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Ultraviolet-excited fluorescent dye and application thereof

A technology for exciting fluorescence and ultraviolet light, which is applied in the field of fluorescent dyes, can solve the problems of reduced fluorescence quantum yield, reduced sensitivity, and increased dye dosage, and achieves the effects of stable solubility, increased solubility, and reduced negative charge

Active Publication Date: 2020-07-10
BIOTIUM BIOLOGICAL SCI & TECH SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, many known dyes will be quenched in aqueous solution, resulting in a decrease in fluorescence quantum yield, which will lead to a decrease in detection sensitivity or the need to increase the amount of dye used.

Method used

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  • Ultraviolet-excited fluorescent dye and application thereof
  • Ultraviolet-excited fluorescent dye and application thereof
  • Ultraviolet-excited fluorescent dye and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0098] Preparation of "dye-conjugates"

[0099] A method for coupling an ultraviolet light-excited fluorescent dye of the present invention to a carrier molecule or a solid support, comprising the steps of:

[0100] (1) contacting the carrier molecule or solid support with the dye to form a combined sample;

[0101] (2) incubating the combined sample for a certain period of time to form a covalent bond between the compound of the general formula I and the carrier molecule or solid support to obtain a mixture of dye-conjugates;

[0102] (3) Separating the compound not connected to the carrier molecule or the solid support from the compound connected to the carrier molecule or the solid support in the dye-conjugate mixture to obtain the dye-conjugate.

[0103] Conjugates of dyes and carrier molecules or solid supports, for example: drugs, polypeptides, toxins, nucleic acids, phospholipids and other organic substances prepared by organic synthesis methods and reactive dyes of th...

Embodiment 1

[0123] Embodiment 1: the preparation of compound 5:

[0124] (1) Synthesis of compound 1:

[0125]

[0126] According to the synthesis method of compound 6 in US2012004397, compound 1 was prepared.

[0127] Compound 1 was subjected to nuclear magnetic resonance (NMR) characterization, and the characterization results were as follows:

[0128] Compound 1: 1 H NMR: 1.1(t,3H),1.3-3(m,8H),4-5(m,4H),7.03(d,2H),7.1(S,1H),7.66(d,2H),7.9 -8.8(m,4H)

[0129] (2) Synthesis of compound 2:

[0130]

[0131] 1g of compound 1 (2.63mmol) was suspended in 10ml of concentrated hydrochloric acid, and reacted overnight at 65°C. The reaction was followed by TLC. After the reaction, the hydrochloric acid and water were removed by rotary evaporation, and it could be used in the next reaction without drying. A small amount was subjected to column chromatography and the resulting solid product, compound 2, was sucked dry.

[0132] Compound 2 was characterized by NMR, and the characterizat...

Embodiment 2

[0150] Preparation of compound 6A:

[0151]

[0152] 1 g of compound 5 (0.64 mmol) was dissolved in 20 ml of anhydrous DMA, 0.16 g of DSC and 6.2 mg of DMAP were added to the reaction solution, and the suspension was stirred at room temperature for 2 days. After the reaction was over, the solvent was concentrated to 3ml under reduced pressure, 300ml ethyl acetate was added and stirred for 0.5h, the solid was collected, filtered and washed with ethyl acetate to obtain compound 6.

[0153] Compound 6A was subjected to NMR characterization, and the characterization results were as follows:

[0154] Compound 6A: 1 H NMR: 1.3-2.5(m,20H),3-5(m,99H),7.5(d,1H),7.1(S,1H),8.1(d,1H),8.3(s,1H),7.9 -8.8(m,4H)

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Abstract

The invention discloses an ultraviolet-excited fluorescent dye and application thereof, and particularly relates to a compound shown as a general formula (I), a dye-conjugate and application of the dye-conjugate in antibody detection, wherein groups in the general formula (I) are as shown in the specification. The fluorescent dye provided by the invention has active groups and water-soluble polymer groups at the same time, can be excited by 405nm laser, has very good water solubility, significantly reduces the influence on biological activity and has a relatively high fluorescence signal effect in a relatively short wavelength.

Description

technical field [0001] The present invention relates to fluorescent dyes, in particular to ultraviolet light-excited fluorescent dyes and their applications, especially their applications in neuropathology, immunology, pathology and proteomics. Background technique [0002] With the development of new microscopy techniques and the emergence of various synthetic and natural fluorescent molecules, fluorescence microscopy has become a fundamental tool in cell biology. Fluorescently labeled target molecules or organelles can be used to study cell structure and function. Fluorescent dyes can be used as tracers to localize biological structures using fluorescence microscopy, quantify analytes using fluorescent immunoassays, analyze cells using flow cytometry, determine the physical state of cells, and other applications. Compared with other types of absorbing dyes, fluorescent dyes usually have high sensitivity, and their absorption wavelength is different from the emission wavel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B69/10C09K11/06G01N33/53
CPCC09B69/109C09K11/06G01N33/56972C09K2211/1466C09K2211/1483C09K2211/1475Y02A50/30
Inventor 王晓飞毛飞
Owner BIOTIUM BIOLOGICAL SCI & TECH SHANGHAI
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