Aryliden-imidazolones as fluorogens of NanoLuc protein

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Abstract

We report a series of orto-substituted aryliden-imidazolones and their derivatives containing styrene moiety. These compounds can be used like ligands of NanoLuc protein. Together with NanoLuc this fluorogens can be used for genetically encoded labeling in fluorescence microscopy, as demonstrated by staining HEK293 cells.

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About the authors

E. R. Zaitseva

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: nsbaleeva@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

Yu. А. Bogdanova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: nsbaleeva@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

N. S. Baleeva

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Author for correspondence.
Email: nsbaleeva@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. Y. Smirnov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: nsbaleeva@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

M. S. Baranov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: nsbaleeva@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

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Supplementary files

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1. JATS XML
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2. Scheme 1. Structures of luciferase substrates, chromophores of fluorescent proteins, our previously proposed fluorogens for the NanoLuc protein and the fluorogen for the NanoLuc protein obtained in this work.

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3. Scheme 2. Scheme for the synthesis of compounds (I) and (II).

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4. Fig. 1. Microphotographs of living HEK293 cells expressing the nuclear-localized H2B-NanoLuc construct in the presence of 5 μM compound (IIc): (a) – image obtained in transmitted light; (b) – the same area visualized using the TxRed cube. Scale bar—10 µm.

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