Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity
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...
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MDPI AG
2022-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/19/6218 |
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| author | Artemiy Nichugovskiy Varvara Maksimova Ekaterina Trapeznikova Elizaveta Eshtukova-Shcheglova Igor Ivanov Marianna Yakubovskaya Kirill Kirsanov Dmitry Cheshkov Gian Cesare Tron Mikhail Maslov |
| author_facet | Artemiy Nichugovskiy Varvara Maksimova Ekaterina Trapeznikova Elizaveta Eshtukova-Shcheglova Igor Ivanov Marianna Yakubovskaya Kirill Kirsanov Dmitry Cheshkov Gian Cesare Tron Mikhail Maslov |
| author_sort | Artemiy Nichugovskiy |
| collection | DOAJ |
| description | 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 PhSiH<sub>3</sub>. 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. |
| first_indexed | 2024-03-09T21:26:39Z |
| format | Article |
| id | doaj.art-7e2b58fcfbd747c5a29687d748becc48 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T21:26:39Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7e2b58fcfbd747c5a29687d748becc482023-11-23T21:07:40ZengMDPI AGMolecules1420-30492022-09-012719621810.3390/molecules27196218Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer ActivityArtemiy Nichugovskiy0Varvara Maksimova1Ekaterina Trapeznikova2Elizaveta Eshtukova-Shcheglova3Igor Ivanov4Marianna Yakubovskaya5Kirill Kirsanov6Dmitry Cheshkov7Gian Cesare Tron8Mikhail Maslov9Lomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, 86 Vernadsky Ave., 119571 Moscow, RussiaN.N. Blokhin National Medical Research Center of Oncology, 23 Kashirskoe Sh., 115478 Moscow, RussiaI.M. Sechenov First Moscow State Medical University, 8-2 Trubetskaya Str., 119991 Moscow, RussiaLomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, 86 Vernadsky Ave., 119571 Moscow, RussiaLomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, 86 Vernadsky Ave., 119571 Moscow, RussiaN.N. Blokhin National Medical Research Center of Oncology, 23 Kashirskoe Sh., 115478 Moscow, RussiaN.N. Blokhin National Medical Research Center of Oncology, 23 Kashirskoe Sh., 115478 Moscow, RussiaState Scientific Research Institute of Chemistry and Technology of Organoelement Compounds, 38 Shosse Entuziastov, 105118 Moscow, RussiaDipartimento di Scienza del Farmaco, Università del Piemonte Orientale, 2 Largo Donegani, 28100 Novara, ItalyLomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, 86 Vernadsky Ave., 119571 Moscow, RussiaNatural 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 PhSiH<sub>3</sub>. 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.https://www.mdpi.com/1420-3049/27/19/6218polyaminesmulticomponent Ugi reactionlipophilic polyaminesanticancer activity |
| spellingShingle | Artemiy Nichugovskiy Varvara Maksimova Ekaterina Trapeznikova Elizaveta Eshtukova-Shcheglova Igor Ivanov Marianna Yakubovskaya Kirill Kirsanov Dmitry Cheshkov Gian Cesare Tron Mikhail Maslov Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity Molecules polyamines multicomponent Ugi reaction lipophilic polyamines anticancer activity |
| title | Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity |
| title_full | Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity |
| title_fullStr | Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity |
| title_full_unstemmed | Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity |
| title_short | Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity |
| title_sort | synthesis of novel lipophilic polyamines via ugi reaction and evaluation of their anticancer activity |
| topic | polyamines multicomponent Ugi reaction lipophilic polyamines anticancer activity |
| url | https://www.mdpi.com/1420-3049/27/19/6218 |
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