Novel carboxylate-based glycolipids: TLR4 antagonism, MD-2 binding and self-assembly properties View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2019-12

AUTHORS

Florent Cochet, Fabio A. Facchini, Lenny Zaffaroni, Jean-Marc Billod, Helena Coelho, Aurora Holgado, Harald Braun, Rudi Beyaert, Roman Jerala, Jesus Jimenez-Barbero, Sonsoles Martin-Santamaria, Francesco Peri

ABSTRACT

New monosaccharide-based lipid A analogues were rationally designed through MD-2 docking studies. A panel of compounds with two carboxylate groups as phosphates bioisosteres, was synthesized with the same glucosamine-bis-succinyl core linked to different unsaturated and saturated fatty acid chains. The binding of the synthetic compounds to purified, functional recombinant human MD-2 was studied by four independent methods. All compounds bound to MD-2 with similar affinities and inhibited in a concentration-dependent manner the LPS-stimulated TLR4 signaling in human and murine cells, while being inactive as TLR4 agonists when provided alone. A compound of the panel was tested in vivo and was not able to inhibit the production of proinflammatory cytokines in animals. This lack of activity is probably due to strong binding to serum albumin, as suggested by cell experiments in the presence of the serum. The interesting self-assembly property in solution of this type of compounds was investigated by computational methods and microscopy, and formation of large vesicles was observed by cryo-TEM microscopy. More... »

PAGES

919

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41598-018-37421-w

DOI

http://dx.doi.org/10.1038/s41598-018-37421-w

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1111747608

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30696900


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