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Fluorescent probe for detecting formaldehyde in cytolysosome and preparation method thereof

A technology of fluorescent probes and lysosomes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of few fluorescent probes and achieve the effect of increasing fluorescence intensity

Inactive Publication Date: 2016-10-12
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the past two years, researchers have successively reported some formaldehyde fluorescent probes. For example, we reported a two-photon formaldehyde that recognizes endogenous formaldehyde in cells and tissues in Angew. Chem. Int. Ed in 2016. Fluorescent probes, but there are still few fluorescent probes that can highly recognize formaldehyde or specifically recognize formaldehyde, especially formaldehyde fluorescent probes that can recognize special organelles (such as lysosomes) in cells have never been reported. Therefore, at this stage, it is necessary to develop some formaldehyde fluorescent probes with less background interference, less scattering interference, higher sensitivity and selectivity, and can avoid photobleaching and phototoxicity, especially those that can recognize special organelles in cells (such as lysosomes). ) formaldehyde fluorescent probe is particularly important

Method used

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  • Fluorescent probe for detecting formaldehyde in cytolysosome and preparation method thereof
  • Fluorescent probe for detecting formaldehyde in cytolysosome and preparation method thereof
  • Fluorescent probe for detecting formaldehyde in cytolysosome and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Synthesis of compound 4-bromo-N-(2-morpholinoethyl)naphthalimide (3):

[0031]

[0032] In a 100 mL round bottom flask, add 1 mmol of 4-bromo-1,8-naphthalene dicarboxylic anhydride (1), 1.2 mmol of aminoethylmorpholine (2), then add 5 mL of ethanol, and heat to reflux for 2-3 h Then, cool to room temperature, filter under reduced pressure, wash the filter cake 2-3 times with ethanol, and dry in vacuo to obtain 4-bromo-N-(2-morpholinoethyl)naphthalimide (3) as a light gray solid. Yield: 81%. H NMR and C spectra such as figure 1 and figure 2 shown.

[0033] 1 H NMR (400 MHz, DMSO- d 6 ) δ 8.57 (dd, J 1 = 7.2 Hz, J 2 = 0.8 Hz, 1H), 8.55 (dd, J 1 = 8.4 Hz, J 2= 0.8 Hz, 1H), 8.34 (d, J = 7.6 Hz, 1H), 8.22 (d, J = 7.6 Hz, 1H), 8.00 (dd, J 1 = 8.4 Hz, J 2 = 7.2 Hz, 1H), 4.18 (t, J = 6.8Hz, 2H), 3.53 (t, J = 4.8 Hz, 4H), 2.57 (t, J = 7.2 Hz, 2H), 2.47 (s, 4H); 13 CNMR (100 MHz, DMSO- d 6 ): 163.30, 163.25, 133.09, 132.07, 131.82, 131.44, ...

Embodiment 2

[0039] The selectivity of compound Na-FA-Lyso formaldehyde fluorescent probe to different molecules or ions

[0040] Prepare 5 mL of PBS aqueous solutions of various conventional ions and amino acids with a concentration of 40 mM and the mother solution of the fluorescent probe for detecting formaldehyde of the present invention with a concentration of 1 mM as backup.

[0041] Add 25 μL of probe master solution, 225 μL DMSO and 500 equivalents of each ion (or amino acid) solution, dilute to 5 mL with phosphate buffered solution PBS, shake well and perform fluorescence detection (λ ex = 440 nm, λ em = 543 nm), and establish the curves of fluorescence intensity and each ion (or amino acid, active oxygen, active nitrogen) (results in image 3 ). After 30 min, the fluorescence emission spectrum of the solution was detected, which was determined by image 3 It can be found that other ions (or amino acids) have almost no effect on the fluorescence of the compound Na-FA-Lyso, wh...

Embodiment 3

[0043] Fluorescence titration detection of the compound Na-FA-Lyso formaldehyde fluorescent probe with different concentrations of formaldehyde

[0044] Prepare 10 mL of an aqueous solution with a concentration of 100 mM formaldehyde and a mother solution of a fluorescent probe for detecting formaldehyde of the present invention with a concentration of 1 mM as backup.

[0045] Prepare the probe at a concentration of 5 μM, interact with different concentrations of formaldehyde (0 – 100 μM), and perform fluorescence detection (λ ex = 440 nm, λ em = 543 nm), calculate the fluorescence intensity in each system, and establish the standard curve of fluorescence intensity and formaldehyde concentration. Such as Figure 4 As shown, as the concentration of formaldehyde increases, the fluorescence intensity of the reaction system increases gradually, and when the concentration of formaldehyde reaches 40 μM, the fluorescence intensity of the reaction system reaches a saturated state....

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Abstract

The invention discloses a fluorescent probe for detecting formaldehyde in a cytolysosome and a preparation method thereof. The chemical name of the fluorescent probe is 4-hydrazino-N-(2-morpholinyl ethyl)naphthalimide. The fluorescence intensity of the fluorescent probe is remarkably enhanced along with the increase of the formaldehyde content. The fluorescent probe is utilized to detect the content of formaldehyde in cells through a fluorescence imaging technology, particularly the content of formaldehyde in the cytolysosome, and can be used for evaluating and studying physiological functions of formaldehyde in the cells.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting formaldehyde in cell lysosomes and a preparation method thereof, belonging to the field of small organic molecule fluorescent probes. Background technique [0002] Formaldehyde is widely used in chemical engineering such as dyestuffs, wood processing, and textile industries, as well as in pharmaceuticals and food engineering. In addition, because formaldehyde has a good ability to bind to proteins and DNA, it is also a common antiseptic agent for cells, tissues and living organisms. However, the World Health Organization has evaluated formaldehyde as the third indoor chemical pollutant. Exposure to leaked formaldehyde can lead to a range of diseases such as Alzheimer's, cancer, stroke and miscarriage. Studies have shown that endogenous formaldehyde is mainly produced by histone demethylation and DNA methylation. In addition, methylamine compounds can also be metabolized to formaldehyde throug...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029C09K2211/1033G01N21/6486
Inventor 林伟英刘展榕徐安唐永和
Owner UNIV OF JINAN
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