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 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.
Department of Chemistry, Moscow State University, Leninskie Gory 1, Moscow, 119992, Russia ; Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, Russia.
Nadezhda V
NV
Sokolova
Department of Chemistry, Moscow State University, Leninskie Gory 1, Moscow, 119992, Russia ; A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991 Moscow, Russian Federation.
Valentine G
VG
Nenajdenko
Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, Russia.
Vladimir B
VB
Sokolov
Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, Russia.
Daria V
DV
Vinogradova
Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, Russia.
Elena F
EF
Shevtsova
Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, Russia.
Ludmila G
LG
Dubova
Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severny proezd 1, Chernogolovka, 142432, Russia.
Sergey O
SO
Bachurin
Ugi multicomponent reaction; mitochondrial membrane potential; mitochondrial permeability transition; multicomponent; peptides; tetrahydro-γ-carbolines