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Near infrared meso-position nitrogen and sulfur substituted hepta-methyl-cyanine fluorochrome for bioanalysis

A technology of near-infrared and cyanine dyes, applied in the field of fluorescent dyes, which can solve the problems of decreased light stability, complex dye synthesis, separation and purification, small Stokes shift, etc., and achieve the effect of improving stability

Inactive Publication Date: 2005-11-30
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Second, it has been confirmed that the increase of methionine chain leads to the decrease of photostability
[0008] Second, the current polymethylcyanine dyes generally have a symmetrical structure and lack a single active site for fluorescent labeling reactions
But this method makes the synthesis and separation and purification of dyes complicated and difficult
[0009] Third, the spectral properties of cyanine dyes also have shortcomings: short fluorescence lifetime; low fluorescence quantum yield; self-polymerization often occurs in aqueous solution, etc.
On the other hand, measurement errors often occur in fluorescence detection because the wavelength of the excitation light source is too close to the emission detection wavelength.
Two recent literatures have mentioned that common polymethine dyes have the weakness of small Stokes shift

Method used

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  • Near infrared meso-position nitrogen and sulfur substituted hepta-methyl-cyanine fluorochrome for bioanalysis
  • Near infrared meso-position nitrogen and sulfur substituted hepta-methyl-cyanine fluorochrome for bioanalysis
  • Near infrared meso-position nitrogen and sulfur substituted hepta-methyl-cyanine fluorochrome for bioanalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Synthetic route of parent dye Ib containing chlorine bridged ring

[0059]

[0060] (1) Synthesis of intermediate 2,3,3-trimethyl-3H-indoline-5-potassium sulfonate

[0061] In a 1000ml three-neck flask, add 150ml of glacial acetic acid, 84ml (0.8mol) of 3-methyl-2-butanone and 50g (0.26mol) of p-hydrazinobenzenesulfonic acid in sequence. The mixture was heated to reflux for 3 hours, the reactant was poured into a beaker, and after standing to cool, a pink solid precipitated out. Filtration and vacuum drying gave 48 grams of 2,3,3-trimethyl-3H-indoline-5-sulfonate, 75% yield, R1=0.58, and the developer was n-butanol: acetic acid: water ( 2:1:5).

[0062] In a 250ml round bottom flask, add 50ml methanol, 50ml isopropanol, 48g (0.2mol) 2,3,3-trimethyl-3H-indoline-5-sulfonate and 12.3 grams (0.22mol) KOH successively . The mixture was heated to reflux, the pink color quickly receded, and a large amount of yellow solid precipitated out upon cooling. Filtration and va...

Embodiment 2

[0070] Synthesis and characterization of target dye IIa:

[0071]

[0072] The parent dye Ib was vacuum-dried at 50-60°C for 8 hours in advance, and the nucleophile aniline was purified by vacuum distillation in advance. The glassware used was pre-dried at 120°C for 3 hours, and the 50mL three-necked round-bottomed flask was cooled under a nitrogen atmosphere, and 100mg (0.12mmol) of the raw material dye Ib and 1.2mmol of the nucleophile and a magnetic stirrer were added. Under nitrogen atmosphere, about 15 mL of anhydrous DMF was added by syringe. The reaction mixture was kept at 100° C. and stirred for 2 hours under the protection of nitrogen. The reaction solution was poured into rapidly stirred 300mL ether, and a large amount of green solid precipitated. Filter the filtrate with a sand-cored funnel, dissolve the solid from the funnel with methanol, evaporate the methanol to dryness, and purify the crude dye with a reverse-phase packed column.

[0073] Dye IIa, 1 H N...

Embodiment 3

[0075] Synthesis and characterization of target dye IIb:

[0076]

[0077] The synthesis method is the same as in Example 2, wherein the nucleophilic reagent uses γ-aminobutyric acid, and the reaction temperature is 40°C.

[0078] Dye IIb, 1 H NMR (400MHz, DMSO-d6): δ0.86 (m, 2H, CH 2 ), 1.25 (m, 4H, CH 2 ), 1.63 (s, 12H, CH 3 ), 1.93 (m, 2H, CH 2 ), 2.29(t, 4H, CH 2 ), 5.20 (s, 4H, CH 2 ), 5.72(d, 2HJ=13.2Hz, CH), 7.00-7.02(d, 2H, CH), 7.25(m, 6H, CH), 7.34(m, 4H, CH), 7.53(m, 4H, CH ), 7.64 (s, 2H, CH). MS, m / z: 861.3 (M-).

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Abstract

The invention relates to a near-infrared new methenyl fluorescence dye, which is made by displacement at mid-position of methine colors by nucleophilic reagent containing nitrogen and sulfur. Mid-position nitrogen derivative replaces methine colors to generate ICT effect, Stokes displacement (70-170nm) and fine fluorescence. It can be used as high fidelity fluorescence labeling probe of biomolecules such as protein, sugar and DNA. When mid-position sulfer derivative replaces methine colours, PET phenomenon occurs in molecule.

Description

technical field [0001] The invention belongs to the fluorescent dye used in the technical field of biological fluorescence analysis. Background technique [0002] With the rapid development of biological science, fluorescence analysis technology has been applied more and more in gene sequencing, gene expression and clinical diagnosis. In medicine, enzyme-catalyzed immunoassay and fluorescence polarization immunoassay with fluorescence technology as the core have become the standard means of medical diagnosis. In cell biology, fluorescence spectroscopy is used to track the location and movement of components within cells. In addition, the identification and classification of cells also rely on flow cytometry with fluorescence technology as the core. The development of fluorescent dyes is the most decisive factor in the development of fluorescence analysis technology. Fluorescent dyes are used in biological analysis. The early landmark achievement was in the mid-1980s. DNA ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08
Inventor 彭孝军宋锋玲周伟舒凡
Owner DALIAN UNIV OF TECH
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