640nm excited near-infrared fluorescent dye and preparation method thereof

A fluorescent dye and near-infrared technology, applied in the field of fluorescent dyes, can solve the problems of few near-infrared dyes and unclear structure-activity relationship

Active Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF4 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research on silicon-based rhodamine has just started, and the structure-activity relatio

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
  • 640nm excited near-infrared fluorescent dye and preparation method thereof
  • 640nm excited near-infrared fluorescent dye and preparation method thereof
  • 640nm excited near-infrared fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0070] Example 1

[0071] Synthesis of target fluorescent dye SiR-1

[0072] Synthesis of intermediate 5-bromotetrahydroquinoline

[0073]

[0074] 5-Bromoquinoline (3.5g) was dissolved in 45mL of acetic acid. Under ice bath conditions, add sodium cyanoborohydride in small amounts, a total of 2.5g, warm to room temperature and stir for 2h, then add paraformaldehyde and continue stirring for 4h Afterwards, most of the acetic acid was removed under reduced pressure, the pH was adjusted to weakly alkaline with a saturated aqueous sodium carbonate solution, extracted with ethyl acetate, the organic phase was collected, dried over anhydrous sodium sulfate, and the organic solvent was removed under reduced pressure to obtain a crude product. The crude product was separated by a silica gel column, and the eluent was pure petroleum ether. After removing the organic solvent, 1.7 g of a colorless liquid was obtained with a yield of 46%. The hydrogen spectrum data of the NMR spectrum are as f...

Example Embodiment

[0097] Example 2

[0098] Synthesis of target fluorescent dye SiR-2

[0099] Synthesis of Intermediate 5

[0100]

[0101] 3.5 g of 4-bromoindole was dissolved in 45 mL of acetic acid. Under ice bath conditions, small amounts of sodium cyanoborohydride (2.2 g in total) were added in small quantities. The reaction was stopped after raising to room temperature and stirring for 4 hours. After removing most of the acetic acid under reduced pressure, adjust the pH to weakly alkaline with saturated sodium carbonate solution, extract three times with ethyl acetate, collect the organic phase, dry with anhydrous sodium sulfate, and remove the organic solvent to obtain 3.2 g of a colorless liquid product. The rate is 91%.

[0102] Synthesis of Intermediate 6

[0103]

[0104] Weigh 381 mg of sodium hydride 70% oily dispersion in a Shrek bottle, under nitrogen protection and ice bath, add 1.0 g of 4-bromoindoline dissolved in tetrahydrofuran solution, 1.6 g of methyl iodide, and stir at room tem...

Example Embodiment

[0127] Example 3

[0128] Synthesis of target fluorescent dye SiR-3

[0129] Synthesis of Intermediate 10

[0130]

[0131] Dissolve 270mg of N-methyl-4-bromoindoline in 5mL DMF, add 140μL of phosphorous oxychloride, heat to 80-100℃ and stir, adjust the acid-base to weakly alkaline after cooling, extract with dichloromethane, wash After drying and removing the organic solvent under reduced pressure, add 10 mL of methanol, slowly add 40 mg of sodium borohydride, and stir at room temperature for 1-4 h. After the methanol was removed under reduced pressure, it was quenched with water, extracted with dichloromethane, the organic phase was collected, washed and dried, and the organic solvent was removed under reduced pressure to obtain a crude product of white solid 247 mg, with a yield of 80%. The hydrogen spectrum data of the NMR spectrum are as follows:

[0132] 1 H NMR(400MHz, CDCl 3 )δ7.10(d,J=7.9Hz,1H), 6.33(d,J=7.9Hz,1H), 4.63(s,2H), 3.38(t,J=8.3Hz,2H), 2.98(t, J=8.3Hz, 2H), 2.75...

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 provides 640nm excited near-infrared fluorescent dye and a preparation method thereof. The structure of the dye is modified by nitrogen ends of a five-membered ring and a six-membered ring with different rigidities, the dye is specifically shown as a formula (1), absorption and red shift of a fluorescence spectrum are realized, and the maximum red shift is 45 nm. Meanwhile, the dye provided by the invention is high in light stability and high in quantum yield (reaching 0.3 or above in methanol), the spiral ring opening and closing forms of a bottom ring of the dye respectively correspond to colourlessness and colorless, light regulation and control can be carried out, and the dye is used for a biological fluorescent probe and super-resolution imaging of the biological fluorescent probe.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, in particular to a class of near-infrared fluorescent dyes excited by 640nm and a preparation method thereof. Background technique [0002] With the continuous rapid development of life sciences, fluorescence imaging technology, as an emerging analysis technology, has the advantages of high sensitivity, high selectivity and real-time observation, and has a wide range of applications in the fields of medicine, biology, and environmental science. . At the same time, near-infrared fluorescent dyes (usually refer to the fluorescence emission wavelength in the 650-1000nm band) are in the silent region of biological autofluorescence, with little background interference and deep tissue penetration characteristics, which have attracted widespread attention. [0003] At present, the commercial near-infrared fluorescent dyes are mainly cyanine dyes, and the 640nm fluorescent dye is mainly Cy5, which has po...

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
IPC IPC(8): C09B57/00C09K11/06G01N21/64A61K49/00
CPCC09B57/00C09K11/06G01N21/6428G01N21/643A61K49/0021C09K2211/1029C09K2211/1088C09K2211/1096
Inventor 徐兆超周伟乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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