Single\two-photon calcium ion fluorescent probe compound and preparation and application thereof

A calcium ion fluorescent probe and compound technology, applied in the direction of fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of increasing the difficulty of observing living biological samples, increasing the thermal damage of biological samples, etc., achieving good selectivity, The effect of good sensitivity and good membrane penetration

Inactive Publication Date: 2012-10-03
QILU UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, traditional Ca 2+ When fluorescently labeled probes such as fluo-2, BAPTA-1(OG1), and Indo-1 are used in two-photon technology, their two-photon fluorescence active absorption cross section (δ×Φ) is relatively small. For example, the commonly used fluorescent reagent Indo-1 for calcium ions δ×Φ of -1 is 1.2GM
Therefore, in the experiment, high-intensity lasers must be used to excite high-concentration fluorescent substances to obtain sufficiently strong up-conversion fluorescence, which makes a large part of the light energy absorbed by the fluorescent compound not converted into fluorescent light energy, but released in the form of heat. out, increasing the thermal damage to biological samples and increasing the difficulty of observing living biological samples

Method used

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  • Single\two-photon calcium ion fluorescent probe compound and preparation and application thereof
  • Single\two-photon calcium ion fluorescent probe compound and preparation and application thereof
  • Single\two-photon calcium ion fluorescent probe compound and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1, the preparation method of calcium ion fluorescent probe compound, the steps are as follows:

[0029] Add BAPTA-CH to the three-necked bottle 3 -CHO 10g (15.87mmol), then weighed 4.5g (19.05mmol) of 4-methyl-N-methylpyridinium iodide salt, then poured 100mL of ethanol into it, added 2.5mL of piperidine dropwise, heated to 80 The reaction was refluxed at ℃ for 10 hours. After the reaction was stopped, the reaction solution turned dark red, and the precipitate was precipitated after cooling. It was filtered, rinsed with ethanol and water, dried and recrystallized in ethanol to obtain 11.6 g of the product.

[0030] The calcium ion fluorescent probe compound synthesized by the present invention, 1 H NMR (CDC1 3 ,400MHz,TMS)δ(ppm):8.54(d,J=7.2Hz,2H),8.03(d,J=6.8Hz,2H),7.25(m,4H),6.76(m,4H),4.21( m,20H),2.28(s,3H),1.94(s,3H),1.18(t,J=4.4Hz,12H).

[0031] The synthetic route of the described two-photon calcium ion fluorescent probe compound is as follows:

...

Embodiment 2

[0033] Example 2. Two-photon solvent effect of calcium ion fluorescent probe compound.

[0034] The calcium ion fluorescent probe compound synthesized in Example 1 was formulated into a solution. Then its two-photon solvent effect was tested, and its two-photon absorption cross section and active absorption cross section in different solvents were calculated.

[0035] Weigh 0.0424g of the calcium ion fluorescent probe compound into a 5mL volumetric flask, and then dilute to the volume with chromatographically pure N,N-dimethylformamide (DMF) to obtain a concentration of 1×10 -2 mol / L probe stock solution. Then use a micro-sampler to take 500 μL of the mother liquor and put it into a 5mL capacity, and use chromatographically pure acetone, ethanol, DMF, acetonitrile, and water to make up a volume of 1×10 -4 mol / L solution, after shaking well, the laser pulse emitted by the Ti:sapphire Mira 900-F mode-locked laser was used as the irradiation light source, the repetition frequen...

Embodiment 3

[0040] Embodiment 3, performance experiment of calcium ion fluorescent probe compound on calcium ion

[0041] The calcium ion fluorescent probe compound synthesized in Example 1 was formulated into a solution. Its performance was then tested to determine its selectivity and sensitivity.

[0042] (1) Selectivity of calcium ion probe

[0043] Common metal ions may interfere with the detection of calcium ions, so it is necessary to determine whether the synthesized calcium ion probe has good selectivity in recognizing calcium ions.

[0044] in 1×10 -5 Add Cu(NO 3 ) 2 .3H 2 0, Fe(NO 3 ) 3 .9H 2 O, Zn(NO 3 ) 2 .6H 2 O, KNO 3 ,Mg(ClO 4 ) 2 .6H 2 O, NaClO 4 .H 2 O, AgNO 3 , AlCl 3 ·6H 2 O and other solids, so that the molar ratio of metal ions to compounds is 10:1. Then use a single-photon fluorescence detector to measure the fluorescence emission intensity, manually input the scanning wavelength range of 440~700nm, and the excitation wavelength of 419nm, the rel...

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Abstract

The invention provides a single\two-photon calcium ion fluorescent probe compound and preparation and application thereof. The calcium ion fluorescent probe compound has the structure of formula I. The preparation method comprises the following steps of: heating BAPTA-CH3-CHO and 4-methyl-N-methylpyridine iodate at a molar ratio of 1:(1.1-1.3) in the presence of ethanol solvent and piperidine catalyst to 78-83 DEG C for a reflux reaction; cooling to separate out precipitates; and filtering, washing, drying and recrystallizing to obtain a product. The fluorescent probe compound has good selectivity and sensitivity on calcium ions, and performs simple pretreatment of the detection sample; and moreover, the fluorescent probe compound has certain water solubility and excellent single\two-photon fluorescence, and can be widely used for detecting the calcium content in animals / plants, human cells, soil or water.

Description

technical field [0001] The invention relates to a calcium ion fluorescent probe compound and its preparation and application, belonging to the technical field of fluorescent probes. technical background [0002] Ca 2+ As an intracellular messaging substance, it plays a role in regulating many important cellular functions. As a second messenger, Ca 2+ It participates in the transmembrane transmission of biological signals, mediates the response of cells to external stimuli, and also participates in blood coagulation, cell growth and division, bone formation, heart beating and so on. There are many methods for detecting calcium ions: Ca 2+ Organic chromogenic reagent method, calcium ion fluorescent indicator method, Ca 2+ Sensor method and NMR method etc. These methods are more sensitive, but there are disadvantages such as time-consuming, complicated pretreatment of samples, and easy damage to cells. [0003] Fluorescence method is one of the feasible methods to elimina...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/36C09K11/06G01N21/64
Inventor 张献谢瑞兴姚金水刘伟良李梅丁碧妍
Owner QILU UNIV OF TECH
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