Molecular Assembly of Rhodanine with Torus-Shaped Cyclodextrins and Their Innovative Applications by Physicochemical Contrivance Simultaneously Optimized by Computational Study

To increase the bioavailability of Rhodanine (RH), inclusion complexes (ICs) of RH with both a-cyclodextrin (alpha-CD) and beta-cyclodextrin (beta-CD) were prepared. The complexes were characterized by different physicochemical as well as spectroscopic techniques thereby indicating encapsulation of RH molecule into the cavities of alpha-CD and beta-CD cavity. DSC analysis showed that the thermal stability of RH was enhanced after complexation. Computational study suggests the most preferred orientation of RH molecule within both CD cavities. In vitro antibacterial activity test illustrates that the IC2 RH-alpha-CD displayed better activity than pure RH and IC1 RH-beta-CD. IC2 RH-alpha-CD (IC50=7.88 mu M) shows the remarkable in vitro cytotoxic activity than pure RH (IC50=44 mu M) and IC1 RH-b beta-CD towards human kidney cancer cell line (ACHN). Furthermore, interaction of RH, IC1 RH-beta-CD and IC2 RH-alpha-CD with CT-DNA was investigated and found that alpha-CD enhances bioavailability of RH to greater extent compared to beta-CD. Additionally, photostability studies reveals that inclusion of RH using alpha-CD induces better stabilization of RH as compared to beta-CD.