In vivo modulated <i>N</i>‐acyl side chain of <i>N</i>‐acetylneuraminic acid modulates the cell contact‐dependent inhibition of growth

Wieser, Johannes; Heisner, Anja; Stehling, Peer; Oesch, Franz; Reutter, Werner

doi:10.1016/0014-5793(96)01029-0

Cited by 46 publications

(25 citation statements)

References 18 publications

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“…In this regard, the use of unnatural synthetic monosaccharides in the cellular glycosynthetic pathway has been proposed as an alternative method for overcoming the aforementioned limitations in the glycan analysis. This metabolic approach stemmed from the early work by Reutter and coworkers (15)(16)(17)(18), who used the N-acyl derivatives of N-acetyl-D-mannosamine (ManNAc) and N-acetyl-D-glucosamine in in vitro and in vivo metabolic synthesis of sialic acids to investigate the biological effects of incorporated unnatural sialoglycoconjugates. N-propanoyl-D-mannosamine (ManNProp), differing from natural ManNAc by an additional methylene (CH 2 ) group, has intensively been used and applied to neuroblastoma, nonneuronal glia, and…”

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confidence: 99%

Tissue-based metabolic labeling of polysialic acids in living primary hippocampal neurons

Kang

Joo

Choi

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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The posttranslational modification of neural cell-adhesion molecule (NCAM) with polysialic acid (PSA) and the spatiotemporal distribution of PSA-NCAM play an important role in the neuronal development. In this work, we developed a tissue-based strategy for metabolically incorporating an unnatural monosaccharide, peracetylated N-azidoacetyl-D-mannosamine, in the sialic acid biochemical pathway to present N-azidoacetyl sialic acid to PSA-NCAM. Although significant neurotoxicity was observed in the conventional metabolic labeling that used the dissociated neuron cells, neurotoxicity disappeared in this modified strategy, allowing for investigation of the temporal and spatial distributions of PSA in the primary hippocampal neurons. PSA-NCAM was synthesized and recycled continuously during neuronal development, and the two-color labeling showed that newly synthesized PSANCAMs were transported and inserted mainly to the growing neurites and not significantly to the cell body. This report suggests a reliable and cytocompatible method for in vitro analysis of glycans complementary to the conventional cell-based metabolic labeling for chemical glycobiology.

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confidence: 99%

Tissue-based metabolic labeling of polysialic acids in living primary hippocampal neurons

Kang

Joo

Choi

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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“…Treatment of lymphoma cells with ManNProp reduced their infectibility by several sialic acid-dependent viruses, e.g., influenza A virus (Keppler et al, 1995). Human diploid lung fibroblasts displayed a loss of density-dependent growth control after biochemical engineering (Wieser et al, 1996). Treatment of neural cell cultures of newborn rats with ManNProp led to proliferation of astrocytes and microglia and increased the number of oligodendrocyte progenitor cells (Schmidt et al, 1998).…”

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Biochemical Engineering of Cell Surface Sialic Acids Stimulates Axonal Growth

et al. 2002

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Sialylation is essential for development and regeneration in mammals. Using N-propanoylmannosamine, a novel precursor of sialic acid, we were able to incorporate unnatural sialic acids with a prolonged N-acyl side chain (e.g., N-propanoylneuraminic acid) into cell surface glycoconjugates. Here we report that this biochemical engineering of sialic acid leads to a stimulation of neuronal cells. Both PC12 cells and cerebellar neurons showed a significant increase in neurite outgrowth after treatment with this novel sialic acid precursor. Furthermore, also the reestablishment of the perforant pathway was stimulated in brain slices. In addition, we surprisingly identified several cytosolic proteins with regulatory functions, which are differentially expressed after treatment with N-propanoylmannosamine. Because sialic acid is the only monosaccharide that is activated in the nucleus, we hypothesize that transcription could be modulated by the unnatural CMP-Npropanoylneuraminic acid and that sialic acid activation might be a general tool to regulate cellular functions, such as neurite outgrowth.

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“…This modification inhibits the sialic acid-dependent infection of these cells with primate polyomaviruses (3). Furthermore, human fibroblasts lose their density-dependent inhibition of proliferation when treated with P-NAP (12).…”

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Biochemical Engineering of Neural Cell Surfaces by the SyntheticN-Propanoyl-substituted Neuraminic Acid Precursor

Schmidt¹,

Stehling²,

Schnitzer³

et al. 1998

Journal of Biological Chemistry

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Sialylation of glycoproteins and glycolipids plays an important role during development, regeneration, and pathogenesis of diseases. During times of intense plasticity within the nervous system, such as development and regeneration, sialylation of neural cells is distinct from the time of its maintenance. In this study, a synthetic precursor of neuraminic acid, N-propanoylmannosamine (N-propanoyl neuraminic acid precursor (P-NAP)), is applied to the culture medium of oligodendrocyte progenitor cells, microglia, astrocytes, and neurons from neonatal rat brains to alter sialylation of glycoconjugates within these cells. P-NAP is metabolized and incorporated as N-propanoyl neuraminic acid into glycoproteins of the cell membrane. P-NAP stimulates the proliferation of astrocytes and microglia but not of oligodendrocyte progenitor in vitro. However, P-NAP increases the number of oligodendrocyte progenitor cells expressing the early oligodendroglial surface marker A2B5 epitope. In the presence of P-NAP, cerebellar neurons (but not astrocytes) in microexplant cultures start to express the oligodendroglial progenitor marker A2B5 epitope, which is normally undetectable on these cells. The controls, which were performed in the absence of any additive or in the presence of the physiological precursor of neuraminic acid, N-acetylmannosamine, did not show any increase in A2B5 expression.

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In vivo modulated N‐acyl side chain of N‐acetylneuraminic acid modulates the cell contact‐dependent inhibition of growth

Cited by 46 publications

References 18 publications

Tissue-based metabolic labeling of polysialic acids in living primary hippocampal neurons

Tissue-based metabolic labeling of polysialic acids in living primary hippocampal neurons

Biochemical Engineering of Cell Surface Sialic Acids Stimulates Axonal Growth

Biochemical Engineering of Neural Cell Surfaces by the SyntheticN-Propanoyl-substituted Neuraminic Acid Precursor

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