Development of a Pillar[6]arene Carboxylic Acid Derivative for the Extraction of a Cationic Protein

IF 5.4 2区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Biomacromolecules Pub Date : 2025-03-10 Epub Date: 2025-02-17 DOI:10.1021/acs.biomac.4c01371

Yu Ikushima, Tatsuya Oshima

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Abstract

Pillararenes are macrocyclic compounds that can have multiple functional groups and can provide a platform to develop multivalent ligands. Herein, a pillar[6]arene carboxylic acid derivative (OctP[6]CH₂COOH) was prepared to extract the cationic protein cytochrome c (Cyt-c) into organic solvents. OctP[6]CH₂COOH was synthesized by the condensation of ethyl 2-(4-octoxyphenoxy) acetate to obtain the pillar[6]arene derivative, followed by alkali hydrolysis. OctP[6]CH₂COOH showed high extractability for Cyt-c, while a monomer analog and a neutral pillar[6]arene ester derivative did not. The lysine-rich protein Cyt-c was selectively extracted using OctP[6]CH₂COOH over other cationic proteins because the complexation was a result of the inclusion of the NH₃ ⁺ groups of the lysine residues by the macrocyclic molecule. Cyt-c complexed with OctP[6]CH₂COOH partially underwent a structural change and exhibited peroxidase activity in organic solvents. This is the first report of protein extraction using pillararene derivatives that can be applied for the separation and modification of proteins.

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柱状[6]芳烃羧酸衍生物萃取阳离子蛋白的研究。

柱芳烃是具有多个官能团的大环化合物，为开发多价配体提供了平台。本文制备了一种柱状[6]芳烃羧酸衍生物（OctP[6]CH2COOH），用于将阳离子蛋白细胞色素c （Cyt-c）萃取到有机溶剂中。采用2-（4-八氧苯氧基）乙酸乙酯缩合得到柱状[6]芳烃衍生物，再经碱水解合成OctP[6]CH2COOH。OctP b[6]CH2COOH对Cyt-c具有较高的可提取性，而单体类似物和中性柱[6]芳烃酯衍生物则没有。由于赖氨酸残基的NH3+基团被大环分子包涵，因此用OctP[6]CH2COOH选择性地提取了富含赖氨酸的蛋白Cyt-c。在有机溶剂中，Cyt-c与OctP[6]CH2COOH配合后发生了部分结构变化，并表现出过氧化物酶活性。这是首次报道利用柱芳烃衍生物提取蛋白质，并将其应用于蛋白质的分离和修饰。

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来源期刊

Biomacromolecules 化学-高分子科学

CiteScore

10.60

自引率

4.80%

发文量

417

审稿时长

1.6 months

期刊介绍： Biomacromolecules is a leading forum for the dissemination of cutting-edge research at the interface of polymer science and biology. Submissions to Biomacromolecules should contain strong elements of innovation in terms of macromolecular design, synthesis and characterization, or in the application of polymer materials to biology and medicine. Topics covered by Biomacromolecules include, but are not exclusively limited to: sustainable polymers, polymers based on natural and renewable resources, degradable polymers, polymer conjugates, polymeric drugs, polymers in biocatalysis, biomacromolecular assembly, biomimetic polymers, polymer-biomineral hybrids, biomimetic-polymer processing, polymer recycling, bioactive polymer surfaces, original polymer design for biomedical applications such as immunotherapy, drug delivery, gene delivery, antimicrobial applications, diagnostic imaging and biosensing, polymers in tissue engineering and regenerative medicine, polymeric scaffolds and hydrogels for cell culture and delivery.