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

Org Biomol Chem. 2022 May 4;20(17):3598-3604. doi: 10.1039/d2ob00372d.

Authors

M Stahlberger¹, O Steinlein², C R Adam¹, M Rotter¹, J Hohmann¹, M Nieger³, B Köberle², S Bräse^{1

4}

Affiliations

¹ Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany. [email protected].
² Institute of Applied Biosciences, Department of Food Chemistry and Toxicology, Karlsruhe Institute of Technology (KIT), Adenauerring 20, 76131 Karlsruhe, Germany.
³ Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio 1), 00014, Finland.
⁴ Institute of Biological and Chemical Systems - IBCS-FMS, Karlsruhe Institute of Technology (KIT), Herman-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.

PMID: 35420107
DOI: 10.1039/d2ob00372d

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
DNA*
Electrophoresis, Polyacrylamide Gel
Electrophoretic Mobility Shift Assay
Isoquinolines* / chemistry
Plasmids

Substances

Isoquinolines
DNA