Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity

Artemiy Nichugovskiy; Varvara Maksimova; Ekaterina Trapeznikova; Elizaveta Eshtukova-Shcheglova; Igor Ivanov; Marianna Yakubovskaya; Kirill Kirsanov; Dmitry Cheshkov; Gian Cesare Tron; Mikhail Maslov

doi:10.3390/molecules27196218

Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity

Artemiy Nichugovskiy, Varvara Maksimova, Ekaterina Trapeznikova, Elizaveta Eshtukova-Shcheglova, Igor Ivanov, Marianna Yakubovskaya, Kirill Kirsanov, Dmitry Cheshkov, Gian Cesare Tron, Mikhail Maslov

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

Natural polyamines (PAs) are involved in the processes of proliferation and differentiation of cancer cells. Lipophilic synthetic polyamines (LPAs) induce the cell death of various cancer cell lines. In the current paper, we have demonstrated a new method for synthesis of LPAs via the multicomponent Ugi reaction and subsequent reduction of amide groups by PhSiH₃. The anticancer activity of the obtained compounds was evaluated in the A-549, MCF7, and HCT116 cancer cell lines. For the first time, it was shown that the anticancer activity of LPAs with piperazine fragments is comparable with that of aliphatic LPAs. The presence of a diglyceride fragment in the structure of LPAs appears to be a key factor for the manifestation of high anticancer activity. The findings of the study strongly support further research in the field of LPAs and their derivatives.

Original language	English
Article number	6218
Journal	Molecules
Volume	27
Issue number	19
DOIs	https://doi.org/10.3390/molecules27196218
Publication status	Published - Oct 2022

Keywords

anticancer activity
lipophilic polyamines
multicomponent Ugi reaction
polyamines

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.3390/molecules27196218

Cite this

@article{0356690454de4929a22cc8d674330b48,

title = "Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity",

abstract = "Natural polyamines (PAs) are involved in the processes of proliferation and differentiation of cancer cells. Lipophilic synthetic polyamines (LPAs) induce the cell death of various cancer cell lines. In the current paper, we have demonstrated a new method for synthesis of LPAs via the multicomponent Ugi reaction and subsequent reduction of amide groups by PhSiH3. The anticancer activity of the obtained compounds was evaluated in the A-549, MCF7, and HCT116 cancer cell lines. For the first time, it was shown that the anticancer activity of LPAs with piperazine fragments is comparable with that of aliphatic LPAs. The presence of a diglyceride fragment in the structure of LPAs appears to be a key factor for the manifestation of high anticancer activity. The findings of the study strongly support further research in the field of LPAs and their derivatives.",

keywords = "anticancer activity, lipophilic polyamines, multicomponent Ugi reaction, polyamines",

author = "Artemiy Nichugovskiy and Varvara Maksimova and Ekaterina Trapeznikova and Elizaveta Eshtukova-Shcheglova and Igor Ivanov and Marianna Yakubovskaya and Kirill Kirsanov and Dmitry Cheshkov and Tron, {Gian Cesare} and Mikhail Maslov",

note = "Publisher Copyright: {\textcopyright} 2022 by the authors.",

year = "2022",

month = oct,

doi = "10.3390/molecules27196218",

language = "English",

volume = "27",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "19",

}

TY - JOUR

T1 - Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity

AU - Nichugovskiy, Artemiy

AU - Maksimova, Varvara

AU - Trapeznikova, Ekaterina

AU - Eshtukova-Shcheglova, Elizaveta

AU - Ivanov, Igor

AU - Yakubovskaya, Marianna

AU - Kirsanov, Kirill

AU - Cheshkov, Dmitry

AU - Tron, Gian Cesare

AU - Maslov, Mikhail

PY - 2022/10

Y1 - 2022/10

N2 - Natural polyamines (PAs) are involved in the processes of proliferation and differentiation of cancer cells. Lipophilic synthetic polyamines (LPAs) induce the cell death of various cancer cell lines. In the current paper, we have demonstrated a new method for synthesis of LPAs via the multicomponent Ugi reaction and subsequent reduction of amide groups by PhSiH3. The anticancer activity of the obtained compounds was evaluated in the A-549, MCF7, and HCT116 cancer cell lines. For the first time, it was shown that the anticancer activity of LPAs with piperazine fragments is comparable with that of aliphatic LPAs. The presence of a diglyceride fragment in the structure of LPAs appears to be a key factor for the manifestation of high anticancer activity. The findings of the study strongly support further research in the field of LPAs and their derivatives.

AB - Natural polyamines (PAs) are involved in the processes of proliferation and differentiation of cancer cells. Lipophilic synthetic polyamines (LPAs) induce the cell death of various cancer cell lines. In the current paper, we have demonstrated a new method for synthesis of LPAs via the multicomponent Ugi reaction and subsequent reduction of amide groups by PhSiH3. The anticancer activity of the obtained compounds was evaluated in the A-549, MCF7, and HCT116 cancer cell lines. For the first time, it was shown that the anticancer activity of LPAs with piperazine fragments is comparable with that of aliphatic LPAs. The presence of a diglyceride fragment in the structure of LPAs appears to be a key factor for the manifestation of high anticancer activity. The findings of the study strongly support further research in the field of LPAs and their derivatives.

KW - anticancer activity

KW - lipophilic polyamines

KW - multicomponent Ugi reaction

KW - polyamines

UR - http://www.scopus.com/inward/record.url?scp=85139812746&partnerID=8YFLogxK

U2 - 10.3390/molecules27196218

DO - 10.3390/molecules27196218

M3 - Article

SN - 1420-3049

VL - 27

JO - Molecules

JF - Molecules

IS - 19

M1 - 6218

ER -

Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity

Abstract

Keywords

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this