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A Profile of the In Vitro Anti-Tumor Activity and In Silico ADME Predictions of Novel Benzothiazole Amide-Functionalized Imidazolium Ionic Liquids

1
Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia
2
Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf, Laboratoire de Chimie et Electrochimie des Complexes Metalliques (LCECM) USTO-MB, P.O. Box 1505, El M‘nouar, Oran 31000, Algeria
3
Department of Pharmaceutical Sciences, School of Pharmacy, University of Jordan, Amman 11942, Jordan
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(12), 2865; https://doi.org/10.3390/ijms20122865
Received: 7 April 2019 / Revised: 1 June 2019 / Accepted: 1 June 2019 / Published: 12 June 2019
(This article belongs to the Section Molecular Pharmacology)
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Abstract

A focused array of green imidazolium ionic liquids (ILs) encompassing benzothiazole ring and amide linkage were designed and synthesized using quaternization and metathesis protocols. The synthesized ILs have been fully characterized by usual spectroscopic methods and screened for their anticancer activities against human cancer cell lines originating from breast and colon cancers. Collectively, our biological data demonstrate that the newly synthesized series has variable anticancer activities in the examined cancer types. The synthesized ILs 8, 10 and 21–29 comprising the methyl and methyl sulfonyl benzothiazole ring emerged as the most potent compounds with promising antiproliferative activities relative to their benzothiazole ring counterparts. Furthermore, the mechanism underlying the observed anticancer activity was investigated. The most active compound 22 appears to exert its anticancer effect through apoptosis dependent pathway in breast cancer cells. Interestingly, compound 22 has also shown good in silico absorption (81.75%) along with high gastro-intestinal absorption as per ADME predictions. View Full-Text
Keywords: ionic liquids; imidazole; benzothiazole; anticancer; ionic liquids; ADME ionic liquids; imidazole; benzothiazole; anticancer; ionic liquids; ADME
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Al-blewi, F.; Rezki, N.; Naqvi, A.; Qutb Uddin, H.; Al-Sodies, S.; Messali, M.; Aouad, M.R.; Bardaweel, S. A Profile of the In Vitro Anti-Tumor Activity and In Silico ADME Predictions of Novel Benzothiazole Amide-Functionalized Imidazolium Ionic Liquids. Int. J. Mol. Sci. 2019, 20, 2865.

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