DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides

Matić, Josipa; Šupljika, Filip; Tandarić, Tana; Dukši, Marko; Piotrowski, Patryciusz; Vianello, Robert; Brozović, Anamaria; Piantanida, Ivo; Schmuck, Carsten; Radić Stojković, Marijana (2019) DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides. International journal of biological macromolecules, 134 . pp. 422-434. ISSN 0141-8130

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Abstract

The binding of four phenanthridine-guanidine peptides to DNA/RNA was evaluated via spectrophotometric/microcalorimetric methods and computations. The minor structural modifications-the type of the guanidine group (pyrrole guanidine (GCP) and arginine) and the linker length (presence or absence of glycine)- greatly affected the conformation of compounds and consequently the binding to double- (ds-) and single- stranded (ss-) polynucleotides. GCP peptide with shorter linker was able to distinguish between RNA (A-helix) and DNA (Bhelix) by different circular dichroism response at 295 nm and thus can be used as a chiral probe. Opposed to the dominant stretched conformation of GCP peptide with shorter linker, the more flexible and longer linker of its analogue enabled the molecule to adopt the intramolecularly stacked form which resulted in weaker yet selective binding to DNA. Beside efficient organization of ss-polynucleotide structures, GCP peptide with shorter linker bound stronger to ss-DNA/RNA compared to arginine peptides which emphasize the importance of GCP unit.

Item Type:	Article
Uncontrolled Keywords:	DNA/RNA recognition ; Pyrrole guanidine peptide ; DNA/RNA chiral probe
Subjects:	NATURAL SCIENCES NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Dizajn i sinteza novih dušikovih heterocikličkih fluorofora i fluorescentnih nanomaterijala kao kemijskih senzora za pH i metalne ione-iNFiNiTE–SENS Robert Vianello IP-2014-09-3386 HRZZ Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina-BioMultiChromoProbes Ivo Piantanida IP-2018-01-5475 HRZZ Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavima-DNARNAHyB-MolBio Marijana Radić Stojković IP-2018-01-4694 HRZZ
Depositing User:	Marijana Radić Stojković
Date Deposited:	04 Dec 2020 11:47
URI:	http://fulir.irb.hr/id/eprint/6052
DOI:	10.1016/j.ijbiomac.2019

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