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Hemicyanine compound for detecting polarity of mitochondria

A technology of cyanine compounds and mitochondria, applied in the field of fluorescent probe compounds, can solve the problems of no literature reports

Active Publication Date: 2015-07-01
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorescent probes that can detect the polarity of specific subcellular organelles have not been reported. So far, fluorescent probes that can be used to detect the polarity of mitochondria are still a "blank area", and there are no reports in the literature.

Method used

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  • Hemicyanine compound for detecting polarity of mitochondria
  • Hemicyanine compound for detecting polarity of mitochondria
  • Hemicyanine compound for detecting polarity of mitochondria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The synthesis of embodiment 1. fluorescent probe compound BOB:

[0055] It is the synthetic method of representative compound BOB of the present invention, and its synthetic route is as follows:

[0056]

[0057] The synthetic method comprises the following steps

[0058] (1) 0.85g benzyl bromide and 0.90g 2-methylbenzothiazole were reacted at 65°C for 3h under nitrogen protection, and cooled to room temperature. After the solid was completely settled, it was vacuum filtered, the obtained solid was washed with ether, and finally the solid was dried in vacuum to obtain the white intermediate 1a;

[0059] In this step, no solvent is needed when 2-methylbenzothiazole reacts with benzyl bromide;

[0060] This step reacts under inert gas protection;

[0061] (2) 0.97g 4-diethylamino salicylaldehyde, 1.6g diethyl malonate and 1.0mL piperidine were stirred and refluxed in 30mL ethanol solution for 6 hours (80°C). After ethanol was distilled off under reduced pressure, 2...

Embodiment 2

[0067] Embodiment 2. Synthesis of fluorescent probe compound BOB-1:

[0068]

[0069] Dissolve 0.67g of intermediate 1a in ethanol, add 0.23g of intermediate 2b, and heat to reflux to form a purple dye BOB-1. After the reaction was completed, the solvent was distilled off. The product is preferably purified by chromatographic column separation using dichloromethane / methanol as the eluent. The product was characterized by NMR and high-resolution mass spectrometry. R 1 for H, R 2 for para-CH 3 : 1 H NMR (400MHz, MeOD): 8.29(s, 2H), 8.24(d, J=7.3Hz, 1H), 8.16(d, J=8.3Hz, 1H), 8.08(d, J=15.0Hz, 1H) ,7.75(t,J=7.2Hz,1H),7.53(s,1H),7.38(d,J=10.8Hz,5H),6.88(dd,J=9.1,2.4Hz,1H),6.62(d, J=2.3Hz,1H),6.03(s,2H),3.58(q,J=7.1Hz,4H),2.34,(s,3H),1.26(dd,J=12.5,5.5Hz,10H).

[0070] 13 C NMR (101MHz, MeOD): δ195.60, 137.40, 123.98, 122.67, 121.29, 116.29, 93.76, 82.22, 80.91, 28.35, 26.27, 21.47, 19.50.

[0071] HRMS-ESI: m / z calcd M + for C 30 h 29 N 2 o 2 S + , 481.1944; fou...

Embodiment 3

[0072] Example 3. Absorption and emission spectra of dye BOB in ethanol

[0073] The dye BOB was dissolved in ethanol, respectively, to prepare solutions with a final concentration of 5.0 μM.

[0074] The test results are attached figure 1 As shown, the maximum absorption of the dye BOB in ethanol is at 425 / 560nm, and the maximum emission spectrum is at 467 / 645nm.

[0075] The instruments used are ultraviolet-visible spectrophotometer, model: Perkin Elmer Lambda 35UV / VIS; fluorescence spectrophotometer, model: FL0812M018.

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PUM

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Abstract

The invention discloses a hemicyanine compound for detecting polarity of mitochondria. The hemicyanine compound has a structure as shown in formula I, wherein R1 and R2 are independently selected from H, C1-18 alkyl, SO3R5 and COOR5; R3 and R4 are independently selected from H, C1-18 alkyl, SO3R5 and COOR5; R5 is selected from H and C1-18 alkyl, Y<-> is Cl<->, Br<->, I<->, I<-> or OTs<->. The compound has a structure with a formula I. The probe is very sensitivity to the environmental polarity, and can be used for detecting the polarity of the solution. The probe can be used for positioning mitochondria, and detecting polarity of the mitochondria of cells in different states, normal cells and cancerous cells through fluorescence ratio imaging.

Description

technical field [0001] The invention relates to a class of fluorescent probe compounds suitable for polarity detection of intracellular mitochondria in the fine chemical industry field. Such compounds can detect intracellular mitochondrial polarity by fluorescence ratiometric imaging. Background technique [0002] Polarity is an important parameter in the course of chemical reactions. The rate of some organic or inorganic reactions depends significantly on the polarity of the environment surrounding the reaction. In biological systems, especially at the cellular level, changes in polarity affect the interactions of proteins, enzymes, etc., and to some extent reflect the permeability of cell membranes. In addition, its abnormal changes are closely related to some diseases, such as diabetes and liver cirrhosis. [0003] Mitochondria are the energy-making factories in cells, which are sensitive to cancer, Alzheimer's, Parkinson's and other diseases. Mitochondrial polarity c...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06G01N21/64C09B23/10C09B57/02
CPCC07D417/06C09B23/102C09B23/105C09K11/06C09K2211/1088G01N21/6486
Inventor 彭孝军姜娜樊江莉王静云
Owner DALIAN UNIV OF TECH
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