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The Effect of Oleanolic Acid and Its Four New Semisynthetic Derivatives on Human MeWo and A375 Melanoma Cell Lines

Overview
Publisher MDPI
Specialty Chemistry
Date 2023 May 27
PMID 37242529
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Abstract

This study aimed to synthesize four new semisynthetic derivatives of natural oleanolic acid (OA) and, based on an analysis of their cytotoxic and anti-proliferative effects against human MeWo and A375 melanoma cell lines, select those with anti-cancer potential. We also screened the treatment time with the concentration of all four derivatives. We synthesized oxime 2 and performed its acylation with carboxylic acids into new derivatives and according to the methods previously described. Colorimetric MTT and SRB assays were used to measure the anti-proliferative and cytotoxic activity of OA and its derivatives , , and against melanoma cells. Selected concentrations of OA, the derivatives, and different time periods of incubation were used in the study. The data were analyzed statistically. The present results revealed the possible anti-proliferative and cytotoxic potential of two selected OA derivatives and , on A375 and MeWo melanoma cells, especially at concentrations of 50 μM and 100 μM at 48 h of incubation ( < 0.05). Further studies will be necessary to analyze the proapoptotic and anti-cancer activities of and against skin and other cancer cells. The bromoacetoxyimine derivative () of OA morpholide turned out to be the most effective against the tested cancer cells.

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References
1.
Mioc M, Milan A, Malita D, Mioc A, Prodea A, Racoviceanu R . Recent Advances Regarding the Molecular Mechanisms of Triterpenic Acids: A Review (Part I). Int J Mol Sci. 2022; 23(14). PMC: 9322890. DOI: 10.3390/ijms23147740. View

2.
Jannus F, Medina-ODonnell M, Rivas F, Diaz-Ruiz L, Rufino-Palomares E, Lupianez J . A Diamine-PEGylated Oleanolic Acid Derivative Induced Efficient Apoptosis through a Death Receptor and Mitochondrial Apoptotic Pathway in HepG2 Human Hepatoma Cells. Biomolecules. 2020; 10(10). PMC: 7601263. DOI: 10.3390/biom10101375. View

3.
Ayeleso T, Matumba M, Mukwevho E . Oleanolic Acid and Its Derivatives: Biological Activities and Therapeutic Potential in Chronic Diseases. Molecules. 2017; 22(11). PMC: 6150249. DOI: 10.3390/molecules22111915. View

4.
Rashid S, Shaughnessy M, Tsao H . Melanoma classification and management in the era of molecular medicine. Dermatol Clin. 2022; 41(1):49-63. DOI: 10.1016/j.det.2022.07.017. View

5.
Guo Y, Han B, Luo K, Ren Z, Cai L, Sun L . NOX2-ROS-HIF-1α signaling is critical for the inhibitory effect of oleanolic acid on rectal cancer cell proliferation. Biomed Pharmacother. 2016; 85:733-739. DOI: 10.1016/j.biopha.2016.11.091. View