Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
Sapozhnikova K. A., Slesarchuk N. A., Orlov A. A., Khvatov E. V., Radchenko E. V., Chistov A. A., Ustinov A. V., Palyulin V. A., Kozlovskaya L. I., Osolodkin D. I., Korshun V. A., Brylev V. A.
RSC Advances
Vol.9, Issue45, P. 26014-26023
Опубликовано: 2019
Тип ресурса: Статья
Аннотация:
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 EC50 values against TBEV in cell culture. © The Royal Society of Chemistry 2019.
Ключевые слова:
Acetic acid; Cell culture; Molecules; pH; Synthesis (chemical); Viruses; Absorbances; Antiviral properties; Antivirals; Click reaction; Cluster compounds; High activity; Perylenes; Self-quenching; Aromatic compounds
Язык текста: Английский
ISSN: 2046-2069
Sapozhnikova K. A.
Slesarchuk N. A.
Orlov A. A. Anton Anatolyevich 1991-
Khvatov E. V.
Radchenko E. V.
Chistov A. A.
Ustinov A. V.
Palyulin V. A.
Kozlovskaya L. I. Lyubov` Igorevna 1984-
Osolodkin D. I. Dmitrij Ivanovich 1985-
Korshun V. A.
Brylev V. A.
Сапожникова К. А.
Слесарчук Н. А.
Орлов А. А. Антон Анатольевич 1991-
Хватов Е. В.
Радченко Е. В.
Чистов А. А.
Устинов А. В.
Палюлин В. А.
Козловская Л. И. Любовь Игоревна 1984-
Осолодкин Д. И. Дмитрий Иванович 1985-
Коршун В. А.
Брyлев В. А.
Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties
Текст визуальный непосредственный
RSC Advances
Vol.9, Issue45 P. 26014-26023
2019
Статья
Acetic acid Cell culture Molecules pH Synthesis (chemical) Viruses Absorbances Antiviral properties Antivirals Click reaction Cluster compounds High activity Perylenes Self-quenching Aromatic compounds
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 EC50 values against TBEV in cell culture. © The Royal Society of Chemistry 2019.