530.
[19]	Akira N,Mikio Y,Manami N,et al.Direct Extract Derivatization for Determination of Amino Acids in Human Urine by Gas Chromatography and Mass Spectrometry[J]. J Chromatogr B,2002,776:49-55.
[20]	Cao G P,Yang R Y,Zhuang Y F,et al.Simple and Sensitive Determination of Trace Nitrite in Water by Zero-Crossing First-Derivative Synchronous Fluorescence Spectrometry Using 6-Amino-1,3-naphthalenedisulfonic Acid as a New Fluorescent Probe[J]. Anal Bioanal Chem,2017,409(19):4637-4646.
[21]	Prasad S,Mandal I,Singh S,et al.Near UV-Visible Electronic Absorption Originating from Charged Amino Acids in a Monomeric Protein[J]. Chem Sci,2017,8(8):5416-5433.
[22]	Smidlehner T,Piantanida I. Novel DNA/RNA-targeting Amino Acid Beacon for the Versatile Incorporation at Any Position Within the Peptide Backbone[J]. Amino Acids,2017,49(8):1381-1388
[23]	Chen C,Huang Q F,Zou S,et al.Asymmetric Alkyne Addition to Aldehydes Catalyzed by Schiff Bases Made from 1,1'-Bi-2-naphthol and Chiral Benzylic Amines[J]. Tetrahedron:Asymmetry,2014,25(3):199-201.
[24]	Huang Z,Yu S S,Zhao X,et al.A Convenient Fluorescent Method to Simultaneously Determine the Enantiomeric Composition and Concentration of Functional Chiral Amines[J]. Chem Eur J,2014,20(50):16458-16461.
[25]	Xu X C,Trindle C O,Zhang G Q,et al.Fluorescent Recognition of Hg2+ by a 1,1'-Binaphthyl-based Macrocycle:A Highly Selective Off-On-Off Response[J]. Chem Commun,2015,51(40):8469-8472.