Template-Directed Synthesis of Bivalent, Broad-Spectrum Hosts for Neuromuscular Blocking Agents

30 September 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report on the synthesis of bivalent water soluble calix[4]arene and calix[5]arene hosts, Super-sCx4 and Super-sCx5 as new broad-spectrum supramolecular binders of neuromuscular blocking agents (NMBAs). Synthesis was achieved using the target bisquaternary amine NMBAs as a template to link two highly anionic p-sulfonatocalixarene building blocks in aqueous solution. Bivalent anionic hosts Super-sCx4 and Super-sCx5 bind by engaging both quaternary amines present on a variety of NMBAs. We report low μM binding to structurally diverse alkyl, steroidal, curarine and benzylisoquinoline NMBAs with high selectivity over the neurotransmitter acetylcholine.

Keywords

Neuromuscular blockade
Host-guest chemistry
Molecular recognition
Templation
Fluorescence
Calixarene

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