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Solution Structures of 1:1 Complexes of Oxyphenonium Bromide With Beta- And Gamma-Cyclodextrins

Solution Structures of 1:1 Complexes of Oxyphenonium Bromide With Beta- And Gamma-Cyclodextrins

Noriaki Funasaki, Tomoko Sumiyoshi, Seiji Ishikawa, Saburo Neya

Mol Pharm. Mar-Apr 2004;1(2):166-72.

PMID: 15832513

Abstract:

The solution structures of complexes of oxyphenonium bromide (OB) with beta- and gamma-cyclodextrins (beta- and gamma-CDs, respectively) in deuterium oxide have been investigated by 500 MHz proton NMR spectroscopy and molecular mechanics calculations. The chemical shifts induced by complex formation provide the 1:1 binding constants and the chemical shift variations, DeltadeltaOB-CD, with complexation for the protons of OB and the CDs. The observed binding constants are very close to those obtained by other methods and are in the following order: beta-CD > gamma-CD > alpha-CD. Initial structures of the complexes are constructed on the basis of the ROESY spectra and the DeltadeltaOB-CD values and are optimized by molecular mechanics calculations. The intermolecular distances between the protons of OB and CD calculated for these structures are well-correlated with the observed ROESY intensities. The cyclohexyl group of OB penetrates deeply into a beta-CD cavity, and the phenyl group is close to the wide rim of the cavity. The phenyl and cyclohexyl groups of OB are both incorporated into a gamma-CD cavity. Furthermore, these structures of the complexes are consistent with the suppression of bitter taste and basic hydrolysis of OB by CDs and the polarity of binding sites of OB.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13536599-A	Deuterium bromide solution		13536-59-9	Price

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