8-Styryl-substituted coralyne derivatives as DNA binding fluorescent probes

RSC Advances
P M PithanY Voß

Abstract

Six new 8-styryl-substituted coralyne derivatives 4a-f were synthesized from coralyne (2) by a base catalysed Knoevenagel type reaction. It was shown by photometric and fluorimetric titrations of double stranded and quadruplex DNA to 4b-d as well as by fluorimetric DNA denaturation experiments that these ligands bind to DNA with different binding modes at varying ligand-DNA ratios (LDR). Specifically, the addition of DNA caused initially a hypochromic effect in absorbance and, at a particular LDR, the development of a new red shifted absorption band with a hyperchromic effect. Furthermore, 4b-d induced a significant and selective stabilization of quadruplex DNA towards unfolding (ΔTm = 31.6-32.9 °C at LDR = 5), which is even more pronounced as compared to the parent compound coralyne (2). Most notably, the addition of DNA to the dimethylamino-substituted derivative 4b leads to a new, strongly red-shifted emission band at 695 nm. Hence, this derivative is a fluorescent probe that changes its fluorescence colour from green to red in the presence of DNA and even allows the fluorimetric analysis of living cells by staining of the nucleoli.

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Citations

May 29, 2020·Beilstein Journal of Organic Chemistry·Phil M PithanHeiko Ihmels
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Peter Jonas Wickhorst, Heiko Ihmels

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Methods Mentioned

BETA
NMR
fluorescence microscopy

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