2017
DOI: 10.1021/jacs.6b08894
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Carbohydrate–Neuroactive Hybrid Strategy for Metabolic Glycan Engineering of the Central Nervous System in Vivo

Abstract: Sialic acids are abundant in the central nervous system (CNS) and are essential for brain development, learning, and memory. Dysregulation in biosynthesis of sialo-glycoconjugates is known to be associated with neurological disorders, CNS injury, and brain cancer. Metabolic glycan engineering (MGE) and bioorthogonal ligation have enabled study of biological roles of glycans in vivo; however, direct investigations of sialoglycans in brain have been intractable. We report a simple strategy utilizing carbohydrate… Show more

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Cited by 26 publications
(22 citation statements)
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“…Similarly, incorporation of azido‐sugars was significantly increased during cardiac hypertrophy . Dysregulation of sialoglycan biosynthesis is also found in neurological disorders and central nervous system injuries . These recent findings inspire novel applications in cell‐based therapies and tissue engineering with innate pathophysiological‐responsive monitoring.…”
Section: Cell‐rich Assembliesmentioning
confidence: 85%
“…Similarly, incorporation of azido‐sugars was significantly increased during cardiac hypertrophy . Dysregulation of sialoglycan biosynthesis is also found in neurological disorders and central nervous system injuries . These recent findings inspire novel applications in cell‐based therapies and tissue engineering with innate pathophysiological‐responsive monitoring.…”
Section: Cell‐rich Assembliesmentioning
confidence: 85%
“…This method uses endogenous metabolic tracers that consist of sialic acid analogs or N-acetylmannosamine (ManNAc) linked with chemical reporters such as azide. In vivo brain imaging of these glycans manipulation techniques has been reported recently ( Gagiannis et al, 2007 ; Sampathkumar et al, 2008 ; Xie et al, 2016 ; Shajahan et al, 2017 ). However, it is difficult to monitor the sialoglycans in the brain tissues because of the labeled glycan’s impermeability through the blood–brain barrier (BBB).…”
Section: Imaging Techniques For the Brain Glycomementioning
confidence: 99%
“…To this aim, new unnatural monosaccharides have been designed to use specific metabolite transporters through the blood–brain barrier. 71 ManNAz analogs have been synthesized by linking at position 1 or 6 either nicotinic acid, valproic acid, or theophylline-7-acetic acid (mimic of caffeine). These metabolites are vectorized to the brain respectively by nicotinate receptors, medium-chain fatty acids transporters, and adenine transporters.…”
Section: Addressing the Reporter To The Right Placementioning
confidence: 99%