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Guanidiniocarbonyl-pyrrole-aryl derivatives : structure tuning for spectrophotometric recognition of specific DNA and RNA sequences and antiproliferative activity


Hernandez-Folgado, Laura; Baretić, Domagoj; Piantanida, Ivo; Marjanović, Marko; Kralj, Marijeta; Rehm, Thomas; Schmuck, Carsten
Guanidiniocarbonyl-pyrrole-aryl derivatives : structure tuning for spectrophotometric recognition of specific DNA and RNA sequences and antiproliferative activity // Chemistry : a European journal, 16 (2010), 10; 3036-3056 doi:10.1002/chem.200901999 (međunarodna recenzija, članak, znanstveni)


Naslov
Guanidiniocarbonyl-pyrrole-aryl derivatives : structure tuning for spectrophotometric recognition of specific DNA and RNA sequences and antiproliferative activity

Autori
Hernandez-Folgado, Laura ; Baretić, Domagoj ; Piantanida, Ivo ; Marjanović, Marko ; Kralj, Marijeta ; Rehm, Thomas ; Schmuck, Carsten

Izvornik
Chemistry : a European journal (0947-6539) 16 (2010), 10; 3036-3056

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

Ključne riječi
DNA/RNA binding ; intercalation ; molecular recognition ; antiproliferation

Sažetak
We present here a systematic study of different guanidiniocarbonyl-pyrrole-aryl derivatives designed to interact with DNA or RNA both by intercalation of an aromatic moiety into the base stack of the nucleotide as well as groove binding of a guanidinio-carbonyl pyrrole cation. We varied 1.) the size of the aromatic ring (benzene, naphthalene, pyrene and acridine), 2.) the length and flexibility of the linker connecting the two binding groups, as well as 3.) the total number of positive charges present at different pH values. The compounds and their interaction with DNA and RNA were studied by UV/Vis-, fluorescence and CD spectroscopy. Also the antiproliferative activity against human tumour cell lines was determined. Our studies show that efficient interaction with e.g. DNA requires a significantly large aromatic ring (pyrene) connected via a flexible linker to the pyrrole moiety. However, a positive charge as in 12 is also needed. Compound 12 allows for a base pair selective recognition of ds-DNA at physiological pH. The antiproliferative activity correlates with the binding affinity of these compounds towards DNA suggesting that the biological effect is most likely due to DNA binding.

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, )

Ustanove
Institut "Ruđer Bošković", 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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