Oxidant-based anticancer activity of a novel synthetic analogue of capsaicin, capsaicin epoxide

Lewińska, Anna; Chochrek, Paweł; Smoląg, Karolina I.; Rawska, Ewa; Wnuk, Maciej

doi:10.1179/1351000214y.0000000113

Cited by 27 publications

(29 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a positive control of apoptosis induction, cells were treated for 30 min with 10 mM hydrogen peroxide (HP) [18]. UA- and BA-mediated changes in mitochondrial membrane potential were evaluated using Muse™ Cell Analyzer and Muse™ Mitopotential Assay Kit (Merck Millipore) according to manufacturer’s instructions.…”

Section: Methodsmentioning

confidence: 99%

Ursolic acid-mediated changes in glycolytic pathway promote cytotoxic autophagy and apoptosis in phenotypically different breast cancer cells

et al. 2017

Self Cite

View full text Add to dashboard Cite

Plant-derived pentacyclic triterpenotids with multiple biological activities are considered as promising candidates for cancer therapy and prevention. However, their mechanisms of action are not fully understood. In the present study, we have analyzed the effects of low dose treatment (5–20 µM) of ursolic acid (UA) and betulinic acid (BA) on breast cancer cells of different receptor status, namely MCF-7 (ER+, PR+/−, HER2−), MDA-MB-231 (ER−, PR−, HER2−) and SK-BR-3 (ER−, PR−, HER2+). UA-mediated response was more potent than BA-mediated response. Triterpenotids (5–10 µM) caused G0/G1 cell cycle arrest, an increase in p21 levels and SA-beta-galactosidase staining that was accompanied by oxidative stress and DNA damage. UA (20 µM) also diminished AKT signaling that affected glycolysis as judged by decreased levels of HK2, PKM2, ATP and lactate. UA-induced energy stress activated AMPK that resulted in cytotoxic autophagy and apoptosis. UA-mediated elevation in nitric oxide levels and ATM activation may also account for AMPK activation-mediated cytotoxic response. Moreover, UA-promoted apoptosis was associated with decreased pERK1/2 signals and the depolarization of mitochondrial membrane potential. Taken together, we have shown for the first time that UA at low micromolar range may promote its anticancer action by targeting glycolysis in phenotypically distinct breast cancer cells.

show abstract

Section: Methodsmentioning

confidence: 99%

Ursolic acid-mediated changes in glycolytic pathway promote cytotoxic autophagy and apoptosis in phenotypically different breast cancer cells

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…Capsaicin may induce the death of human lung and prostate cancer cells through DNA and chromosomal damage while the capsaicin epoxide is a better antiproliferative agent according to Lewinska et al 36,37 On the other hand, dihydrocapsaicin was found active against the human colon and breast cancer cells. 38 Two other main compounds found in chili peppers, the reduced ascorbate and dehydroascorbate, are cofactors in hydroxylation reactions and play an important antioxidant role in the body.…”

Section: Pure Capsaicin Vs Extractmentioning

confidence: 99%

Synthesis and characterization of a polyurethane carrier used for a prolonged transmembrane transfer of a chili pepper extract

Borcan

Dudás

Len

et al. 2018

IJN

View full text Add to dashboard Cite

PurposeRed chili peppers have been highly valued in gastronomy and traditional medicine since ancient times; it seems that it is not just an ingredient for food but also a good remedy for various medical conditions such as increased blood pressure and high levels of serum triglycerides and cholesterol, myocardial infarction, arthritis, and migraines. The objective of this study is the characterization of a new carrier used for encapsulated extract.MethodsChili pepper extract was obtained and was physically entrapped inside polyurethane microparticles in order to diminish the irritative potential of this extract. The particles were evaluated by Zetasizer measurements, small-angle neutron scattering and thermal analysis, scanning electron microscopy (SEM), and Fourier transform infrared spectroscopy; the encapsulation efficacy and the drug release profile were assessed by UV-Vis spectroscopy. Bioevaluations on mice skin were performed to predict the irritative potential of the samples.ResultsTwo different types of samples were compared: hollow polyurethane microparticles vs polyurethane particles containing the natural extract. The sizes of the particles were very similar, but the sample containing the extract presents three particle populations (the polydispersity index increases from 0.3 to 0.6 from one sample to another). The zeta-potential measurements and SEM images indicate a medium tendency to form clusters, while the UV-Vis study revealed an almost 70% encapsulation efficacy.ConclusionThe results suggest that encapsulation of a chili pepper extract inside polyurethane microparticles leads to a non-irritative product with a prolonged release: ~30% of encapsulated extract is released within the first 8 days and a maximum 45% is reached in 2 weeks.

show abstract

“…Most remarkably, the growthsuppressive activity of RPF151 is independent of the TRPV1 receptor. Lewinska et al (2015) synthesized a constrained capsaicin analog that contained an epoxide motif in Region C of the capsaicin (Fig. 6C).…”

Section: Antineoplastic Activity Of Synthetic Capsaicin Analogsmentioning

confidence: 99%

“…6C). The growth-suppressive activity of capsaicin epoxide (CE) compared with capsaicin was studied in a diverse array of cell lines using the MTT assay (Lewinska et al, 2015). Both capsaicin and CE did not reduce the viability of human dermal fibroblasts.…”

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

View full text Add to dashboard Cite

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.

show abstract

Oxidant-based anticancer activity of a novel synthetic analogue of capsaicin, capsaicin epoxide

Cited by 27 publications

References 31 publications

Ursolic acid-mediated changes in glycolytic pathway promote cytotoxic autophagy and apoptosis in phenotypically different breast cancer cells

Ursolic acid-mediated changes in glycolytic pathway promote cytotoxic autophagy and apoptosis in phenotypically different breast cancer cells

Synthesis and characterization of a polyurethane carrier used for a prolonged transmembrane transfer of a chili pepper extract

Anticancer Activity of Natural and Synthetic Capsaicin Analogs

Contact Info

Product

Resources

About