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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Main Authors:	Nadezhda V. Sokolova, Valentine G. Nenajdenko, Vladimir B. Sokolov, Daria V. Vinogradova, Elena F. Shevtsova, Ludmila G. Dubova, Sergey O. Bachurin
Format:	Article
Language:	English
Published:	Beilstein-Institut 2014-01-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	mitochondrial membrane potential mitochondrial permeability transition multicomponent peptides tetrahydro-γ-carbolines Ugi multicomponent reaction
Online Access:	https://doi.org/10.3762/bjoc.10.13

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spelling	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
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Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues

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