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Preparation and application of hydrogen peroxide near-infrared fluorescent probe

A fluorescent probe and hydrogen peroxide technology, applied in the field of fluorescent probes, can solve the problems of short emission wavelength and small Stokes shift of fluorescent probes, and achieve the effect of good spectral response performance and rapid response.

Active Publication Date: 2019-12-06
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these hydrogen peroxide fluorescent probes have shortcomings: the emission wavelength of the fluorescent probe is short, and the Stokes shift is small.
However, there are currently no benzopyranonitrile-xanthene dye-based probes for the detection of H2O2

Method used

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  • Preparation and application of hydrogen peroxide near-infrared fluorescent probe
  • Preparation and application of hydrogen peroxide near-infrared fluorescent probe
  • Preparation and application of hydrogen peroxide near-infrared fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of fluorescent probes

[0027] Synthetic route such as figure 1 . in N 2 Under protection, in a 50mL round bottom flask, DCX-OH (83.6mg, 0.2mmol), 4-bromomethylphenylboronic acid pinacol ester (71.2mg, 0.24mmol), potassium carbonate (55.2mg, 0.4mmol) Dissolved in 5.0 mL of DMF and the reaction was stirred at 60 °C for 4 h. After the reaction is complete, dilute with water and wash with CH 2 Cl 2 For extraction, the organic layer was collected, washed with brine, anhydrous Na 2 SO 4 Dry, filter and concentrate. Crude product with CH 2 Cl 2 The eluent was subjected to column chromatography to obtain a dark blue solid product DCX-B (54.5 mg, yield 43%), which was a fluorescent probe. 1 H NMR (400MHz, CDCl 3 )δ=8.89(d,J=8.3,1H),8.09(d,J=15.4,1H),7.88(d,J=7.8,2H),7.74(t,J=7.8,1H),7.53(d ,J=8.3,1H),7.47(d,J=7.8,2H),7.39(d,J=7.8,1H),7.02(d,J=8.3,1H),6.75-6.66(m,3H), 6.48(s,1H),6.06(d,J=15.4,1H),5.16(s,2H),2.61-2.50(m,2H),2.46(t,J=5.6,2H),1.87-1.81(m ,2H...

Embodiment 2

[0029] Fluorescent probes and H 2 o 2 Solution preparation

[0030] Preparation of probe solution: Weigh a certain amount of probe solid and dissolve it in DMSO to make 1×10 -4 M probe solution. h 2 o 2 Solution preparation: measure a certain amount of H with a volume fraction of 30% 2 o 2 solution, and then dilute it to a 50mL volumetric flask with distilled water to make 1×10 -2 M detection solution. will be 1.0×10 -2 M of H 2 o 2 The solution was gradually diluted to obtain 1.0 × 10 -5 -2.0×10 -3 M of H 2 o 2 solution. Mix 1.0 mL of probe stock solution and 1.0 mL of HO 2 o 2 The solution was added to a 10mL volumetric flask, and after constant volume with buffer solution, the concentration was 1.0×10 -5 M fluorescent probes and 1.0 x 10 -6 -2.0×10 -4 M of H 2 o 2 Mix the solutions to be tested.

Embodiment 3

[0032] Fluorescent probes with H 2 o 2 Determination of the fluorescence spectrum of the action

[0033] figure 2 as a fluorescent probe with H 2 o 2 The fluorescence spectrum of the action, the concentration of the fluorescent probe is 10 μM, H 2 o 2 The concentrations are 0, 0.5, 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 120, 150, 200 μM. The excitation wavelength used in the experiment is 590nm, and the emission wavelength range is 680-900nm. The slit width is 10.0 nm / 10.0 nm, and the fluorescence measurement instrument used is a Hitachi F4600 fluorescence spectrophotometer. from figure 2 It can be seen that adding H 2 o 2 Before, due to the quenching effect of boronate, the fluorescent probe had almost no fluorescence emission peak; adding H 2 o 2 Afterwards, a near-infrared fluorescence emission peak appeared in the near-infrared region (748nm). This is because the probe molecules are H 2 o 2 Oxidation, resulting in the breakage of borate ester bonds...

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Abstract

The invention relates to preparation and application of a hydrogen peroxide (H2O2) near-infrared fluorescent probe. A structural formula of the probe is as shown in the specification. The invention provides a preparation method for synthesizing the fluorescent probe by using a benzopyranitrile-xanthene dye, potassium carbonate, 4-(bromomethyl)benzeneboronic acid pinacol ester and other raw materials. The fluorescent probe is a hydrogen peroxide fluorescent probe with near-infrared emission and large Stoke shift. Firstly, the probe shows high sensitivity to H2O2, and fluorescence intensity is increased by 24 times. Secondly, the fluorescent probe shows high selectivity to H2O2, and is not affected by other active oxygen, active nitrogen, various ions and biothiols. Moreover, the fluorescentprobe reacts quickly with H2O2, and a response time is within 30 min. In addition, the fluorescent probe is applied to detection of hydrogen peroxide content in living cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to the preparation and application of hydrogen peroxide fluorescent probes based on benzopyranonitrile-xanthene dyes. Background technique [0002] Hydrogen peroxide (H 2 o 2 ) is one of the important reactive oxygen species, which plays an important role in cell signaling and homeostasis (B.D'Authreaux, M.B.Toledano, Nat. Rev. Mol. Cell Biol. 2007, 8, 813-814). h 2 o 2 It is a short-lived endogenous substance produced by cellular respiration, which is regulated by a series of free radical scavenging enzymes. At the same time, H 2 o 2 Can be used as a marker of oxidative stress in vivo. More and more evidence shows that the abnormal expression of hydrogen peroxide is closely related to various diseases (T.Finkel, N.J.Holbrook, Nature.2000,408,239-240; K.J.Barnham, C.L.Masters, A.I.Bush, Nat.Rev.Drug . Discov. 2004, 3, 205-214; M.T. Lin, M.F. Beal, Nature. 2006, 443...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/02C09B23/10G01N21/64
CPCC09K11/06C07F5/025C09B23/105G01N21/6428C09K2211/1088C09K2211/1096
Inventor 李春艳王文新
Owner XIANGTAN UNIV
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