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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
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  • 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 relationship is not very clear. Based on this parent structure, there are few near-infrared dyes in different bands.

Method used

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  • 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

Embodiment 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 the condition of ice bath, sodium cyanoborohydride was added in a small amount in batches, a total of 2.5g, raised to room temperature and stirred for 2h, then added paraformaldehyde and continued to stir for 4h Finally, most of the acetic acid was removed under reduced pressure, the pH was adjusted to be weakly alkaline with 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 on a silica gel column with pure petroleum ether as the eluent. After removal of the organic solvent, 1.7 g of a colorless liquid was obtained, with a yield of 46%. Its nuclear magnetic spectrum hydr...

Embodiment 2

[0098] Synthesis of target fluorescent dye SiR-2

[0099] Synthesis of intermediate 5

[0100]

[0101] 3.5g of 4-bromoindole was dissolved in 45mL of acetic acid, and sodium cyanoborohydride was added in small amounts in batches under ice-bath conditions, totaling 2.2g, raised to room temperature and stirred for 4 hours, then the reaction was stopped. After most of the acetic acid was removed under reduced pressure, the pH was adjusted to weak alkalinity with saturated sodium carbonate solution, extracted three times with ethyl acetate, the organic phase was collected, dried over anhydrous sodium sulfate, and the organic solvent was removed 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 70% oily dispersion of sodium hydride 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 ...

Embodiment 3

[0128] Synthesis of target fluorescent dye SiR-3

[0129] Synthesis of intermediate 10

[0130]

[0131] Dissolve 270 mg of N-methyl-4-bromoindoline in 5 mL of DMF, add 140 μL of phosphorus oxychloride, raise the temperature to 80-100 ° C and stir, adjust the acidity and alkalinity to weak alkalinity after cooling, extract with dichloromethane, and 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 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 247 mg of crude product as a white solid, with a yield of 80%. Its nuclear magnetic spectrum hydrogen spectrum data 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....

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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

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Application Information

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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
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