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Synthesis and Evaluation of Antioxidant and Cytotoxicity of the N-Mannich Base of Berberine Bearing Benzothiazole Moieties. | LitMetric
Background : Berberine, a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids has drawn high attention for its several biological potencies.Objective : To furnish new rationalized derivatives based on berberine core which can deliver promising antioxidant and cytotoxic activities.Method : The N-Mannich base of an isoquinoline alkaloid, berberine, bearing substituted benzothiazole moieties was obtained. Novel synthesized analogues were in vitro screened for antioxidant efficacy toward 2,2-diphenyl- 1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) free radicals and in vitro cytotoxicity towards cervical cancer cell lines (HeLa and CaSki), an ovarian cancer cell line (SK-OV-3) and human renal cancer cell line (Caki-2). Cytotoxicity of the compounds toward normal cell lines was examined using the Madin-Darby canine kidney (MDCK) non-cancer cell line.Results : Analogues bearing a methoxy functional group (5e), acid functionality (5c), and a cyano group (5m) showed remarkable radical scavenging potential in DPPH and ABTS bioassays. Potent cytotoxicity exhibited by berberine against the HeLa cell line was attributable to the presence of a 2-aminobenzothaizole moiety (5a) and its 6-chloro congener (5g) on the berberine core, and the 6-cyano group (5m) on the benzothiazole ring revealed strong sensitivity for the CaSki cell line, whereas subjected scaffolds demonstrated diminished activity against the SK-OV-3 cell line. In addition, the compound with a 2-aminobenzothaizole moiety (5a), compound with methoxy functional group (5e) and compound with cyano group appeared with the most significant cytotoxicity effect in Caki-2 cell line. Their structures have been elucidated by FT-IR, 1H NMR, 13C NMR, and elemental analyses (CHN) essential research.Conclusion : N-Mannich bases of berberine were efficiently generated utilizing pharmacologically diverse substituted 2-aminobenzothiazole entities and final compounds were found remarkably active in antioxidant and cytotoxic assay. Hence, such types of compounds can be further studied or rationalized in future drug discovery studies.
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