Cyanine fluorescent compound as well as preparation method and application thereof

A technology for fluorescent compounds and cyanines, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of limited, unusable confirmatory diagnosis, high cost, low background fluorescence interference, and enhanced fluorescence quantum yield. , the effect of low cost

Active Publication Date: 2019-01-11
SOUTH CHINA UNIV OF TECH
View PDF3 Cites 16 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Cyanine fluorescent compound as well as preparation method and application thereof
  • Cyanine fluorescent compound as well as preparation method and application thereof
  • Cyanine fluorescent compound as well as preparation method and application thereof

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention belongs to the field of specific molecular recognition materials and discloses a cyanine fluorescent compound as well as a preparation method and application thereof. The structural general formula of the cyanine fluorescent compound is shown as a formula (I). The fluorescent compound disclosed by the invention adopts a classic cyanine dye structure, an electroneutral electron-drawing group is introduced into the R-group position, a conjugated structure of push-pull electron interaction is formed between the electron-donating group and the electron-drawing group in the structure,and the conjugated system for transition is increased by carbon-carbon double bonds, so that fluorescence produced by compound molecules moves to a near infrared region. Meanwhile, due to the introduced electroneutral group, the problem that most of the charged cyanine compounds cannot pass through the blood brain barrier is solved. The compound molecule has affinity to Abeta plaques, can be successfully applied to near infrared fluorescence imaging of the Abeta plaques, and has the advantages of being safe, non-radioactive, low in cost, low in background fluorescence interference, high in penetrating power in biological tissues and the like. The structural formula is as shown in the specification.

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap