Cytotoxicity of Some Azines of Acetophenone Derived Mono-Mannich Bases against Jurkat Cells
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概要
- 論文の詳細を見る
Acetophenone derived mono-Mannich bases (Ig1-Ig4), 1-aryl-3-amino-1-propanone hydrochlorides, which are known to have cytotoxicity in Jurkat cells, were synthesized. Then, they were converted to corresponding azine derivatives (D1-D4), N,N'-bis(3-amino-1-aryl-propylidenc)hydrazine dihydrochlorides, which are bifunctional agents. The aryl part was replaced by phenyl in Ig1, Ig2, Ig3, D1, D2, and D3, and by p-hydroxyphenyl in Ig4 and D4. The amine part was replaced by dimethylamine in Ig1, D1, Ig4 and D4, by piperidine in Ig2 and D2, and by morpholine in Ig3 and D3. The aim of this study was to investigate whether the modification in chemical structure, converting the mono-Mannich base to a corresponding azine derivative, improves the cytotoxicity. In addition, the effect of the representative compound, D3, N,N'-bis(3-morpholine-4-yl-1-phenylpropylidene)hydrazine dihydrochloride, on cellular glutathione level after 1 h exposure in phosphate buffer at 37℃ was also determined to provide information on a possible mechanism of eytotoxic action. Compounds D2-D4 are reported for the first time in this study. Except for Ig2 and D2, the cytotoxicity of mono-Mannich bases, Igl, Ig3 and Ig4 and corresponding azine derivatives, D1, D3 and D4 were higher than the reference compound 5-FU. Azine derivatives D1 and D4 had almost equal eytotoxic potency with corresponding mono-Mannich bases Ig1 and Ig4, respectively. On the other hand, azine derivatives D2 and D3, had 1.28 and 1.90-timcs less cytotoxicity in Jurkat cells compared with the mono-Mannich bases, Ig2 and Ig3, respectively, from which they are derived. Azine derivative D3 dose-dependently decreased the total cellular glutathione level, suggesting that azine derivatives may exert cytotoxicity by thiol alkylation. Azine derivatives with equal or less eytotoxic potency compared to the mono-Mannich bases they are derived from seemed to be less suitable derivatives for the development of new eytotoxic compounds.
- 公益社団法人日本薬学会の論文
- 2003-05-01
著者
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HANNINEN Osmo
Department of Physiology, Kuopio University Hospital
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Gul M
Department Of Physiology Faculty Of Medicine Ataturk University : Department Of Physiology Faculty O
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Hanninen Osmo
Department Of Physiology University Of Kuopio
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Haenninen O
Department Of Physiology Faculty Of Medicine University Of Kuopio
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GuL Halise
Department of Pharmaceutical Chemistry, Faculty of Pharmacy Ataturk University
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Gul H
Department Of Pharmaceutical Chemistry Faculty Of Pharmacy Ataturk University : Department Of Chemis
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Gul Halise
Department Of Pharmaceutical Chemistry Faculty Of Pharmacy Ataturk University
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GuL Mustafa
Department of Physiology, Faculty of Medicine, Ataturk University
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Gul Mustafa
Department Of Clinical Microbiology Kahramanmaras Sutcu Imam University Faculty Of Medicine
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VEPSALAINEN Jouko
Department of Chemistry, University of Kuopio
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ERCIYAS Ercin
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University
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Erciyas Ercin
Department Of Pharmaceutical Chemistry Faculty Of Pharmacy Ege University
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Vepsalainen Jouko
Department Of Chemistry University Of Kuopio
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Vespalainen Jouko
Department of Chemistry, University of Kuopio
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