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Publication details

Document type
Journal articles

Document subtype
Full paper

Title
Sugar-based bactericides targeting phosphatidylethanolamine-enriched membranes

Participants in the publication
Catarina Dias (Author)
João P. Pais (Author)
Rafael Nunes (Author)
BIOISI - Instituto de Biossistemas e Ciências Integrativas
CQB - Centro de Química e Bioquímica 
Maria-Teresa Blázquez-Sánchez (Author)
CQB - Centro de Química e Bioquímica 
CQE-Ciências - Centro de Química Estrutural-Ciências
Joaquim T. Marquês (Author)
Andreia F. Almeida (Author)
Patrícia Serra (Author)
CQB - Centro de Química e Bioquímica 
Nuno M. Xavier (Author)
CQB - Centro de Química e Bioquímica 
CQE-Ciências - Centro de Química Estrutural-Ciências
Diogo Vila-Viçosa (Author)
CQB - Centro de Química e Bioquímica 
BIOISI - Instituto de Biossistemas e Ciências Integrativas
Miguel Machuqueiro (Author)
Dep. Química e Bioquímica
CQB - Centro de Química e Bioquímica 
BIOISI - Instituto de Biossistemas e Ciências Integrativas
Ana S. Viana (Author)
Alice Martins (Author)
CQB - Centro de Química e Bioquímica 
Maria S. Santos (Author)
Dep. Química e Bioquímica
CQB - Centro de Química e Bioquímica 
Ana Pelerito (Author)
Ricardo Dias (Author)
Rogério Tenreiro (Author)
Dep. Biologia Vegetal
BIOISI - Instituto de Biossistemas e Ciências Integrativas
Maria C. Oliveira (Author)
Marialessandra Contino (Author)
Nicola A. Colabufo (Author)
Rodrigo F. M. de Almeida (Author)
CQB - Centro de Química e Bioquímica 
CQE-Ciências - Centro de Química Estrutural-Ciências
Amélia P. Rauter (Author)
Dep. Química e Bioquímica
CQB - Centro de Química e Bioquímica 

Scope
International

Refereeing
Yes

Summary
Anthrax is an infectious disease caused by Bacillus anthracis, a bioterrorism agent that develops resistance to clinically used antibiotics. Therefore, alternative mechanisms of action remain a challenge. Herein, we disclose deoxy glycosides responsible for specific carbohydrate-phospholipid interactions, causing phosphatidylethanolamine lamellar-to inverted hexagonal phase transition and acting over B. anthracis and Bacillus cereus as potent and selective bactericides. Biological studies of the synthesized compound series differing in the anomeric atom, glycone configuration and deoxygenation pattern show that the latter is indeed a key modulator of efficacy and selectivity. Biomolecular simulations show no tendency to pore formation, whereas differential metabolomics and genomics rule out proteins as targets. Complete bacteria cell death in 10 min and cellular envelope disruption corroborate an effect over lipid polymorphism. Biophysical approaches show monolayer and bilayer reorganization with fast and high permeabilizing activity toward phosphatidylethanolamine membranes. Absence of bacterial resistance further supports this mechanism, triggering innovation on membrane-targeting antimicrobials.

Date of Submisson/Request
2018-01-06
Date of Acceptance
2018-09-06
Date of Publication
2018-11-19

Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
Nature Communications

Publication Identifiers
ISSN - 2041-1723

Publisher
Springer Nature

Volume
9

Number of pages
12
Starting page
4857

Document Identifiers
URL - http://dx.doi.org/10.1038/s41467-018-06488-4
DOI - https://doi.org/10.1038/s41467-018-06488-4

Awards
Nature Communications Top 2% Chemistry Miscellaneous

Rankings
Web Of Science Q1 (2018) - 11.878 - Multidisciplinary Sciences
SCIMAGO Q1 (2018) - 5.992 - Biochemistry, Genetics and Molecular Biology (miscellaneous)
SCIMAGO Q1 (2018) - 5.992 - Chemistry (miscellaneous)
SCIMAGO Q1 (2018) - 5.992 - Physics and Astronomy (miscellaneous)

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APA
Catarina Dias, João P. Pais, Rafael Nunes, Maria-Teresa Blázquez-Sánchez, Joaquim T. Marquês, Andreia F. Almeida, Patrícia Serra, Nuno M. Xavier, Diogo Vila-Viçosa, Miguel Machuqueiro, Ana S. Viana, Alice Martins, Maria S. Santos, Ana Pelerito, Ricardo Dias, Rogério Tenreiro, Maria C. Oliveira, Marialessandra Contino, Nicola A. Colabufo, Rodrigo F. M. de Almeida, Amélia P. Rauter, (2018). Sugar-based bactericides targeting phosphatidylethanolamine-enriched membranes. Nature Communications, 9, ISSN 2041-1723. eISSN . http://dx.doi.org/10.1038/s41467-018-06488-4

IEEE
Catarina Dias, João P. Pais, Rafael Nunes, Maria-Teresa Blázquez-Sánchez, Joaquim T. Marquês, Andreia F. Almeida, Patrícia Serra, Nuno M. Xavier, Diogo Vila-Viçosa, Miguel Machuqueiro, Ana S. Viana, Alice Martins, Maria S. Santos, Ana Pelerito, Ricardo Dias, Rogério Tenreiro, Maria C. Oliveira, Marialessandra Contino, Nicola A. Colabufo, Rodrigo F. M. de Almeida, Amélia P. Rauter, "Sugar-based bactericides targeting phosphatidylethanolamine-enriched membranes" in Nature Communications, vol. 9, 2018. 10.1038/s41467-018-06488-4

BIBTEX
@article{35975, author = {Catarina Dias and João P. Pais and Rafael Nunes and Maria-Teresa Blázquez-Sánchez and Joaquim T. Marquês and Andreia F. Almeida and Patrícia Serra and Nuno M. Xavier and Diogo Vila-Viçosa and Miguel Machuqueiro and Ana S. Viana and Alice Martins and Maria S. Santos and Ana Pelerito and Ricardo Dias and Rogério Tenreiro and Maria C. Oliveira and Marialessandra Contino and Nicola A. Colabufo and Rodrigo F. M. de Almeida and Amélia P. Rauter}, title = {Sugar-based bactericides targeting phosphatidylethanolamine-enriched membranes}, journal = {Nature Communications}, year = 2018, volume = 9 }