High-Affinity Binding of Metallacarborane Cobalt Bis(dicarbollide) Anions to Cyclodextrins and Application to Membrane Translocation | Zendy

Khaleel I. Assaf | Zendy; Barbara Begaj | Zendy; Angelina Frank | Zendy; Mohamed Nilam | Zendy; Ali S. Mougharbel | Zendy; Ulrich Kortz | Zendy; Jan Nekvinda | Zendy; Bohumı́r Grüner | Zendy; Detlef Gabel | Zendy; Werner M. Nau | Zendy

Open Access

High-Affinity Binding of Metallacarborane Cobalt Bis(dicarbollide) Anions to Cyclodextrins and Application to Membrane Translocation

Author(s) -

Khaleel I. Assaf,

Barbara Begaj,

Angelina Frank,

Mohamed Nilam,

Ali S. Mougharbel,

Ulrich Kortz,

Jan Nekvinda,

Bohumı́r Grüner,

Detlef Gabel,

Werner M. Nau

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b01688

Subject(s) - isothermal titration calorimetry , chemistry , cobalt , titration , membrane , aqueous solution , cyclic voltammetry , molecule , cyclodextrin , nuclear magnetic resonance spectroscopy , inorganic chemistry , electrochemistry , stereochemistry , organic chemistry , biochemistry , electrode

Metallacarboranes are a class of inorganic boron clusters that have recently been recognized as biologically active compounds. Herein, we report on the host-guest complexation of several cobalt bis(1,2-dicarbollide) anions (COSANs) with cyclodextrins (CDs) in aqueous solution. The binding affinities reach micromolar values, which are among the highest known values for native CDs, and exceed those for neutral hydrophobic organic guest molecules. The entrapment of the COSANs inside the cavity of CDs was confirmed using NMR and UV-visible spectroscopy, mass spectrometry, cyclic voltammetry, and isothermal titration calorimetry. Complexation by CDs greatly influences the photophysical and electrochemical properties of COSANs. In combination with indicator displacement assays, a label-free fluorescence-based method was developed to allow real-time monitoring of the translocation of COSANs through lipid bilayer membranes.

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