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Novel biologically active nitro and amino substituted benzimidazo[1, 2-a]quinolines


Perin, Nataša; Uzelac, Lidija; Piantanida, Ivo; Karminski-Zamola, Grace; Kralj, Marijeta; Hranjec, Marijana
Novel biologically active nitro and amino substituted benzimidazo[1, 2-a]quinolines // Bioorganic & medicinal chemistry, 19 (2011), 21; 6329-6339 doi:10.1016/j.bmc.2011.09.002 (međunarodna recenzija, članak, znanstveni)


Naslov
Novel biologically active nitro and amino substituted benzimidazo[1, 2-a]quinolines

Autori
Perin, Nataša ; Uzelac, Lidija ; Piantanida, Ivo ; Karminski-Zamola, Grace ; Kralj, Marijeta ; Hranjec, Marijana

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 19 (2011), 21; 6329-6339

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

Ključne riječi
Benzimidazoles ; benzimidazo[1 ; 2-a]quinolines ; antiproliferative activity ; interaction with ct-DNA ; cytometry analysis

Sažetak
This manuscript described the synthesis and biological activity of novel nitro substituted E-2-styryl-benzimidazoles and E-2-(2-benzimidazolyl)-3-phenylacrylonitriles and nitro and amino substituted benzimidazo[1, 2-a]quinolines (4-5, 6-11, 17-20 and 21-32). All of the compounds showed significant growth inhibitory effect towards five tumor cell lines, whereby the IC50 concentrations of 11, 20, 28, 29, 30, 32 are in the low micromolar range (IC50 = 2 – 19 M). The DNA binding experiments did not show significant affinity of two selected compounds towards ds-DNA. The flow cytometry analysis of potential cell cycle perturbations after the treatment with compounds 9, 11, 25 and 29 demonstrated that all of the compounds (5 μM ≈ IC50) significantly delayed the progression through G1 phase, as demonstrated by the accumulation of cells in G1 phase, accompanied with the reduction of the cell number in the cells in S phase, which does not point to DNA damage as the main mechanism of action. Also, fluorescence microscopy study showed cytoplasmic distribution of the compounds, demonstrating that DNA is not the primary target of compounds. Thus, considerable antiproliferative effects of studied compounds are due to interactions with other biological targets within cells.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
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


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