Bioorganic and Medicinal Chemistry, volume 76, pages 117089
Symmetric lipophilic polyamines exhibiting antitumor activity
Publication type: Journal Article
Publication date: 2022-12-01
Journal:
Bioorganic and Medicinal Chemistry
Quartile SCImago
Q2
Quartile WOS
Q1
Impact factor: 3.5
ISSN: 09680896, 14643391
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
Unsymmetric lipophilic polyamine derivatives are considered as potential antitumor agents. Here, a series of novel symmetric lipophilic polyamines (LPAs) based on norspermine and triethylenetetramine (TETA) backbones bearing alkyl substituents with different lengths (from decyl to octadecyl) at C(1) atom of glycerol were synthesized. Performed screening of the cytotoxicity of novel compounds on the panel of tumor cell lines (MCF-7, KB-3-1, B16) and non-malignant fibroblasts hFF3 in vitro revealed a correlation between the length of the aliphatic moieties in LPAs and their toxic effects - LPAs with the shortest decyl substituent were found to exhibit the highest cytotoxicity. Furthermore, norspermine-based LPAs displayed somewhat more pronounced cytotoxicity compared with their TETA-based counterparts. Further mechanistic studies demonstrated that hit LPAs containing the norspermine backbone and tetradecyl or decyl substituents efficiently induced apoptosis in KB-3-1 cells. Moreover, decyl-bearing LPA inhibited motility and enhanced adhesiveness of murine B16 melanoma cells in vitro, showing promising antimetastatic potential. Thus, developed novel symmetric norspermine-based LPAs can be considered as promising anticancer chemotherapeutic candidates.
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Chemico-Biological Interactions
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Chemico-Biological Interactions
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Elsevier
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Perevoshchikova K. A. et al. Symmetric lipophilic polyamines exhibiting antitumor activity // Bioorganic and Medicinal Chemistry. 2022. Vol. 76. p. 117089.
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Perevoshchikova K. A., Eshtukova Shcheglova E. A., Markov O. V., Марков А. В., Chernikov I. V., Maslov M., Zenkova M. A. Symmetric lipophilic polyamines exhibiting antitumor activity // Bioorganic and Medicinal Chemistry. 2022. Vol. 76. p. 117089.
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TY - JOUR
DO - 10.1016/j.bmc.2022.117089
UR - https://doi.org/10.1016%2Fj.bmc.2022.117089
TI - Symmetric lipophilic polyamines exhibiting antitumor activity
T2 - Bioorganic and Medicinal Chemistry
AU - Perevoshchikova, K A
AU - Eshtukova Shcheglova, E A
AU - Markov, Oleg V
AU - Марков, А. В.
AU - Chernikov, Ivan V.
AU - Maslov, Michael
AU - Zenkova, Marina A
PY - 2022
DA - 2022/12/01 00:00:00
PB - Elsevier
SP - 117089
VL - 76
SN - 0968-0896
SN - 1464-3391
ER -
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@article{2022_Perevoshchikova,
author = {K A Perevoshchikova and E A Eshtukova Shcheglova and Oleg V Markov and А. В. Марков and Ivan V. Chernikov and Michael Maslov and Marina A Zenkova},
title = {Symmetric lipophilic polyamines exhibiting antitumor activity},
journal = {Bioorganic and Medicinal Chemistry},
year = {2022},
volume = {76},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016%2Fj.bmc.2022.117089},
pages = {117089},
doi = {10.1016/j.bmc.2022.117089}
}
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