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Pregled bibliografske jedinice broj: 1050064

Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1, 2, 3-triazolyl)-appended benzimidazo[1, 2-a]quinoline derivatives


Meščić Macan, Andrijana; Perin, Nataša; Jakopec, Silvio; Mioč, Marija; Radić Stojković, Marijana; Kralj, Marijeta; Hranjec, Marijana; Raić- Malić, Silvana
Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1, 2, 3-triazolyl)-appended benzimidazo[1, 2-a]quinoline derivatives // European journal of medicinal chemistry, 185 (2020), 111845, 11 doi:10.1016/j.ejmech.2019.111845 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1050064 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1, 2, 3-triazolyl)-appended benzimidazo[1, 2-a]quinoline derivatives

Autori
Meščić Macan, Andrijana ; Perin, Nataša ; Jakopec, Silvio ; Mioč, Marija ; Radić Stojković, Marijana ; Kralj, Marijeta ; Hranjec, Marijana ; Raić- Malić, Silvana

Izvornik
European journal of medicinal chemistry (0223-5234) 185 (2020); 111845, 11

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

Ključne riječi
antiproliferative activity ; DNA/RNA binding ; benzimidazo[1, 2-a]quinolines ; 1, 2, 3-triazoles ; fluorescent microscopy

Sažetak
The three series of 5-mono- and 2, 5-bis-1, 2, 3-triazolyl-substituted benzimidazo[1, 2-a]quinolines as potential antitumor agents were synthesized. Their growth-inhibitory activity is influenced by the introduction of fluorine at C-2 and the mono-triazolyl nuclei at C-5 of the tetracyclic skeleton, particularly containing short aliphatic side chain. Thus, chloropropyl side chain in all three series had the highest impact on inhibitory effect. 1, 2, 3-Triazolyl−2-fluorobenzimidazo[1, 2-a]quinoline conjugates 8a and 8b with 3-chloropropyl and 2-hydroxyethyl substituents, respectively, exhibited the most pronounced cytostatic effect on colon cancer (HCT116) cells in submicromolar range. The compound 8a emerged as the most promising candidate because of its higher potency and some selectivity in non- tumor HaCaT cells. Fluorescence and CD spectroscopy, as well as thermal denaturation assays revealed moderate to high DNA/RNA binding affinities of selected compounds, and identified intercalation, as a dominant binding mode to both polynucleotides. However, intracellular distribution assay in H460 cells showed that none of the evaluated compounds enters the nucleus, suggesting that they do not target nuclear DNA, as a potential mechanism of action.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-4682 - Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja (PurBioCaPa) (Raić-Malić, Silvana, HRZZ - 2018-01) ( POIROT)
IP-2018-01-4379 - Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa (AntioxPot) (Hranjec, Marijana, HRZZ - 2018-01) ( POIROT)
HRZZ-IP-2018-01-4694 - Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavima (DNARNAHyB-MolBio) (Radić Stojković, Marijana, HRZZ - 2018-01) ( POIROT)

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

Citiraj ovu publikaciju

Meščić Macan, Andrijana; Perin, Nataša; Jakopec, Silvio; Mioč, Marija; Radić Stojković, Marijana; Kralj, Marijeta; Hranjec, Marijana; Raić- Malić, Silvana
Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1, 2, 3-triazolyl)-appended benzimidazo[1, 2-a]quinoline derivatives // European journal of medicinal chemistry, 185 (2020), 111845, 11 doi:10.1016/j.ejmech.2019.111845 (međunarodna recenzija, članak, znanstveni)
Meščić Macan, A., Perin, N., Jakopec, S., Mioč, M., Radić Stojković, M., Kralj, M., Hranjec, M. & Raić- Malić, S. (2020) Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1, 2, 3-triazolyl)-appended benzimidazo[1, 2-a]quinoline derivatives. European journal of medicinal chemistry, 185, 111845, 11 doi:10.1016/j.ejmech.2019.111845.
@article{article, year = {2020}, pages = {11}, DOI = {10.1016/j.ejmech.2019.111845}, chapter = {111845}, keywords = {antiproliferative activity, DNA/RNA binding, benzimidazo[1, 2-a]quinolines, 1, 2, 3-triazoles, fluorescent microscopy}, journal = {European journal of medicinal chemistry}, doi = {10.1016/j.ejmech.2019.111845}, volume = {185}, issn = {0223-5234}, title = {Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1, 2, 3-triazolyl)-appended benzimidazo[1, 2-a]quinoline derivatives}, keyword = {antiproliferative activity, DNA/RNA binding, benzimidazo[1, 2-a]quinolines, 1, 2, 3-triazoles, fluorescent microscopy}, chapternumber = {111845} }
@article{article, year = {2020}, pages = {11}, DOI = {10.1016/j.ejmech.2019.111845}, chapter = {111845}, keywords = {antiproliferative activity, DNA/RNA binding, benzimidazo[1, 2-a]quinolines, 1, 2, 3-triazoles, fluorescent microscopy}, journal = {European journal of medicinal chemistry}, doi = {10.1016/j.ejmech.2019.111845}, volume = {185}, issn = {0223-5234}, title = {Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1, 2, 3-triazolyl)-appended benzimidazo[1, 2-a]quinoline derivatives}, keyword = {antiproliferative activity, DNA/RNA binding, benzimidazo[1, 2-a]quinolines, 1, 2, 3-triazoles, fluorescent microscopy}, chapternumber = {111845} }

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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