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Near-infrared fluorescent probe for detecting nitroreductase and application

A fluorescent probe and near-infrared technology, applied in the field of near-infrared fluorescent probes, can solve the problems of background autofluorescence and weak tissue penetration depth.

Active Publication Date: 2022-03-08
SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, most probes emit in the ultraviolet and visible spectral range (below 650nm), plagued by background autofluorescence and poor tissue penetration depth capabilities

Method used

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  • Near-infrared fluorescent probe for detecting nitroreductase and application
  • Near-infrared fluorescent probe for detecting nitroreductase and application
  • Near-infrared fluorescent probe for detecting nitroreductase and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A specific synthesis method of a near-infrared fluorescent probe for detecting nitroreductase

[0035]1.67g of 2-hydroxyl-4-nitrobenzaldehyde 1 (10mmol) and 1.44g of cyclohexenone 2 (15mmol) were dissolved in 25mL of methanol, and then 1.12g of 1,4-diazabicyclo[2.2. 2] Octane (DABCO, 10mmol), the mixture was heated to reflux for 18h. After the reaction was completed, the solvent was removed under reduced pressure, and then purified by column chromatography to obtain compound 3 (yellow powder, 270 mg, yield 10%). 1H NMR (400MHz, CDCl3): δ7.81 (dd, J=8.0, 2.2Hz, 1H), 7.71 (d, J=2.0Hz, 1H), 7.38 (d, J=2.4Hz, 1H), 7.34( d, J=8.0Hz, 1H), 5.07-5.15(m, 1H), 2.60-2.70(m, 1H), 2.50-2.60(m, 1H), 2.36-2.47(m, 1H), 2.10-2.20( m, 1H), 1.98-2.08 (m, 1H), 1.66-1.80 (m, 1H). 13CNMR (100MHz, DMSO-d6): δ197.2, 155.6, 149.2, 134.6, 134.6, 130.9, 128.3, 127.7, 117.4, 110.9, 75.5, 38.9, 29.4, 17.5. HRMS m / z: calcd for C13H10NO4-[M-H]-m / z: 244.0610; found: 244.0616.

[0036]

[0037] ...

Embodiment 2

[0040] Cultivation of single crystals of probe ZY-2

[0041] Dissolve 50mg of probe ZY-2 in 50mL of a mixed solvent of dichloromethane and ethyl acetate with a volume ratio of 1:1, ultrasonically dissolve and let it stand for 1 hour, filter the supernatant, and place the supernatant separately In 10 10mL vials, control the degree of sealing to allow the solvent to evaporate slowly, and finally obtain ZY-2 single crystal. Through analysis, it was found that the probe molecule existed in a lactone structure, as shown in Figure 1.

Embodiment 3

[0043] Responsiveness of probe ZY-2 of the present invention to nitroreductase

[0044] Probe ZY-2 was prepared as 1 mM stock solution with dimethyl sulfoxide, nitroreductase was prepared with pH 7.4 PBS buffer solution as 200 μg / mL stock solution, and NADH was prepared as 50 mM with pH 7.4 PBS buffer solution stock solution.

[0045] In the PBS solution of probe ZY-2 with a concentration of 10 μM, after adding 1 μg / mL nitroreductase, the maximum absorption position of the probe was red-shifted from 565nm to 605nm, and the absorption intensity increased. Before adding nitroreductase, the probe ZY-2 had almost no fluorescence, but after adding 1 μg / mL nitroreductase, the probe emitted strong fluorescence at 740nm.

[0046] The experimental results show that the probe can achieve high sensitivity response to nitroreductase, such as figure 2 As shown, among them, figure 2 A is the absorption spectrum of the probe before (a figure) and after (b figure) adding nitroreductase; ...

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Abstract

The invention discloses a near-infrared fluorescent probe for detecting nitroreductase and application of the near-infrared fluorescent probe. Relates to the technical field of small-molecule probes. The invention provides a chemical structure, a preparation process and application of the near-infrared fluorescent probe. According to the prepared fluorescent probe ZY-2, under the condition that nitroreductase does not exist, due to the quenching effect of nitryl, background fluorescence of the probe can be ignored; when the probe reacts with nitroreductase, nitryl is specifically reduced into amino, and the probe emits near-infrared fluorescence at 740nm, so that the nitroreductase is recognized. Cell experiments find that the probe can evaluate the hypoxia degree of HeLa and HepG2 cells by detecting the expression condition of nitroreductase. In addition, the probe ZY-2 can also be used for imaging analysis of tumors of tumor-bearing mice.

Description

technical field [0001] The invention relates to the technical field of small molecule probes, and more specifically relates to a near-infrared fluorescent probe for detecting nitroreductase and its application. Background technique [0002] Cancer has become one of the important causes of human death. Surgical resection is currently the most effective means of treating cancer clinically. However, how to accurately identify the boundary between tumor and normal tissue has become a difficult problem for clinicians. Therefore, it is of great significance to develop methods for accurate identification of tumors. [0003] Hypoxia is one of the important characteristics of tumor cells. Oxygen concentration is low in some solid tumors, even locally as low as 0%. Nitroreductase (a flavoproteinase) is an endogenous reductase highly expressed in hypoxic tumor cells, and its expression level is closely related to the degree of tumor hypoxia. Nitroreductase is a reductase that can re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20C09K11/06A61K49/00G01N21/64
CPCC07D493/20C09K11/06A61K49/0021G01N21/6428G01N21/6456C09K2211/1088Y02P20/55
Inventor 申世立曹晓群张瑜
Owner SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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