Near infrared boron fluoride complexed dipyrrolyl methine fluorescent dye for biological analysis

Abstract

The new type of styryl radical substituted boron fluoride complexed dipyrrolyl methane fluorescent dyes are prepared through complexing boron fluoride and dipyrrolyl methane fluorescent dye and further reaction with benzaldehyde compound. Partial single styryl radical substituted dyes have absorption spectrum and emission spectrum in near infrared region, while all double styryl radical substituted dyes have absorption spectrum and emission spectrum in near infrared region. When the dye structure has amino radical, it will produce ICT under the excitation of light to raise fluorescent quantum efficiency rapidly. Therefore, the present invention may be used as pH probe in testing pH value and in designing high sensitivity ion probe and sugar probe.

Description

Technical field [0001] The invention belongs to a fluorescent dye used in the technical field of biological fluorescence analysis. Background technique [0002] Fluorescence analysis technology is currently one of the most important biological analysis and detection methods. It has been widely and in-depth applications in DNA sequencing, drug metabolism analysis, and determination of intracellular tissue components. Fluorescent dyes are an important part of the fluorescence analysis system. Its properties will affect or even determine the sensitivity and practical value of the entire fluorescence detection. Even if different fluorescent dyes are used in the analysis of the same substance, their detection results may have greater results. The difference, which mainly depends on the physicochemical properties of the fluorescent dye itself. A fluorescent dye with excellent performance and suitable for fluorescence analysis applications usually has the following main characteristics:...

AI Technical Summary

Problems solved by technology

However, the currently developed near-infrared cyanine dyes still have fatal shortcomings: poor photostability, short fluorescence lifetime, low fluorescence quantum yield, frequent accumulation in solution, etc.

[0010] Kevin Burgess et al. introduced phenyl and naphthyl at the 3-position and 5-position of the boron fluoride-complexed dipyrromethene fluorescent dye parent to red-shift the spectral wavelength of the dye, but the degree of red-shift is not ideal, generally red shifted around 50nm [BurghartA., Kim H., Welch M.B., Thoresen L. H., Reibenspies J. and K. Burgess, 3, 5-Diaryl-4, 4-difluoro-4-bora-3a, 4a-diaza-s- indacene (BODIPY) Dyes: Synthesis, Spectroscopic, Electrochemical, and Structural Properties.J.Org.Chem.1999, 64, 7813-7819], which shows that phenyl and naphthyl are not well conjugated with the dye parent, and There is a certain angle, and the crystal structure of the naphthyl-substituted dye also proves this

In order to enhance the rigidity of dye molecules, Kevin Burgess et al. designed the reaction of conjugated heterocyclic pyrrole and acid chloride to generate new dyes [Chen, J.; Burghart, A.; Derecskei-Kovacs, A. and Burgess, K., 4, 4-Difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations.J.Org.Chem.2000, 65, 2900-2906.], the result is the spectrum The red shift is nearly 120nm, and the improvement of molecular planarity promotes the occurrence of this spectral red shift, but the quantum yield is not high and remains below 0.4

Erick M. Carreira et al. still used conjugated heterocyclic pyrrole as the reaction substrate, and introduced two benzene rings at the 1 and 7 positions of the parent dye, and synthesized an aza-boron fluoride complexed dipyrromethene fluorescent dye [Zhao, W. and Carreira, E.M. Conformationally Restricted Aza-Bodipy: A Highly Fluorescent, Stable, Near-Infrared-Absorbing Dye. Angew. Chem. Int. Ed. 2005, 44, 1677-1679.], the absorption spectrum reached 740nm , unfortunately the quantum yield is lower than 0.3, and the synthesis steps are very cumbersome

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