Biological Activity of Naphthoquinones Derivatives in the Search of Anticancer Lead Compounds

Abstract

Naphthoquinones are a valuable source of secondary metabolites that are well known for their dye properties since ancient times. A wide range of biological activities have been described highlighting their cytotoxic activity, gaining the attention of researchers in recent years. In addition, it is also worth mentioning that many anticancer drugs possess a naphthoquinone backbone in their structure. Considering this background, the work described herein reports the evaluation of the cytotoxicity of different acyl and alkyl derivatives from juglone and lawsone that showed the best activity results from a etiolated wheat coleoptile bioassay. This bioassay is rapid, highly sensitive to a wide spectrum of activities, and is a powerful tool for detecting biologically active natural products. A preliminary cell viability bioassay was performed on cervix carcinoma (HeLa) cells for 24 h. The most promising compounds were further tested for apoptosis on different tumoral (IGROV-1 and SK-MEL-28) and non-tumoral (HEK-293) cell lines by flow cytometry. Results reveal that derivatives from lawsone (particularly derivative 4) were more cytotoxic on tumoral than in non-tumoral cells, showing similar results to those obtained with of etoposide, which is used as a positive control for apoptotic cell death. These findings encourage further studies on the development of new anticancer drugs for more directed therapies and reduced side effects with naphthoquinone skeleton.

Novel N,S-Substituted naphthoquinone analogues from aminonaphthoquinones

“…The most important industrial applications of aromatic thiols are as intermediates in the production of pharmaceuticals, agrochemicals, dyes and pigments, and chemicals for the electronics industry (Vollhardt et al 2009;Roy et al 2000). The biological activity properties of amino and thionaphthoquinones are known from the literature (Durán et al, 2023;Kavaliauskas et al, 2022;Liu et al, 2023;López-López et al, 2022;Souza et al, 2023). In this study, novel N,S-substituted naphthoquinone analogues 2, 4, 6, and 8 were synthesized from the reactions of previously known aminonaphthoquinone derivatives 1 (Kalmayer et al 1991), 3 (Tadashi et al 1996, 5 (Vanallan et al 1963), and7 (Fries et al 1922) with allyl mercaptan.…”

Synthetic naphthoquinone derivatives suppressed nitric oxide and prostaglandin E2 production

“…Quinones, and particularly naphthoquinones (NQs), are widespread among the secondary metabolites of plants and microorganisms [5] . Their molecular structures endow them with redox properties, which confer activity in various biological oxidative processes [6] .…”