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Start Over Author "Pannecouque, Christophe" Journal bioorganic chemistry
15 results on '"Pannecouque, Christophe"'

15. Silibinin phosphodiester glyco-conjugates: Synthesis, redox behaviour and biological investigations

Author

Armando Zarrelli, Christophe Pannecouque, Valeria Romanucci, Rajesh Agarwal, Chapla Agarwal, Gaetano De Tommaso, Giovanni Di Fabio, Tonino Caruso, Mauro Iuliano, Romanucci, Valeria, Agarwal, Chapla, Agarwal, Rajesh, Pannecouque, Christophe, Iuliano, Mauro, De Tommaso, Gaetano, Caruso, Tonino, Di Fabio, Giovanni, and Zarrelli, Armando

Subjects
0301 basic medicine, Antioxidant, DPPH, Cell Survival, medicine.medical_treatment, Silibinin, urologic and male genital diseases, Biochemistry, Antiviral Agents, 03 medical and health sciences, chemistry.chemical_compound, Structure-Activity Relationship, DU145, Cell Line, Tumor, Drug Discovery, LNCaP, medicine, Flavonolignan, Humans, Molecular Biology, ABTS, Cell Death, Dose-Response Relationship, Drug, Molecular Structure, Chemistry, Organic Chemistry, HIV, Flavonolignans, Silibinin, Silybin, Glyco-conjugates, Phosphoramidite chemistry, Organophosphates, 030104 developmental biology, Silybin, Phosphodiester bond, PC-3 Cells, Glycoconjugates, Oxidation-Reduction
Abstract

New silibinin phosphodiester glyco-conjugates were synthesized by efficient phosphoramidite chemistry and were fully characterized by 2D-NMR. A wide-ranging study focused on the determination of their pKa and E° values as well as on their radical scavenging activities by different assays (DPPH, ABTS+ and HRSA) was conducted. The new glyco-conjugates are more water-soluble than silibinin, and their radical scavenging activities are higher than those of silibinin. The conjugation therefore improves both the water solubilities and antioxidant activities of the flavonolignan moieties. The serum stability was evaluated under physiological conditions, and the glyco-conjugates degraded with half-lives of 40-70 h, making them useful in pro-drug approaches. We started by treating androgen-dependent prostate cancer (PCa) LNCaP cells and then expanded our studies to androgen-independent PCa PC3 and DU145 cells. In most cases, the new derivatives significantly reduced both total and live cell numbers, albeit at different levels. Anti-HIV activities were evaluated and the glucosamine-phosphate silibinin derivative showed higher activity (IC50 = 73 μM) than silibinin.

Published
2017

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