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Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties

The propargylamide of N3-Pom-protected 5-(perylen-3-ylethynyl)uracil acetic acid, a universal precursor, was used in a CuAAC click reaction for the synthesis of several derivatives, including three ramified molecules with high activities against tick-borne encephalitis virus (TBEV). Pentaerythritol-...

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Autores principales: Sapozhnikova, Ksenia A., Slesarchuk, Nikita A., Orlov, Alexey A., Khvatov, Evgeny V., Radchenko, Eugene V., Chistov, Alexey A., Ustinov, Alexey V., Palyulin, Vladimir A., Kozlovskaya, Liubov I., Osolodkin, Dmitry I., Korshun, Vladimir A., Brylev, Vladimir A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070374/
https://www.ncbi.nlm.nih.gov/pubmed/35531032
http://dx.doi.org/10.1039/c9ra06313g
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author Sapozhnikova, Ksenia A.
Slesarchuk, Nikita A.
Orlov, Alexey A.
Khvatov, Evgeny V.
Radchenko, Eugene V.
Chistov, Alexey A.
Ustinov, Alexey V.
Palyulin, Vladimir A.
Kozlovskaya, Liubov I.
Osolodkin, Dmitry I.
Korshun, Vladimir A.
Brylev, Vladimir A.
author_facet Sapozhnikova, Ksenia A.
Slesarchuk, Nikita A.
Orlov, Alexey A.
Khvatov, Evgeny V.
Radchenko, Eugene V.
Chistov, Alexey A.
Ustinov, Alexey V.
Palyulin, Vladimir A.
Kozlovskaya, Liubov I.
Osolodkin, Dmitry I.
Korshun, Vladimir A.
Brylev, Vladimir A.
author_sort Sapozhnikova, Ksenia A.
collection PubMed
description The propargylamide of N3-Pom-protected 5-(perylen-3-ylethynyl)uracil acetic acid, a universal precursor, was used in a CuAAC click reaction for the synthesis of several derivatives, including three ramified molecules with high activities against tick-borne encephalitis virus (TBEV). Pentaerythritol-based polyazides were used for the assembly of molecules containing 2⋯4 antiviral 5-(perylen-3-ylethynyl)uracil scaffolds, the first examples of polyvalent perylene antivirals. Cluster compounds showed enhanced absorbance, however, their fluorescence was reduced due to self-quenching. Due to the solubility issues, Pom group removal succeeded only for compounds with one peryleneethynyluracil unit. Four compounds, including one ramified cluster 9f, showed remarkable 1⋯3 nM EC(50) values against TBEV in cell culture.
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spelling pubmed-90703742022-05-05 Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties Sapozhnikova, Ksenia A. Slesarchuk, Nikita A. Orlov, Alexey A. Khvatov, Evgeny V. Radchenko, Eugene V. Chistov, Alexey A. Ustinov, Alexey V. Palyulin, Vladimir A. Kozlovskaya, Liubov I. Osolodkin, Dmitry I. Korshun, Vladimir A. Brylev, Vladimir A. RSC Adv Chemistry The propargylamide of N3-Pom-protected 5-(perylen-3-ylethynyl)uracil acetic acid, a universal precursor, was used in a CuAAC click reaction for the synthesis of several derivatives, including three ramified molecules with high activities against tick-borne encephalitis virus (TBEV). Pentaerythritol-based polyazides were used for the assembly of molecules containing 2⋯4 antiviral 5-(perylen-3-ylethynyl)uracil scaffolds, the first examples of polyvalent perylene antivirals. Cluster compounds showed enhanced absorbance, however, their fluorescence was reduced due to self-quenching. Due to the solubility issues, Pom group removal succeeded only for compounds with one peryleneethynyluracil unit. Four compounds, including one ramified cluster 9f, showed remarkable 1⋯3 nM EC(50) values against TBEV in cell culture. The Royal Society of Chemistry 2019-08-20 /pmc/articles/PMC9070374/ /pubmed/35531032 http://dx.doi.org/10.1039/c9ra06313g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Sapozhnikova, Ksenia A.
Slesarchuk, Nikita A.
Orlov, Alexey A.
Khvatov, Evgeny V.
Radchenko, Eugene V.
Chistov, Alexey A.
Ustinov, Alexey V.
Palyulin, Vladimir A.
Kozlovskaya, Liubov I.
Osolodkin, Dmitry I.
Korshun, Vladimir A.
Brylev, Vladimir A.
Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
title Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
title_full Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
title_fullStr Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
title_full_unstemmed Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
title_short Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
title_sort ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070374/
https://www.ncbi.nlm.nih.gov/pubmed/35531032
http://dx.doi.org/10.1039/c9ra06313g
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