5-Ene-4-thiazolidinones induce apoptosis in mammalian leukemia cells

Julia Senkiv; Nataliya Finiuk; Danylo Kaminskyy; Dmytro Havrylyuk; Magdalena Wojtyra; Iryna Kril; Andrzej Gzella; Rostyslav Stoika; Roman Lesyk

doi:10.1016/j.ejmech.2016.03.089

5-Ene-4-thiazolidinones induce apoptosis in mammalian leukemia cells

Julia Senkiv, Nataliya Finiuk, Danylo Kaminskyy, Dmytro Havrylyuk, Magdalena Wojtyra, Iryna Kril, Andrzej Gzella, Rostyslav Stoika, Roman Lesyk

Chemistry

Research output: Contribution to journal › Article › peer-review

55 Scopus citations

Abstract

The article presents the synthesis of 5-ene-4-thiazolidinone derivatives with pyrazole core linked by enamine group. The structure and purity of compounds were confirmed by analytical and spectral data including X-ray analysis. Target compounds were screened for their anticancer activity and selective antileukemic action was confirmed. 5-[5-(2-Hydroxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-ylmethylene]-3-(3-acetoxyphenyl)-2-thioxothiazolidin-4-one (compound 1) was selected as most active agent against HL-60 and HL-60/ADR cell lines; IC₅₀ Combining double low line 118 nM/HL-60 with low toxicity towards pseudonormal cells. The mitochondria-depended apoptosis was identified as the main mode of 1 action. Moreover compound's effect induces G₀/G₁ arrest of the treated cells and causes inhibition of cell division and is related with activation of ROS production.

Original language	English
Pages (from-to)	33-46
Number of pages	14
Journal	European Journal of Medicinal Chemistry
Volume	117
DOIs	https://doi.org/10.1016/j.ejmech.2016.03.089
State	Published - Jul 19 2016

Bibliographical note

Funding Information:
The authors support all people of good will currently struggling for the liberty and justice in Ukraine. The authors thank the Association for Regional Cooperation in the Fields of Health, Science and Technology (RECOOP HST Association) and Dr. Sandor Vari (president of the RECOOP HST Association) for their support. This work was partially supported by the West-Ukrainian Biomedical Research Center (for Julia Senkiv and Natalia Finiuk in 2015/2016).

Publisher Copyright:
© 2016 Elsevier Masson SAS All rights reserved.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Keywords

5-Ene-4-thiazolidinones
Anticancer activity
Apoptosis
Leukemia
ROS

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2016.03.089

Cite this

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title = "5-Ene-4-thiazolidinones induce apoptosis in mammalian leukemia cells",

abstract = "The article presents the synthesis of 5-ene-4-thiazolidinone derivatives with pyrazole core linked by enamine group. The structure and purity of compounds were confirmed by analytical and spectral data including X-ray analysis. Target compounds were screened for their anticancer activity and selective antileukemic action was confirmed. 5-[5-(2-Hydroxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-ylmethylene]-3-(3-acetoxyphenyl)-2-thioxothiazolidin-4-one (compound 1) was selected as most active agent against HL-60 and HL-60/ADR cell lines; IC50 Combining double low line 118 nM/HL-60 with low toxicity towards pseudonormal cells. The mitochondria-depended apoptosis was identified as the main mode of 1 action. Moreover compound's effect induces G0/G1 arrest of the treated cells and causes inhibition of cell division and is related with activation of ROS production.",

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note = "Funding Information: The authors support all people of good will currently struggling for the liberty and justice in Ukraine. The authors thank the Association for Regional Cooperation in the Fields of Health, Science and Technology (RECOOP HST Association) and Dr. Sandor Vari (president of the RECOOP HST Association) for their support. This work was partially supported by the West-Ukrainian Biomedical Research Center (for Julia Senkiv and Natalia Finiuk in 2015/2016). Publisher Copyright: {\textcopyright} 2016 Elsevier Masson SAS All rights reserved. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

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AU - Senkiv, Julia

AU - Finiuk, Nataliya

AU - Kaminskyy, Danylo

AU - Havrylyuk, Dmytro

AU - Wojtyra, Magdalena

AU - Kril, Iryna

AU - Gzella, Andrzej

AU - Stoika, Rostyslav

AU - Lesyk, Roman

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PY - 2016/7/19

Y1 - 2016/7/19

N2 - The article presents the synthesis of 5-ene-4-thiazolidinone derivatives with pyrazole core linked by enamine group. The structure and purity of compounds were confirmed by analytical and spectral data including X-ray analysis. Target compounds were screened for their anticancer activity and selective antileukemic action was confirmed. 5-[5-(2-Hydroxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-ylmethylene]-3-(3-acetoxyphenyl)-2-thioxothiazolidin-4-one (compound 1) was selected as most active agent against HL-60 and HL-60/ADR cell lines; IC50 Combining double low line 118 nM/HL-60 with low toxicity towards pseudonormal cells. The mitochondria-depended apoptosis was identified as the main mode of 1 action. Moreover compound's effect induces G0/G1 arrest of the treated cells and causes inhibition of cell division and is related with activation of ROS production.

AB - The article presents the synthesis of 5-ene-4-thiazolidinone derivatives with pyrazole core linked by enamine group. The structure and purity of compounds were confirmed by analytical and spectral data including X-ray analysis. Target compounds were screened for their anticancer activity and selective antileukemic action was confirmed. 5-[5-(2-Hydroxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-ylmethylene]-3-(3-acetoxyphenyl)-2-thioxothiazolidin-4-one (compound 1) was selected as most active agent against HL-60 and HL-60/ADR cell lines; IC50 Combining double low line 118 nM/HL-60 with low toxicity towards pseudonormal cells. The mitochondria-depended apoptosis was identified as the main mode of 1 action. Moreover compound's effect induces G0/G1 arrest of the treated cells and causes inhibition of cell division and is related with activation of ROS production.

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KW - Apoptosis

KW - Leukemia

KW - ROS

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5-Ene-4-thiazolidinones induce apoptosis in mammalian leukemia cells

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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