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Structure–Activity Relationship Study of Vitamin K Derivatives Yields Highly Potent Neuroprotective Agents

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† Department of Drug Discovery and Biomedical Sciences, South Carolina College of Pharmacy, Medical University of South Carolina, Charleston, South Carolina 29425, United States
‡ Department of Chemical and Life Science Engineering, Virginia Commonwealth University, Richmond, Virginia, 23284, United States
*Phone: (843) 792-1289. E-mail: [email protected]
Cite this: J. Med. Chem. 2013, 56, 3, 1007–1022
Publication Date (Web):January 17, 2013
https://doi.org/10.1021/jm301485d
Copyright © 2013 American Chemical Society
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    Abstract

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    Historically known for its role in blood coagulation and bone formation, vitamin K (VK) has begun to emerge as an important nutrient for brain function. While VK involvement in the brain has not been fully explored, it is well-known that oxidative stress plays a critical role in neurodegenerative diseases. It was recently reported that VK protects neurons and oligodendrocytes from oxidative injury and rescues Drosophila from mitochondrial defects associated with Parkinson’s disease. In this study, we take a chemical approach to define the optimal and minimum pharmacophore responsible for the neuroprotective effects of VK. In doing so, we have developed a series of potent VK analogues with favorable drug characteristics that provide full protection at nanomolar concentrations in a well-defined model of neuronal oxidative stress. Additionally, we have characterized key cellular responses and biomarkers consistent with the compounds’ ability to rescue cells from oxidative stress induced cell death.

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    Figures and tables and detailed experimental procedures; HPLC and all spectral data. This material is available free of charge via the Internet at http://pubs.acs.org.

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