Proapoptotic Effect and Molecular Docking Analysis of Curcumin–Resveratrol Hybrids in Colorectal Cancer Chemoprevention
Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determin...
Ausführliche Beschreibung
Autor*in: |
Gustavo Moreno-Q [verfasserIn] Angie Herrera-R [verfasserIn] Andres F. Yepes [verfasserIn] Tonny W. Naranjo [verfasserIn] Wilson Cardona-G [verfasserIn] |
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E-Artikel |
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Sprache: |
Englisch |
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2022 |
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Übergeordnetes Werk: |
In: Molecules - MDPI AG, 2003, 27(2022), 11, p 3486 |
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Übergeordnetes Werk: |
volume:27 ; year:2022 ; number:11, p 3486 |
Links: |
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DOI / URN: |
10.3390/molecules27113486 |
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Katalog-ID: |
DOAJ042872251 |
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10.3390/molecules27113486 doi (DE-627)DOAJ042872251 (DE-599)DOAJfba02650ba524b02a8d100e70dbba01b DE-627 ger DE-627 rakwb eng QD241-441 Gustavo Moreno-Q verfasserin aut Proapoptotic Effect and Molecular Docking Analysis of Curcumin–Resveratrol Hybrids in Colorectal Cancer Chemoprevention 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determine the possible mechanism of action of the hybrids. The results indicated that the evaluated curcumin/resveratrol hybrids induce mitochondrial instability in SW620 and SW480 cells. Moreover, these molecules caused a loss in membrane integrity, suggesting an apoptotic process mediated by caspases after the treatment with compounds <b<3i</b< (SW480) and <b<3k</b< (SW620). In addition, the results suggest that the mechanism of action of the hybrids could be independent of the p53 status. Furthermore, hybrids <b<3e</b< and <b<3i</b< caused G0/G1 phase arrest, which highlights the potential of these molecules not only as cytotoxic but also as cytostatic compounds. Hybrids <b<3e</b< and <b<3i</b< caused a negative modulation of the matrix metalloproteinase 7 (MMP7) on SW480 cells. These curcumin resveratrol hybrids could be potential candidates for further investigations in the search for potential chemopreventive agents, even in those cases with resistance to conventional chemotherapy because of the lack of p53 expression or function. Molecular docking simulations showed that compounds <b<3e</b<, <b<3i</b<, and <b<3k</b< bind efficiently to proapoptotic human caspases 3/7 proteins, as well as human MMP-7 and p53, which, in turn, could explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 and SW620 colon cancer cell lines. curcumin resveratrol hybrid molecules colorectal cancer cell death apoptosis Organic chemistry Angie Herrera-R verfasserin aut Andres F. Yepes verfasserin aut Tonny W. Naranjo verfasserin aut Wilson Cardona-G verfasserin aut In Molecules MDPI AG, 2003 27(2022), 11, p 3486 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:11, p 3486 https://doi.org/10.3390/molecules27113486 kostenfrei https://doaj.org/article/fba02650ba524b02a8d100e70dbba01b kostenfrei https://www.mdpi.com/1420-3049/27/11/3486 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 11, p 3486 |
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10.3390/molecules27113486 doi (DE-627)DOAJ042872251 (DE-599)DOAJfba02650ba524b02a8d100e70dbba01b DE-627 ger DE-627 rakwb eng QD241-441 Gustavo Moreno-Q verfasserin aut Proapoptotic Effect and Molecular Docking Analysis of Curcumin–Resveratrol Hybrids in Colorectal Cancer Chemoprevention 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determine the possible mechanism of action of the hybrids. The results indicated that the evaluated curcumin/resveratrol hybrids induce mitochondrial instability in SW620 and SW480 cells. Moreover, these molecules caused a loss in membrane integrity, suggesting an apoptotic process mediated by caspases after the treatment with compounds <b<3i</b< (SW480) and <b<3k</b< (SW620). In addition, the results suggest that the mechanism of action of the hybrids could be independent of the p53 status. Furthermore, hybrids <b<3e</b< and <b<3i</b< caused G0/G1 phase arrest, which highlights the potential of these molecules not only as cytotoxic but also as cytostatic compounds. Hybrids <b<3e</b< and <b<3i</b< caused a negative modulation of the matrix metalloproteinase 7 (MMP7) on SW480 cells. These curcumin resveratrol hybrids could be potential candidates for further investigations in the search for potential chemopreventive agents, even in those cases with resistance to conventional chemotherapy because of the lack of p53 expression or function. Molecular docking simulations showed that compounds <b<3e</b<, <b<3i</b<, and <b<3k</b< bind efficiently to proapoptotic human caspases 3/7 proteins, as well as human MMP-7 and p53, which, in turn, could explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 and SW620 colon cancer cell lines. curcumin resveratrol hybrid molecules colorectal cancer cell death apoptosis Organic chemistry Angie Herrera-R verfasserin aut Andres F. Yepes verfasserin aut Tonny W. Naranjo verfasserin aut Wilson Cardona-G verfasserin aut In Molecules MDPI AG, 2003 27(2022), 11, p 3486 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:11, p 3486 https://doi.org/10.3390/molecules27113486 kostenfrei https://doaj.org/article/fba02650ba524b02a8d100e70dbba01b kostenfrei https://www.mdpi.com/1420-3049/27/11/3486 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 11, p 3486 |
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10.3390/molecules27113486 doi (DE-627)DOAJ042872251 (DE-599)DOAJfba02650ba524b02a8d100e70dbba01b DE-627 ger DE-627 rakwb eng QD241-441 Gustavo Moreno-Q verfasserin aut Proapoptotic Effect and Molecular Docking Analysis of Curcumin–Resveratrol Hybrids in Colorectal Cancer Chemoprevention 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determine the possible mechanism of action of the hybrids. The results indicated that the evaluated curcumin/resveratrol hybrids induce mitochondrial instability in SW620 and SW480 cells. Moreover, these molecules caused a loss in membrane integrity, suggesting an apoptotic process mediated by caspases after the treatment with compounds <b<3i</b< (SW480) and <b<3k</b< (SW620). In addition, the results suggest that the mechanism of action of the hybrids could be independent of the p53 status. Furthermore, hybrids <b<3e</b< and <b<3i</b< caused G0/G1 phase arrest, which highlights the potential of these molecules not only as cytotoxic but also as cytostatic compounds. Hybrids <b<3e</b< and <b<3i</b< caused a negative modulation of the matrix metalloproteinase 7 (MMP7) on SW480 cells. These curcumin resveratrol hybrids could be potential candidates for further investigations in the search for potential chemopreventive agents, even in those cases with resistance to conventional chemotherapy because of the lack of p53 expression or function. Molecular docking simulations showed that compounds <b<3e</b<, <b<3i</b<, and <b<3k</b< bind efficiently to proapoptotic human caspases 3/7 proteins, as well as human MMP-7 and p53, which, in turn, could explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 and SW620 colon cancer cell lines. curcumin resveratrol hybrid molecules colorectal cancer cell death apoptosis Organic chemistry Angie Herrera-R verfasserin aut Andres F. Yepes verfasserin aut Tonny W. Naranjo verfasserin aut Wilson Cardona-G verfasserin aut In Molecules MDPI AG, 2003 27(2022), 11, p 3486 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:11, p 3486 https://doi.org/10.3390/molecules27113486 kostenfrei https://doaj.org/article/fba02650ba524b02a8d100e70dbba01b kostenfrei https://www.mdpi.com/1420-3049/27/11/3486 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 11, p 3486 |
allfieldsGer |
10.3390/molecules27113486 doi (DE-627)DOAJ042872251 (DE-599)DOAJfba02650ba524b02a8d100e70dbba01b DE-627 ger DE-627 rakwb eng QD241-441 Gustavo Moreno-Q verfasserin aut Proapoptotic Effect and Molecular Docking Analysis of Curcumin–Resveratrol Hybrids in Colorectal Cancer Chemoprevention 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determine the possible mechanism of action of the hybrids. The results indicated that the evaluated curcumin/resveratrol hybrids induce mitochondrial instability in SW620 and SW480 cells. Moreover, these molecules caused a loss in membrane integrity, suggesting an apoptotic process mediated by caspases after the treatment with compounds <b<3i</b< (SW480) and <b<3k</b< (SW620). In addition, the results suggest that the mechanism of action of the hybrids could be independent of the p53 status. Furthermore, hybrids <b<3e</b< and <b<3i</b< caused G0/G1 phase arrest, which highlights the potential of these molecules not only as cytotoxic but also as cytostatic compounds. Hybrids <b<3e</b< and <b<3i</b< caused a negative modulation of the matrix metalloproteinase 7 (MMP7) on SW480 cells. These curcumin resveratrol hybrids could be potential candidates for further investigations in the search for potential chemopreventive agents, even in those cases with resistance to conventional chemotherapy because of the lack of p53 expression or function. Molecular docking simulations showed that compounds <b<3e</b<, <b<3i</b<, and <b<3k</b< bind efficiently to proapoptotic human caspases 3/7 proteins, as well as human MMP-7 and p53, which, in turn, could explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 and SW620 colon cancer cell lines. curcumin resveratrol hybrid molecules colorectal cancer cell death apoptosis Organic chemistry Angie Herrera-R verfasserin aut Andres F. Yepes verfasserin aut Tonny W. Naranjo verfasserin aut Wilson Cardona-G verfasserin aut In Molecules MDPI AG, 2003 27(2022), 11, p 3486 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:11, p 3486 https://doi.org/10.3390/molecules27113486 kostenfrei https://doaj.org/article/fba02650ba524b02a8d100e70dbba01b kostenfrei https://www.mdpi.com/1420-3049/27/11/3486 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 11, p 3486 |
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Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determine the possible mechanism of action of the hybrids. The results indicated that the evaluated curcumin/resveratrol hybrids induce mitochondrial instability in SW620 and SW480 cells. Moreover, these molecules caused a loss in membrane integrity, suggesting an apoptotic process mediated by caspases after the treatment with compounds <b<3i</b< (SW480) and <b<3k</b< (SW620). In addition, the results suggest that the mechanism of action of the hybrids could be independent of the p53 status. Furthermore, hybrids <b<3e</b< and <b<3i</b< caused G0/G1 phase arrest, which highlights the potential of these molecules not only as cytotoxic but also as cytostatic compounds. Hybrids <b<3e</b< and <b<3i</b< caused a negative modulation of the matrix metalloproteinase 7 (MMP7) on SW480 cells. These curcumin resveratrol hybrids could be potential candidates for further investigations in the search for potential chemopreventive agents, even in those cases with resistance to conventional chemotherapy because of the lack of p53 expression or function. Molecular docking simulations showed that compounds <b<3e</b<, <b<3i</b<, and <b<3k</b< bind efficiently to proapoptotic human caspases 3/7 proteins, as well as human MMP-7 and p53, which, in turn, could explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 and SW620 colon cancer cell lines. |
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Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determine the possible mechanism of action of the hybrids. The results indicated that the evaluated curcumin/resveratrol hybrids induce mitochondrial instability in SW620 and SW480 cells. Moreover, these molecules caused a loss in membrane integrity, suggesting an apoptotic process mediated by caspases after the treatment with compounds <b<3i</b< (SW480) and <b<3k</b< (SW620). In addition, the results suggest that the mechanism of action of the hybrids could be independent of the p53 status. Furthermore, hybrids <b<3e</b< and <b<3i</b< caused G0/G1 phase arrest, which highlights the potential of these molecules not only as cytotoxic but also as cytostatic compounds. Hybrids <b<3e</b< and <b<3i</b< caused a negative modulation of the matrix metalloproteinase 7 (MMP7) on SW480 cells. These curcumin resveratrol hybrids could be potential candidates for further investigations in the search for potential chemopreventive agents, even in those cases with resistance to conventional chemotherapy because of the lack of p53 expression or function. Molecular docking simulations showed that compounds <b<3e</b<, <b<3i</b<, and <b<3k</b< bind efficiently to proapoptotic human caspases 3/7 proteins, as well as human MMP-7 and p53, which, in turn, could explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 and SW620 colon cancer cell lines. |
abstract_unstemmed |
Different hybrids based on curcumin and resveratrol were previously synthesized and characterized by spectroscopic techniques. The most active molecules (<b<3a</b<, <b<3e</b<, <b<3i</b<, and <b<3k</b<) were evaluated in vitro as an approach to determine the possible mechanism of action of the hybrids. The results indicated that the evaluated curcumin/resveratrol hybrids induce mitochondrial instability in SW620 and SW480 cells. Moreover, these molecules caused a loss in membrane integrity, suggesting an apoptotic process mediated by caspases after the treatment with compounds <b<3i</b< (SW480) and <b<3k</b< (SW620). In addition, the results suggest that the mechanism of action of the hybrids could be independent of the p53 status. Furthermore, hybrids <b<3e</b< and <b<3i</b< caused G0/G1 phase arrest, which highlights the potential of these molecules not only as cytotoxic but also as cytostatic compounds. Hybrids <b<3e</b< and <b<3i</b< caused a negative modulation of the matrix metalloproteinase 7 (MMP7) on SW480 cells. These curcumin resveratrol hybrids could be potential candidates for further investigations in the search for potential chemopreventive agents, even in those cases with resistance to conventional chemotherapy because of the lack of p53 expression or function. Molecular docking simulations showed that compounds <b<3e</b<, <b<3i</b<, and <b<3k</b< bind efficiently to proapoptotic human caspases 3/7 proteins, as well as human MMP-7 and p53, which, in turn, could explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 and SW620 colon cancer cell lines. |
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11, p 3486 |
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Proapoptotic Effect and Molecular Docking Analysis of Curcumin–Resveratrol Hybrids in Colorectal Cancer Chemoprevention |
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https://doi.org/10.3390/molecules27113486 https://doaj.org/article/fba02650ba524b02a8d100e70dbba01b https://www.mdpi.com/1420-3049/27/11/3486 https://doaj.org/toc/1420-3049 |
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Angie Herrera-R Andres F. Yepes Tonny W. Naranjo Wilson Cardona-G |
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