Nucleotide Recognition by a Guanidinocalixarene Receptor in Aqueous Solution

doi:10.1007/s40242-022-2204-9

高等学校化学研究 ›› 2023, Vol. 39 ›› Issue (1): 144-150.doi: 10.1007/s40242-022-2204-9

Nucleotide Recognition by a Guanidinocalixarene Receptor in Aqueous Solution

GENG Wenchao¹, ZHENG Zhe², JIANG Huifeng¹, GUO Dongsheng²

1. Key Laboratory of Systems Microbial Biotechnology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, P. R. China;
2. College of Chemistry, Key Laboratory of Functional Polymer Materials of Ministry of Education, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. China

收稿日期:2022-06-16 出版日期:2023-02-01 发布日期:2023-02-02
通讯作者: GUO Dongsheng E-mail:dshguo@nankai.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (Nos.U20A20259, 31961143004) and the Nankai University & Cangzhou Bohai New Area Institute of Green Chemical Engineering Fund, China (No.NCC2020FH04).

Nucleotide Recognition by a Guanidinocalixarene Receptor in Aqueous Solution

GENG Wenchao¹, ZHENG Zhe², JIANG Huifeng¹, GUO Dongsheng²

1. Key Laboratory of Systems Microbial Biotechnology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, P. R. China;
2. College of Chemistry, Key Laboratory of Functional Polymer Materials of Ministry of Education, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. China

Received:2022-06-16 Online:2023-02-01 Published:2023-02-02
Contact: GUO Dongsheng E-mail:dshguo@nankai.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (Nos.U20A20259, 31961143004) and the Nankai University & Cangzhou Bohai New Area Institute of Green Chemical Engineering Fund, China (No.NCC2020FH04).

摘要/Abstract

摘要： Nucleotides participate in various physiological processes through their supramolecular interactions with biomolecules. Therefore, the molecular recognition of nucleotides became an important topic in supramolecular chemistry and exhibited many biomedical applications. Guanidinocalixarenes showed very strong binding affinities towards nucleotides, even reaching the nanomolar level. In this work, we systematically determined the binding constants between a typical guanidinocalixarene(guanidinium-modified calix[5]arene, GC5A) and various nucleotides and revealed the driving forces behind the molecular recognition using theoretical calculations. The electrostatic interactions and hydrogen bonding provided by the phosphate groups of the nucleotides dominated the binding between the nucleotides and GC5A. The lower rim alkyl chains and the skeleton of GC5A provide preorganized cavity and upper guanidinium groups. The difference in the type of nucleobase is also attributed to the different binding affinities. This work provides insight into the molecular recognition of nucleotides and facilitates the development of new supramolecular hosts for nucleotides and related biological applications.

关键词: Calixarene, Nucleotide, Molecular recognition, Indicator displacement assay, Theoretical calculation

Abstract: Nucleotides participate in various physiological processes through their supramolecular interactions with biomolecules. Therefore, the molecular recognition of nucleotides became an important topic in supramolecular chemistry and exhibited many biomedical applications. Guanidinocalixarenes showed very strong binding affinities towards nucleotides, even reaching the nanomolar level. In this work, we systematically determined the binding constants between a typical guanidinocalixarene(guanidinium-modified calix[5]arene, GC5A) and various nucleotides and revealed the driving forces behind the molecular recognition using theoretical calculations. The electrostatic interactions and hydrogen bonding provided by the phosphate groups of the nucleotides dominated the binding between the nucleotides and GC5A. The lower rim alkyl chains and the skeleton of GC5A provide preorganized cavity and upper guanidinium groups. The difference in the type of nucleobase is also attributed to the different binding affinities. This work provides insight into the molecular recognition of nucleotides and facilitates the development of new supramolecular hosts for nucleotides and related biological applications.

Key words: Calixarene, Nucleotide, Molecular recognition, Indicator displacement assay, Theoretical calculation

GENG Wenchao, ZHENG Zhe, JIANG Huifeng, GUO Dongsheng. Nucleotide Recognition by a Guanidinocalixarene Receptor in Aqueous Solution[J]. 高等学校化学研究, 2023, 39(1): 144-150.

GENG Wenchao, ZHENG Zhe, JIANG Huifeng, GUO Dongsheng. Nucleotide Recognition by a Guanidinocalixarene Receptor in Aqueous Solution[J]. Chemical Research in Chinese Universities, 2023, 39(1): 144-150.

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Nucleotide Recognition by a Guanidinocalixarene Receptor in Aqueous Solution

Nucleotide Recognition by a Guanidinocalixarene Receptor in Aqueous Solution

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