Fluorescent annulated imidazo[4,5-c]isoquinolines via a GBB-3CR/imidoylation sequence – DNA-interactions in pUC-19 gel electrophoresis mobility shift assay

M. Stahlberger; O. Steinlein; C. R. Adam; M. Rotter; J. Hohmann; M. Nieger; B. Köberle; S. Bräse

doi:10.1039/D2OB00372D

Fluorescent annulated imidazo[4,5-c]isoquinolines via a GBB-3CR/imidoylation sequence – DNA-interactions in pUC-19 gel electrophoresis mobility shift assay†

M. Stahlberger,

^a O. Steinlein,^b C. R. Adam,^a M. Rotter,^a J. Hohmann,^a M. Nieger,^c B. Köberle^b and S. Bräse

*^ad

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
E-mail: braese@kit.edu

^b Institute of Applied Biosciences, Department of Food Chemistry and Toxicology, Karlsruhe Institute of Technology (KIT), Adenauerring 20, 76131 Karlsruhe, Germany

^c Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio 1), Finland

^d Institute of Biological and Chemical Systems – IBCS-FMS, Karlsruhe Institute of Technology (KIT), Herman-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany

Abstract

Herein we report the development of a sequential synthesis route towards annulated imidazo[4,5-c]isoquinolines comprising a GBB-3CR, followed by an intramolecular imidoylative cyclisation. X-Ray crystallography revealed a flat 3D structure of the obtained polyheterocycles. Thus, we evaluated their interactions with double-stranded DNA by establishing a pUC-19 plasmid-based gel electrophoresis mobility shift assay, revealing a stabilising effect on ds-DNA against strand-break inducing conditions.

Supplementary files

Article information

DOI: https://doi.org/10.1039/D2OB00372D
Article type: Paper
Submitted: 22 Feb 2022
Accepted: 06 Apr 2022
First published: 07 Apr 2022
This article is Open Access

Download Citation

Org. Biomol. Chem., 2022,20, 3598-3604

Permissions

Request permissions

Fluorescent annulated imidazo[4,5-c]isoquinolines via a GBB-3CR/imidoylation sequence – DNA-interactions in pUC-19 gel electrophoresis mobility shift assay

M. Stahlberger, O. Steinlein, C. R. Adam, M. Rotter, J. Hohmann, M. Nieger, B. Köberle and S. Bräse, Org. Biomol. Chem., 2022, 20, 3598 DOI: 10.1039/D2OB00372D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Organic & Biomolecular Chemistry

Fluorescent annulated imidazo[4,5-c]isoquinolines via a GBB-3CR/imidoylation sequence – DNA-interactions in pUC-19 gel electrophoresis mobility shift assay†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Fluorescent annulated imidazo[4,5-c]isoquinolines via a GBB-3CR/imidoylation sequence – DNA-interactions in pUC-19 gel electrophoresis mobility shift assay

Social activity

Search articles by author

Spotlight

Advertisements