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Near-infrared window II emission type fluorescent dye as well as preparation method and application thereof

A fluorescent dye, near-infrared technology, used in luminescent materials, organic dyes, azo dyes, etc., can solve the problems of reduced molar extinction coefficient, fluorescence quenching, limited performance, etc., to achieve a large molar extinction coefficient, not easy to lyochromic , The effect of wide adjustable range

Active Publication Date: 2019-03-01
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, all the reported cyanine fluorescent dyes with wavelengths reaching the second window of the near-infrared show a large decrease in molar extinction coefficient in water, broadened wavelength and blue shift, significant fluorescence quenching, poor stability and other shortcomings, which are serious. Limits its performance in subsequent biological applications
In contrast, xanthene dyes such as rhodamine have good structural rigidity and better stability than cyanine dyes, but it is not yet possible to redshift the wavelength of these dyes to above 1000 nm

Method used

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  • Near-infrared window II emission type fluorescent dye as well as preparation method and application thereof
  • Near-infrared window II emission type fluorescent dye as well as preparation method and application thereof
  • Near-infrared window II emission type fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation of near-infrared fluorescent dye 1a, the compound structural formula is as follows:

[0038]

[0039] Concrete synthetic route is as follows:

[0040]

[0041] Concrete synthetic steps are as follows:

[0042] Compound 4 (237 mg, 0.5 mmol), compound 5 (177.5 mg, 0.5 mmol), paraformaldehyde (15 mg, 0.5 mmol), sodium acetate (41 mg, 0.5 mmol) were mixed in 10 mL of acetic anhydride, under nitrogen Under protection, react at 80°C for 1 hour. After the reaction was completed, filter while hot, dissolve the filter cake with dichloromethane, and separate by column chromatography (dichloromethane / methanol=100 / 1, v / v) to obtain the final fluorescent dye 1a with a yield of 50%. 1 H NMRδ8.02 (d, J = 6.28 Hz, 1H), 7.57 (t, J = 7.24 Hz, 1H), 7.51 (t, J = 7.56 Hz, 1H), 7.47 (s, 1H), 7.16 (d, J = 7.48Hz, 1H), 6.87 (d, J = 8.16 Hz, 1H), 6.60 (d, J = 8.92 Hz, 1H), 6.46 (s, 1H), 6.41 (d, J = 8.92 Hz, 1H), 6.30 (d, J = 7.76 Hz, 2H), 6.25 (s, 1H), 3...

Embodiment 2

[0044] The preparation of near-infrared fluorescent dye 2a, the compound structural formula is as follows:

[0045]

[0046] Concrete synthetic route is as follows:

[0047]

[0048] The specific synthesis steps are as follows

[0049] Intermediate 5 (177.5 mg, 0.5 mmol), malondialdehyde dianiline hydrochloride (64.7 mg, 0.25 mmol), sodium acetate (41 mg, 0.5 mmol) were mixed in 10 mL of acetic anhydride, under nitrogen protection, The reaction was carried out at 80° C. for 2 hours. After the reaction was completed, the solvent was spin-dried by a rotary evaporator, and then 50 mL of water was added and extracted with dichloromethane. The organic phase was concentrated and separated by column chromatography (dichloromethane / methanol=100 / 1, v / v) to obtain the final fluorescent dye 2a , yield 67%. 1 H NMRδ 7.81 (d, J =12.20 Hz, 2H), 7.39 (s, 2H), 7.35 (d, J = 8.72 Hz, 2H), 6.81 (d, J = 8.12 Hz,2H), 6.78 (s, 2H), 6.43 (t, J = 12.20 Hz, 1H), 3.48-3.45 (m, 8H), 2.6...

Embodiment 3

[0051] The preparation of near-infrared fluorescent dye 3a, the compound structural formula is as follows:

[0052]

[0053] Concrete synthetic route is as follows:

[0054]

[0055] The specific synthesis steps are as follows

[0056] Intermediate 5 (177.5 mg, 0.5 mmol), pentadiene acetal diphenylamine hydrochloride (71 mg, 0.25 mmol), sodium acetate (41 mg, 0.5 mmol) were mixed in 10 mL of acetic anhydride, under nitrogen protection , reacted at 80°C for 2 hours. After the reaction was completed, the solvent was spin-dried by a rotary evaporator, and then 50 mL of water was added and extracted with dichloromethane. The organic phase was concentrated and separated by column chromatography (dichloromethane / methanol=100 / 1, v / v) to obtain the final fluorescent dye 3a , yield 61%. 1 H NMR δ 7.68 (d, J = 9.36 Hz, 2H), 7.43 (s, 2H), 7.39 (d, J = 8.96 Hz, 2H), 7.31 (t, J = 12.72Hz, 1H), 6.84 (dd, J = 8.84 Hz, 1.88 Hz, 2H), 6.69 (d, J = 1.88 Hz, 2H), 6.64(d, J = ...

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Abstract

The invention belongs to the technical field of biological materials, and particularly relates to a near-infrared window II emission type fluorescent dye as well as a preparation method and application thereof. The near-infrared fluorescent dye provided by the invention has the advantages of being large in molar extinction coefficient, long in absorption and emission wavelength and wide in adjustable range, and therefore the dye can be applied to deep-tissue multi-channel imaging, fluorescent encoding microspheres and the like; and in addition, the dye is not liable to generate solvatochromismin a polar solvent, has better stability in water compared with an existing common near-infrared window II heptamethine cyanine fluorescent dye and has very good chemical stability within a relatively large acid-base range.

Description

technical field [0001] The invention belongs to the technical field of biomaterials, and in particular relates to a kind of near-infrared fluorescent dye emitted from a second near-infrared window and a preparation method thereof, and the use of the fluorescent dye in the preparation of deep tissue single-channel or multi-channel imaging and fluorescence-encoded micelles or fluorescence-encoded Applications of microspheres as contrast agents. Background technique [0002] Currently common molecular imaging techniques such as tomography imaging (CT), X-ray, ultrasound imaging (US) and magnetic resonance imaging (MRI) are used for medical diagnosis of diseases, etc., but these methods have poor spatial resolution And its shortcomings such as the inability to realize dynamic real-time monitoring. Fluorescence imaging has been widely used in life sciences and medicine due to its advantages of non-invasiveness, real-time, small amount of sample required, and high resolution. In...

Claims

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Application Information

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IPC IPC(8): C07D311/82C09K11/06C09B57/00A61K49/00
CPCA61K49/0021A61K49/0054A61K49/0082A61K49/0091C09K11/06C07D311/82C09B57/00C09K2211/1007C09K2211/1088
Inventor 张凡雷祖海
Owner FUDAN UNIV
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