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Evaluation of polyanionic cyclodextrins as high affinity binding scaffolds for fentanyl
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Evaluation of polyanionic cyclodextrins as high affinity binding scaffolds for fentanyl
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Journal Article
Evaluation of polyanionic cyclodextrins as high affinity binding scaffolds for fentanyl
2023
Overview
Cyclodextrins (CDs) have been previously shown to display modest equilibrium binding affinities (
K
a
~ 100–200 M
-1
) for the synthetic opioid analgesic fentanyl. In this work, we describe the synthesis of new CDs possessing extended thioalkylcarboxyl or thioalkylhydroxyl moieties and assess their binding affinity towards fentanyl hydrochloride. The optimal CD studied displays a remarkable affinity for the opioid of
K
a
= 66,500 M
−1
, the largest value reported for such an inclusion complex to date. One dimensional
1
H Nuclear Magnetic Resonance (NMR) as well as Rotational Frame Overhauser Spectroscopy (2D-ROESY) experiments supported by molecular dynamics (MD) simulations suggest an unexpected binding behavior, with fentanyl able to bind the CD interior in one of two distinct orientations. Binding energies derived from the MD simulations work correlate strongly with NMR-derived affinities highlighting its utility as a predictive tool for CD candidate optimization. The performance of these host molecules portends their utility as platforms for medical countermeasures for opioid exposure, as biosensors, and in other forensic science applications.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
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