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Issue 27, 2020
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Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA

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Abstract

A series of aryl-substituted guanidines revealed a pKa of about 10 in aqueous medium, thus positioning themselves between the more basic aliphatic guanidines (pKa > 13) and the acidic guanidinocarbonyl-pyrrole (pKa 6). The study revealed that for the biorelevant (micromolar) affinity toward ds-DNA and ds-RNA, the minimal size of the aryl-unit is anthracene. Further aryl-increase (pyrene, porphyrin) did not result in a stronger affinity toward ds-DNA/RNA, nor give significant thermal stabilisation of the DNA/RNA double helix, thus suggesting that aromatic stacking interactions between the compounds and DNA/RNA are not the dominant binding interaction. Generally, the results suggested that aryl-guanidines bind to DNA/RNA grooves by a combination of hydrophobic, electrostatic, H-bonding and van der Waals interactions, whereby fluorescence of the two largest aromatics (pyrene, porphyrin) was highly sensitive in the fine probing of the DNA/RNA groove properties. In addition, pyrene and porphyrin analogues at excess polynucleotide binding sites aggregated within the polynucleotide groove, yielding fine recognition between various ds-DNA and ds-RNA by induced circular dichroism signals.

Graphical abstract: Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA

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Supplementary files

Article information


Submitted
15 Apr 2020
Accepted
09 Jun 2020
First published
10 Jun 2020

New J. Chem., 2020,44, 11537-11545
Article type
Paper

Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA

M. Đud, Z. Glasovac, D. Margetić and I. Piantanida, New J. Chem., 2020, 44, 11537
DOI: 10.1039/D0NJ01879A

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