Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents
New pyrazoline derivatives were synthesized and evaluated for their cytotoxic effects on AsPC-1 human pancreatic adenocarcinoma, U87 and U251 human glioblastoma cell lines. 1-[((5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetyl]-3-(2-thienyl)-5-(4-chlorophenyl)-2-pyrazoline (11) was found to be th...
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doaj-912b566621df4952b782502d1cbc74da2020-11-24T20:55:03ZengMDPI AGMolecules1420-30492015-10-012010190661908410.3390/molecules201019066molecules201019066Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer AgentsMuhammed Karabacak0Mehlika Dilek Altıntop1Halil İbrahim Çiftçi2Ryoko Koga3Masami Otsuka4Mikako Fujita5Ahmet Özdemir6Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, TurkeyDepartment of Bioorganic Medicinal Chemistry, School of Pharmacy, Kumamoto University, Kumamoto 862-0973, JapanDepartment of Bioorganic Medicinal Chemistry, School of Pharmacy, Kumamoto University, Kumamoto 862-0973, JapanDepartment of Bioorganic Medicinal Chemistry, School of Pharmacy, Kumamoto University, Kumamoto 862-0973, JapanResearch Institute for Drug Discovery, School of Pharmacy, Kumamoto University, Kumamoto 862-0973, JapanDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, TurkeyNew pyrazoline derivatives were synthesized and evaluated for their cytotoxic effects on AsPC-1 human pancreatic adenocarcinoma, U87 and U251 human glioblastoma cell lines. 1-[((5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetyl]-3-(2-thienyl)-5-(4-chlorophenyl)-2-pyrazoline (11) was found to be the most effective anticancer agent against AsPC-1 and U251 cell lines, with IC50 values of 16.8 µM and 11.9 µM, respectively. Tumor selectivity of compound 11 was clearly seen between Jurkat human leukemic T-cell line and human peripheral blood mononuclear cells (PBMC). Due to its promising anticancer activity, compound 11 was chosen for apoptosis/necrosis evaluation and DNA-cleavage analysis in U251 cells. Compound 11-treated U251 cells exhibited apoptotic phenotype at low concentration (1.5 µM). DNA-cleaving efficiency of this ligand was more significant than cisplatin and was clearly enhanced by Fe(II)-H2O2-ascorbic acid systems. This result pointed out the relationship between the DNA cleavage and the cell death.http://www.mdpi.com/1420-3049/20/10/19066pyrazolineoxadiazoleanticancer activityapoptosisDNA cleavage |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Muhammed Karabacak Mehlika Dilek Altıntop Halil İbrahim Çiftçi Ryoko Koga Masami Otsuka Mikako Fujita Ahmet Özdemir |
spellingShingle |
Muhammed Karabacak Mehlika Dilek Altıntop Halil İbrahim Çiftçi Ryoko Koga Masami Otsuka Mikako Fujita Ahmet Özdemir Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents Molecules pyrazoline oxadiazole anticancer activity apoptosis DNA cleavage |
author_facet |
Muhammed Karabacak Mehlika Dilek Altıntop Halil İbrahim Çiftçi Ryoko Koga Masami Otsuka Mikako Fujita Ahmet Özdemir |
author_sort |
Muhammed Karabacak |
title |
Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents |
title_short |
Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents |
title_full |
Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents |
title_fullStr |
Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents |
title_full_unstemmed |
Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents |
title_sort |
synthesis and evaluation of new pyrazoline derivatives as potential anticancer agents |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2015-10-01 |
description |
New pyrazoline derivatives were synthesized and evaluated for their cytotoxic effects on AsPC-1 human pancreatic adenocarcinoma, U87 and U251 human glioblastoma cell lines. 1-[((5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetyl]-3-(2-thienyl)-5-(4-chlorophenyl)-2-pyrazoline (11) was found to be the most effective anticancer agent against AsPC-1 and U251 cell lines, with IC50 values of 16.8 µM and 11.9 µM, respectively. Tumor selectivity of compound 11 was clearly seen between Jurkat human leukemic T-cell line and human peripheral blood mononuclear cells (PBMC). Due to its promising anticancer activity, compound 11 was chosen for apoptosis/necrosis evaluation and DNA-cleavage analysis in U251 cells. Compound 11-treated U251 cells exhibited apoptotic phenotype at low concentration (1.5 µM). DNA-cleaving efficiency of this ligand was more significant than cisplatin and was clearly enhanced by Fe(II)-H2O2-ascorbic acid systems. This result pointed out the relationship between the DNA cleavage and the cell death. |
topic |
pyrazoline oxadiazole anticancer activity apoptosis DNA cleavage |
url |
http://www.mdpi.com/1420-3049/20/10/19066 |
work_keys_str_mv |
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