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Communication

Adamantane Containing Peptidoglycan Fragments Enhance RANTES and IL-6 Production in Lipopolysaccharide-Induced Macrophages

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Department of Synthetic Biology and Immunology, National Institute of Chemistry, Hajdrihova 19, P.O. Box 660, SI-1001 Ljubljana, Slovenia
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Centre of Excelence EN-FIST, SI-1000 Ljubljana, Slovenia
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University Center Varaždin, University North, Jurja Križanića 31b, HR-42 000 Varaždin, Croatia
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Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000 Ghent, Belgium
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Univ. Lille, Inserm, Institut Pasteur de Lille, CHU Lille, U1167—Labex DISTALZ—RID-AGE—Risk Factors and Molecular Determinants of Aging-Related Diseases, F-59000 Lille, France
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CNRS, ERL9002—Integrative Structural Biology, F-59000 Lille, France
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Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102A, HR-10 000 Zagreb, Croatia
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Heidelberg Institute for Theoretical Studies, Schloss-Wolfsbrunnenweg 35, 69118 Heidelberg, Germany
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Molecular Recognition and Interaction Research Group, Hungarian Academy of Sciences, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2020, 25(16), 3707; https://doi.org/10.3390/molecules25163707
Received: 2 January 2020 / Revised: 8 July 2020 / Accepted: 6 August 2020 / Published: 14 August 2020
(This article belongs to the Section Medicinal Chemistry)
We report the enhancement of the lipopolysaccharide-induced immune response by adamantane containing peptidoglycan fragments in vitro. The immune stimulation was detected by Il-6 (interleukine 6) and RANTES (regulated on activation, normal T cell expressed and secreted) chemokine expression using cell assays on immortalized mouse bone-marrow derived macrophages. The most active compound was a α-D-mannosyl derivative of an adamantylated tripeptide with L-chirality at the adamantyl group attachment, whereby the mannose moiety assumed to target mannose receptors expressed on macrophage cell surfaces. The immune co-stimulatory effect was also influenced by the configuration of the adamantyl center, revealing the importance of specific molecular recognition event taking place with its receptor. The immunostimulating activities of these compounds were further enhanced upon their incorporation into lipid bilayers, which is likely related to the presence of the adamantyl group that helps anchor the peptidoglycan fragment into lipid nanoparticles. We concluded that the proposed adamantane containing peptidoglycan fragments act as co-stimulatory agents and are also suitable for the preparation of lipid nanoparticle-based delivery of peptidoglycan fragments. View Full-Text
Keywords: peptidoglycan; immunostimulation; lipid incapsulation; adamantane; mannose peptidoglycan; immunostimulation; lipid incapsulation; adamantane; mannose
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MDPI and ACS Style

Manček-Keber, M.; Ribić, R.; Chain, F.; Sinnaeve, D.; Martins, J.C.; Jerala, R.; Tomić, S.; Fehér, K. Adamantane Containing Peptidoglycan Fragments Enhance RANTES and IL-6 Production in Lipopolysaccharide-Induced Macrophages. Molecules 2020, 25, 3707. https://doi.org/10.3390/molecules25163707

AMA Style

Manček-Keber M, Ribić R, Chain F, Sinnaeve D, Martins JC, Jerala R, Tomić S, Fehér K. Adamantane Containing Peptidoglycan Fragments Enhance RANTES and IL-6 Production in Lipopolysaccharide-Induced Macrophages. Molecules. 2020; 25(16):3707. https://doi.org/10.3390/molecules25163707

Chicago/Turabian Style

Manček-Keber, Mateja, Rosana Ribić, Fernando Chain, Davy Sinnaeve, José C. Martins, Roman Jerala, Srđanka Tomić, and Krisztina Fehér. 2020. "Adamantane Containing Peptidoglycan Fragments Enhance RANTES and IL-6 Production in Lipopolysaccharide-Induced Macrophages" Molecules 25, no. 16: 3707. https://doi.org/10.3390/molecules25163707

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