Silver(I) N-Heterocyclic Carbene Complexes Derived from Clotrimazole: Antiproliferative Activity and Interaction with an Artificial Membrane-Based Biosensor
2020
With the aim of combining
the potential anticancer properties of
both clotrimazole, an imidazole based antifungal agent, and silver(I)
N-heterocyclic carbenes, 13 novel silver(I) N-heterocyclic carbene
complexes derived from clotrimazole were synthesized. The complexes
were fully characterized, and the partition coefficient of each was
determined to provide a measure of hydrophobicity. The antiproliferative
properties of the complexes against cancerous and noncancerous cell
lines found optimum cytotoxicity when the complex displays an “intermediate
lipophilicity”, which describes a complex that possesses both
water-soluble groups and lipophilic aromatic groups. The silver complexes
were screened on a synthetic biomembrane-like device using a chip-based
phospholipid-coated Pt/Hg electrode embedded in a flow cell system.
The results are recorded as rapid cyclic voltammograms (RCVs), which
give insight into the interactions of the complexes with a cell membrane.
Interestingly the principle of “intermediate lipophilicity”
also applies to the monolayer interaction to which the silver atom
significantly implements an irreversibility.
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