New Oleoyl Hybrids of Natural Antioxidants: Synthesis and In Vitro Evaluation as Inducers of Apoptosis in Colorectal Cancer Cells.

DNA damage HCT-116 apoptosis colorectal cancer cytotoxicity oleic acid pancreatic porcine lipase polyphenol hybrids quercetin

Journal

Antioxidants (Basel, Switzerland)
ISSN: 2076-3921
Titre abrégé: Antioxidants (Basel)
Pays: Switzerland
ID NLM: 101668981

Informations de publication

Date de publication:
03 Nov 2020
Historique:
received: 08 10 2020
revised: 27 10 2020
accepted: 30 10 2020
entrez: 6 11 2020
pubmed: 7 11 2020
medline: 7 11 2020
Statut: epublish

Résumé

Nowadays, the beneficial role of a healthy lifestyle, particularly emphasizing the quality of foods and cancer management, is accepted worldwide. Polyphenols and oleic acid play a key role in this context, but are still scarcely used as anti-cancer agents due to their bio-accessibility limits. Therefore, we aimed to synthesize a set of new oleoyl-hybrids of quercetin, morin, pinocembrin, and catechin to overcome the low bioavailability of polyphenols, throughout a bio-catalytic approach using pancreatic porcine lipase as a catalyst. The in vitro assays, using a wide panel of human cancer cell lines showed, mainly for two novel regioisomer oleoyl-hybrids of quercetin, a remarkable increase in apoptotic cell populations. We suggested that the DNA damage shown as ɣH2AX signals might be the major cause of apoptotic cell death. Finally, we demonstrated convincing data about two novel polyphenol-based hybrids displaying a highly selective anti-cancer cytotoxicity and being superior compared to their reference/parental compounds.

Identifiants

pubmed: 33153029
pii: antiox9111077
doi: 10.3390/antiox9111077
pmc: PMC7692320
pii:
doi:

Types de publication

Journal Article

Langues

eng

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Auteurs

Gabriele Carullo (G)

Department of Biotechnology, Chemistry and Pharmacy, Department of Excellence 2018-2022, University of Siena, Via Aldo Moro 2, 53100 Siena, Italy.
Department of Pharmacy, Health and Nutritional Sciences, Department of Excellence 2018-2022, University of Calabria, Edificio Polifunzionale, 87036 Rende (CS), Italy.

Sarah Mazzotta (S)

Department of Pharmacy, Health and Nutritional Sciences, Department of Excellence 2018-2022, University of Calabria, Edificio Polifunzionale, 87036 Rende (CS), Italy.
Department of Pharmaceutical Sciences, University of Milan Via Luigi Mangiagalli 25, 20133 Milano, Italy.
Department of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Seville, Profesor García González 2, 41071 Seville, Spain.

Adrian Koch (A)

Institiute of Pathology, University Hospital, Friedrich-Alexander University Erlangen-Nürnberg Universitätsstr. 22, 91054 Erlangen, Germany.
Experimental Tumorpathology, University Hospital, Friedrich-Alexander University Erlangen-Nürnberg Universitätsstr. 22, 91054 Erlangen, Germany.

Kristin M Hartmann (KM)

Institute of Medical Biotechnology Friedrich-Alexander-University Erlangen-Nürnberg, Paul-Gordan-Str. 3, 91052 Erlangen, Germany.
Erlangen Graduate School in Advanced Optical Technologies (SAOT), Friedrich-Alexander-University Erlangen-Nürnberg, Paul-Gordan-Str. 6, 91052 Erlangen, Germany.

Oliver Friedrich (O)

Institute of Medical Biotechnology Friedrich-Alexander-University Erlangen-Nürnberg, Paul-Gordan-Str. 3, 91052 Erlangen, Germany.

Daniel F Gilbert (DF)

Institute of Medical Biotechnology Friedrich-Alexander-University Erlangen-Nürnberg, Paul-Gordan-Str. 3, 91052 Erlangen, Germany.

Margarita Vega-Holm (M)

Department of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Seville, Profesor García González 2, 41071 Seville, Spain.

Regine Schneider-Stock (R)

Institiute of Pathology, University Hospital, Friedrich-Alexander University Erlangen-Nürnberg Universitätsstr. 22, 91054 Erlangen, Germany.
Experimental Tumorpathology, University Hospital, Friedrich-Alexander University Erlangen-Nürnberg Universitätsstr. 22, 91054 Erlangen, Germany.

Francesca Aiello (F)

Department of Pharmacy, Health and Nutritional Sciences, Department of Excellence 2018-2022, University of Calabria, Edificio Polifunzionale, 87036 Rende (CS), Italy.

Classifications MeSH