Mitochondrial pH fluorescent probe based on benzothiazole and preparation method thereof

A technology of methylbenzothiazole and fluorescent probe, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of far difference and low sensitivity, and achieve reduced interference, high sensitivity, and good selectivity Effect

Active Publication Date: 2019-02-01
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, some organic small molecule fluorescent probes have been reported in the literature for pH mito detection of changes, but the pKa of most of these probes is far from mitochondrial pH (~8.0) and thus less sensitive

Method used

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  • Mitochondrial pH fluorescent probe based on benzothiazole and preparation method thereof
  • Mitochondrial pH fluorescent probe based on benzothiazole and preparation method thereof
  • Mitochondrial pH fluorescent probe based on benzothiazole and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] 1, compound 3-(6-bromohexyl)-2-methylbenzothiazole-3-bromide (BMBI), compound 2-methyl-3-(6-(triphenylphosphoryl)hexyl)benzo Thiazole-3-bromide (MTBI) and the probe 2-(2-(6-hydroxynaphthalen-2-yl)vinyl)-3-(6-(triphenylphosphono)hexyl)benzothiazole-3 - Preparation of Bromide (HTBT2):

[0031]

[0032] (1) A mixed solution of 2-methylbenzothiazole (15 mmol, 1.90 mL) and 1,6-dibromohexane (75 mmol, 12.11 mL) was reacted in a locked tube at 140° C. for 5 h. After the reaction was cooled to room temperature in CH 2 Cl 2 The product (5.43 g, 92%) was obtained as a gray solid by precipitation with diethyl ether. 1 H NMR (400MHz, CDCl 3 )δ8.32(d, J=8.1Hz, 1H), 8.06(d, J=8.4Hz, 1H), 7.81(t, J=7.7Hz, 1H), 7.69(t, J=7.7Hz, 1H) ,5.09–4.75(m,2H),3.49(s,3H),3.40(t,J=6.5Hz,2H),2.25–1.75(m,8H). 13 C NMR (101MHz, CDCl 3 )δ175.69,140.93,130.00,129.23,128.67,124.72,116.57,51.00,33.77,32.28,28.67,27.68,25.98,19.30.MS(ESI-MS):m / z Calcd 313.0402[M] + ;found 312.0416,314.0387[M] +...

Embodiment 2

[0036] The concentration of the probe HTBT2 in Example 1 was maintained at 200 μM, and Tris-hydrochloric acid buffer solution (V DMSO :V H2O =2:1,0.05M) measured its absorption spectrum in the system ( figure 1 ). As the pH value decreased from 9.30 to 6.40, the absorption peak at 566nm decreased gradually, the absorption peak at 436nm increased correspondingly, and there was an isosbestic point at 479nm. The color of the solution also changed from the original yellow to yellow-green ( figure 2 ).

Embodiment 3

[0038] The probe concentration in Example 1 was kept at 10 μM, and its fluorescence emission spectrum was measured in Tris-hydrochloric acid buffer (VDMSO:VH2O=2:1, 0.05M) system with different pHs, and the fixed excitation wavelength was 436nm ( image 3 ). As the pH value decreased from 9.30 to 6.40, the solution had a new fluorescence emission peak at 612nm and gradually increased. The color of the solution changed from colorless to orange-red ( Figure 4 ). By fitting the fluorescence intensity value of HTBT2 at 612nm with the Boltzmann function of pH value, the calculated pKa value was 8.04±0.02( Figure 5 ), the pH response linear range is 7.20-8.70. The linear regression equation is F=764314.81192-79080.76184×pH, the correlation coefficient R 2 =0.9991( Figure 6 ).

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Abstract

The invention discloses a mitochondrial pH fluorescent probe based on benzothiazole, and a preparation method and an application thereof. The probe is specifically named as 2-(2-(6-hydroxynaphthalene-2-yl)vinyl)-3-(6-(triphenylphosphonyl)hexyl)benzothiazole-3-bromide (HTBT2). The preparation method comprises the steps: firstly, carrying out a reaction of 2-methylbenzothiazole and 1,6-dibromohexaneunder heating conditions to prepare 3-(6-bromohexyl)-2-methylbenzothiazole-3-bromide (BMBI), and then carrying out mixed reflux of the prepared BMBI with triphenylphosphine and acetonitrile to prepare 2-methyl-3-(6-(triphenylphosphorus)hexyl)benzothiazole-3-bromide (MTBI); and finally, dissolving MTBI and 6-hydroxy-2-naphthaldehyde in ethanol, and adding a small amount of piperidine, refluxing, and then separating and purifying to obtain HTBT2. The probe has the pKa value of 8.04+/-0.02 and is quite close to that of a mitochondrial matrix (with the pH of 8.0). At the same time, the probe hasthe advantages of high sensitivity to the changes of the pH, good selectivity and large Stokes displacement, and can be used for monitoring the changes of the pH in cell mitochondria.

Description

technical field [0001] The invention relates to a mitochondrial pH fluorescent probe, in particular to a benzothiazole-based mitochondrial pH fluorescent probe and a preparation method thereof, and its application in monitoring pH changes in living cell mitochondria. Background technique [0002] Mitochondria are very important organelles in eukaryotic cells, which are closely related to physiological processes such as cell division and apoptosis, information transmission, and ion regulation. In particular, most of the energy required for cell metabolism comes from the redox process of mitochondria, so mitochondria Also known as the "energy factory" of the cell. Under normal physiological conditions, the pH in the mitochondrial matrix (pH mito ) value is about 8.0. Many physiological activities of cells, such as cell information transmission, Na + / K + / Ca 2+ balance, and ROS generation is inseparable from mitochondrial pH mito Balance, and more importantly, studies ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6541C09K11/06G01N21/64
CPCC07F9/6541C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1037G01N21/6486
Inventor 林博樊丽贾晶黄文成双少敏董川
Owner SHANXI UNIV
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