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A bodipy-like dye that generates near-infrared fluorescence in situ and its preparation and application

A near-infrared and dye technology, applied in the direction of luminescent materials, organic dyes, azo dyes, etc., can solve the problems of poor labeling effect, large cell damage, and insufficient long emission wavelength

Inactive Publication Date: 2018-10-23
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The "turn on" multiples of these dyes' fluorescence to the near-infrared region are not high, so the labeling effect is not good. The "turn on" multiples can be done better, but the emission wavelength is not long enough, which will cause greater damage to cells.

Method used

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  • A bodipy-like dye that generates near-infrared fluorescence in situ and its preparation and application
  • A bodipy-like dye that generates near-infrared fluorescence in situ and its preparation and application
  • A bodipy-like dye that generates near-infrared fluorescence in situ and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1. Under nitrogen protection and stirring at room temperature, add 10 μL (0.0878 mmol) aniline dropwise to 2 mL of acetonitrile solution containing 25 mg (0.0438 mmol) of the compound of formula 1-1, stir at room temperature for 12 hours after the dropwise addition, stop the reaction, reduce Concentrate under reduced pressure to remove acetonitrile, and separate by column chromatography (the eluent is a mixture of petroleum ether and ethyl acetate with a volume ratio of 5:1) to obtain 11.2 mg of the compound of formula 2-1 as a red solid, with a yield of 57%. The reaction equation is as follows:

[0033]

[0034] The structural characterization data of the resulting product are: 1 H NMR (400MHz, CDCl 3 )δ:3.88(s,3H),6.35-6.36(d,J=3.88Hz,1H),6.43-6.45(d,J=4.8Hz,1H),6.94-6.95(d,J=4.92Hz,1H ),6.98-7.01(m,2H),7.24-7.26(m,4H),7.30-7.44(m,3H),8.12(s,1H); 13 C NMR (100MHz, CDCl 3 )δ: 55.43, 111.66, 113.87, 116.78, 117.29, 122.07, 122.50, 126.00, 126.17, 129.82, 131.73, ...

Embodiment 2

[0039] 1. Under nitrogen protection and stirring at room temperature, add 5.78 μL (0.052 mmol) of phenylacetylene dropwise to 2 mL of acetonitrile solution containing 20 mg (0.0439 mmol) of the compound of formula 1-1, stir at room temperature for 2 hours after the dropwise addition, and stop the reaction , concentrated under reduced pressure to remove acetonitrile, separated by column chromatography (eluent is toluene), obtained 11 mg of red solid formula 2-2 compound, and its yield was 68%. The reaction equation is as follows:

[0040]

[0041] The structural characterization data of the resulting product are: 1 H NMR (400MHz, CDCl 3 )δ: 3.9 (s, 3H) 6.53-6.54 (d, J = 4.28Hz, 1H), 6.72-6.73 (d, J = 4.32Hz, 1H), 6.82-6.83 (d, J = 4.24Hz, 1H) ,6.91-6.90(d,J=4.24Hz,1H),7.03-7.05(m,2H),7.37-7.39(m,2H),7.49-7.47(m,2H),7.69-7.66(m,2H) ; 13 C NMR (100MHz, CDCl 3 )δ: 161.96, 142.79, 137.77, 136.12, 135.79, 132.35, 131.47, 130.97, 130.70, 129.60, 129.04, 128.40, 125.63, 123.97,...

Embodiment 3

[0046] 1. Under nitrogen protection and stirring at room temperature, add 7 mg (0.045 mmol) of the compound of formula a-1 dropwise to 2 mL of acetonitrile solution containing 21 mg (0.045 mmol) of the compound of formula 1-1, and stir at room temperature for 12 hours after the addition is complete. Stop the reaction, concentrate under reduced pressure to remove acetonitrile, separate by column chromatography (eluent is the mixed solution of sherwood oil and ethyl acetate with a volume ratio of 5:1), obtain 11 mg of red solid formula 2-3 compound, and its yield is 52%, the reaction equation is as follows:

[0047]

[0048] The structural characterization data of the resulting product are: 1 H NMR (400MHz, CDCl 3 )δ:3.88(s,3H),3.92(s,3H),6.37-6.38(d,J=3.92Hz,1H),6.49-6.50(d,J=3.92Hz,1H),6.55-6.54(d ,J=4.88Hz,1H),6.98-7.01(m,3H),7.29-7.27(m,2H),7.42-7.40(d,J=8.64Hz,2H),8.07-8.09(d,J=8.6 Hz,2H),8.21(s,1H); 13 C NMR (100MHz, CDCl 3 )δ: 166.12, 161.02, 156.96, 141.72, 135.4...

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Abstract

The invention discloses BODIPY dyes for generating near infrared fluorescence in situ as well as a preparation method for BODIPY dyes and an application of BODIPY dyes. A structural formula of the dyes is FORMULA as shown in the specification. Starting from existing dibromo BODIPY, tetrazine is firstly introduced into a BODIPY matrix structure by introducing different groups to a site 2, 2' of BODIPY and increasing conjugation through two-step coupling, so that BODIPY dyes for generating near infrared fluorescence in situ are obtained; maximum ultraviolet absorption wavelength of the BODIPY dyes is 623 nm, and maximum emission wavelength of the BODIPY dyes is 645 nm; the BODIPY dyes emit fluorescence " turn on" exceeding 1000 times, and have a fluorescent quantum yield of 0.36, so that fluorescence of BODIPY is completely quenched; and biomarkers can be made without background markers, and cell imaging without background is realized.

Description

technical field [0001] The invention belongs to the technical field of biomolecular labeling, and in particular relates to a BODIPY fluorescent dye capable of generating near-infrared fluorescence in situ, a preparation method of the dye and its application in biomolecular labeling. Background technique [0002] Existing biomarker dyes that can generate fluorescence in situ, such as fluorescein, silorodamine, rhodamine, coumarin, etc. These fluorescent dyes can be used for cell labeling and glucose metabolism labeling, but they all have their shortcomings and are not perfect biomarker dyes. For example, when fluorescein is used as a biomarker dye, its emission wavelength is only 517nm, and the "turn on" multiple is only 34 times (Shieh P, et.al, J.Am.Chem.Soc.2012, 134, 17428-17431); When it is used as a labeling dye, its emission wavelength can reach 668nm, and the "turn on" multiple is only 48 times (Shieh P, et.al, 5456–5461|PNAS|April 15, 2014|vol.111|no.15); When rhod...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00G01N21/64
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055C09K2211/1074G01N21/6486
Inventor 杨俊杜作灵
Owner SHAANXI NORMAL UNIV
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