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Novel amidino-substituted thienyl- and furyl-vinyl-benzimidazole derivatives and their photochemical conversion into corresponding diaza-cyclopenta[c]fluorenes. Synthesis, interactions with DNA and RNA and antitumor evaluation. Part 4.


Hranjec, Marijana; Piantanida, Ivo; Kralj, Marijeta; Šuman, Lidija; Pavelić, Krešimir; Karminski-Zamola, Grace
Novel amidino-substituted thienyl- and furyl-vinyl-benzimidazole derivatives and their photochemical conversion into corresponding diaza-cyclopenta[c]fluorenes. Synthesis, interactions with DNA and RNA and antitumor evaluation. Part 4. // Journal of Medicinal Chemistry, 51 (2008), 16; 4899-4910 (međunarodna recenzija, članak, znanstveni)


Naslov
Novel amidino-substituted thienyl- and furyl-vinyl-benzimidazole derivatives and their photochemical conversion into corresponding diaza-cyclopenta[c]fluorenes. Synthesis, interactions with DNA and RNA and antitumor evaluation. Part 4.

Autori
Hranjec, Marijana ; Piantanida, Ivo ; Kralj, Marijeta ; Šuman, Lidija ; Pavelić, Krešimir ; Karminski-Zamola, Grace

Izvornik
Journal of Medicinal Chemistry (0022-2623) 51 (2008), 16; 4899-4910

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Benzimidazoles; amidines; cyclopenta[c]fluorenes; interaction with DNA and RNA; antitumor evaluation

Sažetak
Synthesis of novel non-fused amidino-substituted thienyl- and furyl-vinyl-benzimidazole derivatives and their photochemical cyclization into corresponding diaza-cyclopenta[c]fluorenes is described. All studied compounds showed prominent growth inhibitory effect. The fused compounds showed stronger activity than non-fused ones, whereby imidazolyl-substituted compound 11 proved to be the most active one. Besides, it induced strong G2/M arrest of the cell cycle followed by drastic apoptosis, which is in accordance with the DNA intercalative binding mode determined by the spectroscopic studies. Non-fused derivatives induced strong S phase arrest of the cell cycle followed by apoptosis that together with DNA minor groove binding mode, pointed to topoisomerase I inhibition. In addition, all non-fused compounds revealed pronounced selectivity toward tumor cells in comparison with non-tumor cells. Based on the presented results, both non-fused and fused tiophene-containing imidazolyl-derivatives should be considered as promising lead compounds for further investigation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Marijeta Kralj, )
098-0982914-2918 - Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima (Ivo Piantanida, )
125-0982464-1356 - Novi heterocikli kao antitumorski i antivirusni ("pametni") lijekovi (Marijana Hranjec, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE