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Lysosome targeted fluorescent probe and preparation method and application thereof

A technology of lysosomes and compounds, applied in biochemical equipment and methods, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of large background signal, poor selectivity, low sensitivity, etc., achieve high anti-interference ability, good Effects of reversibility, fluorescence signal stabilization

Inactive Publication Date: 2016-05-11
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently commercially available lysosome-targeted fluorescent probes have limitations such as high cost, large background signal, low sensitivity, and poor selectivity, and new products need to be further developed

Method used

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  • Lysosome targeted fluorescent probe and preparation method and application thereof
  • Lysosome targeted fluorescent probe and preparation method and application thereof
  • Lysosome targeted fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of probe RS1

[0044]

[0045](1) Synthesis of rhodamine B acid chloride: In a 50ml dry round bottom flask, add 0.48g (1.0mmol) rhodamine B, 5ml dry 1,2-dichloroethane and 1.0ml phosphorus oxychloride, install Condensation drying device and tail gas treatment device, control the reaction temperature at 90°C for 8 hours. After the reaction, the reaction mixture was cooled to room temperature, and the solvent was removed to obtain a dark red viscous solid for future use.

[0046] (2) Synthesis of RS1: Take 2.5ml of dry acetonitrile, dissolve all the solids obtained in the above (1), and dissolve 1.0ml of triethylamine, 1.2mmol (about 0.13g) of 2,6-di A mixture of aminopyridine in acetonitrile (5ml) was slowly added dropwise to the above reaction solution, and the reaction mixture was refluxed at 82°C for 6 hours. After the reaction, the reaction solution was cooled to room temperature, the solvent was removed, and the product was extracted...

Embodiment 2

[0051] Embodiment 2: the synthesis of probe RS2

[0052]

[0053] (1) Preparation of Compound 2: Dissolve 0.5ml (4.85mmol) acetylacetone and 0.5g (4.85mmol) 2,6-diaminopyridine in 2.5ml phosphoric acid, and reflux for 2 hours under magnetic stirring. After the reaction is complete, cool the reaction mixture to room temperature, pour it into 100ml of ice-water mixture, adjust the pH to neutral with concentrated ammonia water, obtain a large amount of precipitate, filter it with suction, wash it with water several times, and dry it to obtain an off-white crude product. The target product was obtained by column chromatography with a volume ratio of 20:1.

[0054] Compound 2: off-white solid Yield: 70.3%.

[0055] 1 HNMR(400MHz,MeOD):δ8.06(dd,J=8.9,2.8Hz,1H),6.95(s,1H),6.80(d,J=8.9Hz,1H),4.91(s,2H),2.54 (d,J=6.3Hz,6H).

[0056] 13 CNMR (101MHz, MeOD) δ160.76, 160.50, 155.73, 146.21, 134.07, 119.12, 114.58, 111.54, 23.17, 16.50.

[0057] MS (ESI) calad.forC 10 h 11 N 3 ...

Embodiment 3

[0064] Embodiment 3: the synthesis of probe RS3

[0065]

[0066] Dissolve 0.53g RS1 (1.0mmol) and 0.15g (1.2mmol) salicylaldehyde in 10ml absolute ethanol, stir and reflux for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and spin-dried, and the crude product was purified by column chromatography with dichloromethane and methanol at a volume ratio of 30:1.

[0067] Probe RS3: Yellow solid 0.32 g, yield 50.3%.

[0068] 1 HNMR (400MHz, CDCl 3 )δ13.57(s,1H),8.86(s,1H),8.50(d,J=8.3Hz,1H),8.00(d,J=6.8Hz,1H),7.73–7.63(m,2H), 7.42(s,2H),7.40–7.35(m,1H),7.10(d,J=7.2Hz,1H),7.04–6.94(m,2H),6.86(d,J=7.5Hz,1H),6.54 (d,J=8.8Hz,2H),6.38(d,J=2.5Hz,2H),6.16(dd,J=8.8,2.5Hz,2H),3.29–3.17(m,8H),1.04(t, J=7.0Hz,12H).

[0069] 13 CNMR (101MHz, CDCl 3 )δ169.03,165.16,161.92,154.96,154.45,152.18,150.03,148.35,139.31,133.82,133.32,133.22,128.82,128.04,127.40,124.06,123.38,119.51,118.80,117.14,115.83,115.18,108.46,107.70,97.91 ,66.10,44.25,...

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Abstract

The invention relates to a lysosome targeted fluorescent probe as shown in a structural formula and used for lactam ring leuco body regulation and control. The fluorescent probe responds to weakly acidic environment (with pH of 4-6) in a highly sensitive and highly selective manner in a complex buffer solution through lactam ring OFF-ON allosterism. Fluorescent confocal imaging experiments of the probe show that the probe can recognize lysosomes in tumor cells in a targeted manner and has certain promising application prospect in the diagnosing of diseases such as cancers.

Description

technical field [0001] The invention relates to a kind of lysosome targeting fluorescent probe regulated by lactam ring, its preparation method and its application in biological detection system and disease diagnosis. Background technique [0002] As an organelle, lysosome exists in almost all eukaryotic cells, which contains more than 60 kinds of acid hydrolases, cathepsins and various membrane proteases with specific functions. These enzymes that exist inside lysosomes can not only control the degradation of macromolecules in organisms, but also play a very important role in many special endocrine functions, such as cell growth, apoptosis, endocytosis, efflux, and ion regulation. It plays a special role in the process. In the inner cavity of lysosomes, compared with the weakly acidic environment of normal cell lysosomes (pH between 5-6), the pH of lysosomes in tumor cells is more acidic (pH between 4.5-5.5) ). Based on this, exploring the pH distribution and fluctuation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/052C07D519/00C12Q1/02G01N21/64
Inventor 李剑利李红梅厍梦尧王翠玲刘萍
Owner NORTHWEST UNIV(CN)
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