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Use of chalcone fluorescent probe in detection of thiophenol compound in water solution

A technology of fluorescent probes and chalcones, applied in the field of analysis, to achieve the effect of simple, fast and accurate experimental methods

Active Publication Date: 2019-01-11
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing molecular probe reports, there is no report on the application of the probe to the detection of thiophenol compounds in seawater samples

Method used

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  • Use of chalcone fluorescent probe in detection of thiophenol compound in water solution
  • Use of chalcone fluorescent probe in detection of thiophenol compound in water solution
  • Use of chalcone fluorescent probe in detection of thiophenol compound in water solution

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The design synthesis of embodiment 1 probe molecule probe-KCN1

[0037] Cs was added to a solution of probe-OH (0.5mmol) in dichloromethane (20ml) 2 CO 3 (1 mmol) was stirred at room temperature for 30 min, 2,4-dinitrofluorobenzene (0.625 mmol) was added to the above solution, and stirred overnight at room temperature, a solid precipitated out. The solvent was dried by filtration, and recrystallized from ethyl acetate:petroleum ether (V:V=2:8) to obtain a yellow powdery solid. Yield: 85%.Probe-KCN1: 1 H NMR (500Hz, DMSO-d 6 )δ9.03(s,1H),8.96(d,J=2.7Hz,1H),8.77(s,1H),8.49(dd,J=9.2,2.8Hz,1H),8.37(d,J=8.9 Hz,1H),8.25(d,J=7.9Hz,2H),8.16(d,J=15.4Hz,1H),8.08(d,J=8.7Hz,2H),8.05(d,J=15.5Hz, 1H), 7.89(d, J=2.1Hz, 1H), 7.73(d, J=8.6Hz, 1H), 7.67(d, J=8.2Hz, 1H), 7.60(dd, J=8.9, 2.3Hz, 1H), 7.52(t, J=7.7Hz, 1H), 7.40(d, J=9.2Hz, 1H), 7.29(t, J=7.4Hz, 1H), 4.51(q, J=6.9Hz, 2H) ,1.35(t,J=7.1Hz,3H)ppm; 13 C NMR (125Hz, DMSO-d 6 )δ188.89(s),154.79(s),154.14(s),146.37(s),142.4...

Embodiment 2

[0039] Spectral properties of embodiment 2 probe molecule probe-KCN1

[0040]The experimental method is as follows: the probe molecule probe-KCN1 is dissolved in DMSO to obtain a 5 mM probe mother solution, and stored at 4°C. In the experimental determination, the buffer solution of DMSO / PBS buffer (1:1, v / v, 20mM, pH=7.4) was used to dilute it into a 5μM standard solution. Dissolve 4-methoxythiophenol in DMSO solvent, make 5mM mother solution, store at 4°C, dilute with DMSO / PBSbuffer (1:1, v / v, 20mM, pH=7.4) buffer solution in the experimental measurement Make a standard solution of 0-30μM, set 2.5μM as a concentration gradient. Add 100 μL of probe solution to the 96-well black plate and mix with different concentrations of thiophenol test solution, mix well, incubate at 37°C for 60 minutes, and then measure its spectrum. The results are as follows: figure 2 and image 3 Shown: Adding thiophenol to the probe-KCN1 solution enhanced its fluorescence intensity by 40 times. ...

Embodiment 3

[0046] Example 3 Selectivity experiment of probe molecule probe-KCN1.

[0047] The experimental method is as follows: the probe molecule probe-KCN1 is dissolved in DMSO to obtain a 5 mM probe mother solution, and stored at 4°C. In the experimental determination, the buffer solution of DMSO / PBS buffer (1:1, v / v, 20mM, pH=7.4) was used to dilute it into a 5μM standard solution. 4-Methoxythiophenol, 4-fluorothiophenol and 4-methylthiophenol were dissolved in DMSO solvent to prepare a 2.5mM mother solution, stored at 4°C, and used in DMSO / PBS buffer (1 :1, v / v, 20mM, pH=7.4) buffer solution diluted to 30μM standard solution. Amino acids such as: GSH, Cys, Hcy, Ala, Gly, Thr and Ser; general interfering substances such as: Ph-NH 2 , Ph-OH, NaSH and C 2 h 5 SH; common inorganic salts such as: KI, (AcO) 2 Co,NaHSO 3 ,KBr,SnCl 2 ,FeCl 3 ,CuSO 4 .5H 2 O,Pb(AcO) 4 ,CuI,CaCl 2 ,KF,NaCl,MgSO 4 ,FeSO 4 and NiSO 4 Dissolved in deionized water, configured as a 5mM mother solut...

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Abstract

The invention discloses a closing-opening molecular fluorescent probe of chalcone linked to a 2, 4-dinitrophenyl group. The closing-opening molecular fluorescent probe is used for detection of toxic thiophenol in the offshore waters. The closing-opening molecular fluorescent probe has no fluorescence. Thiophenol improves the fluorescence and strong yellow-green fluorescence is produced. Through use of thiophenol in the probe molecule probe-KCN1 solution, the fluorescence intensity is increased by 40 times. When the thiophenol has a concentration of 0-10 micromoles per liter, the fluorescence intensity of the probe-KCN1 detection system shows a good linear relationship with the concentration of thiophenol. The closing-opening molecular fluorescent probe can be used for detecting a thiophenol compound at a low concentration in the seawater sample and has a practical application value.

Description

technical field [0001] The invention belongs to the technical field of analysis, and in particular relates to the design and synthesis of molecular fluorescent probes and the recognition and response to thiophenol compounds. The probe molecule can be used to identify thiophenol compounds under experimental conditions, and can detect thiophenol compounds under low-concentration conditions in seawater samples, and has practical application value. Background technique [0002] Thiophenol is a highly toxic colorless liquid with a suffocating odor. It is widely used in the fields of medicine, pesticide, chemical industry and polymer materials, such as the preparation of medical pharmaceuticals, pesticides, and industrial additives. In nature, highly toxic thiophenols endanger the living environment of aquatic organisms and animals. The half-lethal concentration of thiophenol to fish (LC 50 ) ranges from 0.01 to 0.4mM, the half-lethal dose (LD) for mice 50 ) is 46.2mg / kg. There...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029G01N21/643
Inventor 史大永刘华郭传龙王立军郭书举江波
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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