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Organic double-state fluorescent molecular probe for viscosity detection as well as preparation method and application of organic double-state fluorescent molecular probe

A fluorescent molecular probe and viscosity technology, applied in organic chemistry, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve problems such as life-threatening patients and thrombosis in tumor patients, achieve good sensitivity, reduce background fluorescence interference and light damage effect

Pending Publication Date: 2022-04-26
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

High viscosity can easily lead to thrombus in tumor patients, directly endangering the lives of patients

Method used

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  • Organic double-state fluorescent molecular probe for viscosity detection as well as preparation method and application of organic double-state fluorescent molecular probe
  • Organic double-state fluorescent molecular probe for viscosity detection as well as preparation method and application of organic double-state fluorescent molecular probe
  • Organic double-state fluorescent molecular probe for viscosity detection as well as preparation method and application of organic double-state fluorescent molecular probe

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Experimental program
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Effect test

Embodiment 1

[0023] The present invention designs and synthesizes the indole squaraine fluorescent molecular probe (Z)-2-((4-(anthracene-1-yl)-2-(methoxycarbonyl)phenyl)amino)- 3-Oxo-4-((1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene)cyclobutene-1-alkoxylate (SQ-1) , its chemical structure is:

[0024]

[0025] Probe preparation method comprises the following steps, synthetic route such as figure 1 Shown:

[0026] (1) Pour 2-amino-5-bromobenzoic acid methyl ester and phenylboronic acid pinacol ester (molar ratio 1:1) into the flask, add tetrakis (triphenylphosphine) palladium, cesium carbonate, di Oxyhexane and water were heated and reacted for 12h under the protection of nitrogen. After the reaction was completed and cooled to room temperature, 1-bromoanthracene was added, and the reaction was heated for 12 h under nitrogen protection to obtain methyl 2-amino-5-(anthracene-1-yl)benzoate (1-an).

[0027] (2) 3-hydroxyl-4-((1,3,3-trimethylindol-2-ylidene) methyl)-3-cyclobutene-1,2-dio...

Embodiment 2

[0030] From figure 2 and image 3 It can be clearly seen that the ultraviolet-visible absorption spectrum (450-600nm) and fluorescence emission spectrum (525-675nm) of SQ-1 in different polar solvent conditions present a mirror-image symmetrical relationship, accompanied by obvious double peaks. Among them, the maximum absorption peak is located at 530-550nm, and the maximum emission peak is concentrated at 550-570nm. And with the increase of solvent polarity from n-hexane, dichloromethane, tetrahydrofuran to dimethyl sulfoxide, the positions of SQ-1's ultraviolet absorption and fluorescence emission peaks gradually shifted red, which may be caused by the charge transfer effect. Because the twisted conformation in SQ-1 can well suppress the π-π stacking interaction between conjugated molecules, reduce the loss of non-radiative energy, and exhibit a larger Stokes shift and a higher quantum yield.

[0031] In order to study the emission behavior of SQ-1 in the aggregated stat...

Embodiment 3

[0033] The luminescent behavior of SQ-1 was further explored in glycerol / methanol solvents with different proportions ( Figure 6), SQ-1 is a typical molecular rotor structure, showing different fluorescence responses to environmental changes with different viscosities. With the increasing proportion of glycerol, the short peak of SQ-1 at 400-530nm gradually weakened, and the long peak at 530-650nm gradually strengthened. The correlation curve of fluorescence intensity (570nm) and viscosity is as follows Figure 7 As shown, in the viscosity range of 3.4-627.5cP, the logarithm of the fluorescence intensity is linearly positively correlated with the logarithm of the viscosity, and the viscosity value can be detected accordingly. The probe is thus capable of quantitatively detecting changes in viscosity with high sensitivity.

[0034] In view of the differences in the fluorescence properties of SQ-1 under different viscosities, the corresponding CIE chromaticity coordinate diag...

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Abstract

The invention discloses an organic double-state fluorescent molecular probe for viscosity detection as well as a preparation method and application of the organic double-state fluorescent molecular probe, and relates to the field of small-molecule fluorescent probes. According to the method, the indolyl squarylium cyanine fluorescent molecular probe (Z)-2-((4-(anthracene-1-yl)-2-(methoxycarbonyl) phenyl) amino)-3-oxo-4-((1, 3, 3-trimethyl-3H-indole-1-onium-2-yl) methylene) cyclobutene-1-alkyd salt is designed and synthesized through an epitaxial anthryl group. The molecular probe shows different fluorescence response / color development in environmental changes of different viscosities, can realize rapid quantitative determination / visual monitoring of viscosities in different solution systems, is convenient and rapid, and is suitable for preparing a kit / test strip for detecting the viscosities. And the molecular probe can realize double-state luminescence, shows bright red fluorescence in a dilute solution state and an aggregation state, has excellent sensitivity, stably emits light without quenching, and is also suitable for biological imaging.

Description

technical field [0001] The invention relates to the field of small molecule fluorescent probes, in particular to an organic two-state fluorescent molecular probe used for viscosity detection and its preparation method and application. Background technique [0002] Viscosity levels in biological environments play a vital role in overall living systems. Studies have found that abnormal viscosity is related to many diseases, such as atherosclerosis, diabetes, Alzheimer's disease, malignant tumors, etc. High viscosity can easily lead to thrombus in tumor patients, directly endangering the lives of patients. Therefore, there is an urgent need to develop tools for effective detection of viscosity, which can be used to detect and diagnose diseases in time, which plays an important role in promoting disease prevention and clinical diagnosis. [0003] As the advantages of organic two-state fluorescent materials are gradually highlighted in practical applications, many organic two-s...

Claims

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Application Information

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IPC IPC(8): C07D209/14C09K11/06G01N11/00G01N21/64
CPCC07D209/14C09K11/06G01N11/00G01N21/6456C09K2211/1029C09K2211/1007C09K2211/1011G01N2011/008
Inventor 迟宝珠刘姝怡骆晓琳许延王红明
Owner NANCHANG UNIV
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