Nalazite se na CroRIS probnoj okolini. Ovdje evidentirani podaci neće biti pohranjeni u Informacijskom sustavu znanosti RH. Ako je ovo greška, CroRIS produkcijskoj okolini moguće je pristupi putem poveznice www.croris.hr
izvor podataka: crosbi

The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA (CROSBI ID 268807)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

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, 92 (2019), 2; 249-258. doi: 10.5562/cca3542

Podaci o odgovornosti

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

engleski

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

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.

non-covalent binding to polynucleotides ; oligopeptides ; quinone methide precursors

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

Podaci o izdanju

92 (2)

2019.

249-258

objavljeno

0011-1643

1334-417X

10.5562/cca3542

Povezanost rada

Kemija

Poveznice
Indeksiranost