Application of detecting pH of benzothiazole derivative in extremely acidic environment

A technology of benzothiazole and derivatives, applied in the field of benzothiazole compounds, can solve the problems of few pH fluorescent probes and limited types of pH fluorescent probes, and achieve the effects of low cost, good selectivity and high sensitivity

Inactive Publication Date: 2015-07-15
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, very few people have paid attention to the research of pH fluorescent probes in extremely acidic (pH<4) environments, resulting in very limited types of pH fluorescent probes in this area (a.Su, M.H. et al., Chem.Commun., 2001, 960- 961.b.Xu,Y. et al., Analytica Chimica Acta,2014,820:146-151.c.Yang,M.Y. et al.,Angew.Chem.Int.Ed.,2012,51:7674-7679.Niu, W.F. et al., Analytical Chemistry, 2015,87:2788-2793), especially pH fluorescent probes with ratiometric detection properties are rare

Method used

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  • Application of detecting pH of benzothiazole derivative in extremely acidic environment
  • Application of detecting pH of benzothiazole derivative in extremely acidic environment
  • Application of detecting pH of benzothiazole derivative in extremely acidic environment

Examples

Experimental program
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Effect test

Embodiment 1

[0027] The synthesis of probe (benzothiazole derivative) of the present invention:

[0028] (1) Under the protection of inert gas, 2-methylbenzothiazole (0.126ml, 1mmol), 4-(dimethylamino)cinnamaldehyde (0.263g, 1.5mmol) and KOH (0.354g, 6.25mmol) The reaction was stirred at room temperature in 7ml DMF for 24h.

[0029] (2) Remove the KOH solid by filtration, add H to the reaction solution 2 O (10ml), the mixed solution was extracted with dichloromethane. After the organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product.

[0030] (3) The crude product was separated by silica gel column chromatography using dichloromethane as the eluent to obtain an orange-red solid. 1H NMR(300MHz,DMSO-d6):δ2.961-2.976(s,6H),6.674-6.893(m,3H),6.893-7.032(d,2H),7.290-7.476(m,5H),7.890- 8.022(d,1H),8.022-8.047(d,1H).MS: m / z 307.1264for M+.

Embodiment 2

[0032] The probe in Example 1 was used to prepare a stock solution with a concentration of 1 mM in ethanol. In the experiment, the probe was diluted with water / ethanol (V / V=2 / 1) system to make the final concentration 10 μM. Regulate the pH value of this system with the HCl of 1mol / L, record the ultraviolet absorption spectrogram under different pH conditions ( figure 1 ). As the pH value decreased from 7.0 to 1.2, the absorption peak at 418nm decreased gradually, and the absorption peak at 354nm increased in turn, and there was an obvious isoelectric point at 383nm. figure 2 The color of the solution changed from yellow to colorless.

Embodiment 3

[0034]Similarly, the probe was diluted to 10 μM with water / ethanol (V / V=2 / 1) system for fluorescence spectrum titration, the excitation wavelength was fixed at 383 nm, and the fluorescence emission spectra under different pH conditions were recorded. Such as image 3 As shown, under the neutral condition of pH 7.0, the maximum fluorescence emission of the probe is located at 595nm. As the pH decreases, the fluorescence emission at 595nm gradually decreases, and a new fluorescence emission appears at 425nm and is significantly enhanced. At the same time, a clear isoelectric point appears at 522nm. Under the irradiation of ultraviolet light, the color of the solution changed from yellow to blue ( Figure 4 ).

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Abstract

The invention discloses an application of detecting the pH of a benzothiazole derivative in the extremely acidic environment. The structural formula of the benzothiazole derivative is shown in the specification. A probe has the good selectivity and high sensitivity for H+ on the strongly acidic condition, has the obvious ratio fluorescence emission characteristic and has the advantages of having the large Stocks displacement and the like. The probe can be used for detecting the pH changes of escherichia coli in the extremely acidic environment, and can also be used for detecting pH changes in the extremely acidic environment.

Description

technical field [0001] The invention relates to the use of benzothiazole compounds, in particular to the application of a benzothiazole derivative in detecting pH changes in an extremely acidic environment such as Escherichia coli. Background technique [0002] Maintaining pH homeostasis is very important for all organisms (a.Baker-Austin.C. et al., Trends Microbiol.2007, 15:165-171.b.Krulwich, T.A. et al., Nat.Rev.Microbiol. ., 2011, 9:330-343). The pH values ​​within different subcellular organelles of different prokaryotes and eukaryotic cells range from alkaline to strongly acidic (a. Baker-Austin, C. et al., Trends Microbiol., 2007, 15:165-171.b. Krulwich, T.A. et al., Nat. Rev. Microbiol., 2011, 9:330-343. c. Foster, J.W. et al., Nat. Rev. Microbiol., 2004, 2:898-907). Although extreme acidity (pH<4) is fatal to most organisms, studies have shown that a large number of microorganisms (such as Helicobacter pylori and "acidophiles") have evolved to survive in this e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C09K11/06
Inventor 张雯佳樊丽李增波双少敏董川
Owner SHANXI UNIV
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