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Dual-photon methylglyoxal fluorescent probe and preparation method and application thereof

A methylglyoxal, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of large scattering interference, large probe background interference, low sensitivity and selectivity, etc. Achieve the effect of high yield, convenient purification and simple steps

Inactive Publication Date: 2018-08-17
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems of large background interference, large scattering interference, and low sensitivity and selectivity of existing probes, the present invention provides an MGO fluorescent probe with sensitive response, low detection limit, and good specificity with two-photon properties, which can deeply Layer penetration and avoid photobleaching and phototoxicity phenomena

Method used

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  • Dual-photon methylglyoxal fluorescent probe and preparation method and application thereof
  • Dual-photon methylglyoxal fluorescent probe and preparation method and application thereof
  • Dual-photon methylglyoxal fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Synthesis of Fluorescent Probes

[0038] (1) Synthesis of compound 4-bromo-N-(3-nitro-4-aminophenyl)naphthalimide (3):

[0039]

[0040] In a 100 mL round bottom flask, add 1 mmol of 4-bromo-1,8-naphthalic anhydride (1), 1 mmol of 2-nitro-1,4-phenylenediamine (2), and then add 10 mL of ethanol , heated to reflux for 5-6 h, cooled to room temperature, filtered under reduced pressure, the filter cake was washed 2-3 times with ethanol, and dried in vacuo to obtain light yellow solid 4-bromo-N-(3-nitro-4-aminobenzene base) naphthalimide (3). Yield: 91%. The product is directly carried out to the next step without purification;

[0041] (2) Synthesis of compound 4-n-butylamine-N-(3-nitro-4-aminophenyl)naphthalimide (5):

[0042]

[0043] Mix 0.2 mmol of compound 4-bromo-N-(3-nitro-4-aminophenyl)naphthalimide (3) with 1 mmol of n-butylamine (4), and heat in 20 mL of ethylene glycol monomethyl ether Reflux overnight, then cool to room temperature, filter u...

Embodiment 2

[0051] Example 2 Selectivity of Fluorescent Probes to Different Molecules or Ions

[0052] Prepare 5 mL of calcium chloride, magnesium chloride, sodium nitrate, sodium nitrite, sodium bisulfite, sodium sulfide, sodium sulfate, ferrous sulfate, potassium iodide, sodium bromide, sodium hypochlorite, hydrogen peroxide, tert-butyl Hydrogen peroxide, cysteine, homocysteine, glutathione, nitric oxide, glucose, 2,4-dinitrobenzene, sodium pyruvate, formaldehyde, acetaldehyde, chloral, The PBS mother solution of glyoxal and methylglyoxal and the fluorescent probe NB-MGO mother solution synthesized in Example 1 at a concentration of 1 mM were used for later use.

[0053] Add 25 μL probe mother solution, 225 μL DMSO and each ion (or amino acid) solution, and use phosphate buffer PBS to make the volume to 5 mL, the concentration of the test ion (or amino acid) is 2.5 mM, and the concentration of reactive oxygen and nitrogen is 100 mM, the concentration of aldehydes and ketones is 100 μM....

Embodiment 3

[0054] Example 3 Fluorescence titration detection of probe NB-MGO by different concentrations of methylglyoxal

[0055] Prepare 10 mL of an aqueous solution with a concentration of 100 mM methylglyoxal and a mother solution of the fluorescent probe NB-MGO synthesized in Example 1 with a concentration of 1 mM as backup.

[0056] Prepare the probe at a concentration of 5 μM, interact with different concentrations of methylglyoxal (0-200 μM), and perform fluorescence detection (λex = 440 nm, λem = 543 nm), such as Figure 4 Shown fluorescence titration result, along with the increase of methylglyoxal concentration, reaction system fluorescence intensity increases gradually, calculates fluorescence intensity in each system, establishes fluorescence intensity and methylglyoxal concentration standard curve ( Figure 5 ). Depend on Figure 5 It can be seen that as the concentration of methylglyoxal increases, the fluorescence intensity of the reaction system increases gradually. Wh...

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Abstract

The invention provides a methylglyoxal (MGO) fluorescent probe with a dual-photon property. The MGO fluorescent probe is sensitive in response, low in detection limit, good in specificity, capable ofachieving deep penetration and avoiding photo-bleaching and photo-poisoning, good in optical stability and specificity response and capable of detecting methylglyoxal in living tissue. The invention also provides a synthesizing method of the probe. The synthesizing method is simple in steps, convenient in purification and high in yield. The probe can be used for evaluating and researching the content of physiological function of methylglyoxal in cells through the fluorescent imaging technology, is especially applicable to the detection of methylglyoxal in the living tissue and has an application value in the researching and acquiring of the physiological function of the methylglyoxal in biological samples.

Description

technical field [0001] The invention relates to a two-photon methylglyoxal fluorescent probe and its preparation method and application, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Methylglyoxal (MGO) is a relatively simple active carbonyl compound that is relatively common in the body. Endogenous MGO mainly comes from the metabolic degradation of sugar, lipid and amino acid in the body. As a saccharification reagent, MGO can modify or transform proteins and DNA without being catalyzed by biological enzymes. However, when the concentration of MGO in the body increases, it often induces a series of diseases, such as cardiovascular disease, hyperalgesia, kidney disease, etc. Medical research shows that MGO is directly related to the occurrence and development of diabetes. According to reports, the concentration of MGO in the blood plasma of diabetic patients shows a state of substantial increase. Therefore, studying the...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 林伟英唐永和徐安
Owner UNIV OF JINAN
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