Fluorine-Containing Isosteres Enable a Structure-Activity Relationship Study Of Gingerol Derivatives
Document Type
Article
Publication Date
2-1-2025
Abstract
A series of fluorinated and non-fluorinated [6]-gingerol, [6]-paradol, [6]-shogaol and ferulate derivatives were synthesized. Testing these analogs in anti-proliferation assays with MCF-7, A549, HCT-116 and HEK-293 cell lines provided insight into the structural features that contribute to the anti-proliferative activity of naturally occurring ginger constituents. In particular, the use of both vinyl and alkyl trifluoromethyl isosteres allowed us to evaluate the structure-activity impact of the enone motif found in shogaols. Our results indicate that enone-containing derivatives have a higher potency, suggesting the conjugated enone motif characteristic of shogaols may be primarily responsible for the anti-cancer activity of the broader natural product family.
Recommended Citation
Cooper, Shelby; Kabashi, Diarta; Yacoub, Marlin; Molen, Jessica; Farhan, Osman; Farley, Christina; Yencha, Samantha; Figueiredo, Michelle; Phadnis, Nidheesh; Henry, Wynter; Harris, Julian; Wilkinson, Frank; and Milligan, John, "Fluorine-Containing Isosteres Enable a Structure-Activity Relationship Study Of Gingerol Derivatives" (2025). College of Life Sciences Faculty Papers. Paper 22.
https://jdc.jefferson.edu/jclsfp/22
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.
Language
English
Comments
This article is the author's final published version in Journal of Fluorine Chemistry, Volume 282, February 2025, Article number 110400.
The published version is available at https://doi.org/10.1016/j.jfluchem.2025.110400.
Copyright © 2025 The Author(s)