Aminocoumaranones as chemiluminescence indicators of the urease activity and hydrogen peroxide

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Abstract

We report a series of 3-aminocoumaranones possess significant chemiluminescence under various conditions. The introduce of the electron-donor groups in the coumaranone moiety and increasing of the conjugated π-system of coumaranones allow to shift 30–40 nm of the chemiluminescence maxima to the long-wavelength region. We showed that some 3-aminocoumaranones can be used for detecting of the urease and hydrogen peroxide.

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About the authors

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

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. S. Mishin

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

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

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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2. Scheme 1. The mechanism of chemiluminescence of coumaranones under the action of oxygen, as well as a possible mechanism of chemiluminescence under the influence of ureases.

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3. Scheme 2. Scheme for the synthesis of compounds (I–VII).

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4. Fig. 1. Normalized chemiluminescence spectra of compounds (V–VII) in acetonitrile after adding 0.1% DBU.

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5. Fig. 2. Graphs of the decline in chemiluminescence of compounds (V–VII) in acetonitrile after adding 0.1% DBU.

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