L-ribose specific recognition surface constructed by pillar[5]arene-based host-guest interaction

Wenhui Liu; Weiwei Xu; Hang-Hang Luan; Guang Li; Junan Liu; Zhiyan Lu; Fan Zhang; Haibing Li

doi:10.1016/j.bios.2023.115678

L-ribose specific recognition surface constructed by pillar[5]arene-based host-guest interaction

Biosens Bioelectron. 2023 Dec 1:241:115678. doi: 10.1016/j.bios.2023.115678. Epub 2023 Sep 7.

Authors

Wenhui Liu¹, Weiwei Xu², Hang-Hang Luan³, Guang Li², Junan Liu⁴, Zhiyan Lu⁵, Fan Zhang⁶, Haibing Li⁷

Affiliations

¹ College of Chemistry, Huazhong Agricultural University, Wuhan, Hubei, 430070, PR China.
² National Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, PR China.
³ Department of Forensic Medicine, Zhongnan Hospital of Wuhan University, No. 169 East Lake Road, Wuchang District, Wuhan, 430071, PR China.
⁴ College of Chemistry, Huazhong Agricultural University, Wuhan, Hubei, 430070, PR China. Electronic address: liujunan@126.com.
⁵ Department of Forensic Medicine, Zhongnan Hospital of Wuhan University, No. 169 East Lake Road, Wuchang District, Wuhan, 430071, PR China. Electronic address: luzhiyan@znhospital.cn.
⁶ Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Health Sciences and Engineering, Hubei University, Wuhan, 430062, PR China. Electronic address: fanzhang@hubu.edu.cn.
⁷ National Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, PR China. Electronic address: lhbing@mail.ccnu.edu.cn.

PMID: 37703641
DOI: 10.1016/j.bios.2023.115678

Abstract

In living organisms, chiral molecules have specific chiral conformations that produce different physiological effects. Ribose is one of the components of RNA, which mainly plays a role in regulating biological activity. Inspired by the biological recognition of sugars, functional chiral surfaces for recognizing L-ribose through non-covalent interactions were constructed. In the strategy of this study, a functional chiral gold surface based on host-guest interactions was constructed through the assembly of the host molecule single-function alynyl pillar[5]arene(SAP5) and the guest molecule (S) -mandelate-violet (SMV). The association constant of SMV and SAP5 was calculated to be 2.95×10⁴ M^-1, with a binding ratio of 1:1. By impedance and contact angle detection, the constructed functional interface has good detection effect on L-ribose in the range of 1×10^-7 M to1× 10^-2 M. In addition, CV was disassembled from the aromatic cavity of pillar[5]arene after adding zinc powder and it can repeat five times with good recyclability, thus achieving the organic combination of interface recognition and intelligence.

Keywords: Biomimetic technology; Chirality recognition; Host-guest interaction; L-ribose; Single-function alynyl pillar[5]arene.