Lysosome-targeted fluorescent dye capable of realizing red emission and near-infrared emission, and preparation method and application thereof

A fluorescent dye and near-infrared technology, applied to luminescent materials, azo dyes, organic dyes, etc., can solve the problems of extended observation time, short excitation wavelength, short emission wavelength, etc., and achieve short dyeing time, good targeting, and The effect of high photostability

Inactive Publication Date: 2017-08-29
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to understand a series of complex physiological activities of lysosomes, a limited number of organic fluorescent dyes such as toluene red and acridine orange (N, N, N', N'-tetramethylacridine-3,6-diamine) has been developed, however, these commercial lysosomal dyes have rather short excitation wavelengths, relatively short emission wavelengths, shall

Method used

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  • Lysosome-targeted fluorescent dye capable of realizing red emission and near-infrared emission, and preparation method and application thereof
  • Lysosome-targeted fluorescent dye capable of realizing red emission and near-infrared emission, and preparation method and application thereof
  • Lysosome-targeted fluorescent dye capable of realizing red emission and near-infrared emission, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Weigh compound I and morpholine indole aldehyde in a three-necked flask, the molar ratio is 1:1.5, and add 30ml of anhydrous toluene as a solvent. Then, nitrogen gas was introduced, and piperidine and glacial acetic acid were added in sequence after the reaction was heated to 110°C. After the reaction mixture was refluxed under nitrogen atmosphere for 16 hours, the solvent was distilled off under reduced pressure, and the obtained residue was subjected to column chromatography (CH 2 Cl 2 / C2 h 5 OH=60 / 1) to obtain the target dye 1 as dark blue solid.

[0035] 1 H NMR (400MHz, DMSO-d 6 ): δ9.82(s,1H),7.93(s,2H),7.79(d,J=16.4Hz,1H),7.62(d,J=7.2Hz,1H),7.46(d,J=16.4Hz ,1H),7.28(m,2H),7.15(d,J=8.2Hz,2H),6.99(s,1H),6.93(d,J=8.2Hz,2H),6.10(s,1H),4.38 (t, J=5.7Hz, 2H), 3.56(s, 4H), 2.70(s, 2H), 2.48(s, 6H), 1.50(s, 3H), 1.42(s, 3H).

[0036] 13 C NMR (100MHz, DMSO-d 6 ):δ158.47,155.61,151.25,143.37,139.94, 139.55,137.75,133.39,132.80,131.22,129.87,125.95,125.19,123.12,...

Embodiment 2

[0040] Weigh compound I and morpholine indole aldehyde in a three-necked flask, the molar ratio is 1:5.5, and add 30ml of anhydrous ethylene glycol methyl ether as a solvent. Then, nitrogen was introduced, and piperidine and glacial acetic acid were added in sequence after the reaction was heated to 140°C. After the reaction mixture was refluxed for 24 hours under a nitrogen atmosphere, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to column chromatography (CH 2 Cl 2 / C 2 h 5 OH=40 / 1) to obtain the target dye 2 as a dark green solid.

[0041] 1 H NMR (400MHz, DMSO-d 6 ):δ9.81(s,1H),8.07(d,J=7.6Hz,2H),7.88(s,2H),7.65(m,6H),7.32(dt,7.6Hz,4H),7.19(d ,J=8.4Hz,2H),6.94(m,4H),4.38(t,J=6.4Hz,4H),3.56(t,J=4.8Hz,8H),2.72(t,J=6.4Hz,4H ),2.47(s,8H),1.51(s,6H).

[0042] 13 C NMR (125MHz, DMSO-d 6 ):δ158.44,152.83,140.98,137.93,136.85, 133.03,132.97,130.66,130.27,125.93,125.53,123.08,121.16,120.42,117.29, 116.34,114.63,114.11,111.43...

Embodiment 3

[0046] Weigh compound II and morpholine indole aldehyde into a three-necked flask, the molar ratio is 1:3, and add 30ml of anhydrous toluene as a solvent. Then, nitrogen was introduced, and piperidine and glacial acetic acid were added in sequence after the reaction was heated to 110°C. After the reaction mixture was refluxed under nitrogen atmosphere for 4 hours, the solvent was distilled off under reduced pressure, and the obtained residue was subjected to column chromatography (CH 2 Cl 2 / C 2 h 5 OH=55 / 1) to obtain the target dye 3 as a dark blue solid.

[0047] 1 H NMR (400MHz, DMSO-d 6 ):δ8.10(s,1H),7.91(dd,1H),7.22(d,1H),7.14(d,1H),7.05(s,1H),6.99(s,2H),6.87(dd, 1H),6.10(s,1H),5.70(s,1H),3.95(t,1H),3,64(t,2H),2.66(t,1H),2.48(t,2H),2.16(s ,1H),2.08(s,2H).

[0048] 13 C NMR (100MHz, DMSO-d 6 ):δ159.28,153.16,150.19,146.92,145.12, 136.68,133.42,132.08,129.89,128.28,125.94,125.02,122.56,122.22,121.56, 120.78,119.53,114.54,110.96,66.79,57.06,53.10,46.57,16.08, 12.6...

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Abstract

The invention discloses a lysosome-targeted fluorescent dye capable of realizing red emission and near-infrared emission, and a preparation method and application thereof, belonging to the field of bioluminescence analysis. The preparation method comprises the following steps: dissolving a compound with the substituent R in an anhydrous organic solvent and adding morpholinoindolal and a catalyst under the condition of introduction of nitrogen, wherein a mol ratio of morpholinoindolal to the compound with the substituent R is 1-10: 1; and carrying out a reaction at a reaction temperature of 25 to 200 DEG C for 1 to 24 h, concentrating an obtained solution and carrying out silica-gel column chromatography so as to obtain the target fluorescent dye. The fluorescent dye prepared in the invention is applicable to targeted imaging of lysosomes in cells, fluorescent probes or laser dyes. The fluorescent dye has the advantages that the emission wavelength of the fluorescent dye is in a range from red zone to near-infrared zone; the fluorescent dye can prevent interference of biological background fluorescence and has high fluorescence quantum efficiency and good light stability; and the fluorescent dye can be specifically localized in lysosomes, so the fluorescent dye has high application value.

Description

technical field [0001] The invention relates to a class of novel red light and near-infrared emitting lysosome-targeting fluorescent dyes that can be used in the field of bioluminescent analysis, as well as their preparation and application. Background technique, [0002] The diameter of lysosome is about 500nm, which is the most important organelle in the terminal degradation zone of mammals. Lysosomes are involved in many physiological processes, such as bone and tissue remodeling, plasma membrane repair, and cholesterol homeostasis in vivo, as well as cell signaling and apoptosis. In addition, lysosomes significantly increase the expression and activity of related biological enzymes, most of which are related to Tumor initiation and metastasis are also altered by lysosomal transport. Therefore, effective fluorescent technology to label cancer cell lysosomes is of great significance for the study of lysosomal transport. [0003] In order to understand a series of complex...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09B57/00C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07F5/022C09B57/00C09K11/06C09K2211/1033G01N21/6486
Inventor 曾林涛叶卓段冲熊超王红颖
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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