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Bifunctional fluorescent probe for detecting Pd concentration and pH value as well as preparation and application thereof

A fluorescent probe and dual-function technology, applied in the field of fluorescent probe detection, can solve problems such as environmental pollution and human health, and achieve the effect of high selectivity, simple preparation method, and accurate quantitative detection

Active Publication Date: 2021-02-26
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, due to frequent use, Pd has been gradually released into the environment, which may cause serious environmental pollution and human health problems

Method used

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  • Bifunctional fluorescent probe for detecting Pd concentration and pH value as well as preparation and application thereof
  • Bifunctional fluorescent probe for detecting Pd concentration and pH value as well as preparation and application thereof
  • Bifunctional fluorescent probe for detecting Pd concentration and pH value as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: the preparation of probe (I)

[0053]

[0054] Compound II, dichloromethane and triethylamine were added to a 25 mL round bottom flask, followed by allyl chloroformate, and stirred overnight at room temperature. The ratio of compound II, triethylamine and allyl chloroformate is 1:2.5:2.5, wherein the compound II is 0.3mmol, and the amount of dichloromethane is 5mL. Stir the reaction at 25°C for 10h, evaporate under reduced pressure Dry solvent, the crude product was separated and purified by column chromatography, the eluent was dichloromethane / methanol=30:1, v / v, and 55 mg of yellow probe (I) was obtained with a yield of 43.7%. For its H NMR spectrum, see figure 1 , C NMR see figure 2 .

[0055] 1 H NMR (400MHz, DMSO-d 6 )δ (ppm) 10.33 (s, 1H), 8.70 (d, J = 8.5Hz, 1H), 8.46 (dd, J = 13.5, 7.7Hz, 2H), 8.17 (d, J = 8.3Hz, 1H), 7.87–7.75(m,1H),6.07(ddt,J=16.0,10.7,5.5Hz,1H),5.46(dd,J=17.2,1.6Hz,1H),5.35–5.24(m,1H),4.75( d, J=5.5Hz, 2H), 4.16(t, J=...

Embodiment 2

[0056] Example 2: Fluorescence spectrum test of probe (I) (5 μM) response to pH.

[0057] Accurately weigh a certain amount of probe (I) (prepared in Example 1), prepare a probe mother solution with a concentration of 0.05mM with dimethyl sulfoxide, pipette 50 μL into 0.45mL PBS buffer, and configure into DMSO / PBS buffer (1:9, v:v, pH is 4.00, 4.50, 4.75, 5.00, 5.25, 5.50, 5.75, 6.00, 6.25, 6.50, 6.75, 7.00, 7.25, 7.40, 8.00, 8.50, 9.00, 9.50), make the probe final concentration 5 μ M, add in the 96-well plate after shaking up, measure the change situation of the fluorescent spectrum of probe (I) with multifunctional microplate reader, and make correlation linear curve.

[0058] Depend on image 3 In (a), it can be seen that as the pH decreases, the fluorescence intensity of the probe (I) is continuously enhanced, and the fluorescence intensity at 485nm and the pH value also show a good linear relationship in the range of 5.25-6.75 (linear regression equation: F =-11835*[pH]...

Embodiment 3

[0059] Embodiment 3: the selectivity research of probe (I) to pH

[0060] Accurately weigh a certain amount of probe (I) (prepared in Example 1), prepare a probe mother solution with a concentration of 1 mM with dimethyl sulfoxide, pipette 50 μL and add it to 0.45 mL containing different metal ions (in order of PBS, Cu + 、Cd 2+ 、Co 2+ 、Cu 2+ , Mn 2+ 、Sr 2+ 、Ba 2+ , Fe 2+ , Zn 2+ , Ca 2+ 、Al 3+ , Pd(PPh 3 ) 4 ) in PBS buffer (pH 4.50 or 7.40), configure DMSO / PBS buffer (1:9, v:v, pH 7.40), make the final concentration of probe 5μM, metal ion final concentration 10μM, shake well Then add it to a 96-well plate and measure the change of the fluorescence spectrum of the probe (I) with a multifunctional microplate reader.

[0061] Fluorescence spectrum see Figure 4 . The data show that several important metal ions have little effect on the fluorescence signal of the probe (I) under the PBS buffer environment with pH 4.50 or 7.40. The above experimental data show tha...

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Abstract

The invention discloses a bifunctional fluorescent probe capable of respectively detecting a pH value and a Pd0 concentration, and the structural formula of the bifunctional fluorescent probe is shownas a formula (I): 1,8-naphthalimide is used as a fluorescent parent nucleus, and the pH value and the Pd0 concentration can be respectively detected through the combination of two fluorescent light-emitting mechanisms: photo-induced electron transfer and intra-molecular charge transfer.

Description

technical field [0001] The invention relates to the technical field of fluorescent probe detection, in particular to a method for detecting Pd 0 Concentration and pH value dual-functional fluorescent probe and its preparation method and application. Background technique [0002] Due to its specific chemical and physical properties, palladium (Pd, different valence states are Pd 0 , Pd +2 , Pd +4 ) as effective catalysts have been widely used in material preparation and drug synthesis. Meanwhile, due to frequent use, Pd has been gradually released into the environment, which may cause serious environmental pollution and human health problems. Pd has been reported to bind DNA, thiol-containing amino acids, proteins, and other biomolecules and interfere with a variety of cellular processes. Therefore, the government has very strict regulations on the content of palladium in food, and it is recommended that the daily intake of each person should be less than 1.5-15 μg. [...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06G01N21/64C09K2211/1029C09K2211/1033G01N2021/6432
Inventor 谢振达周奕宇倪林晨童应鹏李娜杨仲毅王建新
Owner TAIZHOU UNIV
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