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A kind of merocyanine fluorescent compound and its preparation method and application

A technology of fluorescent compounds and cyanines, applied in chemical instruments and methods, organic chemistry, pharmaceutical formulations, etc., can solve problems such as limited, unavailable confirmatory diagnosis, and high cost, and achieve low background fluorescence interference and enhanced fluorescence quantum yield , low-cost effect

Active Publication Date: 2021-05-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

FDA has approved three PET probes [18F] FPIB, [18F] AV-45 and [18F] AV-1, but the clinical utility of these PET imaging agents is limited because they cannot be used for confirmatory diagnosis of AD and are costly and require specialized facilities for cyclotrons of radionuclides

Method used

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  • A kind of merocyanine fluorescent compound and its preparation method and application
  • A kind of merocyanine fluorescent compound and its preparation method and application
  • A kind of merocyanine fluorescent compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The synthesis of a merocyanine fluorescent compound of the present embodiment, the specific synthesis steps are as follows:

[0039] (1) Synthesis of Intermediate 1

[0040] Stir 4.77g of 2,3,3-trimethylindole (30mmol) and 3.22ml of iodomethane (7.08g, 50mmol) in 60ml of ethanol, seal the pressure vessel, and react at 80°C for 12h. After the reaction was completed, it was cooled to room temperature, and the solid was precipitated, and filtered by suction to obtain 7.7 g of the precipitated solid, namely the lavender intermediate 1, with a yield of 85%. NMR data are as follows: 1H NMR (400MHz, DMSO) δ7.92-7.86 (m, 1H), 7.85-7.78 (m, 1H), 7.66-7.58 (m, 2H), 3.96 (s, 3H), 2.76 (s ,3H), 1.52(s,6H).

[0041] (2) Synthesis of Intermediate 2

[0042]Mix 17.5ml of DMF (16.54g, 225mmol) and 18ml of dichloromethane evenly, in an ice bath and under the protection of nitrogen, slowly add 15ml of phosphorus oxychloride (24.68g, 160mmol) drop by drop, stir for 20-40min, then add ...

Embodiment 2

[0067] The maximum absorption wavelength (λ abs ) and maximum emission wavelength (λ em )experiment:

[0068] Experimental method: Fluorescent compounds D1-D9 were dissolved in dimethyl sulfoxide to prepare a 10 mM stock solution. Take 3 μL of the above solution and dilute to 3 mL with different polar organic solvents DCM, EtOH, ACN, MeOH, DMSO, PBS to obtain a 10 μM solution, and use a UV-2450, SHIMADZU and a fluorescence spectrophotometer (F-4500, Hitachi), the maximum absorption wavelength and maximum emission wavelength of the fluorescent compound were measured and recorded.

[0069] The fluorescence spectra of fluorescent compounds D9-D18 in different solvents in this example are shown in Table 1.

[0070] Table 1 The maximum absorption wavelength and emission wavelength of compounds D9~D18 in different solvents

[0071]

[0072]

[0073] It can be seen from Table 1 that the emission wavelength of the fluorescent compound of the present invention red shifts as t...

Embodiment 3

[0075] Fluorescence quantum yield measurement experiments of fluorescent compounds D1-D9 in DCM and PBS;

[0076] Experimental method: select cresyl violet acetate as the reference compound (in methanol, its fluorescence quantum yield is 0.54), and measure the fluorescent compounds D1-D9 on the UV-visible spectrophotometer and the fluorescence spectrophotometer respectively And the ultraviolet absorption spectrum and fluorescence emission spectrum of the reference compound, according to Y u =Y s *F u / F s *A s / A u Perform calculations to obtain the fluorescence quantum yield of the fluorescent compound. Y u , Y s is the fluorescence quantum yield of the substance to be tested and the reference standard substance, F u , F s is the integrated fluorescence intensity of the substance to be tested and the reference substance, A u 、A s is the incident light intensity of the test substance and the reference substance at the excitation wavelength.

[0077] The fluorescenc...

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Abstract

The invention belongs to the field of specific molecular recognition materials, and discloses a merocyanine fluorescent compound, a preparation method and application thereof. The general structural formula of the merocyanine fluorescent compound is shown in formula (I). The fluorescent compound of the present invention adopts a classic cyanine dye structure, and introduces an electrically neutral electron-withdrawing group at the position of the R group, so that the electron-donating group and the electron-withdrawing group in the structure form a push-pull electron interaction The conjugated structure, and the conjugated system that increases the jump through the carbon-carbon double bond, makes the fluorescence generated by the compound molecule move to the near-infrared region, and at the same time, the introduced neutral group solves the problem that most charged cyanine compounds cannot problems passing the blood-brain barrier. The compound molecule has an affinity for Aβ plaques and can be successfully used for near-infrared fluorescence imaging of Aβ plaques. It has the advantages of safety, non-radioactivity, low cost, low background fluorescence interference, and strong penetrating power in biological tissues.

Description

technical field [0001] The invention belongs to the field of specific molecular recognition materials, and specifically relates to a merocyanine fluorescent compound and its preparation method and application. Background technique [0002] Alzheimer's disease (AD), also known as senile dementia, is a neurodegenerative disease that mostly occurs in people over the age of 65, affecting millions of people around the world, with 5 million new cases every year. The clinical manifestations are progressive memory impairment, cognitive impairment, mental symptoms and loss of daily life ability, which brings serious mental and economic pressure to patients, family members and society. However, since the pathogenic mechanism of Alzheimer's disease is still unclear, there is no effective drug to diagnose and treat Alzheimer's disease so far. To date, the U.S. Food and Drug Administration (FDA) has approved only five drugs for use in donepezil (Aricept), rivastigmine (Exelon), galantam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/24C09K11/06A61K49/00
CPCA61K49/0034C07D209/24C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033
Inventor 颜金武张雷谭慧雅李晶
Owner SOUTH CHINA UNIV OF TECH
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