Naphthalene Diimide Bis-guanidinio-carbonyl-pyrrole As a PH-switchable Threading DNA Intercalator

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2020 Sep 28

PMID 32983268

Citations 1

Authors

Poulami Jana

Filip Supljika

Carsten Schmuck

Ivo Piantanida

Affiliations

Soon will be listed here.

Abstract

A novel naphthalene diimde analogue (NDI) equipped at the imide positions with two guanidinio-carbonyl-pyrrole (GCP) pendant arms interacted significantly stronger with ds-DNA at pH 5 than at pH 7, due to reversible protonation of the GCP arms. This was consequence of a pH-switchable threading intercalation into ds-DNAs only at pH 5, while at neutral conditions (pH 7) NDI-GCP switched to the DNA minor groove binding. Intriguingly, NDI-GCP was at both pH values studied bound to the ds-RNA major groove, still showing a higher affinity and thermal denaturation effect at pH 5 due to GCP protonation. At excess over the DNA/RNA conjugate NDI-GCP showed also aggregation along the ds-polynucleotide and AFM and DLS demonstrated that NDI-GCP has pronounced ds-DNA condensation ability.

Citing Articles

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Erben A, Sviben I, Mihaljevic B, Piantanida I, Basaric N Molecules. 2021; 26(14).

PMID: 34299591 PMC: 8306964. DOI: 10.3390/molecules26144315.

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