Evaluation of the antitumour activity of Rinvanil and Phenylacetylrinvanil on the cervical cancer tumour cell lines HeLa, CaSKi and ViBo

Sánchez-Sánchez, Luis; Alvarado-Sansininea, J. Javier; Escobar, María Luisa; López-Muñoz, Hugo; Hernández-Vázquez, José M.V.; Monsalvo-Montiel, Iván; Demare, Patricia; Regla, Ignacio; Weiss‐Steider, Benny

doi:10.1016/j.ejphar.2015.04.003

Cited by 11 publications

(21 citation statements)

References 30 publications

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“…7,16,17 In other research, including synthesis and antituberculosis activity of amides and isoniazides obtained from different renewable fatty acids, it was demonstrated that the fatty acid chain is of fundamental importance to antimicrobial activity, most likely due to its improved permeability in bacterial cells. 7,16,17 In other research, including synthesis and antituberculosis activity of amides and isoniazides obtained from different renewable fatty acids, it was demonstrated that the fatty acid chain is of fundamental importance to antimicrobial activity, most likely due to its improved permeability in bacterial cells.…”

Section: Introductionmentioning

confidence: 99%

“…Results obtained from research on the synthetic fatty acid amides show that their antiproliferative activity against cancer cells depends both on the structure of the acid moiety, and the kind of the amide moiety. 7,16,17 In other research, including synthesis and antituberculosis activity of amides and isoniazides obtained from different renewable fatty acids, it was demonstrated that the fatty acid chain is of fundamental importance to antimicrobial activity, most likely due to its improved permeability in bacterial cells. 6,18 Moreover, acetylation of the hydroxyl group in hydroxyl fatty acid may also have a significant influence on the biological properties of the molecule.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and cytotoxicity of (R)‐ and (S)‐ricinoleic acid amides and their acetates

et al. 2017

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An environment-friendly, free of solvent, process for the synthesis of (R)- and (S)-ricinoleic acid amides has been developed. Starting from methyl ricinoleates and pyrrolidine or ethanolamine, the corresponding amides were obtained with yields ranging from 83-88%. Among 12 synthesized derivatives of ricinoleic acid, including the starting methyl esters, amides, and their acetates, nine compounds were obtained and tested for the first time. Studies on ricinoleic acid derivatives cytotoxicity showed that methyl esters were the least cytotoxic compounds and modification of their structure resulted in increasing cytotoxicity of the obtained products against both cancer cells and normal lymphocytes. Both enantiomers of the ethanolamine-derived amides showed the most promising anticancer potential.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxicity of (R)‐ and (S)‐ricinoleic acid amides and their acetates

et al. 2017

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“…Unsaturated fatty acids such as those present in cellular membranes are a common target for ROS. Sanchez‐Sanchez et al 18 also observed that rinvanil (RA amide) and phenylacetylrinvanil caused cell membrane damage in HeLa, CaSKi, and ViBo cells (release of LDH up to 60% was noted).…”

Section: Resultsmentioning

confidence: 95%

“…To the best of our knowledge, data on such biological properties of fatty acid amides are available for compounds such as N ‐arachidonoylethanolamine (anandamide, arachidonic acid derivative) or those belonging to the group called capsaicinoids (capsaicin, rinvanil, phenylacetylrinvanil). These compounds were found to have many biological activities (among others, induction of apoptotic cell death) and to be of great pharmacological potential 16,18,20 …”

Section: Introductionmentioning

confidence: 99%

Cytotoxic and genotoxic effects of (R)‐ and (S)‐ricinoleic acid derivatives

et al. 2020

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(R)‐ricinoleic acid is the main component of castor oil from Ricinus communis L. Due to the presence of the hydroxyl group in homoallylic position and asymmetrically substituted carbon atom, it may undergo a number of chemical and biochemical transformations resulting in the products with some specific bioactivities. Conversion of (R)‐ricinoleic acid into its (S)‐enantiomer enables synthesis of both (R)‐ and (S)‐ricinoleic acid derivatives and comparison of their biological activities. In the present research, (R)‐ and (S)‐ricinoleic acid amides synthesized from methyl ricinoleates and ethanolamine or pyrrolidine as well as acetate derivatives of ethanolamine amides were studied to demonstrate their biological activities using HT29 cancer cells. Double staining of cells with fluorochromes (Hoechst 33258/propidium iodide) as well as 2,′7′‐dichlorodihydrofluorescein (DCF) and comet assays were performed. Both the tested amides and acetates caused DNA damage and induced apoptotic and necrotic cell death. In the case of (R)‐ and (S)‐enantiomers of one of the tested acetates, significant difference in the ability to induce DNA damage was observed, which showed the impact of the stereogenic center on the activities of these compounds.

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“…Among all synthetic analogs of capsaicin, the N-acylvanillamides (N-AVAMs) are of the most extensively researched for their analgesic activity (Melck et al, 1999;Kobata et al, 2010;Huang et al, 2013). There are numerous studies that have investigated their anticancer activities in diverse human cancer cell lines (Sancho et al, 2003;Stock et al, 2012;Sánchez-Sánchez et al, 2015). This class of compounds is modified in the hydrophobic Region C of capsaicin (Fig.…”

Section: Antineoplastic Activity Of Synthetic Capsaicin Analogsmentioning

confidence: 99%

Anticancer Activity of Natural and Synthetic Capsaicin Analogs

Friedman

Nolan

Brown

et al. 2017

J Pharmacol Exp Ther

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The nutritional compound capsaicin is the major spicy ingredient of chili peppers. Although traditionally associated with analgesic activity, recent studies have shown that capsaicin has profound antineoplastic effects in several types of human cancers. However, the applications of capsaicin as a clinically viable drug are limited by its unpleasant side effects, such as gastric irritation, stomach cramps, and burning sensation. This has led to extensive research focused on the identification and rational design of second-generation capsaicin analogs, which possess greater bioactivity than capsaicin. A majority of these natural capsaicinoids and synthetic capsaicin analogs have been studied for their pain-relieving activity. Only a few of these capsaicin analogs have been investigated for their anticancer activity in cell culture and animal models. The present review summarizes the current knowledge of the growth-inhibitory activity of natural capsaicinoids and synthetic capsaicin analogs. Future studies that examine the anticancer activity of a greater number of capsaicin analogs represent novel strategies in the treatment of human cancers.

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Evaluation of the antitumour activity of Rinvanil and Phenylacetylrinvanil on the cervical cancer tumour cell lines HeLa, CaSKi and ViBo

Cited by 11 publications

References 30 publications

Synthesis and cytotoxicity of (R)‐ and (S)‐ricinoleic acid amides and their acetates

Synthesis and cytotoxicity of (R)‐ and (S)‐ricinoleic acid amides and their acetates

Cytotoxic and genotoxic effects of (R)‐ and (S)‐ricinoleic acid derivatives

Anticancer Activity of Natural and Synthetic Capsaicin Analogs

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