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Fluorescent probe for detecting formaldehyde-targeted mitochondria as well as preparation method and application thereof

A fluorescent probe, mitochondrial technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of unclear content fluctuation, achieve excellent performance and reduce light damage.

Inactive Publication Date: 2018-07-13
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the impact of formaldehyde content fluctuations in the human body, especially in the mitochondria, on human physiology and pathology is still not clear enough.

Method used

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  • Fluorescent probe for detecting formaldehyde-targeted mitochondria as well as preparation method and application thereof
  • Fluorescent probe for detecting formaldehyde-targeted mitochondria as well as preparation method and application thereof
  • Fluorescent probe for detecting formaldehyde-targeted mitochondria as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Synthesis of Fluorescent Probes

[0040] (1) Synthesis of compound 3-aminopropyltriphenylphosphonium: In a 100 mL round bottom flask, add 5 mmol of 3-bromopropylamine and 6 mmol of triphenylphosphine, then add 30 mL of acetonitrile, and heat under reflux for 24 h , cooled to room temperature, evaporated to dryness under reduced pressure, separated by silica gel column (DCM:CH 3 OH=10:1), dried in vacuo to obtain 3-aminopropyltriphenylphosphonium (1) as a white solid. Yield: 60%. 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.97 – 7.76 (m, 15H), 3.83 – 3.68 (m, 2H), 2.99 (t, J = 6 Hz, 2H), 1.84 (m, 2H); 13 C NMR (101 MHz, DMSO- d 6 ) δ 135.59, 135.56, 134.15, 134.04, 130.91, 130.79, 118.96, 118.11, 20.58, 19.11, 18.58.

[0041] (2) Synthesis of compound N-(2-formylethyl)-4-bromo-1,8-naphthalimide: In a 100 mL round bottom flask, compound 4-bromo-1,8 -5 mmol of naphthalic anhydride was added to the β - Reflux and stir in the ethanol solution of aminopropionic acid...

Embodiment 2

[0044] Example 2 Changes in the fluorescence intensity of Na-FA-Mito under different concentrations of formaldehyde

[0045] Prepare 10 mL of aqueous solutions of 100 mM, 10 mM, 1 mM, and 0.1 mM formaldehyde and the fluorescent probe mother solution prepared in Example 1 at a concentration of 1 mM as spares.

[0046] The PBS buffer solution (pH=7.4, 5% DMSO) with a probe concentration of 5 μM was added to interact with different concentrations of formaldehyde (0 – 250 μM), and the fluorescence spectrum was tested after one hour of action, (λex = 440 nm , λem =450-700 nm), detect the fluorescence intensity in each system, and use the fluorescence intensity-formaldehyde concentration to draw a curve, such as Figure 4 As shown in the middle and large picture, the curve is drawn from the 539nm fluorescence intensity-formaldehyde concentration, such as Figure 4 As shown in the middle and small panels: As the concentration of formaldehyde increases, the fluorescence intensity of ...

Embodiment 3

[0047] Example 3 Changes in the fluorescence intensity of Na-FA-Mito under different reaction times

[0048] Prepare 10 mL of an aqueous solution with a concentration of 100 mM formaldehyde and the fluorescent probe mother solution prepared in Example 1 with a concentration of 1 mM as spares.

[0049] Add 150 μM formaldehyde or an equivalent amount of PBS buffer solution (pH=7.4, 5% DMSO) with a probe concentration of 5 μM, test once every 2 min, and test for 1 h. The excitation wavelength is 440 nm, whichever is the maximum Emission peak position λ em The fluorescence intensity at =539nm draws its kinetic curve with time, such as Figure 5 As shown, the fluorescence intensity of the probe did not change significantly when irradiated in PBS buffer solution (pH=7.4, 5% DMSO) for 1 h; however, the kinetic experiment of the probe with formaldehyde (150 μM) showed that the fluorescence intensity was about It tends to saturation at 40 min.

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Abstract

The invention provides a fluorescent probe Na-FA-Mito. The fluorescent probe has the advantages that the reaction is sensitive, the detection limit is low, and the specificity is good; the fluorescentprobe can be used for detecting formaldehyde-targeted mitochondria. The chemical name of the fluorescent probe is brominated N-(2-formamido ethyl-N-(3-triphenyl phosphine propyl))-4-hydrazino-1,8-naphthalimide salt. The fluorescent probe is used for detecting the formaldehyde in solutions or cells.

Description

technical field [0001] The invention relates to a mitochondrial-targeted fluorescent probe for detecting formaldehyde, a preparation method and application thereof, and belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Formaldehyde is a common industrial raw material, which is widely used in chemical industry, wood processing, textile industry and other fields, and most of the formaldehyde pollution in the environment comes from human production emissions. Relevant statistics show that the risk of cancer among practitioners who are more exposed to formaldehyde is significantly higher than that of ordinary people. In 2017, formaldehyde was listed as a first-class carcinogen in the list of carcinogens compiled by the WHO. In addition to its mutagenic risk, excessive direct contact with formaldehyde can also have a strong irritating effect on the eyes, skin, and respiratory tract, which in turn can cause eye allergies, skin inflamm...

Claims

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Application Information

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IPC IPC(8): C07F9/576C09K11/06G01N21/64
CPCC07F9/5765C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 林伟英唐永和徐安
Owner UNIV OF JINAN
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