Synthesis of Binol-based Fluorescence Probe and Recognition of Arginine

doi:10.11944/j.issn.1000-0518.2018.01.170317

Chinese Journal of Applied Chemistry ›› 2018, Vol. 35 ›› Issue (1): 40-45.DOI: 10.11944/j.issn.1000-0518.2018.01.170317

• Full Papers • Previous Articles Next Articles

Synthesis of Binol-based Fluorescence Probe and Recognition of Arginine

LIU Chuantao^‡,XIAO Ting^‡,WANG Fang(),CHEN Xiaoqiang()

National Key Laboratory of Material Chemical Engineering,College of Chemistry and Chemical Engineering,Nanjing University of Technology,Nanjing 210009,China

Received:2017-09-05 Accepted:2017-09-28 Published:2018-01-03 Online:2018-01-03
Contact: WANG Fang,CHEN Xiaoqiang
Supported by:
Supported by the National Natural Science Foundation of China(No.21722605, No.21376117, No.21406109), the Jiangsu Natural Science Funds for Distinguished Young Scholars(No.BK20140043), the Natural Science Foundation of the Jiangsu Higher Education Institutions of China(No.14KJA150005)

Abstract

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

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.

References

[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.

Synthesis of Binol-based Fluorescence Probe and Recognition of Arginine

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hong-Li YU, Si-Yi ZHOU, Chen HONG, Wen LUO. A Flavone-based “Off-On” Fluorescence Probe for Detecting Butyrylcholinesterase in Living Cell [J]. Chinese Journal of Applied Chemistry, 2023, 40(4): 500-508.
[2]	Wei-Qiang ZHANG, Chen WANG, Yu-Rong ZHAO, Dong WANG, Ji-Qian WANG, Hai XU. Research Progress of Regulation of Driving Forces in Short Peptide Supramolecular Self‑Assembly [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1190-1201.
[3]	ZHAO Chang-Li, QIN Ming-Gao, DOU Xiao-Qiu, FENG Chuan-Liang. High Mechanical Stability and Osteogenesis of Chiral Supramolecular Hydrogel Induced by Inorganic Nanoparticles [J]. Chinese Journal of Applied Chemistry, 2022, 39(1): 177-187.
[4]	ZHANG Cheng-Lu, BAO Jin-Di, YU Feng-Ming, DONG Wen-Jing, ZHANG Yang, GONG Rong-Qing, ZHANG Yan-Peng, ZHANG Lu. Synthesis and Application of a Fluorescence Probe with Quinazolinone as the Core Block for Highly Selective and Sensitive Detection of Hypochlorite Ion [J]. Chinese Journal of Applied Chemistry, 2021, 38(8): 986-994.
[5]	LIU Hui, LIU Xiao, CAO Yuan-Qiao, LIU Ming, LIU Ya-Dong, HAN Miao-Miao, JI Sheng-Xiang. Research Progress on Amino Acid-Based Antimicrobial Polymers [J]. Chinese Journal of Applied Chemistry, 2021, 38(5): 559-571.
[6]	DING Ya-Li, HU Xiang-Xiang, FENG Xuan, ZHANG Ran, SHI Tong-Fei, WEI Lai. Mechanism of Enhancing Antifreeze Protein Activity by Low Molecular Mass Molecules [J]. Chinese Journal of Applied Chemistry, 2021, 38(12): 1612-1620.
[7]	XU Liping, LIU Qingshi, DONG Zhichen, GUO Xingjia, DONG Wei. Simple, Fast and Accurate Detection of Ciprofloxacin Based on Fluorescence Enhancement of Nitrogen-Doped Carbon Dots [J]. Chinese Journal of Applied Chemistry, 2020, 37(7): 830-838.
[8]	ZHANG Yingying, WANG Liyan, ZHAO Bing, SONG Bo. A Benzoindole-Based Probe for Recognition of Al³⁺ and Its Application [J]. Chinese Journal of Applied Chemistry, 2020, 37(1): 88-95.
[9]	ZHANG　Chenglu, WANG　Jing, LI Jingyi, YU Xiangkun, YANG Jingyi, CAI Jinhua, LI Yizhen, WANG Huayu, GONG Rongqing. Synthesis of 1,2,4-Triazine-PhenanthrolineCo(Ⅲ) Complexes and Their FluorescenceRecognition on Calf Thymus DNA [J]. Chinese Journal of Applied Chemistry, 2019, 36(2): 212-222.
[10]	WANG Tao,MA Lamaocao,MA Hengchang. Research Progress on Cell Imaging Based on the Aggregation-induced Emission Fluorescent Probes [J]. Chinese Journal of Applied Chemistry, 2018, 35(10): 1155-1165.
[11]	HUANG Zike, LIU Chao, FU Qiangqiang, LI Jin, ZOU Jianmei, XIE Sitao, QIU Liping. Aptamer-based Fluorescence Probe for Bioanalysis and Bioimaging [J]. Chinese Journal of Applied Chemistry, 2018, 35(1): 28-39.
[12]	WANG Dejia, XU Yongqian, SUN Shiguo, LI Hongjuan. Advanced in Fluorescent Probes Based on Excited State Intramolecular Proton Transfer [J]. Chinese Journal of Applied Chemistry, 2018, 35(1): 1-20.
[13]	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): 0-0.
[14]	SHI Weining,XU Yongqian,SUN Shiguo,LI Hongjuan. Research Progress on Application of Fluorescent Sensors Based on Squaraine Dyes [J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1433-1449.
[15]	ZHANG Weijie, HUO Fangjun, YIN Caixia. A Coumarin Based Ratiometric Fluorescent Probe for Fast Sensing of Hypochlorite [J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1457-1461.