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Fluorescent dye with fluorescence opening property and preparation method and application thereof

A technology of fluorescent dyes and properties, applied in the field of fluorescent dyes, can solve the problems of lack of synthesis methods and hinder the development of fluorescent azide probes

Inactive Publication Date: 2018-09-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is obvious that the existing methods using azido-based LFBR cannot fully meet the above standards.
Therefore, despite the potential application of azides, the next major limitation is the lack of complex synthetic methods, which hinders the development of new fluorescent azide probes.

Method used

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  • Fluorescent dye with fluorescence opening property and preparation method and application thereof
  • Fluorescent dye with fluorescence opening property and preparation method and application thereof
  • Fluorescent dye with fluorescence opening property and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1: Synthesis of 5-azido-8-aminoquinoline (DA)

[0063]

[0064] In a 100 mL single-necked flask, 8-benzamide quinoline (10 mmol) and KOH (20 mmol) were dissolved in an appropriate amount of methanol, and the resulting mixture was heated at 80°C for 12 hours and cooled to room temperature. The reaction solution was treated with CH 2 Cl 2 Wash three times, collect CH 2 Cl 2 The solution was washed three times with saturated NaCl aqueous solution and then Na 2 SO 4 Dry and remove the solvent by rotary evaporation to obtain a crude product. The crude product was further purified through a silica gel column using a mixed solvent of PE / EtOAc (v / v; 2:1) as the eluent to obtain the product DA (yield 75%) as a white solid.

[0065] 1H NMR (500MHz, CDCl 3 )δ8.11(s,1H), 8.05(d,J=8.6Hz,1H), 7.70(d,J=16.3Hz,2H), 7.64(dd,J=13.1,8.0Hz,3H),7.44– 7.40(m,2H), 7.36–7.28(m,2H), 7.14(d,J=8.0Hz,1H), 6.94(dd,J=7.5,0.9Hz,1H), 5.08(s,2H);

[0066] 13C NMR(126MHz, CDCl 3 )δ154.23,148.06,135.51...

Embodiment 2

[0067] Example 2: Synthesis of dye precursor compound 2 (DQ)

[0068]

[0069] Add 8-aminoquinoline (10mmol) and triethylamine (15mmol) into a 100mL single-neck flask, and dissolve in CH 2 Cl 2 (30mL). After stirring for 5 minutes at room temperature, the reaction solution was cooled in an ice bath. Add acid chloride (11 mmol) dropwise. The reaction solution was then stirred overnight, then the mixture was filtered through a pad of Celite, and the residue was washed with CH 2 Cl 2 (25mL) Wash the collected CH 2 Cl 2 1M NaHCO for solution 3 Wash with aqueous solution three times. Collect the organic layer and use anhydrous Na 2 SO 4 dry. The solvent was removed by rotary evaporation, and the obtained crude product was purified by a silica gel column with PE / EtOAc (v / v; 10:1) mixed solvent to obtain pure product 2 (yield 80%).

[0070] 1H NMR (500MHz, CDCl 3 )δ10.61(s,1H), 8.90(dd,J=7.6,1.1Hz, 1H), 8.68(dd,J=4.2,1.6Hz,1H), 8.03(dd,J=3.7,2.1Hz,2H ), 7.95 (dd, J = 8.2, 1.6 Hz, 1H),...

Embodiment 3

[0072] Example 3: Synthesis of dye DA-1

[0073]

[0074] Add 6-styrene-5azide-8aminoquinoline (10mmol) and KOH (20mmol) to a 250mL round bottom flask, and dissolve in 100mL methanol. The resulting mixture was heated at 80°C for 12 hours and cooled to room temperature. The mixture was removed by rotary evaporation, and the residue was replaced with CH 2 Cl 2 Wash three times. CH collected 2 Cl 2 The solution was washed three times with aqueous NaCl solution. After that, collect the organic layer and use Na 2 SO 4 dry. The solvent was removed by rotary evaporation. Then the crude product was purified by passing through a silica gel column using a PE / EtOAc (v / v: 2:1) mixed solvent as an eluent. And provide the product DA-1 (yield 75%) yellow solid.

[0075] 1H NMR (500MHz, CDCl 3 ): δ=5.92(s,2H), 7.05(d,J=2.5Hz, 1H), 7.29-7.41(m,5H), 7.60-7.63(m,4H), 7.99(dd,J1=14.0Hz, J2=8.5Hz, 2H);

[0076] 13C NMR(125MHz, CDCl 3 ): δ=105.2, 119.5, 122.2, 127.0, 128.2, 128.3, 128.7, 129.0, 130....

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Abstract

The invention discloses a fluorescent dye with a fluorescence opening property and a preparation method and application thereof. The fluorescent dye is a 5-azido-8-aminoquinoline fluorescent dye, andadopts a structural formula shown as a formula (I), wherein in the formula (I), R1 is H, styrene, buty-1, 3-dien-1-ylbenzene or 4-vinyl phenol, R2 is H or styrene and R3 is H or styrene. The fluorescent dye has the fluorescence opening property, and after 1, 3-dipolar cycloaddition with alkyne, a fluorophore with the high quantum yield is provided for formation of triazole. The fluorescent dye hashigh click-through rate and excellent light stability as a fluorescent probe, and provides a powerful tool for living cell biological imaging.

Description

Technical field [0001] The invention belongs to the technical field of fluorescent dyes, and particularly relates to a fluorescent dye with fluorescence opening properties, a preparation method and application thereof. Background technique [0002] 8-Aminoquinoline is a common drug and chemical intermediate, and 8-aminoquinoline is the first antimalarial drug that was discovered and is still used in clinical synthesis. As early as 1926, the 8-aminoquinoline drug-Prometholine has been used clinically. In recent years, with the development of fluorescent probes, it has been found that the fluorescence generated by 8-aminoquinoline based on the conjugated quinoline structure has excellent properties in small molecule detection and biological activity detection. What is more surprising is that in recent years, researchers have continued to study the value of its drugs and found that functional 8-aminoquinoline has good anti-tumor and anti-Alheimer's properties. Therefore, functiona...

Claims

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Application Information

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IPC IPC(8): C09B23/14C09B23/10C09B23/00C07D215/40C09K11/06G01N21/64
CPCC09B23/145C07D215/40C09B23/00C09B23/107C09B23/141C09K11/06C09K2211/1007C09K2211/1029G01N21/6402
Inventor 朱勍顾晓旭窦言东
Owner ZHEJIANG UNIV OF TECH
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