2-Deoxyglycosylation towards more effective and bioavailable neuroprotective molecules inspired by nature

Dias, Catarina and Matos, Ana M. and Blasquez-Sanchez, Maria T. and Calado, Patricia and Martins, Alice and Daetwyler, Philipp and Ernst, Beat and Macedo, M. Paula and Colabufo, Nicola and Rauter, Amelia. (2019) 2-Deoxyglycosylation towards more effective and bioavailable neuroprotective molecules inspired by nature. Pure and applied chemistry, 91 (7). pp. 1209-1221.

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Official URL: https://edoc.unibas.ch/78085/

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The neuroprotective role of natural polyphenols is well established but phenolics poor water solubility affects their bioavailability and bioactivity. Aiming to overcome this issue, we were encouraged to investigate the 2-deoxyglycosylation of natural or nature inspired neuroprotective molecules, using glycals as easily accessed glycosyl donors. This robust methodology allowed the generation of a set of new resveratrol and caffeic acid ester glycosides, envisioning more effective and bioavailable compounds. Resveratrol 2-deoxyglycosides were more effective at protecting the neuronal cells from peroxide-induced cytotoxicity than resveratrol itself, while the caffeic acid ester glycoside also showed extraordinary neuroprotection activity. Coefficient partition measurements demonstrated the moderate lipophilicity of resveratrol glycosides, which Log D values are typical of a central nervous system (CNS) drug and ideal for blood-brain barrier (BBB) penetration. Passive permeation assessed by the parallel artificial membrane permeability assay (PAMPA) revealed that 2,6-dideoxy- l - arabino -hexopyranosides were more effective than 2-deoxy- d - arabino -hexopyranosides. The lack of toxicity of the neuroprotective glycosides and their promising physicochemical properties revealed the usefulness of sugar coupling towards the modulation of natural product properties and bioactivity.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Ehemalige Einheiten Pharmazie > Molekulare Pharmazie (Ernst)
UniBasel Contributors:Ernst, Beat and D├Ątwyler, Philipp
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:de Gruyter
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:21 Aug 2020 13:48
Deposited On:21 Aug 2020 13:48

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