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Current Topics in Medicinal Chemistry

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ISSN (Print): 1568-0266
ISSN (Online): 1873-4294

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Research Article

Novel [6]-gingerol Triazole Derivatives and their Antiproliferative Potential against Tumor Cells

Author(s): William Cezar de Lima Silva, Raphael Conti, Larissa Costa de Almeida, Pedro Alves Bezerra Morais, Keyller Bastos Borges, Valdemar Lacerda Júnior, Letícia Veras Costa-Lotufo and Warley de Souza Borges*

Volume 20, Issue 2, 2020

Page: [161 - 169] Pages: 9

DOI: 10.2174/1568026620666191227125507

Price: $65

Abstract

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.

Methods: [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%.

Keywords: [6]-gingerol, Cytotoxic activity, Zingiber officinale, Semisynthesis, Triazole derivatives, Tumor cells.

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