Synthesis of the steroidal glycoside (25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl β-d-glucopyranoside and its anti-cancer properties on cervicouterine HeLa, CaSki, and ViBo cells

Fernández-Herrera, María A.; Mohan, Sankar; López-Muñoz, Hugo; Hernández-Vázquez, José M.V.; Pérez‐Cervantes, Esmeralda; Escobar-Sánchez, María L.; Sánchez-Sánchez, Luis; Regla, Ignacio; Pinto, B. Mario; Sandoval‐Ramírez, Jesús

doi:10.1016/j.ejmech.2010.07.051

Cited by 31 publications

(11 citation statements)

References 40 publications

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“…It also inhibits DU145 proliferation . The diosgenin-derivative 26-hydroxy-22-oxocholestanic steroid in human cervical cancer CaSki cells causes apoptosis at non-cytotoxic doses of caspase-3 activation (Fernández-Herrera et al, 2010). Furthermore, it caused the Hepatocellular Carcinoma (HCC) cells to be arrested during the G1 phase of the cell cycle and caused apoptosis by caspase-3 activation leading to PARP cleavage.…”

Section: Activity On Cancermentioning

confidence: 99%

Pharmacological characteristics of a phyto steroidal food saponin: Diosgenin

Manobharathi¹,

Mirunalini²

2020

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Diosgenin, a plant derived steroidal saponin found most abundantly in legumes and yams. It has been used for the treatment of various types of disorder such as leukemia, inflammation, hypercholesterolemia and cancer. Besides being a lactation aid, it has been shown to be gastro-and hepato-protective, antioxidant, antidiabetic and vaso-dilatory compound. It is a precursor for production of several steroidal hormones. This review focuses on the pharmacological properties of diosgenin, a food saponin.

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Section: Activity On Cancermentioning

confidence: 99%

Pharmacological characteristics of a phyto steroidal food saponin: Diosgenin

Manobharathi¹,

Mirunalini²

2020

afjbs

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“…General procedures for the cell culture of HeLa, CaSki and ViBo cell lines can be found in references [45,46]. Cells were seeded in 96-well tissue culture plates, stimulated with phytohemagglutinin (PHA, 10 µg/mL) and treated with title compounds at their IC 50 concentrations; analyses were performed after 72 h of incubation, by measuring carboxyfluorescein incorporation.…”

Section: Cell Culturementioning

confidence: 99%

Phenolic peptides as antioxidant and anti-proliferative agents

2018

J. Mol. Clin. Med.

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We report an efficient synthesis of phenolic peptides starting from 3,4-dihydroxyphenylacetic acid (DOPAC) and L-configured amino acid esters (glycine, phenylalanine, valine, serine, tryptophan, and cystine) using different coupling reagents. The combination of a phenolic scaffold with an amino acid residue might modulate the bioavailability and the therapeutic properties of title derivatives. Moreover, the incorporation of a catechol group, with inherent redox activity, can contribute to alter the redox status of the cancer cells, and therefore, provide anti-proliferative properties. Their activities as antioxidants (i.e. scavenging free radicals and H 2 O 2 as well inhibition of lipid peroxidation) and as anti-proliferative agents against three human cervical carcinoma cell lines (HeLa, ViBo, and CaSki) and normal lymphocytes were evaluated. All compounds exhibited an excellent antioxidant activity; remarkably, the peptide derived from L-cystine exhibited the best antioxidant activity, displaying a 2.5-fold increase in radical-scavenging activity when compared with the natural 2-(3',4'-dihydroxyphenyl)ethanol (hydroxytyrosol, HT). Moreover, this compound was also the most potent antitumor agent against the three human tumor cell lines (IC 50 values 108-122 µM), with a 2-7-fold increase in activity when compared with natural DOPAC and HT, used as reference compounds. Importantly, the cytotoxic activity of these phenolic peptidomimetics against normal human lymphocytes was very low, hence confirming their selectivity towards tumor cells. Moreover, a disulfide-containing peptide also exhibited negligible cell necrosis and a high selectivity against tumor cells when compared to normal lymphocytes. Such derivative incorporates two fragments characterized with redox properties, the catechol moiety, and the disulfide linker. Thus, disulfide-containing phenolic peptidomimetics emerge as good lead candidates for the development of a novel family of anti-tumor agents. This is an open access article under the CC BY-NC 4.0 license. https://creativecommons.org/licenses/by-nc/4.0/ Journal of Molecular and Clinical MedicineScheme 1. Peptide coupling between O-protected phenolic acid 1 and amino acid esters 2-6.

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“…In cancer cell lines, cell cycle arrest is one of the most important strategies used to stop or limit cancer proliferation. 42 As shown in Table 2, compounds 6-7 markedly suppressed the proliferation of HepG2 cells compared with positive drug LODDC with ID 50 values of 0.024 mM. To explore whether the cytotoxicity of compounds 6-7 was due to cell cycle arrest, we rst examined the effect on cell cycle distribution using propidiumiodide (PI) staining with ow cytometry analysis.…”

Section: In Vitro Cytotoxic Activity and Cell Cycle Analysismentioning

confidence: 99%