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Tropolone-Conjugated DNA: A Fluorescent Thymidine Analogue Exhibits Solvatochromism,Enzymatic Incorporation into DNA and HeLa Cell Internalization |
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| Authors: | Sagarika Meher Dr Chandrasekhar Reddy Gade Dr Nagendra K Sharma |
| Affiliation: | 1. School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, Jatani, 752050 Odisha, India
Homi Bhabha National Institute (HBNI), Training School Complex, Anushaktinagar, Mumbai, 400094 India These authors contributed equally to this work.;2. School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, Jatani, 752050 Odisha, India |
| Abstract: | Tropolone is a non-benzenoid aromatic scaffold with unique photophysical and metal-chelating properties. Recently, it has been conjugated with DNA, and the photophysical properties of this conjugate have been explored. Tropolonyl-deoxyuridine (tr-dU) is a synthetic fluorescent DNA nucleoside analogue that exhibits pH-dependent emissions. However, its solvent-dependent fluorescence properties are unexplored owing to its poor solubility in most organic solvents. It would be interesting to incorporate it into DNA primer enzymatically. This report describes the solvent-dependent fluorescence properties of the silyl-derivative, and enzymatic incorporation of its triphosphate analogue. For practical use, its cell-internalization and cytotoxicity are also explored. tr-dU nucleoside was found to be a potential analogue to design DNA probes and can be explored for various therapeutic applications in the future. |
| Keywords: | cell-internalization DNA DNA polymerases fluorescent nucleosides tropolone |