Fluorinated N-quinoxaline-based boron complexes: Synthesis, photophysical properties, and selective DNA/BSA biointeraction

A series of six examples of 1,1-difluoro-3,5-diaryl-1H [1,2,3,5] oxadiazaborinino[3,4-alpha]quinoxalin-11-ium-1-uides as a new N-quinoxaline-based boron complex with variable structures was synthesized at 65-70% yields from the reaction of the respective N-(3-arylquinoxalin-2-yl)benzamides with BF3 center dot & nbsp;Et2O - in which aryl = phenyl, 4-ClC6H4, 4-CH3C6H4, and 4-NMe2C6H4. All new benzamides and BF2-complexes were fully characterized by (1) H-, (13) C, (19) F-, and B-11-NMR spectroscopy and single-crystal X-ray diffraction. Moreover, the photophysical properties, TD-DFT analysis, DNA and BSA-binding experiments, and molecular docking studies for these new organoboron complexes were studied. The new BF2-heterocycles demonstrated to be weak generators of (1) O (2) , although their solutions at 5.0 mu M showed great photostability over the investigated irradiation. Additionally, the results of the DNA and BSA-binding studies indicated that the greatest interactions were selective in the minor groove of DNA and by the tryptophan site in the BSA albumin pocket. (c) 2022 Elsevier B.V. All rights reserved.

Automated summary

A series of new N-quinoxaline-based boron complexes have been successfully synthesized and characterized. These compounds demonstrated weak generation of (1)O(2) but showed excellent photostability under irradiation. Furthermore, selective interactions with DNA and BSA were observed in binding studies.