Novel [6]-gingerol Triazole Derivatives and their Antiproliferative Potential against Tumor Cells
| Autor: | Letícia V. Costa-Lotufo, Warley de Souza Borges, Larissa Costa de Almeida, Keyller Bastos Borges, Pedro Alves Bezerra Morais, William Cezar de Lima Silva, Valdemar Lacerda Júnior, Raphael Conti |
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| Rok vydání: | 2020 |
| Předmět: |
Catechols
Triazole Antineoplastic Agents Pharmacology Structure-Activity Relationship 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Drug Discovery Humans Cytotoxic T cell Cytotoxicity Cell Proliferation 030304 developmental biology 0303 health sciences Natural product Dose-Response Relationship Drug Molecular Structure Cell growth Gingerol General Medicine Triazoles HCT116 Cells Semisynthesis chemistry 030220 oncology & carcinogenesis PLANTAS MEDICINAIS MCF-7 Cells Click chemistry Drug Screening Assays Antitumor Fatty Alcohols |
| Zdroj: | Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP |
| ISSN: | 1568-0266 |
| Popis: | Background: Effective cancer treatment is a major public health challenge. The limitations of current therapies and their adverse effects reduce the efficacy of treatment, leading to significant mortality rates worldwide. Moreover, natural product chemistry occupies a prominent role in the search for new treatment alternatives, by contributing a spectrum of chemical structures that may potentially yield new bioactive compounds. The compound [6]-gingerol (1) is the main active substance in ginger (Zingiber officinale) and several studies have shown it to produce beneficial effects, including antitumor activity. Objective: This work aims to obtain new gingerol derivatives with cytotoxic activity. Method: [6]-gingerol was isolated and its derivatives were produced using click chemistry, obtaining eight new compounds. All chemical structures were determined by means of IR, NMR and HRMS data, and cytotoxicity was evaluated in the HCT 116 (colon carcinoma) and MCF-7 (breast carcinoma) cell lines at concentrations of 5 µmol L-1 and 50 µmol L-1. Results: At 50 µmol L-1, more than 70% inhibition of cell growth was achieved with compounds 2e, 2g against HCT 116, and 2b, 2d, 2e, 2f and 2g against MCF-7. Conclusion: The obtained compounds showed only moderate cytotoxic activity. However, the products with substituents occupying the meta position in relation to the triazole ring showed increased cytotoxic properties. The brominated compound (2g) showed the strongest activity, inhibiting cell proliferation by 87%. |
| Databáze: | OpenAIRE |
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