Napredna pretraga

Pregled bibliografske jedinice broj: 728965

‘Click’ derived 1, 2, 3-triazolium salts as potential anticancer drugs

Steiner, Ivana; Stojanović, Nikolina; Bolje, Aljoša; Ambriović-Ristov, Andreja; Brozovic, Anamaria; Radić Stojković, Marijana; Piantanida, Ivo; Eljuga, Domagoj; Košmrlj, Janez; Osmak, Maja
‘Click’ derived 1, 2, 3-triazolium salts as potential anticancer drugs // Periodicum Biologorum / Ozretić, Petar ; Levanat, Sonja (ur.).
Zagreb, 2014. str. 59-59 (poster, domaća recenzija, sažetak, znanstveni)

‘Click’ derived 1, 2, 3-triazolium salts as potential anticancer drugs

Steiner, Ivana ; Stojanović, Nikolina ; Bolje, Aljoša ; Ambriović-Ristov, Andreja ; Brozovic, Anamaria ; Radić Stojković, Marijana ; Piantanida, Ivo ; Eljuga, Domagoj ; Košmrlj, Janez ; Osmak, Maja

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

Periodicum Biologorum / Ozretić, Petar ; Levanat, Sonja - Zagreb, 2014, 59-59

"From Bench to Clinic" Third Meeting of the Croatian Association for cancer Research with International Participation

Mjesto i datum
Zagreb, Hrvatska, 06-07.11.2014

Vrsta sudjelovanja

Vrsta recenzije
Domaća recenzija

Ključne riječi
1; 2; 3-triazole; 1; 2; 3-triazolium salt; tumor cell; normal cell; anticancer drug; drug resistance

Modern synthetic chemistry is powered by new synthetic protocols that allow the rapid generation of compound scaffolds. Copper-catalysed azide–alkyne cycloaddition reaction, also referred to as the ‘Click’ reaction, producing 1, 4-disubstituted-1, 2, 3-triazoles (‘Click’ triazoles) is one of that kind. 1-(2-Picolyl)-, 4-(2-picolyl)-, 1-(2-pyridyl)-, and 4-(2-pyridyl)-3-methyl-1, 2, 3-triazolium salts have been synthesized and tested for their anticancer activity on human cervical carcinoma HeLa cells. In general, the analogues that are functionalized at the triazole ring with strongly electron donating substituent were more potent in comparison to those with the electron neutral or electron accepting groups. The most active compound was 4-(4-methoxyphenyl)-3-methyl-1-(2-picolyl)-1H-1, 2, 3-triazolium hexafluorophosphate(V) (AB144), with very high cytotoxicity. Its anticancer activity was cell type dependent, being most cytotoxic against large-cell lung carcinoma H460 cells. It is of outmost importance that AB144 was significantly more cytotoxic against tumor cells than to normal cells, with very low therapeutic index (0.0658) for H460 cells. Additionally, this compound was similarly cytotoxic against parent laryngeal carcinoma HEp-2 cells and their carboplatin and cisplatin resistant 7T subline what is, having in mind the importance of inhibitory effect of drug resistance on the success of cancer treatment, of great importance. On the basis of the structural features of triazolium salts it was anticipated that DNA would be the primary target. The fact that no influence of AB144 on thermal stability of calf thymus DNA could be observed, however, discarded this possibility. Compound AB144 arrests tumor cells in the G1 phase of the cell cycle, and induces apoptosis. While our data suggest that the triazolium salt AB144 is an anticancer molecule which preferentially target malignant cells, it holds a promise as simple to make, low molecular mass, non-metalic potential anti-cancer agents.

Izvorni jezik

Znanstvena područja
Kemija, Biologija


Projekt / tema
098-0982913-2748 - Stanični odgovor na citotoksične spojeve i razvoj otpornosti (Maja Osmak, )
098-0982913-2850 - Povećanje transdukcije adenovirusnih vektora i otpornost stanica na citostatike (Andreja Ambriović Ristov, )
098-0982914-2918 - Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima (Ivo Piantanida, )

Institut "Ruđer Bošković", Zagreb