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      Drug Design, Development and Therapy (submit here)

      This international, peer-reviewed Open Access journal by Dove Medical Press focuses on the design and development of drugs, as well as the clinical outcomes, patient safety, and programs targeted at the effective and safe use of medicines. Sign up for email alerts here.

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      Design and preparation of derivatives of oleanolic and glycyrrhetinic acids with cytotoxic properties.

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          Abstract

          The structural modification of natural products with the aim to improve the anticancer activity is a popular current research direction. The pentacyclic triterpenoid compounds oleanolic acid (OA) and glycyrrhetinic acid (GA) are distributed widely in nature.

          Most cited references37

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          Exclusion of Kaposi Sarcoma From Analysis of Cancer Burden—Reply

          Mohsen Naghavi, Christina Fitzmaurice (2017)
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            Cinnamic acid derivatives as anticancer agents-a review.

            M Baltas, Ronald de Vries, F Bedos-Belval (2010)
            Cinnamic acid and its phenolic analogues are natural substances. Chemically, in cinnamic acids the 3-phenyl acrylic acid functionality offers three main reactive sites; substitution at the phenyl ring, addition at the α,β- unsaturation and the reactions of the carboxylic acid functionality. Owing to these chemical aspects cinnamic acid derivatives received much attention in medicinal research as traditional as well as recent synthetic antitumor agents. We observed that in spite of their rich medicinal tradition, cinnamic acid derivatives and their anticancer potentials remained underutilized for several decades since the first published clinical use in 1905. In last two decades, there has been huge attention towards various cinnamoyl derivatives and their antitumor efficacy. This review provides a comprehensive and unprecedented literature compilation concerning the synthesis and biological evaluation of various cinnamoyl acids, esters, amides, hydrazides and related derivatives in anticancer research. We envisage that our effort in this review contributes a much needed and timely addition to the literature of medicinal research.
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              18beta-Glycyrrhetinic acid induces apoptotic cell death in SiHa cells and exhibits a synergistic effect against antibiotic anti-cancer drug toxicity.

              Cheol E. Han, Sang Lee, S Lee … (2008)
              Defects in mitochondrial function have been shown to participate in the induction of cell death in cancer cells. The present study was designed to assess the toxic effect of 18beta-glycyrrhetinic acid against human cervix and uterus tumor cell line SiHa cells in relation to the mitochondria-mediated cell-death process and evaluate the combined toxic effect of 18beta-glycyrrhetinic acid and anti-cancer drugs. 18beta-Glycyrrhetinic acid induced the nuclear damage, changes in the mitochondrial membrane permeability, formation of reactive oxygen species and depletion of glutathione in SiHa cells. It caused cell death by inducing the increase in the pro-apoptotic Bax protein and cytochrome c levels, reduction in anti-apoptotic Bcl-2 level, subsequent caspase-3 activation and loss of the mitochondrial transmembrane potential. Unlike 18beta-glycyrrhetinic acid, a pro-compound glycyrrhizin up to 100 microM did not induce cell death and depletion of glutathione. Combined treatment of mitomycin c (or doxorubicin) and 18beta-glycyrrhetinic acid revealed a synergistic toxic effect. Meanwhile, combination of camptothecin and 18beta-glycyrrhetinic acid exhibited an additive cytotoxic effect. Results suggest that 18beta-glycyrrhetinic acid may cause cell death in SiHa cells by inducing the mitochondrial membrane permeability change, leading to cytochrome c release and caspase-3 activation. The effect may be associated with increased formation of reactive oxygen species and depletion of glutathione. Combined treatment of antibiotic anti-cancer drug and 18beta-glycyrrhetinic acid seems to exhibit a synergistic toxic effect.
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                Author and article information

                Journal
                Journal ID (iso-abbrev): Drug Des Devel Ther
                Title: Drug design, development and therapy
                Publisher: Informa UK Limited
                ISSN (Electronic): 1177-8881
                ISSN (Print): 1177-8881
                Publication date (Electronic): 2018
                Volume: 12
                Affiliations
                [1 ] Marine College, Shandong University, Weihai, China.
                [2 ] Zhong Yuan Academy of Biological Medicine, Liaocheng People's Hospital/Affiliated Liaocheng Hospital, Taishan Medical University, Liaocheng, China.
                [3 ] School of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, China.
                [4 ] School of Marine Science and Technology, Harbin Institute of Technology at Weihai, Weihai, China.
                Article
                Publisher Item ID: dddt-12-1321
                DOI: 10.2147/DDDT.S166051
                PMC ID: 5968802
                PubMed ID: 29861624
                SO-VID: 1e01eec6-0074-488b-a004-7a6b5302de01
                History

                Keywords: apoptosis,cytotoxic properties,glycyrrhetinic acid,oleanolic acid,synthesis
                Data availability:
                Keywords: apoptosis, cytotoxic properties, glycyrrhetinic acid, oleanolic acid, synthesis

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