Preparation and application of a hypoxic fluorescent probe based on hemicyanine dye

A fluorescent probe and semicyanine technology, applied in the field of fluorescent probes, can solve problems such as interference, short emission wavelength of fluorescent probes, unfavorable deep tissue imaging detection, etc.

Active Publication Date: 2022-04-01
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these hypoxic fluorescent probes have disadvantages: (1) The emission wavelength of fluorescent probes is short, which is easily interfered by their own background fluorescence, which is not conducive to deep tissue imaging detection.
However, there are currently no fluorescent probes based on hemicyanine dyes to detect hypoxia

Method used

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  • Preparation and application of a hypoxic fluorescent probe based on hemicyanine dye
  • Preparation and application of a hypoxic fluorescent probe based on hemicyanine dye
  • Preparation and application of a hypoxic fluorescent probe based on hemicyanine dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of fluorescent probes

[0025] Synthetic route such as figure 1 . In a 100mL round bottom flask, add 10mL containing Cy-NH 2 (0.17g, 0.3mmol) CH 3 CN / CH 2 Cl 2 (1:1) mixed solution, added concentrated hydrochloric acid (0.05mL, 1mmol) at 0°C under nitrogen protection, and stirred well. Next, the NaNO 2 (0.02g, 0.3mmol) of distilled aqueous solution was slowly added dropwise to the above reaction solution, and the stirring was continued for 30min. Then, an aqueous solution of sulfamic acid (0.06 g, 0.6 mmol) was added and stirring was continued for 10 min. Subsequently, CH containing phenol (0.16mL, 1.8mmol) 3 The CN solution was added to the reaction solution, and the pH was adjusted to 6.0. Under the same conditions, the stirring was continued for 1.5 h. After the reaction was completed, dilute with water and dilute with CH 2 Cl 2 extraction. The organic layer was collected, washed with brine, anhydrous Na 2 SO 4 Dry, filter and concentrate. Th...

Embodiment 2

[0027] Fluorescent probes and Na 2 S 2 o 4 Solution preparation

[0028] Preparation of probe solution: Weigh a certain amount of probe solid and dissolve it in methanol to make 1×10 -4 M probe solution. Na 2 S 2 o 4 Preparation of the solution (preparation for current use): weigh a certain amount of Na 2 S 2 o 4 Dissolve the solid in distilled water to make 1×10 -1 M detection solution. will be 1.0×10 -1 Na of M 2 S 2 o 4 The solution was gradually diluted to obtain 1.0 × 10 -1 -1.0×10 -3 Na of M 2 S 2 o 4 solution. Mix 1.0 mL of probe stock solution and 1.0 mL of Na 2 S 2 o 4 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 -2 -1.0×10 -4 Na of M 2 S 2 o 4 Mix the solutions to be tested.

Embodiment 3

[0030] Fluorescent probes and Na 2 S 2 o 4 Determination of the fluorescence spectrum of the action

[0031] figure 2 as fluorescent probe and Na 2 S 2 o 4 The fluorescence spectrum of the action, the concentration of the fluorescent probe is 10μM, Na 2 S 2 o 4 The concentrations are 0, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0mM in turn. The excitation wavelength used in the experiment is 680nm, and the emission wavelength range is 705-800nm. 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 Na 2 S 2 o 4 Before, due to the quenching effect of the azo bond, the fluorescent probe had no fluorescence emission peak; adding Na 2 S 2 o 4 Afterwards, a near-infrared fluorescence emission peak appeared in the near-infrared region (725nm). This is because the probe molecules are surrounded by Na 2 S 2 o 4 Reduction, resulting in the bre...

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Abstract

The invention relates to the preparation and application of an anoxic fluorescent probe based on a semicyanine dye. The structural formula of the fluorescent probe is: The preparation method of this fluorescent probe; This fluorescent probe is a kind of anoxic fluorescent probe with near-infrared emission, high selectivity; Because Na 2 S 2 o 4 It has been proved that it can be used to simulate the anoxic reducing environment in biological samples, so we choose Na 2 S 2 o 4 to replace the hypoxic environment outside the body. First, the fluorescent probe for Na 2 S 2 o 4 Exhibiting a high signal-to-noise ratio, the probe with Na 2 S 2 o 4 After the reaction, the fluorescence is significantly enhanced; secondly, the fluorescent probe for Na 2 S 2 o 4 It shows good selectivity and is not interfered by other ions and reducing substances; in addition, this fluorescent probe has been successfully applied in cell imaging research, which can detect hypoxia in cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to the preparation and application of an anoxic fluorescent probe based on a semicyanine dye. Background technique [0002] Hypoxia is a common phenomenon in the occurrence and development of malignant tumors. Its occurrence is mainly related to unrestricted growth of tumors, increased oxygen consumption, and poor development of tumor blood vessels. It is also a pathological process shared by many clinical diseases (A.L.Harris, Nat . Rev. Cancer., 2002, 2, 38-47). Tumor cells in a hypoxic environment are prone to metastasis, and can increase resistance to radiotherapy and chemotherapy, thereby reducing the therapeutic effect (L.J.Walker, R.B.Craig, A.L.Harris, I.D.Hickson, Nucl Acids Res, 1994, 22, 4884- 4889; R.E. Durand, Int J Radiat Oncol Biol Phys, 1991, 20, 253-258; R.E. Durand, In Vivo, 1994, 8, 691-702). Therefore, it is very important to design effec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6428G01N21/6486C09K2211/1007C09K2211/1029C09K2211/1088G01N2021/6439G01N2021/6421
Inventor 李春艳田杨
Owner XIANGTAN UNIV
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