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Fluorescent probe used for identifying hydrogen peroxide

A hydrogen peroxide and fluorescent probe technology, applied in the field of chemical analysis and detection, to achieve the effect of wide application range, good selectivity, anti-interference ability, and large Stokes shift

Inactive Publication Date: 2018-01-19
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are relatively few reports of a near-infrared fluorescent probe with a large Stokes shift for the detection of hydrogen peroxide.

Method used

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  • Fluorescent probe used for identifying hydrogen peroxide
  • Fluorescent probe used for identifying hydrogen peroxide
  • Fluorescent probe used for identifying hydrogen peroxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of intermediate product 2

[0028] Compound 1 (234.0 mg, 1.0 mmol) and potassium carbonate (300.1 mg, 2.2 mmol) were stirred in 8.0 mL of acetone at room temperature for 10 minutes. Then 2-(4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (356.2 mg, 1.2 mmol), the resulting mixture was reacted at 70°C for 3h. After the reaction was cooled to room temperature, the reaction mixture was concentrated under reduced pressure to obtain a crude product. Finally, column chromatography was performed using petroleum ether / dichloromethane (5 / 1, v / v) as eluent to obtain compound 3 (197.2 mg, 43.7%) as a yellow solid. 1 H NMR (500MHz, CDCl 3 )δ H 10.26(s, 1H), 7.83(d, J=7.7Hz, 2H), 7.45(d, J=7.7Hz, 2H), 7.01(s, 1H), 6.04, 1.55(s, 2H), 1.36(s , 12H), 1.16(t, J=7.0Hz, 3H), 1.12(t, J=7.1Hz, 3H)

Embodiment 2

[0029] Embodiment 2: the synthesis of probe molecule

[0030] Dissolve compound 2 (90.3 mg, 0.2 mmol) and ethyl cyanoacetate (48.2 mg, 0.4 mmol) in 5.0 mL of ethanol at room temperature, add piperidine (5.0 μL, 0.05 mmol), and stir at room temperature for 5 minutes , and the resulting solution was refluxed for 1 hour. After the reaction, the reaction solution was concentrated under reduced pressure to obtain a crude product. Finally, column chromatography using petroleum ether / ethyl acetate (4 / 1, v / v) as eluent afforded Probe1 as a red solid (46.0 mg, 39.4% yield). HRMS (ESI) m / z: C 22 h 21 N 6 o 5 [M+1]+, 449.1573; 1 H NMR (400MHz, CDCl 3 )δ H 8.72(s, 1H), 7.82(d, J=8.0Hz, 2H), 7.73(s, 1H), 7.42(d, J=8.0Hz, 2H), 5.98(s, 1H), 5.15(s, 2H) , 4.31(q, J=7.1Hz, 2H), 3.31(m, 8H), 1.35(t, J=15.5, 3H), 1.34(s, 12H), 1.21(t, J=7.0Hz, 3H), 1.07 (t, J = 7.1 Hz, 3H). 13 CNMR (100MHz, CDC l 3 )δ C 165.2, 155.9, 147.1, 143.4, 140.0, 135.1, 128.8, 126.1, 118.8, 109.6, 94.4, 9...

Embodiment 3

[0031] Embodiment 3: the application of fluorescent probe of the present invention

[0032] The probe molecule was dissolved in PBS (10mM, pH=7.4) / EtOH30% to prepare 10.0×10 -6 mol / L solution, adding various active oxygen species and anions and cations (ROO., NO., TBHP, ClO - , KO 2 , ONOO - ,OH - , I - , F - , PO 4 3- , NO2-, NO 3 - , SO 3 2- , S 2 o 3 2- , SCN - , CN - , CO 3 2- , Fe 2+ , Fe 3+ ) did not cause a significant change in fluorescence, when hydrogen peroxide (H 2 o 2 ) and interfering substances (ROO . , NO . , TBHP, ClO - , KO 2 , ONOO - ,OH - , I - , F - , PO 4 3- , NO2-, NO 3 - , SO 3 2- , S 2 o 3 2- , SCN - , CN - , CO 3 2- , Fe 2+ , Fe 3+ ) coexist, the probe is not affected by interference factors, showing a strong anti-interference ability. The probe molecule and hydrogen peroxide (H 2 o 2 ) response within a certain time and concentration range has a good linear relationship. Probe molecules can react to hyd...

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Abstract

The invention relates to a preparation method and application of a fluorescent probe used for identifying hydrogen peroxide and belongs to the technical field of chemical analysis and detection. The molecular structure of the fluorescent probe is described in the specification. Maximum absorption wavelength of the probe molecule is 480nm, after the probe molecule acts with hydrogen peroxide (H2O2), fluorescence spectrum emerges at the intensity of 619nm and is continuously increased, larger Stokes shifts are shown up, self absorption of fluorescent lights can be reduced, and detection sensitivity is improved; and emission wavelength can reduce background fluorescent lights and light damage on living cells in a probe detection process in a red light region, and penetrating power of an organism for tissues is enhanced. The probe molecule has good linearity in a certain time and concentration range, strong hydrogen peroxide (H2O2) identifying capability and strong selectivity and antijamming capability, and the probe has important application value in the fields of biochemistry and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a preparation method of a novel red light-near-infrared fluorescent probe with a large Stokes shift for detecting hydrogen peroxide and its detection of hydrogen peroxide in vitro and inside living cells Applications. Background technique [0002] Hydrogen peroxide (H 2 o 2 ) is one of the most important reactive oxygen species (ROS), which plays a key role in many physiological and pathological processes. Hydrogen peroxide (H 2 o 2 ) can be produced endogenously in cells by activation of the NADPH oxidase complex (NOX) during cellular stimulation by hormones, cytokines, neurotransmitters and peptide growth factors. Endogenous hydrogen peroxide (H 2 o 2 ) are not only major oxidative metabolites that serve as indicators of oxidative stress in biological systems, but also important signaling molecules that regulate many biological process...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64
Inventor 宋相志何龙刘兴江杨柳齐风佩廖立德
Owner CENT SOUTH UNIV
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