Nuclear magnetic resonance spectroscopic study of the inclusion complex of (R)-tedizolid with HDAS-β-CD, β-CD, and γ-cyclodextrin in aqueous solution.

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Nuclear magnetic resonance spectroscopic study of the inclusion complex of (R)-tedizolid with HDAS-β-CD, β-CD, and γ-cyclodextrin in aqueous solution.

J Pharm Biomed Anal. 2019 Feb 23;169:170-180

Authors: Bednarek E, Bocian W, Michalska K

Abstract
NMR spectroscopy is used to investigate the host-guest complexation of (R)-tedizolid, such as tedizolid with the hydroxymethyl substituent at the C5 position of the oxazolidinone ring ((R)-TED) or tedizolid with 5-methyl dihydrogen phosphate ((R)-TED-PO4) with heptakis-(2,3-diacetyl-6-sulfo)-β-cyclodextrin (HDAS-β-CD), β-CD and γ-CD, in particular to obtain information about the mode and strength of the guest complexation into the hydrophobic cavity of the host. The complex stoichiometries of 1:1 (host:guest) and 1:2 were detected in millimolar concentrations for HDAS-β-CD and γ-CD with TED-PO4 complexes, respectively. In the meantime, the mixed of complexes with stoichiometries of 1:1 and 2:1 were found for β-CD with both TED and TED-PO4, however the 1:1 complex had a significant advantage.The binding mode was proposed. The estimated binding constants Ka of the complexes of TED or TED-PO4 with CDs differ significantly in the order HDAS-β-CD<<β-CD<<γ-CD.

PMID: 30921691 [PubMed - as supplied by publisher]