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Impact of α-hydrazino acids embedded in short fluorescent peptides on peptide interaction with DNA and RNA

Suć, Josipa; Tumir, Lidija-Marija; Glavaš-Obrovac, Ljubica; Jukić, Marijana; Piantanida, Ivo; Jerić, Ivanka (2016) Impact of α-hydrazino acids embedded in short fluorescent peptides on peptide interaction with DNA and RNA. Organic and Biomolecular Chemistry, 14 (21). pp. 4865-4874. ISSN 1477-0520

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Abstract

Series of novel hydrazino-based peptidomimetics and analogues comprising N-terminal lysine and C-terminal phenanthridinyl-L-alanine were prepared. Presented results demonstrate up till now unknown possibility to finely modulate peptide interaction with DNA/RNA by α-hydrazino group insertion and how different positioning of two α-hydrazino groups in peptide controls binding to various double stranded and single stranded DNA and RNA. All peptidomimetics bind with 1-10 micromolar affinity to ds-DNA/RNA, whereby binding mode is combination of electrostatic interactions and hydrophobic interactions within DNA/RNA grooves. Insertion of α-hydrazino group into peptide systematically decreased its fluorimetric response to DNA/RNA binding in line: mono-hydrazino<alternating-hydrazino<sequential-hydrazino group. Binding studies to ss-polynucleotides suggest intercalation of phenanthridine between polynucleotide bases, whereby affinity and fluorimetric response decrease with the number of α-hydrazino groups in peptide sequence. Particularly interesting was interaction of two sequential α-hydrazino acids-peptidomimetic with poly rG, characterised by specific strong increase of CD bands, while all other peptide/ssRNA combinations gave only CD-bands decrease. All mentioned interactions could also be reversibly controlled by pH, due to the protonation of the fluorophore.

Item Type: Article
Additional Information: This work has been supported by Croatian Science Foundation projects 1477 and 3102. The support from FP7-REGPOT-2012-2013-1 project, Grant Agreement Number 316289 – InnoMol is gratefully acknowledged.
Uncontrolled Keywords: hydrazino; peptidomimetic; DNA/RNA; interactions
Subjects: NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Višekomponentne reakcije u sintezi peptidnih mimetika-MIMICRyIVANKA JERIĆIP-09-2014-3102HRZZ
Višenamjensko očitavanje DNA / RNA sekundarne strukture molekularnim kemijskim senzorima-DNA/RNA-MolSenseIvo PiantanidaIP-11-2013-1477HRZZ
FP7-REGPOT-2012-2013-1 project Enhancement of the Innovation Potential in SEE through new Molecular Solutions in Research and Development-INNOMOLUNSPECIFIED316289EK
Depositing User: Ivanka Jerić
Date Deposited: 16 Dec 2016 12:45
Last Modified: 06 Apr 2017 07:36
URI: http://fulir.irb.hr/id/eprint/3186
DOI: 10.1039/c6ob00425c

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