The phenanthridine-modified tyrosine dipeptide
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...
| Permalink: | http://skupni.nsk.hr/Record/nsk.NSK01001074261/Details |
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| Matična publikacija: |
Croatica chemica acta (Online) 92 (2019), 2 ; str. 249-258 |
| Glavni autori: | Erben, Antonija (Author), Matić, Josipa, kemijska tehnologinja, Basarić, Nikola, Piantanida, Ivo |
| Vrsta građe: | e-članak |
| Jezik: | eng |
| Predmet: | |
| Online pristup: |
https://doi.org/10.5562/cca3542 Hrčak |
| LEADER | 03048naa a22003854i 4500 | ||
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| 001 | NSK01001074261 | ||
| 003 | HR-ZaNSK | ||
| 005 | 20220214173501.0 | ||
| 006 | m d | ||
| 007 | cr|||||||||||| | ||
| 008 | 200916s2019 ci d |o |0|| ||eng | ||
| 024 | 7 | |2 doi |a 10.5562/cca3542 | |
| 035 | |a (HR-ZaNSK)001074261 | ||
| 040 | |a HR-ZaNSK |b hrv |c HR-ZaNSK |e ppiak | ||
| 041 | 0 | |a eng |b eng | |
| 042 | |a croatica | ||
| 044 | |a ci |c hr | ||
| 080 | 1 | |a 577 |2 2011 | |
| 080 | 1 | |a 615 |2 2011 | |
| 100 | 1 | |a Erben, Antonija |4 aut | |
| 245 | 1 | 4 | |a The phenanthridine-modified tyrosine dipeptide |h [Elektronička građa] : |b synthesis and non-covalent binding to DNA and RNA / |c Antonija Erben, Josipa Matić, Nikola Basarić, Ivo Piantanida. |
| 300 | |b Graf. prikazi. | ||
| 504 | |a Bibliografija: 39 jed. | ||
| 504 | |a Summary. | ||
| 520 | |a 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. | ||
| 653 | 0 | |a Fenantridin |a Deoksiribonukleinska kiselina |a DNK |a Ribonukleinska kiselina |a RNK |a Polinukleotidi |a Oligopeptidi |a Tirozin-dipeptid |a Kinon-metidi |a Kemijska sinteza |a Protutumorski učinak |a Selektivnost |a Fotokemijske reakcije | |
| 700 | 1 | |a Matić, Josipa, |c kemijska tehnologinja |4 aut | |
| 700 | 1 | |a Basarić, Nikola |4 aut | |
| 700 | 1 | |a Piantanida, Ivo |4 aut | |
| 773 | 0 | |t Croatica chemica acta (Online) |x 1334-417X |g 92 (2019), 2 ; str. 249-258 |w nsk.(HR-ZaNSK)000255036 | |
| 981 | |b Be2019 |b B05/19 | ||
| 998 | |b dalo2010 | ||
| 856 | 4 | 0 | |u https://doi.org/10.5562/cca3542 |
| 856 | 4 | 0 | |u https://hrcak.srce.hr/226261 |y Hrčak |
| 856 | 4 | 1 | |y Digitalna.nsk.hr |