Synthesis and antiproliferative activity of novel sugiol β-amino alcohol analogs

Córdova, I.; León, Leticia G.; León, Francisco; Andrés, Lucía S.; Luis, Javier G.; Padrón, José M.

doi:10.1016/j.ejmech.2006.06.001

Cited by 25 publications

(12 citation statements)

References 15 publications

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“…However, sugiol showed less cytotoxicity towards normal ovarian cells (IC 50 ; 62.5 μM), indicating that sugiol targets cancer cells more potently. Our results are in agreement with previous studies in which sugiol was reported to inhibit the growth of several types of cancers including prostate cancer [11,[15][16][17]. Moreover, sugiol treatment triggered several morphological changes in SKOV3 cells that are characteristic of apoptosis.…”

Section: Discussionsupporting

confidence: 83%

Anticancer activity of sugiol against ovarian cancer cell line SKOV3 involves mitochondrial apoptosis, cell cycle arrest and blocking of the RAF/MEK/ERK signalling pathway

Wang¹,

Shi²,

Qi³

et al. 2020

aoms

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A b s t r a c tIntroduction: Ovarian cancer is one of the leading causes of cancer-related deaths in women. Treatments for ovarian cancer include surgery followed by chemotherapy. However, the survival rate for ovarian cancer is still not satisfactory. Moreover, the current chemotherapy has numerous associated side effects. Therefore there is an urgent need to look for novel and more viable treatment options. Against this backdrop the present study was designed to evaluate the anticancer activity of sugiol against ovarian cancer cells. Material and methods: Cell viability was assessed by CCK8 assay, apoptosis by DAPI, AO/ER and annexin V/PI staining. Mitochondrial membrane potential and cell cycle analysis was performed by flow cytometry. Cell migration was investigated by wound healing assay. Protein expression was monitored by western blotting. Results: The results of the present study indicated that sugiol exerts significant (p < 0.0001) anticancer effects on SKOV3 cancer cells with an IC 50 of 25 μM. However, sugiol exhibited less cytotoxicity against normal ovarian cells with an IC 50 of 62.5 μM. The anticancer effects of sugiol were found to be due to G0/G1 cell cycle arrest and mitochondrial apoptosis. Sugiol also inhibited cell migration of SKOV3 cells dose dependently. Moreover, the results showed that sugiol could inhibit the RAF/MEK/ERK signalling pathway in a dose-dependent manner. Conclusions:The results of the present study indicate that sugiol exerts potent anticancer effects on SKOV3 cells via induction of cell cycle arrest, mitochondrial apoptosis and inhibition of the RAF/MEK/ERK signalling pathway.

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Section: Discussionsupporting

confidence: 83%

Anticancer activity of sugiol against ovarian cancer cell line SKOV3 involves mitochondrial apoptosis, cell cycle arrest and blocking of the RAF/MEK/ERK signalling pathway

Wang¹,

Shi²,

Qi³

et al. 2020

aoms

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“…Among them, dehydroabietic acid (DHA, 1 ) is one of the major tricyclic diterpenoid constituents of pine resin and can be readily obtained from commercial disproportionated rosin. DHA and its derivatives have exhibited a broad spectrum of biological activities such as antimicrobial, antitumor, antiviral, antioxidant, anti-inflammatory and gastroprotective activities [ 16 , 17 , 18 , 19 , 20 , 21 ], which indicate that the compound is a potentially useful starting material for the synthesis of industrially or pharmacologically important products. In view of these findings, it would be worthwhile to design, synthesize new derivatives of DHA bearing N -acylhydrazone moiety and evaluate their potential antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of New N-acylhydrazone Derivatives from Dehydroabietic Acid

et al. 2012

Molecules

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A series of new N-acylhydrazone derivatives were synthesized in good yields through the reactions of dehydroabietic acid hydrazide with a variety of substituted arylaldehydes. The structures of the synthesized compounds were confirmed by IR, 1H- and 13C-NMR, ESI-MS, elemental analysis and single crystal X-ray diffraction. From the crystal structure of compound 4l, the C=N double bonds of these N-acylhydrazones showed (E)-configuration, while the NMR data of compounds 4a–q indicated the existence of two rotamers for each compound in solution. The target compounds were evaluated for their antibacterial activities against four microbial strains. The result suggested that several compounds exhibited pronounced antibacterial activities. Particularly, compound 4p exhibited good antibacterial activity against Staphylococcus aureus and Bacillus subtilis comparable to positive control. The possible antibacterial metabolism and the strategy for further optimization of this compound were also discussed.

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“…or abietopinoic acid), its deoxy acid, 12-hydroxydehydroabietic acid(15) and the sugiol methyl ester analog(14) were generally inactive (GI50 > 70 µΜ) in the solid tumor cells asays(Table S2, Supporting Information). The most potent compound in general in solid tumor assays, was compound 10, characterized by an acetate group at C12 and a methyl ester at C18.…”

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confidence: 99%

Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies

et al. 2019

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similar chemistry. The combined findings indicate that these abietane-diterpenoid natural product analogues offer a source of novel bioactive molecules with promising pharmacological and drug-likeness properties. ASSOCIATED CONTENT Supporting Information Available: Complete experimental details for the synthesis of compounds 7 and 9-16, including copies of 1 H NMR and 13 C NMR spectra, and for all the biological assays. A list with the complete results of the docking studies carried out on the analyzed targets and SMILES codes is also available in the S.I.

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Synthesis and antiproliferative activity of novel sugiol β-amino alcohol analogs

Cited by 25 publications

References 15 publications

Anticancer activity of sugiol against ovarian cancer cell line SKOV3 involves mitochondrial apoptosis, cell cycle arrest and blocking of the RAF/MEK/ERK signalling pathway

Anticancer activity of sugiol against ovarian cancer cell line SKOV3 involves mitochondrial apoptosis, cell cycle arrest and blocking of the RAF/MEK/ERK signalling pathway

Synthesis and Antibacterial Evaluation of New N-acylhydrazone Derivatives from Dehydroabietic Acid

Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies

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