Cytotoxic and apoptotic effects of chalcone derivatives of 2-acetyl thiophene on human colon adenocarcinoma cells

Alana de Vasconcelos, Vinicius Farias Campos, Fernanda Nedel, Fabiana Kömmling Seixas, Odir A. Dellagostin, Kevin R. Smith, Cláudio Martin Pereira de Pereira, Francieli Moro Stefanello, Tiago Collares, Alethéa Gatto Barschak

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Recent studies report that chalcones exhibit cytotoxicity to human cancer cell lines. Typically, the form of cell death induced by these compounds is apoptosis. In the context of the discovery of new anticancer agents and in light of the antitumour potential of several chalcone derivatives, in the present study, we synthesized and tested the cytotoxicity of six chalcone derivatives on human colon adenocarcinoma cells. Six derivatives of 3-phenyl-1-(thiophen-2-yl) prop-2-en-1-one were prepared and characterized on the basis of their 1H and 13C NMR spectra. HT-29 cells were treated with synthesized chalcones on two concentrations by three different incubation times. Cells were evaluated by cell morphology, Tetrazolium dye (MTT) colorimetric assay, live/dead, flow cytometry (annexin V) and gene expression analyses to determine the cytotoxic way. Chalcones 3-(4-bromophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C06) and 3-(2-nitrophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C09) demonstrated higher cytotoxicity than other chalcones as shown by cell morphology, live/dead and MTT assays. In addition, C06 induced apoptosis on flow cytometry annexin V assay. These data were confirmed by a decreased expression of anti-apoptotic genes and increased pro-apoptotic genes. Our findings indicate in summary that the cytotoxic activity of chalcone C06 on colorectal carcinoma cells occurs by apoptosis.
Original languageEnglish
Pages (from-to)289-297
Number of pages9
JournalCell Biochemistry and Function
Volume31
Issue number4
Early online date18 Sep 2012
DOIs
Publication statusPublished - Jun 2013

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Chalcones
Chalcone
Thiophenes
Colon
Adenocarcinoma
Cytotoxicity
Derivatives
Assays
Flow cytometry
Annexin A5
Apoptosis
Coloring Agents
Genes
Cells
Flow Cytometry
Cell death
HT29 Cells
Gene expression
Antineoplastic Agents
Nuclear magnetic resonance

Cite this

de Vasconcelos, A., Campos, V. F., Nedel, F., Seixas, F. K., Dellagostin, O. A., Smith, K. R., ... Barschak, A. G. (2013). Cytotoxic and apoptotic effects of chalcone derivatives of 2-acetyl thiophene on human colon adenocarcinoma cells. Cell Biochemistry and Function, 31(4), 289-297. https://doi.org/10.1002/cbf.2897
de Vasconcelos, Alana ; Campos, Vinicius Farias ; Nedel, Fernanda ; Seixas, Fabiana Kömmling ; Dellagostin, Odir A. ; Smith, Kevin R. ; de Pereira, Cláudio Martin Pereira ; Stefanello, Francieli Moro ; Collares, Tiago ; Barschak, Alethéa Gatto. / Cytotoxic and apoptotic effects of chalcone derivatives of 2-acetyl thiophene on human colon adenocarcinoma cells. In: Cell Biochemistry and Function. 2013 ; Vol. 31, No. 4. pp. 289-297.
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abstract = "Recent studies report that chalcones exhibit cytotoxicity to human cancer cell lines. Typically, the form of cell death induced by these compounds is apoptosis. In the context of the discovery of new anticancer agents and in light of the antitumour potential of several chalcone derivatives, in the present study, we synthesized and tested the cytotoxicity of six chalcone derivatives on human colon adenocarcinoma cells. Six derivatives of 3-phenyl-1-(thiophen-2-yl) prop-2-en-1-one were prepared and characterized on the basis of their 1H and 13C NMR spectra. HT-29 cells were treated with synthesized chalcones on two concentrations by three different incubation times. Cells were evaluated by cell morphology, Tetrazolium dye (MTT) colorimetric assay, live/dead, flow cytometry (annexin V) and gene expression analyses to determine the cytotoxic way. Chalcones 3-(4-bromophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C06) and 3-(2-nitrophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C09) demonstrated higher cytotoxicity than other chalcones as shown by cell morphology, live/dead and MTT assays. In addition, C06 induced apoptosis on flow cytometry annexin V assay. These data were confirmed by a decreased expression of anti-apoptotic genes and increased pro-apoptotic genes. Our findings indicate in summary that the cytotoxic activity of chalcone C06 on colorectal carcinoma cells occurs by apoptosis.",
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de Vasconcelos, A, Campos, VF, Nedel, F, Seixas, FK, Dellagostin, OA, Smith, KR, de Pereira, CMP, Stefanello, FM, Collares, T & Barschak, AG 2013, 'Cytotoxic and apoptotic effects of chalcone derivatives of 2-acetyl thiophene on human colon adenocarcinoma cells', Cell Biochemistry and Function, vol. 31, no. 4, pp. 289-297. https://doi.org/10.1002/cbf.2897

Cytotoxic and apoptotic effects of chalcone derivatives of 2-acetyl thiophene on human colon adenocarcinoma cells. / de Vasconcelos, Alana; Campos, Vinicius Farias; Nedel, Fernanda; Seixas, Fabiana Kömmling; Dellagostin, Odir A.; Smith, Kevin R.; de Pereira, Cláudio Martin Pereira; Stefanello, Francieli Moro; Collares, Tiago; Barschak, Alethéa Gatto.

In: Cell Biochemistry and Function, Vol. 31, No. 4, 06.2013, p. 289-297.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Cytotoxic and apoptotic effects of chalcone derivatives of 2-acetyl thiophene on human colon adenocarcinoma cells

AU - de Vasconcelos, Alana

AU - Campos, Vinicius Farias

AU - Nedel, Fernanda

AU - Seixas, Fabiana Kömmling

AU - Dellagostin, Odir A.

AU - Smith, Kevin R.

AU - de Pereira, Cláudio Martin Pereira

AU - Stefanello, Francieli Moro

AU - Collares, Tiago

AU - Barschak, Alethéa Gatto

PY - 2013/6

Y1 - 2013/6

N2 - Recent studies report that chalcones exhibit cytotoxicity to human cancer cell lines. Typically, the form of cell death induced by these compounds is apoptosis. In the context of the discovery of new anticancer agents and in light of the antitumour potential of several chalcone derivatives, in the present study, we synthesized and tested the cytotoxicity of six chalcone derivatives on human colon adenocarcinoma cells. Six derivatives of 3-phenyl-1-(thiophen-2-yl) prop-2-en-1-one were prepared and characterized on the basis of their 1H and 13C NMR spectra. HT-29 cells were treated with synthesized chalcones on two concentrations by three different incubation times. Cells were evaluated by cell morphology, Tetrazolium dye (MTT) colorimetric assay, live/dead, flow cytometry (annexin V) and gene expression analyses to determine the cytotoxic way. Chalcones 3-(4-bromophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C06) and 3-(2-nitrophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C09) demonstrated higher cytotoxicity than other chalcones as shown by cell morphology, live/dead and MTT assays. In addition, C06 induced apoptosis on flow cytometry annexin V assay. These data were confirmed by a decreased expression of anti-apoptotic genes and increased pro-apoptotic genes. Our findings indicate in summary that the cytotoxic activity of chalcone C06 on colorectal carcinoma cells occurs by apoptosis.

AB - Recent studies report that chalcones exhibit cytotoxicity to human cancer cell lines. Typically, the form of cell death induced by these compounds is apoptosis. In the context of the discovery of new anticancer agents and in light of the antitumour potential of several chalcone derivatives, in the present study, we synthesized and tested the cytotoxicity of six chalcone derivatives on human colon adenocarcinoma cells. Six derivatives of 3-phenyl-1-(thiophen-2-yl) prop-2-en-1-one were prepared and characterized on the basis of their 1H and 13C NMR spectra. HT-29 cells were treated with synthesized chalcones on two concentrations by three different incubation times. Cells were evaluated by cell morphology, Tetrazolium dye (MTT) colorimetric assay, live/dead, flow cytometry (annexin V) and gene expression analyses to determine the cytotoxic way. Chalcones 3-(4-bromophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C06) and 3-(2-nitrophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C09) demonstrated higher cytotoxicity than other chalcones as shown by cell morphology, live/dead and MTT assays. In addition, C06 induced apoptosis on flow cytometry annexin V assay. These data were confirmed by a decreased expression of anti-apoptotic genes and increased pro-apoptotic genes. Our findings indicate in summary that the cytotoxic activity of chalcone C06 on colorectal carcinoma cells occurs by apoptosis.

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DO - 10.1002/cbf.2897

M3 - Article

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JO - Cell Biochemistry and Function

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