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Application of photoacoustic probe in preparation of NTR photoacoustic detection reagent

A photoacoustic detection and probe technology, which is applied in measurement devices, material analysis through optical means, instruments, etc., can solve the problems of low resolution of fluorescent probes, unfavorable NTR accurate imaging analysis, etc.

Inactive Publication Date: 2019-07-02
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, more and more probes are based on this principle to evaluate the degree of tumor hypoxia by detecting NTR. However, the probe compounds currently used are all fluorescent probes. Although they can perform qualitative detection and analysis of tumors, fluorescent probes low resolution, which is not conducive to accurate imaging analysis of NTR

Method used

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  • Application of photoacoustic probe in preparation of NTR photoacoustic detection reagent
  • Application of photoacoustic probe in preparation of NTR photoacoustic detection reagent
  • Application of photoacoustic probe in preparation of NTR photoacoustic detection reagent

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preparation example Construction

[0103] And the preparation method of the above photoacoustic probe of the present invention can be referred to as follows: NO 2 -R 1 -R 2 -Y 1 (i) with R 3 -Y 2 (ii) The target photoacoustic probe compound can be obtained by mixing reaction, the preparation method is relatively convenient, and the operation is relatively simple, which is suitable for large-scale expanded production;

[0104] Among them, in compound (i), R 1 C5~C30 arylene, heteroarylene, substituted arylene, or substituted heteroarylene; preferably, R 1 Arylene, heteroarylene, substituted arylene, or substituted heteroarylene of C5-C15; more preferably, R 1 C5-C15 heteroarylene or substituted heteroarylene, wherein the heteroatoms in the heteroarylene or substituted heteroarylene are one or more of nitrogen, oxygen, and sulfur, and each The number of heteroatoms contained in heteroaryl or substituted heteroarylene is one or more; for example, R 1 Can be, but not limited to: furan, thiophene, pyrrole, i...

Embodiment 1

[0139] (1) Preparation of MZ-BOC molecules:

[0140] Dissolve 2-nitroimidazole (0.5 g, 4.42 mmol) in 2 mL of DMF, and then add K 2 CO 3 (0.915g, 6.63mmol) and N-Boc-bromoethylamine (0.99g, 4.42mmol), reacted overnight under nitrogen protection;

[0141] Then, the solvent was removed by rotary evaporation, dried in vacuo, the obtained solid was dissolved in water, extracted with ethyl acetate, the organic phase was collected, the solvent was removed by rotary evaporation, and the crude product was recrystallized with ethyl acetate to obtain a dark yellow solid product MZ-BOC (0.10 g, 89%).

[0142] The product MZ-BOC NMR and mass spectrometry test patterns are respectively referred to figure 1 and figure 2 , the graph analysis is as follows:

[0143] MZ-BOC: 1 H NMR (400MHz, DMSO-d 6 )δ7.46(s, 1H), 7.14(s, 1H), 4.43(t, J=5.6Hz, 2H), 3.36(q, J=5.9Hz, 2H), 1.31(s, 9H);

[0144] HRMS (ESI + ): m / z calcd for C 10 h 16 N 4 o 4 :279.1064[M+Na +], found 279.1060.

[01...

Embodiment 2

[0159] (1) Preparation of MZ-BOC molecules:

[0160] 2-Nitroimidazole (1.0g, 8.84mmol) was dissolved in 4mL of DMF, and then K was added in batches under stirring 2 CO 3 (1.83g, 13.26mmol), and N-Boc-bromoethylamine (1.98g, 8.84mmol), reacted overnight under nitrogen protection.

[0161] The solvent was removed by rotary evaporation, and the obtained solid was dissolved in water, then extracted with ethyl acetate, the organic phase was collected, and the solvent was removed by rotary evaporation. The obtained crude product was recrystallized from ethyl acetate to obtain dark yellow solid product MZ-BOC (0.19g, 83%).

[0162] The product MZ-BOC NMR and mass spectrometry detection spectrum and analysis results are the same as those in Example 1.

[0163] (2) Preparation of MZ molecules

[0164] Dissolve MZ-BOC (1.7g, 6.6mmol) in methanol (4mL), add 1.25M HCl in methanol (4mL) with stirring, and react at room temperature for 8h;

[0165] The solvent was removed by rotary eva...

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Abstract

The invention provides an application of a photoacoustic probe in preparation of an NTR photoacoustic detection reagent. The provided photoacoustic probe adopts 2-(2-nitroimidazole)ethylamine as a specific response group, and is weak in signal; when a nitro group is reduced to an amino group, the photoacoustic signal is greatly enhanced, so that NTR detection can be realized successfully, and thephotoacoustic probe is a first probe compound that can realize NTR photoacoustic detection; meanwhile, the photoacoustic probe is not be disturbed by common reducing substances Vc, GSH and Cys in a biological body; under physiological conditions, pH fluctuation does not affect the photoacoustic detection performance of the IR1048 MZ; furthermore, an excitation wave of the photoacoustic probe is ina near infrared region, so that bio-imaging can be realized more favorably, background influence of a biological body to be detected is smaller, and tissue penetration depth is deeper; since the probe is positively charged, the probe can quickly complete trans-membrane movement under the action of the negative charge of a cell membrane; and meanwhile, the probe is low in toxicity and good in biological compatibility, and can be used for imaging analysis of NTR in vivo.

Description

technical field [0001] The invention relates to the field of tumor detection reagents, in particular to the application of a photoacoustic probe in the preparation of NTR photoacoustic detection reagents. Background technique [0002] As we all know, malignant tumors seriously endanger human life and health. Among them, solid tumors account for more than 85% of clinical malignant tumors, and hypoxia is one of the important characteristics of solid tumors. Tumor hypoxic cells have changes in metabolism, molecular genetics and pathophysiology, which play a very important role in the evolution and progression of tumors, and resistance to chemotherapy and radiotherapy lead to local recurrence, distant metastasis and poor prognosis of tumors. Therefore, the research on tumor cell hypoxia is still a very hot topic. It is well known that hypoxia can lead to increased reducing stress, resulting in the overexpression of nitroreductase (NTR), the level of NTR is directly related to t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/17C07D403/14
CPCC07D403/14G01N21/1702
Inventor 蔡林涛孟晓青龚萍张佳丽周理华
Owner SHENZHEN INST OF ADVANCED TECH
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