Abstract
In this work, we synthesize the sulfonated Schiff bases of the chitosan derivatives 2a-2j without the use of a catalyst in two moderately straightforward steps with good yield within a short reaction time. The morphology and chemical structure of chitosan derivatives were investigated using FT-IR, NMR (1H—13C), XRD, and SEM. Furthermore, our chitosan derivatives were tested for their anticancer activity against the MCF-7 cancer cell line, and doxorubicin was used as a standard. In addition, the normal cell lines of the breast cancer cell MCF-10A, and of the lung cell MRC-5 were tested. Compound 2 h, with a GI50 value of 0.02 µM for MCF-7, is highly active compared with the standard doxorubicin and other compounds. The synthesized compounds 2a-2j exhibit low cytotoxicity, with IC50 > 100 μg/ml, against normal cell lines MCF-10A, MRC-5. We also provide the results of an in-silico study involving the Methoxsalen protein (1Z11). Compound 2h exhibits a higher binding affinity for 1Z11 protein (−5.9 kcal/mol) and a lower binding affinity for Doxorubicin (−5.3 kcal/mol) than certain other compounds. As a result of the aforementioned findings, the use of compound 2h has an anticancer drug will be researched in the future.
Highlights
Cell proliferation becomes abnormal when it expands outside its normal limits, invades adjacent tissues, and/or feeds on other parts of the body, and can cause cancer
The same procedure was followed by the synthesis of other sulfonated chitosan derivatives 2c-2j.The synthesized compounds 2a-2j were assessed for their cytotoxic activities against the MCF-7 cancer cell line and against the normal cell lines breast cancer cell MCF-10A and lung cell MRC-5 using an MTT assay, and doxorubicin was used as a standard
Compound 2 h was found to be highly active, with a GI50 value of 0.02 μM for MCF-7 compared with other compounds
Summary
Cell proliferation becomes abnormal when it expands outside its normal limits, invades adjacent tissues, and/or feeds on other parts of the body, and can cause cancer. Chitosan and its derivatives have been shown to selectively permeate cancer cell membranes and exhibit anticancer activity via cellular enzymatic, antiangiogenic, immune-enhancing, antioxidant defense mechanism, and apoptotic mechanisms. This activity can be reduced in oral administration due to protonation of the amine group (Mahmood et al, 2019). 1H NMR (DMSO-d6), δ (ppm): 8.41 (s, 1H, N CH), 7.85–7.38 (m, 4H, F-Ph), 5.20–3.08 (m, 5H, CS-H), 3.65 (s, 1H, OH), 3.50–3.31 (s, 6H, OCH3 -CS), 3.43–2.68 (m, 4H, OH-(CH2)2), 2.81–2.53 (m, 2H, CH2-NH), 2.66–2.52 (m, 4H, N (CH2)2), 2.03 (s, 2H, NH); 13C NMR (DMSO-d6) δ (ppm): 165.5, 132.2, 130.3, 115.9 (6C, F-Ph), 163.6 (1C,N CH), 112.1, SCHEME 1 | The synthesized Schiff base of sulfonated chitosan derivatives 2a-2j. The compound with the lowest binding affinity value obtained the highest score, which was determined visually using the software Discovery Studio 2019
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