Next Article in Journal
Systematic Profiling of the Multicomponents and Authentication of Erzhi Pill by UHPLC/Q-Orbitrap-MS Oriented Rapid Polarity-Switching Data-Dependent Acquisition and Selective Monitoring of the Chemical Markers Deduced from Fingerprint Analysis
Next Article in Special Issue
Dermal Delivery of Selected Polyphenols from Silybum marianum. Theoretical and Experimental Study
Previous Article in Journal
Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents
Previous Article in Special Issue
Selective Synthesis of 3-O-Palmitoyl-Silybin, a New-to-Nature Flavonolignan with Increased Protective Action against Oxidative Damages in Lipophilic Media
Open AccessArticle

O-Aminoalkyl-O-Trimethyl-2,3-Dehydrosilybins: Synthesis and In Vitro Effects Towards Prostate Cancer Cells

1
Department of Chemistry, California State University, Fresno, 2555 E. San Ramon Avenues, M/S SB70, Fresno, CA 93740, USA
2
Department of Chemistry and RCMI Cancer Research Center, Xavier University of Louisiana, 1 Drexel Drive, New Orleans, LA 70125, USA
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(12), 3142; https://doi.org/10.3390/molecules23123142
Received: 31 October 2018 / Revised: 26 November 2018 / Accepted: 29 November 2018 / Published: 29 November 2018
(This article belongs to the Special Issue Silymarin and Derivatives: From Biosynthesis to Health Benefits)
As part of our ongoing silybin project, this study aims to introduce a basic nitrogen-containing group to 7-OH of 3,5,20-O-trimethyl-2,3-dehydrosilybin or 3-OH of 5,7,20-O-trimethyl-2,3-dehydrosilybin via an appropriate linker for in vitro evaluation as potential anti-prostate cancer agents. The synthetic approaches to 7-O-substituted-3,5,20-O-trimethyl-2,3-dehydrosilybins through a five-step procedure and to 3-O-substituted-5,7,20-O-trimethyl-2,3- dehydrosilybins via a four-step transformation have been developed. Thirty-two nitrogen-containing derivatives of silybin have been achieved through these synthetic methods for the evaluation of their antiproliferative activities towards both androgen-sensitive (LNCaP) and androgen-insensitive prostate cancer cell lines (PC-3 and DU145) using the WST-1 cell proliferation assay. These derivatives exhibited greater in vitro antiproliferative potency than silibinin. Among them, 11, 29, 31, 37, and 40 were identified as five optimal derivatives with IC50 values in the range of 1.40–3.06 µM, representing a 17- to 52-fold improvement in potency compared to silibinin. All these five optimal derivatives can arrest the PC-3 cell cycle in the G0/G1 phase and promote PC-3 cell apoptosis. Derivatives 11, 37, and 40 are more effective than 29 and 31 in activating PC-3 cell apoptosis. View Full-Text
Keywords: silybin; prostate cancer; 2,3-dehydrosilybin; cell proliferation; cell apoptosis silybin; prostate cancer; 2,3-dehydrosilybin; cell proliferation; cell apoptosis
Show Figures

Graphical abstract

MDPI and ACS Style

Vue, B.; Zhang, S.; Vignau, A.; Chen, G.; Zhang, X.; Diaz, W.; Zhang, Q.; Zheng, S.; Wang, G.; Chen, Q.-H. O-Aminoalkyl-O-Trimethyl-2,3-Dehydrosilybins: Synthesis and In Vitro Effects Towards Prostate Cancer Cells. Molecules 2018, 23, 3142. https://doi.org/10.3390/molecules23123142

AMA Style

Vue B, Zhang S, Vignau A, Chen G, Zhang X, Diaz W, Zhang Q, Zheng S, Wang G, Chen Q-H. O-Aminoalkyl-O-Trimethyl-2,3-Dehydrosilybins: Synthesis and In Vitro Effects Towards Prostate Cancer Cells. Molecules. 2018; 23(12):3142. https://doi.org/10.3390/molecules23123142

Chicago/Turabian Style

Vue, Bao; Zhang, Sheng; Vignau, Andre; Chen, Guanglin; Zhang, Xiaojie; Diaz, William; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong. 2018. "O-Aminoalkyl-O-Trimethyl-2,3-Dehydrosilybins: Synthesis and In Vitro Effects Towards Prostate Cancer Cells" Molecules 23, no. 12: 3142. https://doi.org/10.3390/molecules23123142

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop