Improved spin trapping properties by beta-cyclodextrin-cyclic nitrone conjugate

The Journal of Organic Chemistry
Yongbin HanFrederick A Villamena

Abstract

Spin trapping using a nitrone and electron paramagnetic resonance (EPR) spectroscopy is commonly employed in the identification of transient radicals in chemical and biological systems. There has also been a growing interest in the pharmacological activity of nitrones, and there is, therefore, a pressing need to develop nitrones with improved spin trapping properties and controlled delivery in cellular systems. The beta-cyclodextrin (beta-CD)-cyclic nitrone conjugate, 5-N-beta-cyclodextrin-carboxamide-5-methyl-1-pyrroline N-oxide (CDNMPO) was synthesized and characterized. 1-D and 2-D NMR show two stereoisomeric forms (i.e., 5S- and 5R-) for CDNMPO. Spin trapping using CDNMPO shows distinctive EPR spectra for superoxide radical anion (O2(*-)) compared to other biologically relevant free radicals. Kinetic analysis of O2(*-) adduct formation and decay using singular value decomposition and pseudoinverse deconvolution methods gave an average bimolecular rate constant of k = 58 +/- 1 M(-1) s(-1) and a maximum half-life of t(1/2) = 27.5 min at pH 7.0. Molecular modeling was used to rationalize the long-range coupling between the nitrone and the beta-CD, as well as the stability of the O2(*-) adducts. This study demonstrates how a co...Continue Reading

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Citations

Nov 13, 2010·Journal of the American Chemical Society·Shang-U KimFrederick A Villamena
Jun 18, 2009·The Journal of Organic Chemistry·Yongbin HanFrederick A Villamena
Nov 17, 2011·The Journal of Physical Chemistry. a·Shang-U Kim, Frederick A Villamena
Oct 19, 2013·The Journal of Clinical Investigation·Laura L DuganKumar Sharma
Jun 20, 2012·Future Medicinal Chemistry·Frederick A VillamenaKevin M Nash
Apr 16, 2013·Theoretical Chemistry Accounts·Xiaoguang BaoChristopher M Hadad
Jul 18, 2017·Organic & Biomolecular Chemistry·Florent PoulhèsOlivier Ouari
May 14, 2010·The Journal of Physical Chemistry. a·Mariana Spulber, Shulamith Schlick
Jul 27, 2012·The Journal of Physical Chemistry. a·Mariana SpulberFrederick A Villamena
Jun 19, 2013·The Journal of Physical Chemistry. B·Olesya A KrumkachevaElena G Bagryanskaya
Aug 28, 2018·Chemical Reviews·Saba ParvezYimon Aye

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