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Anthracene fluorescent dye synthesis and application

A fluorescent dye, C1-C6 technology, used in anthracene dyes, organic dyes, luminescent materials, etc., can solve the problems of unstable intermediates, unfavorable large-scale synthesis and derivatization, and achieve high quantum yield, wide biological Application prospects, the effect of high absorption coefficient

Active Publication Date: 2016-02-10
CYGNUS BIOSCI BEIJING CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its synthesis involves transition metal catalysis involving special ligands and the generation of unstable intermediates, which is not conducive to large-scale synthesis and derivatization

Method used

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  • Anthracene fluorescent dye synthesis and application
  • Anthracene fluorescent dye synthesis and application
  • Anthracene fluorescent dye synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of anthracene-structured fluorescein "Beijing Orange":

[0039] In the general formula (1), R 1 = Me,R 0 = H, R 2-8，11-13 =H, the synthetic route is as follows

[0040]

[0041] Reagents and reaction conditions: i) THF, -40°C; ii) DCM, PCC, diatomaceous earth; iii) ZnMe 2 , TiCl 4 , DCM-40°C; iv) t-Buli, THF; o-tolualdehyde; v) DCM, PCC; vi) BBr 3 ;MeSO 3 h

[0042] 1. Synthesis of (2-bromo-5-methoxyphenyl)-3-methoxybenzyl alcohol 1a

[0043]

[0044] In a 250ml dry round bottom bottle equipped with a constant pressure dropping funnel, cool the 80ml dry tetrahydrofuran solution of m-methoxyphenylmagnesium chloride to -40°C, and dissolve 3-methoxy-o-bromobenzaldehyde under the protection of argon. (10.8g) of 20ml dry tetrahydrofuran solution was added dropwise into the reaction flask through a constant pressure dropping funnel, kept at -40°C and stirred for 2-6 hours, and the reaction was monitored by TLC. After the disappearance of the raw materi...

Embodiment 2

[0067] Synthesis of Fluorescent Producible Phosphatase Substrate Molecules with Anthracene Structure 2

[0068]

[0069] Add 300 mg of compound 1 to the dry reaction bottle, then add 15 mL of anhydrous dry dichloromethane, and stir. To this suspension was added the proton sponge and stirred for 10 minutes until the mixture was dissolved. Cool to -20~0°C, add 250uL phosphorus oxychloride dropwise, and keep the reaction at low temperature for 0.5~2h. Add 30 mL of sodium phosphate buffer and continue stirring for 1 hour. The resulting solution was separated, the aqueous phase was concentrated, and separated and purified by a C-18 reverse-phase chromatographic column. Separation conditions: AQC-18 preparative chromatographic column (Agela40g), 0-50% acetonitrile / TEAA buffer gradient elution, flow rate 20ml / min. The obtained fractions containing the target product were concentrated and kept refrigerated for future use. MS (ESI): Calcd for C 23 h 20 o 5 P(M-H), 407.1. Foun...

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Abstract

The invention provides a novel fluorescent dye structure and a synthesis method thereof. The anthracene structure fluorescent dye of the type has a high light absorption coefficient similar to that of fluorescein molecules, a high quantum yield and the like and meanwhile has more bathochromic-shift excitation wavelength and emission wavelength. The synthesis method is simple and economical and suitable for large-scale synthesis and group modification of a molecular structure. According to the anthracene fluorescent dye synthesis and application, phosphatase substrate molecules with a fluorescent generation property can be obtained through phosphorylation modification conducted on the molecules, and wide biological application prospect is achieved.

Description

technical field [0001] The invention relates to a class of novel fluorescent dyes with anthracene structure, which provides a synthetic method and changes in fluorescent properties brought about by phosphoric acid derivatization. technical background [0002] With the development of modern biotechnology, fluorescent dye compounds have been widely used as molecular functional probes in various fields such as life sciences and chemical biology, and have become favorable weapons for people to study molecular diagnostic techniques, immunoassays and detection. Among the many fluorescent dyes, there is a kind of dyes with a property, that is, after the dye itself is modified by a certain chemical group, the dye derivative changes its original fluorescent properties, usually manifested as a large increase in fluorescence efficiency. Decrease or disappear, and after such derivatives are used as substrates to participate in enzyme reactions or other types of reactions, their modifica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B1/00C09K11/06
Inventor 黄岩谊段海峰陈子天谢晓亮
Owner CYGNUS BIOSCI BEIJING CO LTD
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