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Probing the carbohydrate recognition domain of E-selectin : the importance of the acid orientation in sLex mimetics

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Datum

2010

Autor:innen

Patton, John
Smiesko, Martin
Radic, Zorana
Schwardt, Oliver
Magnani, John L.
Ernst, Beat

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http://nbn-resolving.de/urn:nbn:de:bsz:352-126161
DOI (zitierfähiger Link)
https://doi.org/10.1016/j.bmc.2009.11.024
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Published

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Bioorganic & Medicinal Chemistry. 2010, 18(1), pp. 19-27. ISSN 0968-0896. eISSN 1464-3391. Available under: doi: 10.1016/j.bmc.2009.11.024

Zusammenfassung

The selectin–leukocyte interaction is the initial event in the early inflammatory cascade. This interplay proceeds via the terminal tetrasaccharide sialyl Lewisx (sLex), present on physiological selectin ligands and E- and P-selectins located on the endothelial surface. Blocking this process is regarded as a promising therapeutic approach for inflammatory diseases where excessive leukocyte efflux is responsible for tissue damage. Selectin antagonists are generally based on sLex as lead structure, containing the essential pharmacophores pre-oriented in the bioactive conformation. In this work, we describe a set of competitive sLex mimetics possessing the carboxylic acid pharmacophore equipped with additional hydrophobic substituents as neuraminic acid (Neu5Ac) replacements. This small library of antagonists derived from Huisgen-1,3-dipolar cycloadditions allows to further probe the carbohydrate recognition domain of E-selectin.

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
540 Chemie

Schlagwörter

E-selectin, Sialyl Lewisx, Pre-organization, Antagonist, Neu5Ac replacement

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ISO 690TITZ, Alexander, John PATTON, Martin SMIESKO, Zorana RADIC, Oliver SCHWARDT, John L. MAGNANI, Beat ERNST, 2010. Probing the carbohydrate recognition domain of E-selectin : the importance of the acid orientation in sLex mimetics. In: Bioorganic & Medicinal Chemistry. 2010, 18(1), pp. 19-27. ISSN 0968-0896. eISSN 1464-3391. Available under: doi: 10.1016/j.bmc.2009.11.024
BibTex
@article{Titz2010-01-01Probi-12616,
  year={2010},
  doi={10.1016/j.bmc.2009.11.024},
  title={Probing the carbohydrate recognition domain of E-selectin : the importance of the acid orientation in sLex mimetics},
  number={1},
  volume={18},
  issn={0968-0896},
  journal={Bioorganic & Medicinal Chemistry},
  pages={19--27},
  author={Titz, Alexander and Patton, John and Smiesko, Martin and Radic, Zorana and Schwardt, Oliver and Magnani, John L. and Ernst, Beat}
}
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