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Based on the established relationship between altered membrane dipole potential and transmembrane protein conformation and function, we investigate\u00a0here polyphenols' ability to induce changes in cell membrane dipole potential. Ultimately, we are interested in finding a tool to prevent polyphenol PAINS-type behavior and produce compounds less prone to untargeted and promiscuous interactions with the cell membrane. Di-8-ANEPPS fluorescence ratiometric measurements suggest that planar lipophilic polyphenols\u2014phloretin, genistein and resveratrol\u2014act by decreasing membrane dipole potential, especially in cholesterol-rich domains such as lipid rafts, which play a role in important cellular processes. These results provide a mechanism for their labelling as PAINS through their ability to disrupt cell membrane homeostasis. Aiming to explore the role of<jats:italic>C<\/jats:italic>-glucosylation in PAINS membrane-interfering behavior, we disclose herein the first synthesis of 4-glucosylresveratrol, starting from 5-hydroxymethylbenzene-1,3-diol, via<jats:italic>C<\/jats:italic>-glucosylation, oxidation and Horner-Wadsworth-Emmons olefination, and resynthesize phloretin and genistein<jats:italic>C<\/jats:italic>-glucosides. We show that C-glucosylation generates compounds which are no longer able to modify membrane dipole potential. Therefore, it can be devised as a strategy to generate bioactive natural product derivatives that no longer act as membrane dipole potential\u00a0modifiers. Our results offer a new technology towards rescuing bioactive polyphenols\u00a0from their PAINS danger label through C\u2013C ligation of sugars.<\/jats:p>","DOI":"10.1038\/s41598-021-83032-3","type":"journal-article","created":{"date-parts":[[2021,2,24]],"date-time":"2021-02-24T11:03:35Z","timestamp":1614164615000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["C-Glucosylation as a tool for the prevention of PAINS-induced membrane dipole potential alterations"],"prefix":"10.1038","volume":"11","author":[{"given":"Ana Marta","family":"de Matos","sequence":"first","affiliation":[]},{"given":"Maria Teresa","family":"Bl\u00e1zquez-S\u00e1nchez","sequence":"additional","affiliation":[]},{"given":"Carla","family":"Sousa","sequence":"additional","affiliation":[]},{"given":"Maria Concei\u00e7\u00e3o","family":"Oliveira","sequence":"additional","affiliation":[]},{"given":"Rodrigo F. 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