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

Author:

Sharma Antara12,Bomzan Pranish3,Roy Debadrita1ORCID,Chhetri Abhijit4,Choudhury Subhankar5,Ghosh Narendra Nath6,Ali Salim1,BK Puja7,Ghosh Shilpi7,Dutta Ankita7,Kumar Anoop7,Roy Mahendra Nath1

Affiliation:

1. Department of Chemistry University of North Bengal Darjeeling 734013 India

2. Department of Chemistry St. Joseph's College Darjeeling 734104 India

3. Department of Chemistry Gorubathan Government College Kalimpong 735231 India

4. Department of Microbiology St. Joseph's College Darjeeling 734104 India

5. Department of Chemistry Malda College Malda 732101 India

6. Pakuahat A.N.M. High School Malda 732138 India

7. Department of Biotechnology University of North Bengal Darjeeling 734013 India

Abstract

AbstractTo increase the bioavailability of Rhodanine (RH), inclusion complexes (ICs) of RH with both α‐cyclodextrin (α‐CD) and β‐cyclodextrin (β‐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 α‐CD and β‐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‐α‐CD displayed better activity than pure RH and IC1 RH‐β‐CD. IC2 RH‐α‐CD (IC50=7.88 μM) shows the remarkable in vitro cytotoxic activity than pure RH (IC50=44 μM) and IC1 RH‐β‐CD towards human kidney cancer cell line (ACHN). Furthermore, interaction of RH, IC1 RH‐β‐CD and IC2 RH‐α‐CD with CT‐DNA was investigated and found that α‐CD enhances bioavailability of RH to greater extent compared to β‐CD. Additionally, photostability studies reveals that inclusion of RH using α‐CD induces better stabilization of RH as compared to β‐CD.

Publisher

Wiley

Subject

General Chemistry

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