Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pKa shift, increased solubility and enhanced antibacterial activity

Guchuan Ping; Yiliang Wang; Lingyun Shen; Yuting Wang; Xiaoshi Hu; Junyi Chen; Bingwen Hu; Lei Cui; Qingbin Meng; Chunju Li

doi:10.1039/C7CC02799K

Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pK_a shift, increased solubility and enhanced antibacterial activity†

Guchuan Ping,‡^a Yiliang Wang,‡^a Lingyun Shen,^a Yuting Wang,^a Xiaoshi Hu,^b Junyi Chen,^ac Bingwen Hu,

^b Lei Cui,*^a Qingbin Meng^c and Chunju Li

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai 200444, P. R. China
E-mail: cuilei@shu.edu.cn, cjli@shu.edu.cn

^b School of Physics and Materials Science, Shanghai Key Laboratory of Magnetic Resonance, East China Normal University, Shanghai 200062, P. R. China

^c State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, P. R. China

Abstract

Encapsulation of a physiologically active substance, sanguinarine (SA), by a water soluble carboxylatopillar[6]arene (CP6A), is described. The efficient complexation by CP6A, giving a K_a value of (2.4 ± 0.3) × 10⁵ M⁻¹ in pH 7.4, served to increase the water solubility by 4.3-fold, cause a 2.02 shift in pK_a, and enhance the antibacterial activity of SA.

This article is part of the themed collection: 2017 Emerging Investigators

Chemical Communications

Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pK_a shift, increased solubility and enhanced antibacterial activity†

Abstract

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Chemical Communications

Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pKa shift, increased solubility and enhanced antibacterial activity†

Abstract

Supplementary files

Article information

Download Citation

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Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pKa shift, increased solubility and enhanced antibacterial activity

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Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pK_a shift, increased solubility and enhanced antibacterial activity†

Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pK_a shift, increased solubility and enhanced antibacterial activity