Natural product honokiol (1) has been used in traditional Chinese medicine for centuries. More recently it has been discovered to cause inhibitory effects against the oral bacterium Streptococcus mutans, one of the causative agents of dental caries. Additionally, honokiol is being heavily studied in the realm of cancer research due to its demonstrated activity against a panel of cancer types. For these reasons, we probed the structure-activity relationship (SAR) of its bisphenol structure by examining modifications to its substitution pattern, linker length and the phenol protections. Through this process, we identified an extended scaffold (C2) that is 100 times more potent than the natural product. Intrigued by the drastic increase in potency, the biological mechanism of the extended scaffold was then investigated. Herein, we present our findings that C2 affects the membrane integrity of S. mutans, causing membrane disruption and ultimately cell death. Moreover, preliminary data shows that C2 is more potent than a commercial oral antiseptic and demonstrates a wider therapeutic window, highlighting its potential to influence future oral care.

Honokiol-inspired analog disrupts Streptococcus mutans membrane integrity

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.