Pentamethine cyanine dye and preparation method thereof

A technology of pentamethyl sichuan cyanine and cyanine dyes, applied in the field of fluorescent probes, can solve the problem of insufficient variety of pentamethyl sichuan cyanine dyes, etc., and achieve the effect of facilitating confirmation of dyeing effect and concise process conditions

Inactive Publication Date: 2019-11-01
SHENZHEN UNIV
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a kind of pentamethyl cyanine dye and preparation method thereof, to solve the technical problem that the existing pentamethyl cyanine dye kind is not abundant enough

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
  • Pentamethine cyanine dye and preparation method thereof
  • Pentamethine cyanine dye and preparation method thereof
  • Pentamethine cyanine dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0053] On the other hand, the present invention also provides a kind of preparation method of described pentamethine dye, comprises the steps:

[0054] S01: reacting alkyl halides containing substituents such as general formulas A, B and C with thioesters to obtain quaternary ammonium salts such as general formulas D, E and F;

[0055]

[0056] S02: the quaternary ammonium salt of the general formula D, E, F and malondialdehyde diphenylamine hydrochloride are heated and condensed under acid catalysis to generate intermediates such as the general formula G, H, and I;

[0057]

[0058] S03: the target product G, H, I of the condensation reaction is condensed with the compound of general formula A, B, C to obtain the thioester J, K, L, M of the cyanine dye;

[0059]

[0060] S04: deacylating the thioesters J, K, L, and M under alkaline conditions to generate intramolecular six-membered heterocyclic compounds N, O, P, and Q;

[0061]

[0062] S05: The six-membered het...

Embodiment 1

[0074] Embodiment 1 wherein a kind of preparation method of probe

[0075] Synthetic route such as figure 1

[0076] Specific steps are as follows:

[0077] Preparation of Compound 1

[0078] Add 1-bromo-3-chloropropane and potassium thioacetate solution (1:1) into THF to reflux for 1 hour, stir at room temperature for 24 hours, filter the inorganic salt, evaporate the organic phase to dryness and dissolve it with acetone, add an equivalent amount of NaI and stir at room temperature for 6 days , the organic phase was diluted with ethyl acetate, washed with sodium thiosulfate, dried and the organic phase was evaporated to dryness to obtain a pale yellow oil.

[0079] Preparation of Compound 2

[0080] Take 3.66g of 2,3,3-trimethyl-3H-indoline and 2.38g of compound 1 in 20ml of acetonitrile, add, under nitrogen atmosphere, heat to reflux for 6h, cool to room temperature, add diethyl ether to wash, pour the liquid organic phase , to obtain a purple oil (yield 40%).

[0081]...

Embodiment 2

[0092] Bioluminescent imaging detection of dyes

[0093] 1), the preparation of dye mother liquor

[0094] Weigh 1 mol of the dyes prepared in Examples 18-19 and place them in a brown glass bottle, add 100 mL of HPLC DMSO solvent, and mix well to obtain 1 mM dye mother liquor.

[0095] 2), HeLa cells were planted in a living cell culture dish, and after 48 hours, the medium was replaced, and the dye mother solution prepared in 1) was added to the culture dish so that the final concentration of the dye was 1uM, and placed in 30 Incubate at 7°C for 10 minutes, discard the culture medium, wash with PBS buffer 3 times, place on the laser confocal microscope stage, select a long-pass filter with an excitation wavelength of 633nm and an emission wavelength of 645nm for observation. Depend on figure 2 As shown, the dye can enter cells, and has different selectivity in cells, and can be applied to the application of live cell fluorescent dyes.

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 discloses pentamethine cyanine dye and a preparation method thereof. Advantages of long wavelength and good stability of the dye are utilized; dye protection and scintillation triggeringcan be achieved through introducing sulfydryl into the molecule to induce dynamic ring opening and closing of the dye at the physiological pH; the sulfydryl is protected through a disulfide bond so that the dye can radiate stable fluorescence, facilitating confirmation of the dyeing effect; and the disulfide bond in cells can be cleaved by intracellular high-activity sulfydryl protein in cells soas to achieve scintillation.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, and in particular relates to a pentamethine dye and a preparation method thereof. Background technique [0002] In recent years, the development of molecular fluorescence detection and imaging technology has provided powerful research and detection tools for the development of life sciences, such as detection instruments using molecular fluorescence imaging analysis technology, confocal fluorescence imaging microscope, fluorescence spectroscopy / lifetime instrument, etc. On the basis of the above theories, the rapidly emerging super-resolution imaging technology breaks through the limitation of the optical diffraction limit and obtains fine-structure imaging of tiny targets with a size less than 200nm. [0003] Stochastic optical reconstruction super-resolution imaging method (STORM) is a new super-resolution imaging method. This method has a great dependence on the performance of fluorescent ma...

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): C09B23/16C07D209/62C09K11/06G01N21/64
CPCC07D209/62C09B23/164C09K11/06C09K2211/1029G01N21/6458G01N21/6486
Inventor 杨志刚李文潘文慧熊佳屈军乐
Owner SHENZHEN UNIV
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