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Synthesis, molecular structure, and metabolic stability of new series of N' -(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-1-(5-phenyl-1 H -pyrazol-1-yl)amidine as potential anti-cancer agents
Abstract
A series of new N'-(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-1-(5-phenyl-1H-pyrazol-1-yl)amidine derivatives have been synthesized and evaluated in vitro by MTT assays for their antiproliferative activity against cell lines of colon cancer HCT-116, cervical cancer HeLa and breast cancer MCF-7. The studied compounds display selective activity mainly against HCT-116 and HeLa cells. Thus, five compounds show selective cytotoxic effect against HCT-116 (IC50 = 3-10 uM) and HeLa (IC50 = 7 uM). Importantly, the noticed values of IC50 for four compounds are almost 4-fold lower for HeLa than nonmalignant HaCaT cells. More-in-depth biological research revealed that the treatment of HCT-116 and HeLa with active compound resulted in increased numbers of cells in sub-G1 phase in a time dependent manner, while non-active derivative does not influence cell cycle. Metabolic stability assays using liver microsomes and NADPH provide important information on compounds susceptibility to phase 1 biotransformation reactions.
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Authors (9)
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Aneta Pogorzelska
- Gdański Uniwersytet Medyczny Katedra Chemii Organicznej
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Jarosław Sławiński
- Gdański Uniwersytet Medyczny Katedra Chemii Organicznej
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Anna Kawiak
- Gdański Uniwersytet Medyczny Laboratorium Fizjologii Człowieka
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Beata Żołnowska
- Gdański Uniwersytet Medyczny Katedra Chemii Organicznej
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Grzegorz Stasiłojć
- Gdański Uniwersytet Medyczny Laboratorium Biologii Komórki
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Szymon Ulenberg
- Gdański Uniwersytet Medyczny Katedra Chemii Farmaceutycznej
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Krzysztof Szafrański dr
- Gdański Uniwersytet Medyczny Katedra Chemii Organicznej
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Tomasz Bączek
- Gdański Uniwersytet Medyczny Katedra Chemii Farmaceutycznej
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
no. 155,
pages 670 - 680,
ISSN: 0223-5234 - Language:
- English
- Publication year:
- 2018
- Bibliographic description:
- Pogorzelska A., Sławiński J., Kawiak A., Żołnowska B., Chojnacki J., Stasiłojć G., Ulenberg S., Szafrański K., Bączek T.: Synthesis, molecular structure, and metabolic stability of new series of N' -(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-1-(5-phenyl-1 H -pyrazol-1-yl)amidine as potential anti-cancer agents// EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. -Vol. 155, (2018), s.670-680
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.ejmech.2018.06.032
- Verified by:
- Gdańsk University of Technology
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