Activated near-infrared small-molecule fluorescent probe as well as preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of biological probes, can solve the problems of reducing the accuracy of imaging results, difficult to monitor the occurrence and progress of acute kidney injury, and easy to be cleared, so as to achieve high imaging detection and analysis, avoid clearing, The effect of high signal-to-background ratio

Active Publication Date: 2021-12-17
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Activated near-infrared small-molecule fluorescent probe as well as preparation method and application thereof
  • Activated near-infrared small-molecule fluorescent probe as well as preparation method and application thereof
  • Activated near-infrared small-molecule fluorescent probe as well as preparation method and application thereof

Examples

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Embodiment 1

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

[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-lutidine, triethylamine, CH 3 CN, 80°C, 24h, 77%.

[0054] Synthesis of compound 1: 2-chloroethoxy-2-ethoxydiethanol (991mg, 5.9mmol), NaN 3 (462mg, 7.1mmol) was dissolved in secondary water (5mL) and stirred at 90°C for 24 hours. After the reaction was completed, 20 mL of ethyl acetate was added to the reaction mixture for extraction, a total of 3 extractions, and the organic layer was washed with anhydrous Na 2 SO 4 dry. The precipitate was removed by filtration, and the solvent was removed by rotary evaporation to obtain compound 1 as a transparent colorless liquid. Yield: 955mg (96%) 1 H NMR (400MHz, Chloroform-d) δ3.74 (dd...

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Abstract

The invention discloses an activated near-infrared small-molecule fluorescent probe as well as a preparation method and application thereof, and a PS (polystyrene) targeted and Casp-3 activated near-infrared fluorescent probe 1-DPA2 is designed and synthesized by combining receptor-mediated binding and a retention effect with a fluorescence activation strategy of enzyme response. By combining with PS, 1-DPA2 can effectively stay in the damaged kidney, so that too fast removal is avoided; through the activation effect of Casp-3, the probe can generate strong near-infrared fluorescence in the damaged kidney, so more accurate and higher signal-to-background ratio imaging detection analysis on the early acute kidney injury is realized.

Description

technical field [0001] The invention belongs to the field of biological probes, and in particular relates to a near-infrared activated small molecule fluorescent probe and its preparation method and application. Background technique [0002] Acute kidney injury is a global disease with high morbidity and mortality, mainly manifested by a significant decline in glomerular filtration, leading to renal dysfunction. There are many causes of acute kidney injury, such as sepsis, hypotension, kidney stones, organ failure, and overuse of drugs. Among the many causes, acute kidney injury caused by overuse of drugs is the most common. The traditional methods for diagnosing acute kidney injury mainly include live kidney biopsy or measuring the content of creatinine and blood urea nitrogen in the blood, but the former may have the potential risk of other organ infection due to its invasive characteristics; The sensitivity is insufficient to detect acute kidney injury in the early stage...

Claims

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Application Information

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Patent Type & Authority Applications(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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