An activated near-infrared small molecule fluorescent probe and its preparation method and application

A fluorescent probe and small molecule technology, applied in the field of biological probes, can solve the problems of reducing the accuracy of imaging results, being easy to be cleared, and difficult to monitor the occurrence and progress of acute kidney injury, achieving high imaging detection and analysis, avoiding clearing, The effect of high signal-to-background ratio

Active Publication Date: 2022-06-07
NANJING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the existing fluorescent probes can basically realize the early detection of acute kidney injury, these probes often only respond to a single molecular event and are easily cleared, which reduces the accuracy of imaging results and makes it difficult to monitor acute kidney injury occurrence and process

Method used

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  • An activated near-infrared small molecule fluorescent probe and its preparation method and application
  • An activated near-infrared small molecule fluorescent probe and its preparation method and application
  • An activated near-infrared small molecule fluorescent probe and its preparation method and application

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Embodiment 1

[0050] Probe 1-DPA 2 Design, synthesis and characterization

[0051] The synthetic route of 2-[2-(2-Azidoethoxy)ethoxy]-N,N-bis (2-pyridinylmethyl) ethanamine intermediate compound 3 (CAS: 1613538-61-6) is as follows:

[0052]

[0053] Reaction conditions: (a) NaN 3 ,H 2 O,90℃,24h,96％； (b) TsCl, triethylamine, DCM, r.t., 4h, 83%; (c) 2,2-Dimethylpyridinamine, triethylamine, CH 3 CN,80℃,24h,77％。

[0054] Synthesis of Compound 1: 2-Chloroethoxy-2-ethoxydiethanol (991 mg, 5.9 mmol), NaN 3 (462mg, 7.1mmol) dissolved in secondary water (5mL), stirred at 90 °C for 24 hours. After the reaction was completed, 20mL of ethyl acetate was added to the reaction mixture for extraction, a total of 3 times, and the organic layer was anhydrous Na 2 SO 4 Dry. After filtering to remove the precipitate, the solvent is removed by steaming to give compound 1 as a transparent colorless liquid. Yield: 955 mg (96%) 1 H NMR(400MHz,Chloroform-d)δ3.74(dd,J＝8.1,3.8Hz,2H),3.69(d,J＝2.8Hz,6H),3.62(dd,J＝5.3,3.8Hz...

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Abstract

The invention discloses an activated near-infrared small-molecule fluorescent probe and its preparation method and application. It combines receptor-mediated binding and retention effects with enzyme-responsive fluorescence activation strategies to design and synthesize a PS target. 1‑DPA, a near-infrared fluorescent probe activated by Casp‑3 2 . By combining with PS, 1‑DPA 2 It can effectively stay in the damaged kidney to avoid excessive clearance; through the activation of Casp-3, the probe can generate strong near-infrared fluorescence in the damaged kidney, thereby achieving more accurate detection of early acute kidney injury , Imaging detection analysis with higher signal-to-background ratio.

Description

Technical field [0001] The present invention belongs to the field of biological probes, specifically relates to a near-infrared activated small molecule fluorescent probe and preparation method and application thereof. Background [0002] Acute kidney injury is a global disease with a high incidence and fatality rate, which is mainly manifested by a significant decrease in glomerular filtration, resulting in renal dysfunction. There are many triggers for acute kidney injury, such as sepsis, hypotension, kidney stones, organ failure and drug overuse, among the many triggers, acute kidney injury caused by drug overuse is the most common. Traditional methods of diagnosing acute kidney injury mainly include live renal aspiration biopsy or measurement of the content of creatinine and blood urea nitrogen in the blood, but the former may have a potential risk of infection of other organs due to its invasive nature; The latter, due to the lack of sensitivity of the test, cannot be detect...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/06C09K11/06G01N21/64
CPCC07F3/06C09K11/06G01N21/6428C09K2211/188G01N2021/6432Y02P20/55
Inventor 叶德举翁剑辉王宇琦
Owner NANJING UNIV
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