Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues
The synthesis of novel peptide conjugates of N-substituted-tetrahydro-γ-carbolines has been performed using the sequence of the Ugi multicomponent reaction and Cu(I)-catalyzed click chemistry. The effect of obtained γ-carboline–peptide conjugates on the rat liver mitochondria was evaluated. It was f...
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doaj-c84cac97a138403c9cd92165e79f80852021-02-02T02:31:40ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-01-0110115516210.3762/bjoc.10.131860-5397-10-13Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residuesNadezhda V. Sokolova0Valentine G. Nenajdenko1Vladimir B. Sokolov2Daria V. Vinogradova3Elena F. Shevtsova4Ludmila G. Dubova5Sergey O. Bachurin6Department of Chemistry, Moscow State University, Leninskie Gory 1, Moscow, 119992, RussiaDepartment of Chemistry, Moscow State University, Leninskie Gory 1, Moscow, 119992, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, RussiaThe synthesis of novel peptide conjugates of N-substituted-tetrahydro-γ-carbolines has been performed using the sequence of the Ugi multicomponent reaction and Cu(I)-catalyzed click chemistry. The effect of obtained γ-carboline–peptide conjugates on the rat liver mitochondria was evaluated. It was found that all compounds in the concentration of 30 µM did onot induce depolarization of mitochondria but possessed some inhibitory effect on the mitochondria permeability transition. The original N-substituted-tetrahydro-γ-carbolines containing an terminal alkyne group demonstrated a high prooxidant activity, whereas their conjugates with peptide fragments slightly inhibited both autooxidation and the t-BHP-induced lipid peroxidation.https://doi.org/10.3762/bjoc.10.13mitochondrial membrane potentialmitochondrial permeability transitionmulticomponentpeptidestetrahydro-γ-carbolinesUgi multicomponent reaction |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Nadezhda V. Sokolova Valentine G. Nenajdenko Vladimir B. Sokolov Daria V. Vinogradova Elena F. Shevtsova Ludmila G. Dubova Sergey O. Bachurin |
spellingShingle |
Nadezhda V. Sokolova Valentine G. Nenajdenko Vladimir B. Sokolov Daria V. Vinogradova Elena F. Shevtsova Ludmila G. Dubova Sergey O. Bachurin Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues Beilstein Journal of Organic Chemistry mitochondrial membrane potential mitochondrial permeability transition multicomponent peptides tetrahydro-γ-carbolines Ugi multicomponent reaction |
author_facet |
Nadezhda V. Sokolova Valentine G. Nenajdenko Vladimir B. Sokolov Daria V. Vinogradova Elena F. Shevtsova Ludmila G. Dubova Sergey O. Bachurin |
author_sort |
Nadezhda V. Sokolova |
title |
Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues |
title_short |
Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues |
title_full |
Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues |
title_fullStr |
Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues |
title_full_unstemmed |
Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues |
title_sort |
synthesis and biological activity of n-substituted-tetrahydro-γ-carbolines containing peptide residues |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2014-01-01 |
description |
The synthesis of novel peptide conjugates of N-substituted-tetrahydro-γ-carbolines has been performed using the sequence of the Ugi multicomponent reaction and Cu(I)-catalyzed click chemistry. The effect of obtained γ-carboline–peptide conjugates on the rat liver mitochondria was evaluated. It was found that all compounds in the concentration of 30 µM did onot induce depolarization of mitochondria but possessed some inhibitory effect on the mitochondria permeability transition. The original N-substituted-tetrahydro-γ-carbolines containing an terminal alkyne group demonstrated a high prooxidant activity, whereas their conjugates with peptide fragments slightly inhibited both autooxidation and the t-BHP-induced lipid peroxidation. |
topic |
mitochondrial membrane potential mitochondrial permeability transition multicomponent peptides tetrahydro-γ-carbolines Ugi multicomponent reaction |
url |
https://doi.org/10.3762/bjoc.10.13 |
work_keys_str_mv |
AT nadezhdavsokolova synthesisandbiologicalactivityofnsubstitutedtetrahydrogcarbolinescontainingpeptideresidues AT valentinegnenajdenko synthesisandbiologicalactivityofnsubstitutedtetrahydrogcarbolinescontainingpeptideresidues AT vladimirbsokolov synthesisandbiologicalactivityofnsubstitutedtetrahydrogcarbolinescontainingpeptideresidues AT dariavvinogradova synthesisandbiologicalactivityofnsubstitutedtetrahydrogcarbolinescontainingpeptideresidues AT elenafshevtsova synthesisandbiologicalactivityofnsubstitutedtetrahydrogcarbolinescontainingpeptideresidues AT ludmilagdubova synthesisandbiologicalactivityofnsubstitutedtetrahydrogcarbolinescontainingpeptideresidues AT sergeyobachurin synthesisandbiologicalactivityofnsubstitutedtetrahydrogcarbolinescontainingpeptideresidues |
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1724309677137723392 |