Phosphate-Linked Silibinin Dimers (PLSd): New Promising Modified Metabolites
| Autor: | Armando Zarrelli, Giovanni Di Fabio, Gilles Mailhot, Valeria Romanucci, Marcello Brigante, Martina Cimafonte, Cinzia Di Marino, Raffaele Gravante |
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| Přispěvatelé: | Department of Chemical Sciences, University of Naples Federico II, Napoli, Italy, Institut de Chimie de Clermont-Ferrand (ICCF), Université Blaise Pascal - Clermont-Ferrand 2 (UBP)-SIGMA Clermont (SIGMA Clermont)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), University of Naples Federico II = Università degli studi di Napoli Federico II, Romanucci, Valeria, Gravante, Raffaele, Cimafonte, Martina, DI MARINO, Cinzia, Mailhot, Gille, Brigante, Marcello, Zarrelli, Armando, DI FABIO, Giovanni |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Antioxidant
medicine.medical_treatment Pharmaceutical Science 01 natural sciences Antioxidants Analytical Chemistry chemistry.chemical_compound Drug Discovery phosphodiester Organic chemistry silibinin oligoflavonoids xanthine/xanthine oxidase assay radical scavengers reactive oxygen species (ROS) chemistry.chemical_classification Singlet oxygen Medicine (all) Free Radical Scavengers Hep G2 Cells Oligoflavonoid Chemistry (miscellaneous) Molecular Medicine Dimerization Oxidation-Reduction Silymarin Xanthine Oxidase Cell Survival Silibinin Radical scavenger 010402 general chemistry Xanthine Article Phosphates lcsh:QD241-441 lcsh:Organic chemistry medicine Humans [CHIM]Chemical Sciences Physical and Theoretical Chemistry Xanthine oxidase Reactive oxygen species Hydroxyl Radical 010405 organic chemistry Organic Chemistry Polyphenols 0104 chemical sciences Oxidative Stress Solubility chemistry Silybin Phosphodiester bond Hydroxyl radical Reactive Oxygen Species |
| Zdroj: | Molecules Molecules, MDPI, 2017, 22 (8), pp.1323. ⟨10.3390/molecules22081323⟩ Molecules; Volume 22; Issue 8; Pages: 1323 Molecules, 2017, 22 (8), pp.1323. ⟨10.3390/molecules22081323⟩ Molecules, Vol 22, Iss 8, p 1323 (2017) Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules22081323⟩ |
| Popis: | International audience; By exploiting the regioselective protection of the hydroxyl groups of silibinin along with the well-known phosphoramidite chemistry, we have developed an efficient strategy for the synthesis of new silibinin-modified species, which we have named Phosphate-Linked Silibinin Dimers (PLSd), in which the monomer units are linked by phosphodiester bonds. The antioxidant abilities of the new PLSd were estimated on HepG2 cells using DPPH free radical scavenging and xanthine/xanthine oxidase assays. The new phosphate-metabolites showed a higher anti-oxidant activity than the silibinin, as well as very low toxicity. The ability to scavenge reactive oxygen species (ROS) such as singlet oxygen () and hydroxyl radical () reveals that the two dimers are able to scavenge about two times more effectively than silibinin. Finally, solubility studies have shown that the PLSd present good water solubility (more than 20 mg·L−1) under circumneutral pH values, whereas the silibinin was found to be very poorly soluble (less than 0.4 mg·L−1) and not stable under alkaline conditions. Together, the above promising results warrant further investigation of the future potential of the PLSd as anti-oxidant metabolites within the large synthetic polyphenols field. |
| Databáze: | OpenAIRE |
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