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Pregled bibliografske jedinice broj: 694235

Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles


Perin, Nataša; Nhili, Raja; Ester, Katja; Laine, William; Karminski-Zamola, Grace; Kralj, Marijeta; David-Cordonnier, Marie-Hélène; Hranjec, Marijana
Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles // European journal of medicinal chemistry, 80 (2014), 218-227 doi:10.1016/j.ejmech.2014.04.049 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 694235 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles

Autori
Perin, Nataša ; Nhili, Raja ; Ester, Katja ; Laine, William ; Karminski-Zamola, Grace ; Kralj, Marijeta ; David-Cordonnier, Marie-Hélène ; Hranjec, Marijana

Izvornik
European journal of medicinal chemistry (0223-5234) 80 (2014); 218-227

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

Ključne riječi
benzimidazo[1 ; 2-a]quinolines ; amino side chains ; antiproliferative activity ; DNA binding properties ; cellular distribution

Sažetak
The synthesis of 5-amino substituted benzimidazo[1, 2-a]quinolines prepared by microwave assisted amination from halogeno substituted precursor was described. The majority of compounds were active at micromolar concentrations against colon, lung and breast carcinoma cell lines in vitro. The N, N-dimethylaminopropyl 9 and piperazinyl substituted derivative 19 showed the most pronounced activity towards all of the three tested tumor cell lines, which could be correlated to the presence of another N heteroatom and its potential interactions with biological targets. The DNA binding studies, consisting of UV/Visible absorbency, melting temperature studies, and fluorescence and circular dichroism titrations, revealed that compounds 9, 19 and 20 bind to DNA as strong intercalators. The cellular distribution analysis, based on compounds’ intrinsic fluorescence, showed that compound 20 does not enter the cell, while compounds 9 and 19 do, which is in agreement with their cytotoxic effects. Compound 9 efficiently targets the nucleus whereas 19, which also showed DNA intercalating properties in vitro, was mostly localised in the cytoplasm suggesting that the antitumor mechanism of action is DNA-independent.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekti:
MZOS-098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Kralj, Marijeta, MZOS ) ( CroRIS)
MZOS-125-0982464-1356 - Novi heterocikli kao antitumorski i antivirusni (pametni) lijekovi (Hranjec, Marijana, MZOS ) ( CroRIS)

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

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com dx.doi.org

Citiraj ovu publikaciju:

Perin, Nataša; Nhili, Raja; Ester, Katja; Laine, William; Karminski-Zamola, Grace; Kralj, Marijeta; David-Cordonnier, Marie-Hélène; Hranjec, Marijana
Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles // European journal of medicinal chemistry, 80 (2014), 218-227 doi:10.1016/j.ejmech.2014.04.049 (međunarodna recenzija, članak, znanstveni)
Perin, N., Nhili, R., Ester, K., Laine, W., Karminski-Zamola, G., Kralj, M., David-Cordonnier, M. & Hranjec, M. (2014) Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles. European journal of medicinal chemistry, 80, 218-227 doi:10.1016/j.ejmech.2014.04.049.
@article{article, author = {Perin, Nata\v{s}a and Nhili, Raja and Ester, Katja and Laine, William and Karminski-Zamola, Grace and Kralj, Marijeta and David-Cordonnier, Marie-H\'{e}l\`{e}ne and Hranjec, Marijana}, year = {2014}, pages = {218-227}, DOI = {10.1016/j.ejmech.2014.04.049}, keywords = {benzimidazo[1, 2-a]quinolines, amino side chains, antiproliferative activity, DNA binding properties, cellular distribution}, journal = {European journal of medicinal chemistry}, doi = {10.1016/j.ejmech.2014.04.049}, volume = {80}, issn = {0223-5234}, title = {Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles}, keyword = {benzimidazo[1, 2-a]quinolines, amino side chains, antiproliferative activity, DNA binding properties, cellular distribution} }
@article{article, author = {Perin, Nata\v{s}a and Nhili, Raja and Ester, Katja and Laine, William and Karminski-Zamola, Grace and Kralj, Marijeta and David-Cordonnier, Marie-H\'{e}l\`{e}ne and Hranjec, Marijana}, year = {2014}, pages = {218-227}, DOI = {10.1016/j.ejmech.2014.04.049}, keywords = {benzimidazo[1, 2-a]quinolines, amino side chains, antiproliferative activity, DNA binding properties, cellular distribution}, journal = {European journal of medicinal chemistry}, doi = {10.1016/j.ejmech.2014.04.049}, volume = {80}, issn = {0223-5234}, title = {Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles}, keyword = {benzimidazo[1, 2-a]quinolines, amino side chains, antiproliferative activity, DNA binding properties, cellular distribution} }

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


Uključenost u ostale bibliografske baze podataka::


  • CA Search (Chemical Abstracts)


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