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A large stokes-shifted fluorescent probe for NO detection and its synthesis method

A fluorescent probe, nitrogen protection technology, applied in the field of biological detection, can solve the problems affecting measurement accuracy, overlapping absorption spectrum and emission spectrum, large radiation energy, etc., to avoid scattered light interference, easy to popularize and apply, and light stability Good results

Inactive Publication Date: 2016-02-10
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the excitation and emission of existing BODIPY fluorescent probes are mostly in the visible light spectral region (500-550nm), and the Stokes shift of the probes is generally only about 10nm
In the visible spectral region, biological samples have strong background fluorescence and self-absorption, which will interfere with detection and imaging and affect the accuracy of measurement
At the same time, the wavelength of visible light is short, and the radiation energy in fluorescence imaging is relatively large, which is easy to cause photodamage to cells and biological tissues
In addition, the Stokes shift of the probe is too small, which will lead to a large overlap of its absorption and emission spectra, resulting in self-absorption and scattered light interference

Method used

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  • A large stokes-shifted fluorescent probe for NO detection and its synthesis method
  • A large stokes-shifted fluorescent probe for NO detection and its synthesis method
  • A large stokes-shifted fluorescent probe for NO detection and its synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1p-MOPB Synthesis.

[0025] 400mg of 3,4-dinitrobenzoyl chloride (1.73mmol) was dissolved in 100mL of 1,2-dichloroethane, and 600mg of 2-(4-methoxyphenyl)-1hydro-pyrrole (3.47 mmol) in 20mL of 1,2-dichloroethane solution, the mixed solution was heated to reflux for 48h. After cooling to room temperature, 0.72 mL of triethylamine (5.19 mmol) was added, stirred at room temperature for 10 min, then 1.1 mL of boron trifluoride ether (8.71 mmol) was added, and heated to reflux for 30 min under nitrogen protection. The organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane / ethyl acetate=2 / 1 / 0.3) to obtain a blue solid 4,4-difluoro- 362 mg of 8-(3',4'-dinitrophenyl)-3,5-bis(4-methoxyphenyl)-dipyrromethane (36.7% yield). 1 HNMR(600MHz,DMSO)δ8.55(s,1H),8.42(d,J=8.2Hz,1H),8.25(dd,J=8.2,1.7Hz,1H),7.91(d,J=8.8Hz, 4H), 7.07(t, J=6.9Hz, 6H), 6.94(d, J=4.4Hz, 2H), 3...

Embodiment 2

[0027] Example 2 Fluorescence properties of p-MOPB.

[0028] The fluorescence spectra of p-MOPB and its NO-derived products are shown in figure 2 As shown, due to the light-induced electron transfer mechanism, the fluorescence of the fluorophore is suppressed, and the fluorescent probe itself has almost no fluorescence; when it reacts with NO to form triazole, there is a significant fluorescence enhancement, and its excitation / emission wavelength is 582 / 620nm, The Stokes shift is 38nm. Depend on image 3 It can be seen that under the continuous irradiation of a 120W mercury lamp, the fluorescence intensity of the NO derivative product of the probe decreased by 1.0% for 3h, but remained above 95.9% within 10h. Studies have shown that the probe has good enough photostability, can withstand strong light irradiation for a long time and meet the needs of fluorescence imaging of biological samples.

Embodiment 3

[0029] Example 3 p-MOPB pre-column derivatization HPLC separation and fluorescence detection of NO in mouse whole blood samples.

[0030]Using p-MOPB as a pre-column derivatized fluorescent probe, an analytical method for NO content in whole blood and cerebral cortex of mice was established by HPLC separation and fluorescence detection. Fluorescent probe p-MOPB can react completely with NO in pH9.0 phosphate buffer solution at 30°C for 9 minutes. In Kromasil C 18 On the chromatographic column, the mobile phase is methanol:buffer solution=90:10 (v / v, buffer solution: 0.1M, pH4.5H 3 Cit-NaOH), 4min separation. Linear range is 5.0×10 -9 M–1.0×10 -6 M; when the signal-to-noise ratio S / N=3, the limit of detection (LOD) reached 0.3nM; the recovery rate of the method was between 96.5-98.7%, and the R.S.D. (n=6) was 1.92-3.17%. This method has the advantages of high sensitivity, simple separation system, short separation time, and fast derivatization speed. It can effectively eli...

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Abstract

The invention discloses a fluorescent probe used for detecting nitric oxide and a preparation method thereof, and belongs to the technical field of biological detection. The probe is 4,4-difluoro-8-(3',4'-diamido phenyl)-3,5-bi(4-methoxyphenyl)-dipyrrylmethane (p-MOPB). The probe has the characteristics that red fluorescence (620nm) is brought, large Strokes displacement (38nm) is generated, the light stability is high, and the interference from the fluorescence and scattered light generated by a biological sample can be avoided during analyzing and detecting. The fluorescent probe can be applied to quantitative analysis and fluorescent imaging of NO in chemical samples, biological samples, medical samples and other samples.

Description

technical field [0001] The invention relates to a large Stokes shift fluorescent probe for NO detection and a preparation method thereof, belonging to the technical field of biological detection. Background technique [0002] As the core and source of active oxygen free radicals and active nitrogen free radicals, NO is widely involved in the physiological and pathological processes of animals and plants. As a vasodilation factor, NO promotes vasodilation and lowers blood pressure; as a messenger molecule, it is involved in the transmission of nerve signals, and has the ability to strengthen memory and enhance learning. At the same time, NO is also involved in immune protection, regulation of inflammation and inhibition of tumor cell proliferation. For plants, NO breaks seed dormancy, promotes root development, induces leaf growth, delays fruit ripening, etc., and is also involved in biotic or abiotic stress responses such as drought, mechanical damage, and resistance to pes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
Inventor 王红张华山陈建波郭小峰
Owner WUHAN UNIV
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