A kind of near-infrared photothermal dye and its preparation method and application

A near-infrared light and dye technology, applied in organic dyes, chemical instruments and methods, methine/polymethine dyes, etc., can solve the problems of drug resistance of Gram-positive bacteria, achieve excellent light-to-heat conversion characteristics, Strong near-infrared absorption and simple preparation method

Active Publication Date: 2022-04-08
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a near-infrared photothermal dye for selectively killing gram-positive bacteria, its preparation method and application, so as to solve the problem of drug resistance of gram-positive bacteria caused by traditional antibiotic therapy

Method used

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  • A kind of near-infrared photothermal dye and its preparation method and application
  • A kind of near-infrared photothermal dye and its preparation method and application
  • A kind of near-infrared photothermal dye and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of near-infrared photothermal dye C

[0033] The synthesis process is as follows:

[0034]

[0035] 1) Weigh compound A (IR780 iodide derivative, 60.1mg, 0.082mmol), compound B (18.7mg, 0.068mmol), EDC (32.7mg, 0.171mmol) and HOAT (23.2mg, 0.170mmol), dissolve in In DMF (3.5mL), react at 60°C for 24h under argon protection;

[0036] 2) After the reaction is over, add ethyl acetate and saturated sodium chloride solution to the reaction solution for extraction, collect the ethyl acetate layer, and successively wash with saturated sodium chloride solution and pure water, dry over anhydrous sodium sulfate, and concentrate under reduced pressure , and purified by column chromatography to obtain dark green near-infrared photothermal dye C (35.1 mg, yield 43.2%).

Embodiment 2

[0037] Embodiment 2: proton nuclear magnetic resonance spectrum test

[0038] Weighed 5.0 mg of C in Example 1 and dissolved it in 0.5 mL of deuterated chloroform, and carried out the H NMR spectrum test. The test result is 1 H NMR (400MHz, CDCl 3 ):δ8.80(s,2H),7.62(d,2H),7.40(t,4H),7.35(d,2H),7.30(d,2H),7.21(t,4H),7.08(m, 2H),6.13(s,2H),5.11(d,1H),4.03(m,4H),3.62(d,1H),3.27(t,2H),3.02(t,2H),2.62(m,4H ), 2.50(t,4H), 2.00(m,2H), 1.90(m,4H), 1.70(s,12H), 1.07(t,6H), demonstrating the successful synthesis of C.

Embodiment 3

[0039] Embodiment 3: mass spectrometry test

[0040] A small amount of C in Example 1 was weighed and dissolved in methanol for mass spectrometry. [M-I] + The experimental value of the mass-to-nucleus ratio (m / z) was 867.47, which was consistent with the theoretical value of 867.47, indicating the successful preparation of C.

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PUM

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Abstract

The invention provides a near-infrared photothermal dye and its preparation method and application to solve the problem of drug resistance of Gram-positive bacteria caused by traditional antibiotic therapy. The near-infrared photothermal dye is a diphenylcyclooctyne-functionalized IR780 iodide near-infrared dye, which can be labeled with metabolic precursors based on the difference in the cell wall structure of Gram-positive bacteria and Gram-negative bacteria. The bacteria undergo a bioorthogonal reaction to achieve selective loading on the surface of Gram-positive bacteria and selective photothermal killing of Gram-positive bacteria under near-infrared light excitation.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a near-infrared photothermal dye and its preparation method and application. Background technique [0002] Diseases caused by bacterial infections pose a serious threat to human life and health, and are also a heavy burden on the medical system. Among them, Gram-positive bacterial infection can cause a variety of diseases, including sepsis, bacteremia, pneumonia, and osteomyelitis. Sepsis was the most expensive disease to treat in U.S. hospitals in 2013, totaling $23.6 billion for approximately 1.3 million hospitalizations. In addition, the fatality rate of sepsis and severe sepsis is 30% and 50%, respectively, while the fatality rate of septic shock is as high as 80%. Meanwhile, surgical site infections, which account for 25% of nosocomial infections, are also mainly caused by Gram-positive bacteria. [0003] Clinically, traditional antibio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/10C07D403/14A61K41/00A61P31/04
CPCC09B23/107C07D403/14A61K41/0052A61P31/04
Inventor 冯涛李鹏叶晓婷陆辉黄维
Owner NORTHWESTERN POLYTECHNICAL UNIV
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