We have prepared several organometallic systems whose structures are closely analogous to that of tamoxifen, the drug used in the treatment of hormone-dependent breast cancers, but which now possess two basic aminoalkyl chains: O(CH 2 ) 3 NMe 2 . Despite the absence of a phenolic functionality, these ferrocenyl compounds 3, 4 and their organic analogue 5 recognize the estrogen receptor but in addition exhibit strong antiproliferative effects on hormone-dependent breast cancer cells (MCF-7), and also on hormone-independent ones (MDA-MB-231) with, in this case, an IC 50 value of about 0.4 mM. The ferrocenyl moiety does not create a major effect here compared to a purely organic aromatic group. On the other hand, the presence within the molecule of two vicinal basic entities, potentially allowing complexation to metal ions such as Zn 2+ , could perhaps be the key to the antiproliferative effectiveness of this series which operates via a different mechanism to that of hydroxytamoxifen 1 and hydroxyferrocifen 2. The behaviour of these new species is discussed. They possess the distinctive feature of combining a strong antiproliferative effect with intense antibacterial and antifungal activity.
Diarylmethanes (DAMs) and triarylmethanes (TAMs), molecules bearing two or three aryl groups (phenyls or heterocycles) bonded to a central carbon atom, have numerous applications. The biological and therapeutic relevancy of this class of molecules has been demonstrated for various applications in the field of antimicrobials, infectious, cardiovascular and nervous system disorders, genital tract diseases, estrogen-related disorders and bone remodeling. These interesting compounds have also been used as starting materials for the development of high value-added molecules. We report here the synthesis of two new diarylmethanes using a McMurry coupling reaction as well as their antibacterial evaluation.
The inhibitory effects of four series of aryl butene derivatives, active against breast cancer, on the monophenolase activity of tyrosinase, in melanin-free ink from Sepia officinalis, have been studied.Hydroxytamoxifen 1, ferrociphenol 17 and several aryl butene analogs have shown strong antiproliferative activity on hormone-dependent and hormone-independent breast cancer cells and were evaluated in leukemia K562 cell proliferation. Their potential to induce skin depigmentation by evaluating their anti-tyrosinase activity was also estimated. In order to better rationalize the tyrosinase inhibitory action and the binding mode of the compounds, docking studies were carried out.Hydroxytamoxifen and some aryl butenes showed strong antiproliferative effects against K562 cells at 1 μM without showing tyrosinase inhibition.If phenolic compounds 16 and 17 showed the best antiproliferative activity on K562,Hydroxytamoxifen and compounds 5, 10, 20 and 21 have been identified as candidates for further development against chronic myeloid leukemia (CML), and are predicted to not induce depigmentation of the skin, a side effect encountered with imatinib, conventionally used for the treatment of CML.
The table olive industry produces a large amount of wastewater that can be expensive to be treated and harmful to the environment. This study aimed to find a way to reuse brine water from the production of black and green table olive brines from Bejaia and Mascara of the Sigoise cultivar in order to create a valuable byproduct and con-tribute to sustainable development. In this context, the high-performance liquid chromatography–diode-array detection (HPLC-DAD) analysis revealed the highest concentration of hydroxytyrosol (4-(2-dihydroxy phenyl ethanol); 69.67 mg/100 mg) for green table olive brines of Mascara (EOGM) and tyrosol (Ty) (28.8 mg/100 mg) for black table olive brines of Bejaia (EOBB). Presence of polyphenols and ortho-diphenols could be responsible for their antioxidant, anti-inflammatory, and antibacterial properties. To assess antioxidant activity, the scavenging effects of DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,20-Azinobis[3-ethylbenzothiazoline-6-sulfonate]) radicals as well as hydrogen peroxide (H2O2) radicals were used. The antimicrobial activity showed that the black olive extract exhibited the best inhibitory effect, with a minimum inhibitory concentration (MIC) ranging from 0.625 mg/mL to 0.31 mg/mL. The anti-inflammatory activity of tested extracts of black olives of Bejaia (EOBB) and green of olives Mascara (EOGM) was 20.06 µg/mL and 20.21 µg/mL, respectively, which demonstrated the anti-inflammatory effect of these extracts on human beings.
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