1. Academic Validation
  2. Toward Resolving the Resveratrol Conundrum: Synthesis and in Vivo Pharmacokinetic Evaluation of BCP-Resveratrol

Toward Resolving the Resveratrol Conundrum: Synthesis and in Vivo Pharmacokinetic Evaluation of BCP-Resveratrol

  • ACS Med Chem Lett. 2017 Apr 24;8(5):516-520. doi: 10.1021/acsmedchemlett.7b00018.
Yi Ling Goh 1 Yan Ting Cui 1 Vishal Pendharkar 2 Vikrant A Adsool 1
Affiliations

Affiliations

  • 1 Institute of Chemical and Engineering Sciences (ICES), Agency for Science Technology and Research (ASTAR), 8 Biomedical Grove, Neuros, #07-01, Singapore 138665, Singapore.
  • 2 Experimental Therapeutic Center (ETC), Agency for Science Technology and Research (ASTAR), 31 Biopolis way, Nanos, #03-01, Singapore 138669, Singapore.
Abstract

Over the last few decades, resveratrol has gained significance due to its impressive array of biological activities; however, its true potential as a drug has been severely constrained by its poor bioavailability. Indeed, several studies have implicated this bioavailability trait as a major road-block to resveratrol's potential clinical applications. To mitigate this pharmacokinetic issue, we envisioned a tactical bioisosteric modification of resveratrol to bicyclo[1.1.1]pentane (BCP) resveratrol. Relying on the beneficial bioisosteric potential demonstrated by the BCP-scaffold, we hypothesized that BCP-resveratrol would have an inherently better in vivo PK profile as compared to its natural counterpart. To validate such a hypothesis, it was necessary to secure a synthetic access to this novel structure. Herein we describe the first synthesis of BCP-resveratrol and disclose its PK properties.

Keywords

BCP; Bioisostere; bicyclo[1.1.1]pentane; pharmacokinetic studies; resveratrol.

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