Citation: 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. doi: 10.11944/j.issn.1000-0518.2018.01.170317 shu

Synthesis of Binol-based Fluorescence Probe and Recognition of Arginine

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

Corresponding author: WANG Fang, fangwang@njtech.edu.cn CHEN Xiaoqiang, chenxq@njtech.edu.cn

^‡

Received Date: 5 September 2017
Revised Date: 22 September 2017
Accepted Date: 28 September 2017

Fund Project: the Natural Science Foundation of the Jiangsu Higher Education Institutions of China 14KJA150005the National Natural Science Foundation of China 21406109the National Natural Science Foundation of China 21722605Supported 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)the Jiangsu Natural Science Funds for Distinguished Young Scholars BK20140043the National Natural Science Foundation of China 21376117

Figures(8)

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.
- binaphthol,
- fluorescence probe,
- arginine,
- chirality
1. [1]
  Gong D Y, Tian Y J, Yang C D. A Fluorescence Enhancement Probe Based on BODIPY for the Discrimination of Cysteine from Homocysteine and Glutathione[J]. Biosens Bioelectron, 2016,85:178-183. doi: 10.1016/j.bios.2016.05.013
2. [2]
  Liu G T, Liu D, Han X. A Hemicyanine-Based Colorimetric and Ratiometric Fluorescent Probe for Selective Detection of Cysteine and Bioimaging in Living Cell[J]. Talanta, 2017,170:406-412. doi: 10.1016/j.talanta.2017.04.038
3. [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. doi: 10.1016/j.jfda.2014.04.006
4. [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. doi: 10.1016/j.snb.2015.06.149
5. [5]
  Shang X F, Li J, Guo K R. 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. doi: 10.1016/j.molstruc.2016.12.105
6. [6]
  Shang X F, Luo L M, Ren K. Synthesis and Cytotoxicity of Azo Nano-Materials as New Biosensors for L-Arginine Determination[J]. Mater Sci Eng C, 2015,51:279-286. doi: 10.1016/j.msec.2015.03.005
7. [7]
  Yu M M, Du W W, Li H. Near-infrared Ratiometric Fluorescent Detection of Arginine in Lysosome with a New Hemicyanine Derivative[J]. Biosens Bioelectron, 2017,92:385-389. doi: 10.1016/j.bios.2016.10.090
8. [8]
  Lu X H, Wang W, Dong Q. 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. doi: 10.1039/C4CC07757A
9. [9]
  YANG Tingting, GUO Zhiqian, SHAO Andong. A Turn-on Fluorescent Probe for Cysteine Based on Benzopyran[J]. Chinese J Appl Chem, 2016,33(4):397-405. doi: 10.11944/j.issn.1000-0518.2016.04.160053
10. [10]
  Wang F, Nandhakumar R, HU Y. BINO(L)-based Chiral Receptors as Fluorescent and Colorimetric Chemosensors for Amino Acids[J]. J Org Chem, 2013,78(22):11571-11576. doi: 10.1021/jo401789a
11. [11]
  Wang F, Nandhakumar R, Moon J H. Ratiometric Fluorescent Chemosensor for Silver Ion at Physiological pH[J]. Inorg Chem, 2011,50(6):2240-2245. doi: 10.1021/ic1018967
12. [12]
  Chen X Q, Nam S W, KIM G H. 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. doi: 10.1039/c0cc03398g
13. [13]
  Liu C T, Xiao T, Wang Y C. Rhodamine Based Turn-on Fluorescent Sensor for Hg²⁺ and Its Application of Microfluidic System and Bioimaging[J]. Tetrahedron, 2017,73(34):5189-5193. doi: 10.1016/j.tet.2017.07.012
14. [14]
  Wanderley M M, Wang C, Wu C D. 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. doi: 10.1021/ja302110d
15. [15]
  CHEN Xiuying, GUO Lin, ZHENG Changge. Synthesis and Spectral Properities of Benzothiazole Cyanine Dyes for Nucleic Acid Fluorescence Probe[J]. Chinese J Appl Chem, 2012,29(8):892-897.
16. [16]
  Alexey S, Monica P, Aaron J R. Anode Catalysts for Direct Hydrazine Fuel Cells:From Laboratory Test to an Electric Vehicle[J]. Angew Chem Int Ed, 2014,53:10336-10339. doi: 10.1002/anie.201404734
17. [17]
  Wang H L, Zhou G D, Mao C. A Fluorescent Sensor Bearing Nitroolefin Moiety for the Detection of Thiols and Its Biological Imaging[J]. Dyes Pigm, 2013,96(1):232-236. doi: 10.1016/j.dyepig.2012.07.013
18. [18]
  Zhou M, Smith A M, Das A K. Self-assembled Peptide-Based Hydrogels as Scaffolds for Anchorage-dependent Cells[J]. Biomaterials, 2009,30(13):2523-2530. doi: 10.1016/j.biomaterials.2009.01.010
19. [19]
  Akira N, Mikio Y, Manami N. 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. doi: 10.1016/S1570-0232(02)00075-2
20. [20]
  Cao G P, Yang R Y, Zhuang Y F. 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. doi: 10.1007/s00216-017-0409-4
21. [21]
  Prasad S, Mandal I, Singh S. Near UV-Visible Electronic Absorption Originating from Charged Amino Acids in a Monomeric Protein[J]. Chem Sci, 2017,8(8):5416-5433. doi: 10.1039/C7SC00880E
22. [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. doi: 10.1007/s00726-017-2438-x
23. [23]
  Chen C, Huang Q F, Zou S. 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. doi: 10.1016/j.tetasy.2013.12.013
24. [24]
  Huang Z, Yu S S, Zhao X. 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. doi: 10.1002/chem.201405143
25. [25]
  Xu X C, Trindle C O, Zhang G Q. 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. doi: 10.1039/C5CC02457A
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