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Near-infrared & two-photon dynamics dual-mode high-stability fluorescent dye, NTR&HClO probe and synthesis method and application

A fluorescent dye and two-photon technology, applied in the field of ROS&, can solve the problems of multiple wavelength coverage and fluorescence ratio dependence, and achieve the effect of enhancing electron transfer

Active Publication Date: 2022-08-09
伊明泰(山东)生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above problems, the present invention finds that in order to realize the synchronous non-interference detection of ROS & AOS, it is necessary to first solve the problem of single-molecule dual-mode excitation and emission region regulation of dual-response probes, so as to overcome the multiple wavelength coverage and fluorescence ratio dependence caused by single-mode excitation.

Method used

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  • Near-infrared & two-photon dynamics dual-mode high-stability fluorescent dye, NTR&HClO probe and synthesis method and application
  • Near-infrared & two-photon dynamics dual-mode high-stability fluorescent dye, NTR&HClO probe and synthesis method and application
  • Near-infrared & two-photon dynamics dual-mode high-stability fluorescent dye, NTR&HClO probe and synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0061] The synthesis of a single-molecule dual-mode excitation probe (CYNA-CN for short) comprises the following steps:

[0062] 1. Synthesis of Y-n series compounds (refer to synthetic route 1): Benzyl bromide (2.59 g, 12 mmol) was dissolved in acetonitrile (20 mL deoxygenated in advance) under anaerobic operation, and heated at 85° C. in the dark until the solution became clear. 2,3,3-Trimethylindole (2.385 g, 16 mmol) was dissolved in deoxygenated acetonitrile (20 mL), then added dropwise to the above clear solution, and the reaction was continued for 12 h in the dark. After stopping the reaction, use a rotary evaporator to steam more than 70% of the solvent, then add the petroleum ether of anhydrous and anaerobic treatment to the solid product and separate out, and wash the solid product 3 times with the petroleum ether to obtain Y-n series compounds (n refers to the para-position). Benzyl bromide series derivatives with different substituents, as shown in Synthetic Scheme...

Embodiment 2

[0073]Near-infrared parent framework stability test: In order to select the most stable fluorescent dye as the parent structure, this embodiment uses the CY-n series compounds prepared in Example 1 to carry out time stability testing, specifically including: Light, no cooling) to analyze the chromatographic components of each CY-n dye (2 mM), and the sample solutions were all prepared with chromatographic grade acetonitrile. The samples were subjected to high performance liquid chromatography (HPLC) analysis at different time intervals (1h, 2h, 3h, 5h, 7h, 9h). HPLC adopts Agilent 1100 series high performance liquid chromatography (Waldbronn, Germany), mobile phase A: organic phase with 100% acetonitrile; mobile phase B: aqueous phase with 5% acetonitrile (containing 0.1% formic acid). Elution gradient: 0min=100%A, 3min=98%A, 10min=97%A, 15min=0%A. The gradient elution flow rate was 1 mL / min, and the injection volume was 10 μL.

[0074] The results are attached Image 6 sho...

Embodiment 3

[0076] The effect of pH on the fluorescence intensity of fluorescent dyes (CY-n series compounds): In order to select the most stable dye as the parent ring, in this example, the CY-n series compounds prepared in Example 1 were used to detect the effect of pH, which specifically included : To prepare PBS buffer solutions of different pH, each CY-n was prepared to 10 μM with buffer solutions of different pH (pH=3.0, 4.0, 5.0, 6.0, 6.8, 7.4, 8.0, 9.0), and then subjected to spectral test.

[0077] as attached Figure 7 As shown, the more stable dyes CY-1, CY-6, CY-7 and CY-8 were placed in the attached Figure 9 In a, that is, the dye whose fluorescence intensity is less affected by pH is the dye containing benzene ring, bromine, phenylboronic acid and nitro group connected to the N-position of cyanine; Figure 9 As can be seen in b, the other probes are relatively more affected by pH.

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Abstract

The present invention relates to ROSamp; the invention belongs to the technical field of AOS detection, and particularly discloses a single-molecule dual-mode excitation probe and a synthesis process and application thereof. The structural formula of the single-molecule dual-mode excitation probe is shown in the specification. According to the invention, firstly, the structure of traditional cyanine is optimized, and a nitrobenzene benzyl structure compound CY-8 with a large light absorption coefficient is synthesized, so that the stability of a near-infrared frame (CY-8) is enhanced. Secondly, naphthol biphenyl alkene dinitrile is combined to form a two-photon response part (compound 2); and then connecting two parts of the CY-8 and the compound 2 to obtain the CYNA-CN. The compound has a dual-mode (near-infrared and two-photon) fluorescence excitation function, so that nitroreductase (NTR) and hypochlorous acid (HClO) in cancer cells can be independently detected in a non-interference excitation mode.

Description

technical field [0001] The invention relates to the technical field of ROS&AOS detection, in particular to a near-infrared&two-photon dynamic dual-mode highly stable fluorescent dye, an NTR&HClO probe, a synthesis method and application. Background technique [0002] The information disclosed in this Background section is intended to enhance understanding of the general background of the invention and should not necessarily be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person of ordinary skill in the art. [0003] Reactive oxygen species (ROS) and reducing species (AOS) coexist dynamically in living systems. Accurate detection of ROS and AOS is very important. At present, ROS&AOS fluorescent molecular probes mainly include three types, among which: type I is ROS single-trigger detection, and type II is AOS single-trigger detection. These two types of probes can be used for the analysis of pure oxidativ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C09K11/06C09B57/00G01N21/64
CPCC07D209/12C09K11/06C09B57/00G01N21/6428C09K2211/1029C09K2211/1011C09K2211/1007
Inventor 陈光苏东亮毕繁荣
Owner 伊明泰(山东)生物科技有限公司
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