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Ultrahigh binding affinity of a hydrocarbon guest inside cucurbit[7]uril enhanced by strong host-guest charge matching

Lambert, H; Mohan, N; Lee, T-C; (2019) Ultrahigh binding affinity of a hydrocarbon guest inside cucurbit[7]uril enhanced by strong host-guest charge matching. Physical Chemistry Chemical Physics 10.1039/c9cp01762c. (In press). Green open access

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Abstract

Cucurbit[7]uril (CB[7]) is an artificial macrocyclic molecule that can form exceptionally strong host-guest complexes with binding constants higher than that of the biotin-avidin complex. Despite notable experimental efforts, there do not exist large-scale computational investigations on finding strongly binding guests of CB[7]. Herein, we develop a computational approach based on large-scale molecular modelling to predict strongly binding hydrocarbon motifs. Our results indicate that an expanded cubane (PubChem ID 101402794) will be the most strongly binding hydrocarbon guest of CB[7] among the hundreds of thousands of hydrocarbons in the PubChem database, achieving a binding affinity significantly stronger than those reported in preceding experimental studies. Our findings highlight the important role of charge complementarity in the form of quadrupole electrostatic interactions in enabling the ultrahigh binding affinity of nonpolar guest molecules with CB[7], in addition to other known contributions such as van der Waals interactions and high-energy water release.

Type: Article
Title: Ultrahigh binding affinity of a hydrocarbon guest inside cucurbit[7]uril enhanced by strong host-guest charge matching
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c9cp01762c
Publisher version: https://doi.org/10.1039/c9cp01762c
Language: English
Additional information: © The Owner Societies 2019. This article is open access licensed under a Creative Commons Attribution 3.0 Unported licence (CC BY 3.0).
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > MAPS Faculty Office
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > MAPS Faculty Office > Institute for Materials Discovery
URI: https://discovery.ucl.ac.uk/id/eprint/10077605
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