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Organic fluorescent small molecule compound capable of regulating and controlling metabolism as well as preparation method and application of organic fluorescent small molecule compound

A small molecule compound and compound technology, applied in the field of biomedical fluorescence imaging applications, can solve problems such as reduction, and achieve the effects of good application prospect, simple synthesis route and high yield

Pending Publication Date: 2022-07-29
SHENZHEN RES INST OF WUHAN UNIVERISTY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, currently developed organic fluorescent molecules for NIR II fluorescence imaging usually accumulate severely in organs of the reticuloendothelial system (RES, such as liver and spleen), which will increase unwanted background interference and affect imaging performance and raises concerns about probe metabolism
Therefore, there is a lack of a near-infrared second region organic molecular structure platform that can effectively control the synthesis of probes for renal metabolism or hepatobiliary metabolism and reduce the uptake of RES in the prior art

Method used

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  • Organic fluorescent small molecule compound capable of regulating and controlling metabolism as well as preparation method and application of organic fluorescent small molecule compound
  • Organic fluorescent small molecule compound capable of regulating and controlling metabolism as well as preparation method and application of organic fluorescent small molecule compound
  • Organic fluorescent small molecule compound capable of regulating and controlling metabolism as well as preparation method and application of organic fluorescent small molecule compound

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Experimental program
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Embodiment 1

[0059] This embodiment provides an organic fluorescent small molecule compound that can regulate metabolism, and the structural formula of the organic fluorescent small molecule compound that can regulate metabolism is shown in formula 1:

[0060]

[0061] wherein Y, Z are independently selected from O, S, Se and N-R, respectively 9 one of the R 9 One selected from H, methyl and ethyl; R 1 , R 2 , R 3 , R 4 individually selected from and one of H, n is taken from an integer from 0 to 18, and m is taken from an integer from 0 to 20;

[0062] R 5 , R 6 , R 7 , R 8 individually selected from One of them, n is an integer from 0 to 18, m is an integer from 0 to 20, X is selected from F, Cl, Br, I and N 3 one of the.

[0063] The preparation route of the above-mentioned metabolically regulated organic fluorescent small molecule compound (the compound represented by formula 1) is as follows:

[0064]

[0065] The following takes HYA0 and HYA12 as examples t...

Embodiment 2

[0105] The following experiment is the imaging of mouse bladder with the organic small molecule fluorescent probe HYAOP obtained in Example 1

[0106] Imaging of mouse bladder with organic small molecule fluorescent probe HYA0P. Specific steps are as follows:

[0107] Mice were anesthetized with sodium pentobarbital and 200 μl of HYAOP was injected via the tail vein using a power density of 120 mW / cm 2 The 808 nm laser irradiated the mice in the supine position. Add a 1000nm long-pass filter in front of the camera lens. Fluorescence images were collected from the abdomen of mice at different time points (0s, 180s, 15min, 30min, 1h, 3h, 6h, 12h) to observe the process of probe enrichment into the bladder. The results are as follows Figure 12 As shown in the figure, after the probe HYAOP was injected into normal mice through the tail vein, the metabolic process of the probe in the body at different time points could be clearly observed, and finally reached the bladder and ex...

Embodiment 3

[0109] The following experiment is the imaging of mouse abdomen with the organic small molecule fluorescent probe HYA12P obtained in Example 1

[0110] The organic small molecule fluorescent probe HYA12P imaged the abdomen of mice. Specific steps are as follows:

[0111] Mice were anesthetized using sodium pentobarbital and 200 μg HYA12P was injected via the tail vein using a power density of 90 mW / cm 2 808 nm laser irradiated mice. Add a 1250nm long-pass filter in front of the camera lens. Fluorescence images were collected at different time points (0s, 5min, 3h, 6h, 12h, 24h, 36h, 60h) of the leg blood vessels of mice. The results are as follows Figure 13 As shown in the figure, after the probe HYA12P was injected into normal mice through the tail vein, the metabolic process of the probe in the body at different time points could be clearly observed, and finally eliminated through the hepatobiliary system; (1000nm LP).

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Abstract

The invention provides an organic fluorescent small-molecule compound capable of regulating and controlling metabolism, the structural formula of the organic fluorescent small-molecule compound capable of regulating and controlling metabolism is as shown in formula 1, and the organic fluorescent small-molecule compound capable of regulating and controlling metabolism can be used for near-infrared two-region tumor detection, bladder imaging and the like after being connected with biomacromolecules such as polypeptide, protein, polyethylene glycol, nucleic acid aptamers, folic acid and derivatives thereof; the fluorescent probe is a brand new compound with the maximum emission wavelength exceeding 1000 nm, the fluorescence emission wavelength of the fluorescent probe is located in the second near-infrared region, and the fluorescent probe is non-toxic, good in biocompatibility and easy to absorb and metabolize by organisms; the invention also provides a preparation method of the organic fluorescent small molecule compound capable of regulating and controlling metabolism, the synthesis route is simple, the reaction efficiency is high, the yield is high, and the industrial application prospect is relatively high.

Description

technical field [0001] The patent of the present invention relates to the technical field of biomedical fluorescence imaging applications, in particular to the organic fluorescent small molecule compounds that can regulate metabolism, and the preparation method and application thereof. Background technique [0002] Fluorescence imaging has the advantages of real-time imaging, high sensitivity and high temporal and spatial resolution, and is widely used in vascular imaging, early diagnosis and imaging-guided surgical navigation, drug delivery, photothermal therapy / photodynamic therapy and other fields. Near-infrared second region (NIR-II, 1000-1700nm) fluorescence imaging has higher penetration depth and spatial resolution than traditional near-infrared region one (NIR-I, 750-900nm) fluorescence imaging, and is considered to be a A more ideal and more promising imaging mode. [0003] Near-infrared second-region fluorescence imaging also requires a large amount of developers ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C09K11/06A61K49/00
CPCC07D513/04C09K11/06A61K49/0021A61K49/0082C09K2211/1007C09K2211/1092C09K2211/1051
Inventor 肖玉玲李扬洪学传
Owner SHENZHEN RES INST OF WUHAN UNIVERISTY
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