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Conformational investigations of mannosylated peptidoglycan derivatives with immunomodulating properties

Krisztina Fehér UGent, Srjdanka Tomič-Pisarovič, László Szilágyi, José Martins UGent and Katalin E Kövér (2012) Young Belgian Magnetic Resonance Scientist, 11th Symposium, Abstracts.
abstract
Bacterial cell wall peptidoglycan (PGN), a polymer of disaccharide-pentapeptide repeating units is one of the most important molecular patterns recognised by innate immune receptors. Although the mechanism of action of PGNs leading to immunostimulation in the host is not yet completely understood, it has been shown that several families of innate immune receptors mediated PGN recognition such as the Toll-like receptors, NOD-like receptors and the recently discovered family of Peptidoglycan Recognition Proteins. Fragments of PGN and related small molecules can also elicit immune response [1]. Mannosylation of the monomeric unit of PGN (PGM) alters its effects on the immune system [2]. In particular, immunostimulating activity of mannosylated derivatives (ManPGM) [3] were decreased in comparison to the parent PGM molecule as well as the type of immune reaction was switched towards Th2. These observations may be rationalised in different ways: a drastic change of the conformation caused by the hydrophilic substituent might hinder/prohibit the binding of ManPGN to known receptors. Alternatively, the immunological observations may point to the involvement of the macrophage mannose receptor (MR) in PGN recognition. As a first take in understanding the immunological behaviour of the new derivatives, we investigated the solution conformation of mannosylated PGM as well as that of the peptapeptide fragment (ManPP) using NMR spectroscopy and molecular modelling and compared the structures with that of the parent moelcule, PGM. 1. Szilagyi L. Pristovsek P. MiniRev.Med.Chem. Vol 7. p.861 2007 2. Ribic R Habjanec L Brgles M Tomic S Tomašic J. Bioorg. Med. Chem 17 6096–6105 2009 3. Fehér, K.; Pristovsek, P.; Szilágyi, L.; Ljevakovic, D.; Tomasic, J. Bioorg. Med. Chem., 2003, 11, 3133
Please use this url to cite or link to this publication:
author
organization
year
type
conference
publication status
published
subject
keyword
NMR spectroscopy, molcular modelling, peptidoglycan, immunomodulation
in
Young Belgian Magnetic Resonance Scientist, 11th Symposium, Abstracts
conference name
11th Young Belgian Magnetic Resonance Scientist (YBMRS) symposium
conference location
Spa, Belgium
conference start
2012-11-26
conference end
2012-11-27
language
English
UGent publication?
yes
classification
C3
id
4108761
handle
http://hdl.handle.net/1854/LU-4108761
date created
2013-08-02 18:08:29
date last changed
2016-12-19 15:35:53
@inproceedings{4108761,
  abstract     = {Bacterial cell wall peptidoglycan (PGN), a polymer of disaccharide-pentapeptide repeating units is one of the most important molecular patterns recognised by innate immune receptors. Although the mechanism of action of PGNs leading to immunostimulation in the host is not yet completely understood, it has been shown that several families of innate immune receptors mediated PGN recognition such as the Toll-like receptors, NOD-like receptors and the recently discovered family of Peptidoglycan Recognition Proteins. Fragments of PGN and related small molecules can also elicit immune response [1]. Mannosylation of the monomeric unit of PGN (PGM) alters its effects on the immune system [2]. In particular, immunostimulating activity of mannosylated derivatives (ManPGM) [3] were decreased in comparison to the parent PGM molecule as well as the type of immune reaction was switched towards Th2. These observations may be rationalised in different ways: a drastic change of the conformation caused by the hydrophilic substituent might hinder/prohibit the binding of ManPGN to known receptors. Alternatively, the immunological observations may point to the involvement of the macrophage mannose receptor (MR) in PGN recognition. As a first take in understanding the immunological behaviour of the new derivatives, we investigated the solution conformation of mannosylated PGM as well as that of the peptapeptide fragment (ManPP) using NMR spectroscopy and molecular modelling and compared the structures with that of the parent moelcule, PGM.
1. Szilagyi L. Pristovsek P. MiniRev.Med.Chem. Vol 7. p.861 2007
2. Ribic R Habjanec L Brgles M Tomic S Toma\v{s}ic J. Bioorg. Med. Chem 17 6096--6105 2009
3. Feh{\'e}r, K.; Pristovsek, P.; Szil{\'a}gyi, L.; Ljevakovic, D.; Tomasic, J. Bioorg. Med. Chem., 2003, 11, 3133},
  author       = {Feh{\'e}r, Krisztina and Tomi\v{c}-Pisarovi\v{c}, Srjdanka and Szil{\'a}gyi, L{\'a}szl{\'o} and Martins, Jos{\'e} and K{\"o}v{\'e}r, Katalin E},
  booktitle    = {Young Belgian Magnetic Resonance Scientist, 11th Symposium, Abstracts},
  keyword      = {NMR spectroscopy,molcular modelling,peptidoglycan,immunomodulation},
  language     = {eng},
  location     = {Spa, Belgium},
  title        = {Conformational investigations of mannosylated peptidoglycan derivatives with immunomodulating properties},
  year         = {2012},
}

Chicago
Fehér, Krisztina, Srjdanka Tomič-Pisarovič, László Szilágyi, José Martins, and Katalin E Kövér. 2012. “Conformational Investigations of Mannosylated Peptidoglycan Derivatives with Immunomodulating Properties.” In Young Belgian Magnetic Resonance Scientist, 11th Symposium, Abstracts.
APA
Fehér, K., Tomič-Pisarovič, S., Szilágyi, L., Martins, J., & Kövér, K. E. (2012). Conformational investigations of mannosylated peptidoglycan derivatives with immunomodulating properties. Young Belgian Magnetic Resonance Scientist, 11th Symposium, Abstracts. Presented at the 11th Young Belgian Magnetic Resonance Scientist (YBMRS) symposium.
Vancouver
1.
Fehér K, Tomič-Pisarovič S, Szilágyi L, Martins J, Kövér KE. Conformational investigations of mannosylated peptidoglycan derivatives with immunomodulating properties. Young Belgian Magnetic Resonance Scientist, 11th Symposium, Abstracts. 2012.
MLA
Fehér, Krisztina, Srjdanka Tomič-Pisarovič, László Szilágyi, et al. “Conformational Investigations of Mannosylated Peptidoglycan Derivatives with Immunomodulating Properties.” Young Belgian Magnetic Resonance Scientist, 11th Symposium, Abstracts. 2012. Print.