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Soluble fluorescent cyanogen dye

A fluorescent cyanine and water-soluble technology, applied in the field of cyanine dyes, can solve problems such as poor photostability and affect analysis reliability, and achieve the effect of improving photostability

Inactive Publication Date: 2007-04-04
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cy3 TM , Cy5 TM and Cy7 TM Although the problems of water solubility and fluorescence are well solved, due to the existence of conjugated double bonds in its molecules, its photostability is poor, which affects the reliability of analysis.

Method used

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  • Soluble fluorescent cyanogen dye
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of (2,3,3-trimethyl-3H-indol-5-yl)acetic acid (5)

[0022]

[0023] i) In a 250ml three-necked flask equipped with a mechanical stirring device, add p-aminophenylacetic acid (7.55g, 0.05mol), 20ml concentrated hydrochloric acid, 25ml ice water, slowly add sodium nitrite (3.45g, 0.05mol) dropwise at 0°C ) in 18ml of ice-water solution, keep the temperature at 0°C for 0.5 hour, and quickly filter to remove a small amount of precipitate. A solution of stannous chloride dihydrate (33.84 g, 0.15 mol) in 35 ml of hydrochloric acid was added dropwise to the filtrate at 0°C, stirred for 0.5 h to stop the reaction, and frozen overnight. The next day, the reaction solution was filtered, and the filter cake was washed successively with a mixture of saturated sodium chloride solution, petroleum ether and diethyl ether (2:1) to obtain 6.5 g of a pink solid with a yield of 64%. The product was directly obtained without purification. for the next reaction.

[0024] ii) ...

Embodiment 2

[0026] Synthesis of 1-ethyl-(2,3,3)-trimethylindole iodide (6)

[0027]

[0028] In a 25ml three-necked flask equipped with a reflux condenser and a drying tube, add 2,3,3-trimethylindole (1.6g, 0.01mol) and ethyl iodide (8ml, 0.1mol) under argon protection, and heat Reflux for 24 hours, add 50ml of acetone after cooling, a solid precipitates, and filter to obtain 1.9g of a khaki solid, with a crude yield of 60%. Recrystallization from ethanol gave a brownish-yellow solid, Mp.229°C (lit.Mp.226-228°C). 1 HNMR (D 2 O): δ7.76-7.60 (m, 4H, 4-H, 5-H, 6-H, 7-H), δ4.50 (q, 2H, J=7.6Hz, 8-H), δ1. 55 (s, 6H, 11-H, 12-H), δ1.53 (t, 3H, J=7.6Hz, 9-H).

Embodiment 3

[0030] Synthesis of 1-(δ-sulfonic acid butyl)-5-carboxymethyl-2,3,3-trimethylindole betaine (7)

[0031]

[0032] In a 25ml three-necked flask equipped with a reflux condenser and a drying tube, add 5-carboxymethyl-2,3,3-trimethylindole (0.65g, 0.003mol), 1,4-butane Sultone (1.23g, 0.09mol) and 2ml of o-dichlorobenzene were heated to 110°C, kept at this temperature for 5 hours, cooled to 60°C after the reaction, added 10ml of acetone and refluxed for one hour, cooled and filtered to obtain a brown powder The solid was 0.9 g, and the crude yield was 85%. Purple crystals were obtained by recrystallization from methanol and isopropanol (1:1.5). Mp.264-267°C (lit.Mp.287-290°C). 1 HNMR (D 2 O): δ7.75(d, 1H, J=8.3Hz, 7-H), δ7.65(s, 1H, 4-H), δ7.51(d, 1H, J=8.3Hz, 6-H ), δ4.50(t, 2H, J=7.6Hz, 11-H), δ3.84(s, 2H, 15-H), δ2.96(t, 2H, J=7.6Hz, 8-H) , δ2.14-2.07 (m, 2H, 10-H), δ1.90-1.85 (m, 2H, 9-H), δ1.55 (s, 6H, 13-H, 14-H).

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Abstract

A soluble fluorescent dicyan dye is prepared by condensing compound (2) with compound (3), by squaric acid and inducing squaric acid bridged ring into linear conjugate polymethin chain. In the structural formula, X is S, CH2 or C(CH3)2; R1 and R2 are selected from any kind of C1-C6 alkyl or (CH2)kSO3H separately; k=1-6; R3 is H or C1-C6 alkyl; R4 is H or CH2COOH; n is 1,2 or 3. It has excellent light stability.

Description

technical field [0001] The invention relates to a cyanine dye, in particular to a water-soluble cyanine dye used for a fluorescent probe. Background technique [0002] In the post-genome era, what awaits scientists is to use modern detection and analysis methods to decipher the biological meaning of the huge genetic language hidden in organisms, which puts forward higher requirements for the accuracy of detection. Due to the radioactive contamination of traditional isotope biolabeling techniques, the application of fluorescent labeling techniques for modern biological analysis has developed rapidly. Especially in the past ten years, the introduction and rapid development of some new science and technology such as laser, microprocessor and electronics have greatly promoted the wide application of fluorescence analysis and accelerated the development of various new fluorescence analysis instruments. The advent of Fluorescence Analysis has continuously developed towards the di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/00
Inventor 钱旭红徐玉芳朱维平刘艳
Owner EAST CHINA UNIV OF SCI & TECH
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