Redox induced pH-responsive type methacrylate fluorine-containing monomer as well as synthetic method and application thereof

Abstract

The invention relates to a synthetic method and application of a redox induced pH-responsive type methacrylate fluorine-containing monomer. The general formula is shown in the specification, wherein a, b, c and d are respectively independent integers. The synthetic method comprises the following steps: with organic alkali as an acid-binding agent, enabling a methacrylate monomer containing a primary amine end group to react with 2,4-dinitrobenzene sulfonyl chloride in anhydrous tetrahydrofuran so as to obtain a sulfamide monomer; and with diethyl azodicarboxylate and triphenylphosphine as catalysts, enabling the sulfamide monomer to have a Mitsunobu reaction with a fluorine alcohol monomer, separating and purifying, and assembling in an aqueous solution. A strong electron withdrawing group2,4-dinitro-benzsulfamide exists in the structure disclosed by the invention and can rapidly have a nucleophilic substitution reaction with mercapto group so as to produce a secondary amine group, and the secondary amine group is protonized under corresponding pKa, so that redox induced pH response is realized. Development of fluorine-containing small molecules is facilitated, and the developmentneed of a 19FMRI probe is met. The synthetic method disclosed by the invention is simple, and the monomer is stable in quality and high in yield. The structural formula is as shown in the specification.

Description

technical field [0001] The invention relates to a redox-induced pH-responsive methacrylate fluorine-containing monomer, a synthesis method and an application. Background technique [0002] 19 F nucleus is a substance that is beneficial to nuclear magnetic resonance (NMR). Because it has almost no endogenous background interference in the body, it has been used in recent years 19 The related research of F elements in magnetic resonance imaging (MRI) has received more and more attention. Based on water molecules ( 1 H proton) nuclear magnetic resonance imaging, although it has high sensitivity, but due to the background signal interference of a large amount of water-containing substances in biological tissues, its imaging effect for specific positions is poor. In contrast, 19 F has almost no endogenous background interference in the organism, and only a very small amount of fluorine exists in human bones and teeth in solid form, so T2 very short, well below 19 Detection ...

AI Technical Summary

Problems solved by technology

Because the fluorine-containing organic ligands are directly grafted into the polymer or liposome molecular structure through chemical bonds, and then form nano-probes, which contributes to the improvement of material stability and toxicity, but due to the reduction of fluorine atoms degrees of freedom, so the T2 of the grafted material will be shortened, the peak width of the fluorine signal will increase, and the imaging signal-to-noise ratio will decrease

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