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Issue 21, 2016
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The impact of α-hydrazino acids embedded in short fluorescent peptides on peptide interactions with DNA and RNA

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Abstract

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

Graphical abstract: The impact of α-hydrazino acids embedded in short fluorescent peptides on peptide interactions with DNA and RNA

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Supplementary files

Article information


Submitted
24 Feb 2016
Accepted
25 Apr 2016
First published
26 Apr 2016

Org. Biomol. Chem., 2016,14, 4865-4874
Article type
Paper

The impact of α-hydrazino acids embedded in short fluorescent peptides on peptide interactions with DNA and RNA

J. Suć, L. Tumir, L. Glavaš-Obrovac, M. Jukić, I. Piantanida and I. Jerić, Org. Biomol. Chem., 2016, 14, 4865
DOI: 10.1039/C6OB00425C

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