Jump to main content
Jump to site search


The reactive group effects on the photophysical and biological properties of the 2-phenyl-1H-phenanthro[9,10-d]imidazole derivatives as fluorescence markers

Abstract

The presented research focuses on the theoretical design and procedures for preparing protein conjugates with markers. For this purpose a series of phenanthroimidazole analogous compounds (PhI) was designed and investigated by means of the first principle methods. Through the judicious choice of cross-linking reagents and the selection of reactive groups, five target fluorescent probes were selected, one of which was previously described using in vitro tests. For the best cognitive purpose and understanding of the nature of protein conjugation, studies describe the impact of the reactive group on the solvatochromism, polarity of the charge transfer of the excited states, Stokes' shift, ECD spectra and two-photon cross sections. The research is also extended to the analysis of PhI-Concanavalin A biocomplexes and changes in photophysical properties after conjugation. In order to identify the valuable alternatives to commercial probes designed for cellular labelling in biological and biomedical imaging, biological properties were described such as ecotoxicity, LogP and LogBCF and the dye-protein binding was quantified by means of AutoDock and molecular dynamics simulations. The study showed that for phenanthroimidazole derivatives the factor limiting the possibility of use in medical imaging will be the presence of a pyridyl disulfides group while the introduction of the N-hydroxysuccinimide ester may be used to create stable and valuable fluorescent probes with a wide spectrum for applications in biomedical imaging.

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Mar 2018, accepted on 16 Apr 2018 and first published on 16 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00729B
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
  •   Request permissions

    The reactive group effects on the photophysical and biological properties of the 2-phenyl-1H-phenanthro[9,10-d]imidazole derivatives as fluorescence markers

    P. Krawczyk, P. Czeleń and P. Cysewski, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB00729B

Search articles by author

Spotlight

Advertisements