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Antioxidant and cytotoxic activity of new di- and polyamine caffeine analogues

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Název: Antioxidant and cytotoxic activity of new di- and polyamine caffeine analogues
Autoři: Lucyna Mrówczyńska, Krzysztof Bielawski, Anna Bielawska, Weronika Piorońska, Agnieszka Górnicka, Wojciech Jankowski, Arleta Sierakowska, Beata Jasiewicz, Marcin Hoffmann
Zdroj: Free Radical Research. 52:724-736
Informace o vydavateli: Informa UK Limited, 2018.
Rok vydání: 2018
Témata: Chelating agents - pharmacology, 0301 basic medicine, Caffeine - analogs & derivatives, Erythrocytes, Cell Survival, Hemolysis - drug effects, Iron, Antioxidants - chemical synthesis, Amidines, Caffeine - pharmacology, Chelating agents - chemical synthesis, Cytotoxins - chemical synthesis, Picrates - chemistry, Amidines - antagonists & inhibitors, Hemolysis, Antioxidants, Inhibitory Concentration 50, Structure-Activity Relationship, 03 medical and health sciences, Picrates, Erythrocytes - drug effects, Caffeine, Polyamines, Cell survival - drug effects, Humans, MCF-7 cells, Chelating Agents, Antioxidants - pharmacology, Oxidants - antagonists & inhibitors, Organ specificity, Cytotoxins, Biphenyl Compounds, Picrates - antagonists & inhibitors, Caffeine - chemical synthesis, Polyamines - chemistry, Biphenyl compounds - chemistry, Structure-activity relationship, Oxidants, Oxidation-reduction, 3. Good health, Oxidants - pharmacology, Organ Specificity, Inhibitory concentration 50, Iron - chemistry, MCF-7 Cells, Cytotoxins - pharmacology, Biphenyl compounds - antagonists & inhibitors, Amidines - pharmacology, Oxidation-Reduction
Popis: A series of new di- and polyamine-caffeine analogues were synthesised and characterised by NMR, FT-IR, and MS spectroscopic methods. To access the stability of the investigated caffeine analogues, molecular dynamic simulations were performed in NAMD 2.9 assuming CHARMM36 force field. To evaluate the antioxidant capacity of new compounds, three different antioxidant assays were used, namely 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH•) scavenging activity, ferrous ions (Fe2+) chelating activity, and Fe3+→Fe2+reducing ability. In vitro, the ability of new derivatives to protect human erythrocytes against oxidative haemolysis induced by free radical from 2,2'-azobis(2-methylpropionamidine) dihydrochloride (AAPH) was estimated. The cytotoxic activity was tested using MCF-7 breast cancer cells and human erythrocytes. All compounds showed the antioxidant capacity depending mostly on their ferrous ions chelating activity. In the presence of AAPH, some derivatives were able to effectively inhibit the oxidative haemolysis. Two derivatives, namely 8-(methyl(2-(methylamino)ethyl)-amino)caffeine and 8-(methyl(3-(methylamino)propyl)amino)caffeine, showed cytotoxic activity against MCF-7 breast cancer cells but not against human erythrocytes. Therefore, it is concluded that the selected di- and polyamine caffeine analogues, depending on their chemical structure, were able to minimise the oxidative stress and to inhibit the tumour cell growth. The confirmed antioxidant and cytotoxic properties of some caffeine derivatives make them attractive for potential applications in food or pharmaceutical industries.
Druh dokumentu: Article
Jazyk: English
ISSN: 1029-2470
1071-5762
DOI: 10.1080/10715762.2018.1467561
Přístupová URL adresa: https://pubmed.ncbi.nlm.nih.gov/29669446
https://www.ncbi.nlm.nih.gov/pubmed/29669446
https://europepmc.org/article/MED/29669446
https://www.tandfonline.com/doi/abs/10.1080/10715762.2018.1467561
Přístupové číslo: edsair.doi.dedup.....a1b315e56138bdff7e0e6575fc57ba89
Databáze: OpenAIRE
Popis
Abstrakt:A series of new di- and polyamine-caffeine analogues were synthesised and characterised by NMR, FT-IR, and MS spectroscopic methods. To access the stability of the investigated caffeine analogues, molecular dynamic simulations were performed in NAMD 2.9 assuming CHARMM36 force field. To evaluate the antioxidant capacity of new compounds, three different antioxidant assays were used, namely 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH•) scavenging activity, ferrous ions (Fe2+) chelating activity, and Fe3+→Fe2+reducing ability. In vitro, the ability of new derivatives to protect human erythrocytes against oxidative haemolysis induced by free radical from 2,2'-azobis(2-methylpropionamidine) dihydrochloride (AAPH) was estimated. The cytotoxic activity was tested using MCF-7 breast cancer cells and human erythrocytes. All compounds showed the antioxidant capacity depending mostly on their ferrous ions chelating activity. In the presence of AAPH, some derivatives were able to effectively inhibit the oxidative haemolysis. Two derivatives, namely 8-(methyl(2-(methylamino)ethyl)-amino)caffeine and 8-(methyl(3-(methylamino)propyl)amino)caffeine, showed cytotoxic activity against MCF-7 breast cancer cells but not against human erythrocytes. Therefore, it is concluded that the selected di- and polyamine caffeine analogues, depending on their chemical structure, were able to minimise the oxidative stress and to inhibit the tumour cell growth. The confirmed antioxidant and cytotoxic properties of some caffeine derivatives make them attractive for potential applications in food or pharmaceutical industries.
ISSN:10292470
10715762
DOI:10.1080/10715762.2018.1467561