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Near-infrared cyanine colorimetric fluorescent probe and preparation method and application thereof

A fluorescent probe, near-infrared technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of scarcity of near-infrared fluorescent probes, poor anti-interference ability, and homeostasis destruction, and achieve the realization of Tracer imaging detection, strong anti-interference ability, good sensing properties

Active Publication Date: 2021-08-10
SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The second is associated morphological changes, including mitochondrial swelling and hypodensity, leading to disruption of homeostasis
At present, a large number of organic small molecule fluorescent probes for the detection of hydrazine have been reported, but the near-infrared fluorescent probes for the detection of hydrazine are relatively rare, and the existing near-infrared hydrazine fluorescent probes can only be used in vivo The detection of non-targeted exogenous hydrazine has low selectivity and sensitivity, poor anti-interference ability, and low detection limit. At present, there is an urgent need for a method with high selectivity and sensitivity, strong anti-interference ability, and low enough detection limit. A near-infrared fluorescent probe that can be used for the visual detection of targeted endogenous hydrazine in vivo

Method used

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  • Near-infrared cyanine colorimetric fluorescent probe and preparation method and application thereof
  • Near-infrared cyanine colorimetric fluorescent probe and preparation method and application thereof
  • Near-infrared cyanine colorimetric fluorescent probe and preparation method and application thereof

Examples

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Embodiment 1

[0075] Example 1 Synthesis of near-infrared cyanine colorimetric fluorescent probe VI

[0076] The fluorescent probe VI of the present embodiment corresponds to the R of the compound of formula (I) 1 for hydrogen, R 2 Is propyl, n is 1.

[0077] The reaction formula for synthesizing near-infrared cyanine-like colorimetric fluorescent probe VI is as follows (A):

[0078]

[0079] Concrete steps for synthesizing near-infrared cyanine-like colorimetric fluorescent probe VI:

[0080] (1) Synthesis of intermediate V: Dissolve IV and sodium acetate in anhydrous N,N-dimethylformamide (15mL) at a molar ratio of 1:5 to 1:2, under an argon atmosphere at 75 to 90°C Heating for 2 to 6 hours. After the mixture was cooled to room temperature, it was filtered, and the resulting solution was concentrated under reduced pressure to obtain an oily crude product. Finally, separation and purification by silica gel column chromatography (dichloromethane as eluent) gave the pure intermediate...

Embodiment 2

[0083] Example 2 Synthesis of near-infrared cyanine-like colorimetric fluorescent probe IX

[0084] Fluorescent probe IX of the present embodiment corresponds to the R of the compound of formula (I) 1 is a benzene ring, R 2 is propyl, n is 0.

[0085] The reaction formula for synthesizing near-infrared cyanine-like colorimetric fluorescent probe IX is as follows (B):

[0086]

[0087] Concrete steps for synthesizing near-infrared cyanine-like colorimetric fluorescent probe IX:

[0088] (1) Synthesis of intermediate VIII: Dissolve VII and sodium acetate in anhydrous N,N-dimethylformamide (15mL) at a molar ratio of 1:1 to 1:4, under an argon atmosphere at 70 to 90°C Heating for 1 to 6 hours. After the mixture was cooled to room temperature, it was filtered, and the resulting solution was concentrated under reduced pressure to obtain an oily crude product. Finally, separation and purification by silica gel column chromatography (dichloromethane as eluent) gave the pure in...

Embodiment 3

[0091] Example 3 Synthesis of near-infrared cyanine-like colorimetric fluorescent probe XII

[0092] The fluorescent probe XII of the present embodiment corresponds to the R of the compound of formula (I) 1 is chlorine, R 2 is a methyl group, and n is 1.

[0093] The reaction formula for synthesizing the near-infrared cyanine-like colorimetric fluorescent probe XII is as follows (C):

[0094]

[0095] Concrete steps for synthesizing near-infrared cyanine-like colorimetric fluorescent probe XII:

[0096] (1) Synthesis of intermediate XI: Dissolve X and sodium acetate in anhydrous N,N-dimethylformamide (15mL) at a molar ratio of 1:3 to 1:1.5, under an argon atmosphere at 75 to 100°C Heating for 2 to 5 hours. After the mixture was cooled to room temperature, it was filtered, and the resulting solution was concentrated under reduced pressure to obtain an oily crude product. Finally, separation and purification by silica gel column chromatography (dichloromethane as the elu...

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Abstract

The invention discloses a near-infrared cyanine colorimetric fluorescent probe and a preparation method and application thereof. The structural formula of the probe is shown as a formula (I). The fluorescent probe can identify and detect N2H4 in a mixed solution of absolute ethyl alcohol and a PBS by utilizing fluorescence and an ultraviolet-visible absorption spectrum. The probe has high selectivity and sensitivity in N2H4 identification, strong anti-interference capability and very low detection limit; the fluorescent probe can be applied to detection of environmental pollution or in-vitro and in-vivo antituberculous drug metabolites N2H4.

Description

technical field [0001] The invention relates to the technical field of detection and identification of toxic substances, in particular to a near-infrared cyanine-like colorimetric fluorescent probe and its preparation method and application. Background technique [0002] Anti-tuberculosis drugs are the most common drug agents, which can cause a series of liver damage in patients. Isoniazid is the first choice for effective treatment of tuberculosis agent, which is widely used to inhibit the activity of mycobacterial tuberculosis. Studies have shown that the hepatotoxicity of isoniazid depends on metabolites (hydrazine) produced by various enzymes. Rifampicin and isoniazid are widely used in the treatment of tuberculosis by enzymatically inducing an increase in hydrazine levels. There is experimental evidence that isoniazid and its major metabolite hydrazine may be associated with mitochondrial dysfunction. The influence of hydrazine (generally referred to as hydrazine) on...

Claims

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Application Information

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IPC IPC(8): C07D409/14C09K11/06G01N21/64
CPCC07D409/14C09K11/06G01N21/6402C09K2211/1029C09K2211/1007C09K2211/1092
Inventor 蔡林涛张秀文江道勇王勇张鹏飞龚萍
Owner SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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