Naslov
Cytotoxic Activity of Ferrocene-substituted Purines Against Several Cancer Cell Lines

Autori
Toma, Mateja ; Marjanović Čermak, Ana Marija ; Pavičić, Ivan ; Vinković Vrček, Ivana ; Vrček, Valerije

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
5th Mini Symposium of Section of Medicinal and Pharmaceutical Chemistry, Book of Abstracts / Gabelica Marković, Vesna - Zagreb : Hrvatsko kemijsko društvo, Sekcija za medicinsku i farmacutsku kemiju, 2021, 15-15

Skup
5th Mini Symposium of Section of Medicinal and Pharmaceutical Chemistry

Mjesto i datum
Zagreb, Hrvatska, 30.11.2021

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Domaća recenzija

Ključne riječi
ferrocene-substituted purines, redox potential, ROS, cytotoxic effect, cancer cell lines

Sažetak
A series of ferrocene-substituted purines with carbonyl group as linker between the organometallic and heterocyclic part were synthesized by regioselective acylation [1] and their cytotoxic activity against several cancer cell lines was investigated. Since ferrocenyl compounds are shown to exhibit diverse biological activity through redox mechanism by generating reactive oxygen species (ROS) [2], electrochemical and ROS generation studies were carried out. Cyclic voltammetry showed that all measured compounds follow a reversible one-electron oxidation in the range of 300-450 mV with the N7 isomers being better oxidants than the N9. While nucleobases coupled with ferrocene generate ROS in acellular media, ferrocene and nucleobases itself were not active. Cytotoxic effect against L929 representing normal cells, and Panc-1, A549 and MCF-7 cancer cell lines was determined based on IC50 values using MTT viability assay. N7 and N9 isomers containing fluorine atom at position 2 and amino group at position 6 of the purine ring, were the most active against all examined cell lines with IC50 value between 1 and 5 µM. Other compounds showed higher IC50 values (50-200 µM). The oxidative status of cells treated with compounds showing low IC50 values was assessed by cellular ROS generation with DCFH reagent and glutathione production with monochlorobimane. Collected data showed no correlation between cytotoxic effect and acellular ROS generation and/or the redox potential of ferrocene-substituted purines.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija

POVEZANOST RADA