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Issue 20, 2018
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Reactive group effects on the photophysical and biological properties of 2-phenyl-1H-phenanthro[9,10-d]imidazole derivatives as fluorescent markers

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Abstract

The presented research focuses on the theoretical design and procedures for preparing protein conjugates with markers. For this purpose a series of phenanthroimidazole (PhI) analogous compounds was designed and investigated by means of 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 the protein conjugation, the studies describe the impact of the reactive group on the solvatochromism, the polarity of the charge transfer of the excited states, the Stokes’ shift, ECD spectra and two-photon cross sections. The research is also extended to an analysis of PhI–Concanavalin A biocomplexes and changes in photophysical properties after conjugation. In order to identify valuable alternatives to commercial probes designed for cellular labelling in biological and biomedical imaging, biological properties were described such as ecotoxicity, log P and log BCF, and dye–protein binding was quantified by means of AutoDock and molecular dynamics simulations. The study showed that for phenanthroimidazole derivatives the factor which limits the possibility of their use in medical imaging is the presence of a pyridyl disulfide group, while the introduction of an N-hydroxysuccinimide ester may be used to create stable and valuable fluorescent probes with a wide spectrum for applications in biomedical imaging.

Graphical abstract: Reactive group effects on the photophysical and biological properties of 2-phenyl-1H-phenanthro[9,10-d]imidazole derivatives as fluorescent markers

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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., 2018,16, 3788-3800
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    Reactive group effects on the photophysical and biological properties of 2-phenyl-1H-phenanthro[9,10-d]imidazole derivatives as fluorescent markers

    P. Krawczyk, P. Czeleń and P. Cysewski, Org. Biomol. Chem., 2018, 16, 3788
    DOI: 10.1039/C8OB00729B

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