Pregled bibliografske jedinice broj: 1018745
The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA
The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA // Croatica chemica acta, 92 (2019), 2; 249-258 doi:10.5562/cca3542 (međunarodna recenzija, članak, znanstveni)
CROSBI ID: 1018745 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA
Autori
Erben, Antonija ; Matić, Josipa ; Basarić, Nikola ; Piantanida, Ivo
Izvornik
Croatica chemica acta (0011-1643) 92
(2019), 2;
249-258
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
non-covalent binding to polynucleotides ; oligopeptides ; quinone methide precursors
Sažetak
Dipeptide 4 containing two unnatural amino acids, a modified tyrosine and a phenanthridine derivative, was synthesized. Binding of the dipeptide to a series of polynucleotides including ct-DNA, poly A - poly U, poly (dAdT)2, poly dG - poly dC and poly (dGdC)2 was investigated by thermal denaturation experiments, fluorescence spectroscopy and circular dichroism. Thermal denaturation experiments indicated that dipeptide 4 at pH 5.0, when phenanthridine is protonated, stabilizes ds-DNA, whereas it destabilizes ds-RNA. At pH 7.0, when the phenanthridine is not protonated, effects of 4 to the polynucleotide melting temperatures are negligible. At pH 5.0, dipeptide 4 stabilized DNA double helices, and the changes in the CD spectra suggest different modes of binding to ds-DNA, most likely the intercalation to poly dG- poly dC and non-specific binding in grooves of other DNA polynucleotides. At variance to ds-DNA, addition of 4 destabilized ds-RNA against thermal denaturation and CD results suggest that addition of 4 probably induced dissociation of ds-RNA into ss-RNA strands due to preferred binding to ss-RNA. Thus, 4 is among very rare small molecules that stabilize ds-DNA but destabilize ds-RNA. However, fluorescence titrations with all polynucleotides at both pH values gave similar binding affinity (log Ka ≈ 5), indicating nonselective binding. Preliminary photochemical experiments suggest that dipeptide 4 reacts in the photochemical reaction, which affects polynucleotides chirality, presumably via quinone methide intermediates that alkylate DNA.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
POVEZANOST RADA
Projekti:
IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (SupraPhotoE) (Basarić, Nikola, HRZZ - 2014-09) ( CroRIS)
HRZZ-IP-2013-11-1477 - Višenamjensko očitavanje DNA/RNA sekundarne strukture molekularnim kemijskim senzorima (DNA/RNA-MolSense) (Piantanida, Ivo, HRZZ - 2013-11) ( CroRIS)
EK-HR.3.2.01.-0254 - Jačanje kapaciteta u medicinskoj kemiji i istraživanju bioaktivnih sustava (Piantanida, Ivo, EK ) ( CroRIS)
Ustanove:
Institut "Ruđer Bošković", Zagreb
Citiraj ovu publikaciju:
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