Synthesis, Characterization, Antiproliferative Activity, Toxicity, and ADME Studies of a New Schiff Base

Abstract

In this study, a new Schiff base 3 was synthesized in a reaction step using N1-phenylbenzene-1,2-diamine and 2-hydroxy-5-methoxybenzaldehyde at 20 h. The structural properties of compound 3 were characterized in detail by ¹H NMR, ¹³C NMR, and IR. The cytotoxic activity of the synthesized molecule was investigated on breast cancer cell lines (MDA-MB-231 and MCF-7) and a healthy human embryonic kidney cell line (HEK-293T). The evaluations revealed that the compound exhibits cytotoxic activity against breast cancer cells (IC₅₀: 22.73 µM for MDA-MB-231 and 51.59 µM for MCF-7). Additionally, analyses on healthy cells revealed that the compound exhibits a high selectivity effect (IC₅₀: 352.40 µM). The ADME and toxicity (ADMET) properties of the molecule 3 were analyzed using in silico approaches; physicochemical parameters, lipophilicity, and solubility predictions were calculated using SwissADME, while acute toxicity predictions were obtained through the Protox-II platform. Acute toxicity predictions were reported using Protox-II, and the estimated toxic dose was reported as 563 mg/kg based on the value specified in the study. The GHS toxicity class assigned by Protox-II is 4, which indicates moderate acute toxicity.

Keywords

• Breast cancer
• Cytotoxic activity
• Schiff base
• Protox-II

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