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New dicationic derivatives of dibenzotetraaza[14]annulene: tuning of the DNA/RNA binding properties


Pawlica, Dariusz; Radić Stojković, Marijana; Dudek, Łukasz; Piantanida, Ivo; Sieroń, Lesław; Eilmes, Julita
New dicationic derivatives of dibenzotetraaza[14]annulene: tuning of the DNA/RNA binding properties // Tetrahedron, 65 (2009), 20; 3980-3989 doi:10.1016/j.tet.2009.03.030 (međunarodna recenzija, članak, znanstveni)


Naslov
New dicationic derivatives of dibenzotetraaza[14]annulene: tuning of the DNA/RNA binding properties

Autori
Pawlica, Dariusz ; Radić Stojković, Marijana ; Dudek, Łukasz ; Piantanida, Ivo ; Sieroń, Lesław ; Eilmes, Julita

Izvornik
Tetrahedron (0040-4020) 65 (2009), 20; 3980-3989

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

Ključne riječi
Dibenzotetraaza[14]annulene; synthesis; crystal structure; DNA binding; UV/Vis titration; DNA thermal denaturation; ethidium bromide displacement

Sažetak
Four new water-soluble derivatives of dibenzotetraaza14]annulene have been synthesized bearing meso substituents different in structure and dimensions: 3-(N, N, N-trimethylammonium)propyl, 3-(N-pyridinium-1-yl)propyl, 2-[3-(N, N, N-trimethylammonium)propoxy]benzoyl and 2-[3-(N-pyridinium-1-yl)propoxy]benzoyl. The crystal structures of 3-(trimethylammonium)propyl and (N, N, N-trimethylammonium)propoxy]benzoyl derivatives have been determined by single crystal X-Ray analysis. According to the UV-Vis titrations, thermal denaturation experiments and ethidium bromide displacements assays all here presented compounds strongly interact with double stranded (ct-) DNA. The product equipped with 3-(trimethylammonium)propyl pendant groups and two positive charges interacts with DNA by one dominant binding mode, whereas other three derivatives revealed more complex mixed-type of non-covalent interactions. The results have been discussed in terms of dimensions, geometry and electronic properties of evaluated compounds on the basis of corresponding crystallographic data.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
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


Uključenost u ostale bibliografske baze podataka:


  • CA Search (Chemical Abstracts)


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