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Publication details

Document type
Journal articles

Document subtype
Full paper

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

Participants in the publication
Catarina Dias (Author)
Ana M. Matos (Author)
CQB - Centro de Química e Bioquímica 
Maria T. Blásquez-Sanchez (Author)
CQB - Centro de Química e Bioquímica 
CQE-Ciências - Centro de Química Estrutural-Ciências
Patrícia Calado (Author)
Alice Martins (Author)
Philipp Dätwyler (Author)
Beat Ernst (Author)
M. Paula Macedo (Author)
Nicola Colabufo (Author)
Amélia P. Rauter (Author)
Dep. Química e Bioquímica
CQB - Centro de Química e Bioquímica 

Scope
International

Refereeing
Yes

Summary
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.

Date of Publication
2019-07-26

Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
Pure and Applied Chemistry

Publication Identifiers
ISSN - 1365-3075
eISSN - 0033-4545

Publisher
Walter de Gruyter GmbH

Volume
91
Number
7

Number of pages
12
Starting page
1209
Last page
1221

Document Identifiers
DOI - https://doi.org/10.1515/pac-2019-0303
URL - http://dx.doi.org/10.1515/pac-2019-0303

Rankings
SCIMAGO Q1 (2018) - 1,24 - Chemistry (miscellaneous)

Keywords
medicinal chemistry resveratrol caffeic acid ester biomolecular chemistry bioactive molecules neuroprotection organic synthesis ICS29

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APA
Catarina Dias, Ana M. Matos, Maria T. Blásquez-Sanchez, Patrícia Calado, Alice Martins, Philipp Dätwyler, Beat Ernst, M. Paula Macedo, Nicola Colabufo, Amélia P. Rauter, (2019). 2-Deoxyglycosylation towards more effective and bioavailable neuroprotective molecules inspired by nature. Pure and Applied Chemistry, 91, 1209-1221. ISSN 1365-3075. eISSN 0033-4545. http://dx.doi.org/10.1515/pac-2019-0303

IEEE
Catarina Dias, Ana M. Matos, Maria T. Blásquez-Sanchez, Patrícia Calado, Alice Martins, Philipp Dätwyler, Beat Ernst, M. Paula Macedo, Nicola Colabufo, Amélia P. Rauter, "2-Deoxyglycosylation towards more effective and bioavailable neuroprotective molecules inspired by nature" in Pure and Applied Chemistry, vol. 91, pp. 1209-1221, 2019. 10.1515/pac-2019-0303

BIBTEX
@article{39349, author = {Catarina Dias and Ana M. Matos and Maria T. Blásquez-Sanchez and Patrícia Calado and Alice Martins and Philipp Dätwyler and Beat Ernst and M. Paula Macedo and Nicola Colabufo and Amélia P. Rauter}, title = {2-Deoxyglycosylation towards more effective and bioavailable neuroprotective molecules inspired by nature}, journal = {Pure and Applied Chemistry}, year = 2019, pages = {1209-1221}, volume = 91 }