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Chem Biodivers ; 20(5): e202200972, 2023 May.
Article in English | MEDLINE | ID: mdl-37058554

ABSTRACT

We present the synthesis and characterization of organic Salphen compounds containing bromine substituents at the para/ortho-para positions, in their symmetric and non-symmetric versions, and describe the X-ray structure and full characterization for the new unsymmetrical varieties. We report for the first time antiproliferative activity in metal-free brominated Salphen compounds, by evaluations in four human cancer cell lines, cervix (HeLa), prostate (PC-3), lung (A549) and colon (LS 180) and one non-cancerous counterpart (ARPE-19). We assessed in vitro cell viability against controls using the MTT assay ((3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide)) and determined the concentration required for 50 % growth inhibition (IC50 ), together with their selectivity vs. non-cancerous cells. We found promising results against prostate (9.6 µM) and colon (13.5 µM) adenocarcinoma cells. We also found a tradeoff between selectivity (up to 3-fold vs. ARPE-19) and inhibition, depending upon the symmetry and bromine-substitution of the molecules, showing up to 20-fold higher selectivity vs. doxorubicin controls.


Subject(s)
Antineoplastic Agents , Bromine , Male , Female , Humans , Bromine/pharmacology , HeLa Cells , Phenylenediamines/pharmacology , Antineoplastic Agents/chemistry , Cell Proliferation , Cell Line, Tumor , Drug Screening Assays, Antitumor , Structure-Activity Relationship , Molecular Structure
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