Literature DB >> 29361218

Single Site Fluorination of the GM4 Ganglioside Epitope Upregulates Oligodendrocyte Differentiation.

Tobias J Kieser1,2, Nico Santschi1,2, Luise Nowack3, Gerald Kehr1, Tanja Kuhlmann3, Stefanie Albrecht3, Ryan Gilmour1,2.   

Abstract

Relapsing multiple sclerosis is synonymous with demyelination, and thus, suppressing and or reversing this process is of paramount clinical significance. While insulating myelin sheath has a large lipid composition (ca. 70-80%), it also has a characteristically large composition of the sialosylgalactosylceramide gangliosde GM4 present. In this study, the effect of the carbohydrate epitope on oligodendrocyte differentiation is determined. While the native epitope had no impact on oligodendroglial cell viability, a single site OH → F substitution is the structural basis of a significant increase in ATP production that is optimal at 50 μg/mL. From a translational perspective, this subtle change increases the amount of MBP+ oligodendrocytes compared to the control studies and may open up novel therapeutic remyelination strategies.

Entities:  

Keywords:  Carbohydrates; fluorine; gangliosides; multiple sclerosis; myelin; oligodendrocytes

Mesh:

Substances:

Year:  2018        PMID: 29361218     DOI: 10.1021/acschemneuro.8b00002

Source DB:  PubMed          Journal:  ACS Chem Neurosci        ISSN: 1948-7193            Impact factor:   4.418


  5 in total

Review 1.  Gangliosides in nervous system development, regeneration, and pathologies.

Authors:  Juliana F Vasques; Renata Guedes de Jesus Gonçalves; Almir Jordão da Silva-Junior; Robertta Silva Martins; Fernanda Gubert; Rosalia Mendez-Otero
Journal:  Neural Regen Res       Date:  2023-01       Impact factor: 6.058

Review 2.  Sphingolipid Players in Multiple Sclerosis: Their Influence on the Initiation and Course of the Disease.

Authors:  Maria Podbielska; Toshio Ariga; Anna Pokryszko-Dragan
Journal:  Int J Mol Sci       Date:  2022-05-10       Impact factor: 6.208

Review 3.  Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design.

Authors:  Rachel Hevey
Journal:  Biomimetics (Basel)       Date:  2019-07-28

4.  Halogen-directed chemical sialylation: pseudo-stereodivergent access to marine ganglioside epitopes.

Authors:  Taiki Hayashi; Alexander Axer; Gerald Kehr; Klaus Bergander; Ryan Gilmour
Journal:  Chem Sci       Date:  2020-03-26       Impact factor: 9.825

5.  Stereocontrolled Synthesis of 2-Fluorinated C-Glycosides.

Authors:  Anna Sadurní; Ryan Gilmour
Journal:  European J Org Chem       Date:  2018-06-07
  5 in total

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