Synlett 2024; 35(06): 691-697
DOI: 10.1055/a-2201-3756
cluster
Special Issue to Celebrate the Centenary Year of Prof. Har Gobind Khorana

Fluorescent 2′-Deoxyuridine (dU) Analogue: Tropolonyl triazolyl-dU (tt-dU) Exhibits Solvatochromism/HeLa Cell Internalization and Its Triphosphate (tt-dUTP) Is Incorporated into DNA Enzymatically

Sagarika Meher
a   School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, Jatani-752050, Odisha, India
b   Homi Bhabha National Institute (HBNI), Training School Complex, Anushaktinagar, Mumbai, 400094, India
,
Chandrasekhar Reddy Gade
a   School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, Jatani-752050, Odisha, India
b   Homi Bhabha National Institute (HBNI), Training School Complex, Anushaktinagar, Mumbai, 400094, India
,
a   School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, Jatani-752050, Odisha, India
b   Homi Bhabha National Institute (HBNI), Training School Complex, Anushaktinagar, Mumbai, 400094, India
› Author Affiliations
This project has been supported by SERB-New Delhi core research grant (grant number: CRG/2020/001028).


Abstract

This era has witnessed the development and extensive application of modified nucleosides, including fluorescent nucleosides that clinically served humankind. Most fluorescent nucleoside analogues are derived from benzenoid aromatic scaffolds. However, the non-benzenoid aromatic moiety, tropolone, which exhibits unique hydrogen bonding and metal chelating properties, also occurs in nature. Recently, we introduced the tropolone unit at deoxyuridine through an ethyne linker and prepared its DNA analogues, which are fluorescent. This report describes the synthesis of a new troponyl triazolyl-dU (tt-dU) analogue, possessing a triazolyl linker, through click chemistry. tt-dU exhibits fluorescence with solvatochromism and enters into Hela cells without any cytotoxicity. Its triphosphate (tt-dUTP) was also synthesized and incorporated enzymatically into DNA, as shown in primer extension experiments. The unique photophysical properties and metal-chelating ability of the tropolone group make tt-dU a promising modified nucleoside.

Supporting Information



Publication History

Received: 27 July 2023

Accepted after revision: 30 October 2023

Accepted Manuscript online:
30 October 2023

Article published online:
27 November 2023

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