2,5-Dimethoxy-benzylidene-rhodanine and its acyclic analogues as selective fluorogenic dyes for lipid droplets of living cells

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Abstract

We report about a series of arylidene-rhodanines and their acyclic analogues. The fluorescent properties of these substances were studied. We showed that the derivatives containing a 2,5-dimethoxybenzylidene fragment or similar groups are characterized by a noticeable variation in the fluorescence quantum yield depending on the properties of the medium. We discovered that two of the synthesized compounds – dimethoxy-benzylidene-rhodanine and dimethoxy-benzylidene-malononitrile – can be used as selective fluorogenic dyes for lipid droplets (adiposomes) of living cells for labeling under fluorescent microscopy conditions.

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About the authors

S. A. Krasnova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; National Research University Higher School of Economics

Author for correspondence.
Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Myasnitskaya 20, Moscow, 101000

Yu. A. Bogdanova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. I. Sokolov

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

Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

I. N. Myasnyanko

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

Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

A. Y. Smirnov

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

Email: svetlanakr2002@mail.ru
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: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

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2. Scheme 1. Synthesis of arylidene rhodanines (Ia–Io) and their acyclic analogues (II–V).

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3. Fig. 1. Microscopy of living HeLa Kyoto cells with the addition of 7 µM compound (In) (a–c) or 5 µM compound (III) (d–f). (a, d) – Fluorescence of samples of compounds (In) and (III), respectively, upon their penetration into lipid droplets in HeLa Kyoto cells; (b, e) – HeLa Kyoto cells in transmitted light; (c, f) – fluorescent signals of samples of compounds (In) and (III), respectively, superimposed on the image of cells in transmitted light. The scale bar in all cases corresponds to a length of 5 µm.

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