Napredna pretraga

Pregled bibliografske jedinice broj: 1018745

The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA


Erben, Antonija; Matić, Josipa; Basarić, Nikola; Piantanida, Ivo
The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA // Croatica chemica acta (2019) doi:10.5562/cca3542 (znanstveni, prihvaćen)


Naslov
The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA

Autori
Erben, Antonija ; Matić, Josipa ; Basarić, Nikola ; Piantanida, Ivo

Vrsta, podvrsta
Radovi u časopisima, znanstveni

Izvornik
Croatica chemica acta (2019)

Status rada
Prihvaćen

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


Projekt / tema
HRZZ-IP-2013-11-1477 - Višenamjensko očitavanje DNA / RNA sekundarne strukture molekularnim kemijskim senzorima (Ivo Piantanida, )
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )

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


Citati