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OFF-ON type TBT-detecting fluorescent probe and preparation method and application thereof

A compound and general formula technology, applied in the OFF-ON type detection TBT fluorescent probe and its preparation and application fields, can solve the problems of non-target biological ecological hazards, human health hazards, aquatic biological hazards, etc., and achieve high selective identification Ability and anti-interference ability, good biological application prospects, high selective effect

Inactive Publication Date: 2016-05-18
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the continuous release of it into the surrounding water body and settlement into the sea mud, it has caused serious ecological hazards to other non-target organisms
Tributyltin chloride not only causes serious harm to aquatic organisms, but also can enter the food chain and even endanger human health
[0003] In recent years, fluorescent chemical labeling and molecular probe technology have been widely used in the fields of internal state information expression of complex biological and environmental systems, high-throughput drug screening, and fluorescence histochemical research. It is widely used as the research object of fluorescent probes. A variety of rhodamine-based molecular fluorescent probes with high sensitivity and high selectivity have been designed and synthesized, but the specific selection of fluorescent probes that recognize TBT has so far No report

Method used

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  • OFF-ON type TBT-detecting fluorescent probe and preparation method and application thereof
  • OFF-ON type TBT-detecting fluorescent probe and preparation method and application thereof
  • OFF-ON type TBT-detecting fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of probes 2a-2c:

[0048]

[0049] a. Synthesis of rhodamine B hydrazide: Rhodamine B (25 g, 56.4 mmol) and 200 mL of absolute ethanol were added to a 500 mL three-necked flask, and excess 60 mL of hydrazine hydrate was added dropwise. The reaction solution was vigorously stirred and refluxed for 24 hours, and the dark red suspension gradually became clear. After the reaction was completed, the temperature was lowered and poured into 500 mL of water, a large amount of light yellow precipitate was produced immediately. Static suction filtration, the solid was washed with a small amount of water and absolute ethanol until it was colorless. The crude product was recrystallized from ethanol and dried.

[0050] Rhodamine B hydrazide: 20.40 g of white solid, yield: 80.2%.

[0051] 1 HNMR (CDCl 3 ,400MHz,TMS):δ(ppm)8.00–7.89(m,1H),7.53–7.40(m,2H),7.17–7.05(m,1H),6.55–6.37(m,4H),6.29(d, J=8.4Hz,2H),3.61(s,2H),3.34(dd,J=13.8Hz,6.8,8H),1.37–1.01(m,12...

Embodiment 2

[0067] Example 2: Synthesis of probes 3a-3c:

[0068]

[0069] a. Synthesis of rhodamine 6G hydrazide: add rhodamine 6G (25g, 60.2mmol) and 200mL absolute ethanol into a 500mL three-necked flask, and add dropwise excess 50mL of hydrazine hydrate. The reaction solution was vigorously stirred and refluxed for 24 hours, and the dark orange-yellow suspension gradually became clear. After the reaction was completed, the temperature was lowered and poured into 500 mL of water, a large amount of light yellow precipitate was produced immediately. Stand still and filter with suction, and wash the solid with a small amount of water and absolute ethanol until it is colorless. The crude product was recrystallized from ethanol and dried.

[0070] Rhodamine 6G hydrazide: 19.46 g of colored solid. Yield: 76.4%.

[0071] 1 HNMR (CDCl 3 ,400MHz,TMS):δ(ppm)7.96(dd,J=5.9Hz,2.7,1H),7.52–7.41(m,2H),7.15–7.02(m,1H),6.40(s,2H),6.26 (s,2H),3.58(s,2H),3.22(q,J=7.1Hz,4H),1.92(s,6H),1.33(t,J=7...

Embodiment 3

[0087] Embodiment 3: Probe 2a-2c and 3a-3c recognize the fluorescence and absorption data and spectrometry of TBT

[0088] Prepare a probe solution with a concentration of 5 μmol / L, and gradually add TBT solution for titration experiments. figure 1 is the optical data (excitation wavelength, maximum emission wavelength, fluorescence quantum yield, response time) of probes 2a-2c and 3a-3c. It can be seen that the synthesized probes have significant fluorescence emission in the range of 550-580nm, and The response time is extremely short, and the TBT content in the solution can be detected immediately. Figure 9 The fluorescence spectrum of probe 2a was titrated for TBT. It can be seen from the results that the probe itself has no fluorescence due to the existence of the lactone structure. For probe 2a, when the fixed concentration was 5μmol / L, with the addition of TBT, the fluorescence intensity at 577nm was gradually enhanced to 207 times of the original intensity. When the ...

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Abstract

The invention relates to an OFF-ON type TBT-detecting fluorescent probe shown by a structural general formula (I). The R1 represents H or CH2CH3, and the R2 is selected from H, Cl, Br or NO2. The fluorescent probe has very good fluorescence response to tributyl tin chloride (TBT), has the advantages of high selectivity, high sensitivity and the like, has the TBT detection capability in a complex environment, can be applied to fluorescent confocal imaging of cells and is wide in application prospect.

Description

technical field [0001] The invention relates to an OFF-ON fluorescent probe for detecting TBT and a preparation method thereof, and its application in the detection of TBT content in complex environmental systems and biological systems. Background technique [0002] Organotin compounds are the general term for metal organic compounds formed by the direct combination of tin and carbon atoms, the general formula is R n wxya 4-n (n=1-4, R is an alkyl group or an aryl group). Organotin compounds are widely used to kill fungi, insects and molluscs. As early as the 1960s, organotins were used as antifouling coatings for ships in the world, which can effectively prevent damage to ship hulls, fishing nets, drilling platforms, etc. by mollusks, seaweeds, sponges and other attached organisms in the ocean. Tributyltin chloride (TBT) is the most widely used and most effective one. However, due to its continuous release into surrounding water bodies and sedimentation into sea mud, it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1022C09K2211/1033C09K2211/1088G01N21/643G01N21/6486
Inventor 李剑利薛智凤金洗郎厍梦尧刘萍史真
Owner NORTHWEST UNIV(CN)
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