ANTIOKSIDATIVNA I CITOTOKSIČNA AKTIVNOST MONO-I BIS- DERIVATA SALICILNE KISELINE
| Autor: | Mihalj Poša, Mihály Szécsi, M Katarina Penov-Gasi, Vesna Kojić, Suzana Jovanović-Šanta, N Marija Sakac, P Marina Savic, M Aleksandar Okljesa, A Evgenija Djurendic |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Quantitative structure–activity relationship
Antioxidant Chemistry DPPH medicine.medical_treatment General Engineering antioxidant activity Medicinal chemistry In vitro Solvent chemistry.chemical_compound Molecular descriptor lcsh:Technology (General) medicine salicylic acid derivatives Organic chemistry lcsh:T1-995 Cytotoxicity QSAR study IC50 cytotoxic activity |
| Zdroj: | Acta Periodica Technologica, Vol 2014, Iss 45, Pp 173-189 (2014) |
| ISSN: | 1450-7188 |
| Popis: | A simple synthesis of mono- and bis-salicylic acid derivatives 1-10 by the transesterification of methyl salicylate (methyl 2-hydroxybenzoate) with 3-oxapentane-1,5-diol, 3,6- dioxaoctane-1,8-diol, 3,6,9-trioxaundecane-1,11-diol, propane-1,2-diol or 1-aminopropan- 2-ol in alkaline conditions is reported. All compounds were tested in vitro on three malignant cell lines (MCF-7, MDA-MB-231, PC-3) and one non-tumor cell line (MRC- 5). Strong cytotoxicity against prostate PC-3 cancer cells expressed compounds 3, 4, 6, 9 and 10, all with the IC50 less than 10 ?mol/L, which were 11-27 times higher than the cytotoxicity of antitumor drug doxorubicin. All tested compounds were not toxic against the non-tumor MRC-5 cell line. Antioxidant activity of the synthesized derivatives was also evaluated. Compounds 2, 5 and 8 were better OH radical scavengers than commercial antioxidants BHT and BHA. The synthesized compounds showed satisfactory scavenger activity, which was studied by QSAR modeling. A good correlation between the experimental variables IC50 DPPH and IC50 OH and MTI (molecular topological indices) molecular descriptors and CAA (accessible Connolly solvent surface area) for the new compounds 1, 3, and 5 was observed. |
| Databáze: | OpenAIRE |
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