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A highly selective ratiometric fluorescent probe for the detection of periodate

A technology of acetic acid solution and compound, which is applied in the field of anion detection, can solve the problems of repeatability difference in periodate detection experiment results, large time, instrument and labor costs, and influence on the quantitative detection of periodate, etc., to achieve solid fluorescence signal stability, Advanced internal calibration function, good selective effect

Active Publication Date: 2019-09-06
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although chromatography and capillary electrophoresis methods have high experimental precision, they require more complicated experimental pretreatment steps, and require specialized experimental operators with high experimental skills to perform operation and analysis, so it is expensive in terms of time, equipment and labor costs. Expensive
At the same time, due to the difference of instruments and operators, the repeatability of periodate detection experiment results will vary.
Although the ultraviolet spectrum analysis method can be used for qualitative and quantitative analysis, it is limited in experimental accuracy due to its weak sensitivity compared with fluorescence analysis and other methods.
Although the electrochemical detection method is widely used in the detection of periodate, it is easily interfered by foreign substances such as various substances with similar oxidation properties to periodate (hypochlorite, hydrogen peroxide, etc.), thus affecting the detection of periodate. Quantitative detection

Method used

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  • A highly selective ratiometric fluorescent probe for the detection of periodate
  • A highly selective ratiometric fluorescent probe for the detection of periodate
  • A highly selective ratiometric fluorescent probe for the detection of periodate

Examples

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specific example

[0074]

[0075] HMBT or its derivatives can be prepared by the method described by Z.Xu et al. (Chemical Communications, 48(88), 10871-10873(2012)).

[0076] It should be understood that although the above preparation scheme only provides the preparation of compound PDS-2, those skilled in the art can prepare the compounds of formula II and formula I of the present invention by changing the groups of the reactants. For example, different trihydric alcohols with different carbon chain lengths can be used to prepare compounds A, B or C with corresponding carbon chain lengths.

[0077] The present invention also includes the compound of formula I of the present invention as a fluorescent probe in the detection of periodate in a chemical system, the fluorescent imaging test of periodate in biological living cells, the construction of a high-throughput hydrolase test platform, and the detection of test strips. Apps in development.

[0078] In a specific embodiment, the detectio...

Embodiment 1

[0084] Embodiment 1: the synthetic route of probe PDS-2

[0085] (1) Preparation of 2-(2-benzothiazolyl)-6-methoxyphenol (HMBT)

[0086]

[0087]Refer to literature (Z.Xu et al., Chemical Communications, 48(88), 10871-10873(2012)).

[0088] (2) Preparation of 2-(2,2-dimethyl-1,3-4-dioxolanyl)ethanol (A)

[0089]

[0090] Weigh 2-4g of 1,2,4-butanetriol and dissolve it in acetone, then add 300-400mg of p-toluenesulfonic acid monohydrate (TsOH), then stir the above reaction mixture at room temperature for two days, Finally, 0.7 mL of triethylamine was added to terminate the reaction, and evaporated to dryness with a rotary evaporator to obtain a crude product, which was then separated by column chromatography on silica gel to obtain a colorless oily product.

[0091] 1 H NMR (400MHz, CDCl 3 )δ4.19(br,1H),4.01(br,1H),3.69(br,2H),3.51(br,1H),1.74(br,2H),1.34(s,3H),1.29(s,3H ); 13 C NMR (100MHz, CDCl 3 )δ108.85,74.53,69.38,59.89,35.79,26.80,25.60; MS(ESI)m / z 147.09[M+H...

Embodiment 2

[0112] Embodiment 2: the influence of pH value on the fluorescence intensity of PDS-2 in the aqueous solution

[0113] Perform pH titration in water. In the pure water system, add 1 mM probe DMSO mother solution to obtain 10 μM probe aqueous solution, use hydrochloric acid and sodium hydroxide aqueous solution to adjust the probe aqueous solution at different pH, and measure the corresponding fluorescence spectrum respectively. A pH titration curve was obtained by plotting the pH and the fluorescence intensity at the maximum emission wavelength (406nm and 462nm). In order to determine the optimum pH condition of the test system.

[0114] The result is as Figure 7 shown. There was no change in the fluorescence intensity of PDS-2 in the pH range of 6-10. Therefore, PBS buffer solution with a pH of 7.4 and containing 1% DMSO was selected as the test medium.

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Abstract

The invention provides a high-selectivity ratio fluorescence probe for detecting periodate radicals. The probe has a structure represented by formula I. In the formula I, R1 is selected from H or C1-C4 alkyl groups; R2 is selected from C2-C8 alkyl groups with two adjacent carbon atoms respectively being substituted by one hydroxyl group; R3 is selected from H and C1-C4 alkyl groups; and R4 is selected from H and C1-C4 alkyl groups. The invention also provides an intermediate compound represented by formula II and used for preparing the compound of the formula I, a preparation method of the compound of the formula I, a detection composition containing the compound of the formula I, a detection kit containing the compound of the formula I, and an application of the compound of the formula I in detection of the periodate radicals in a chemical system, fluorescence imaging test of the periodate radicals in biological living cells, construction of high-flux hydrolase test platforms, and exploitation of detection test strips as a fluorescence probe.

Description

technical field [0001] The invention belongs to the technical field of anion detection, specifically relates to the periodate content determination technology in biological and chemical systems, and is a high-selectivity ratio probe that can be used for imaging determination of periodate in chemical systems and living cells. Background technique [0002] Periodate is an oxoacid anion composed of heptavalent iodine and oxygen atoms. It mainly exists in two forms in water, namely metaperiodate (IO 4- ) and periodate (IO 6- ), usually in the form of potassium periodate (KIO 4 ) or sodium periodate (NaIO 4 ) form exists. In neutral solution, periodate mainly exists in the form of metaperiodate. The most important feature of periodate is that it can selectively oxidize and break the carbon-carbon bond containing two adjacent hydroxyl groups to generate the corresponding aldehyde group or carbonyl group. This characteristic makes periodate widely used in organic synthesis an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/66C07D417/12C09K11/06G01N21/64
Inventor 黄楚森贾能勤贾倜于丛军章阿敏
Owner SHANGHAI NORMAL UNIVERSITY
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