We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Artificial and Natural Sialic Acid Precursors Influence the Angiogenic Capacity of Human Umbilical Vein Endothelial Cells.
- Authors
Bayer, Nils B.; Schubert, Uwe; Sentürk, Zehra; Rudloff, Silvia; Frank, Sandra; Hausmann, Heike; Geyer, Hildegard; Geyer, Rudolf; Preissner, Klaus T.; Galuska, Sebastian P.
- Abstract
N-acetylneuraminic acid (Neu5Ac) represents the most common terminal carbohydrate residue in many mammalian glycoconjugates and is directly involved in a number of different physiological as well as pathological cellular processes. Endogenous sialic acids derive from the biosynthetic precursor molecule N-acetyl-D-mannosamine (ManNAc). Interestingly, N-acyl-analogues of D-mannosamine (ManN) can also be incorporated and converted into corresponding artificial sialic acids by eukaryotic cells. Within this study, we optimized a protocol for the chemical synthesis of various peracetylated ManN derivatives resulting in yields of approximately 100%. Correct molecular structures of the obtained products ManNAc, N-propanoyl-ManN (ManNProp) and N-butyl-ManN (ManNBut) were verified by GC-, ESI-MS- and NMR-analyses. By applying these substances to human umbilical vein endothelial cells (HUVECs), we could show that each derivative was metabolized to the corresponding N-acylneuraminic acid variant and subsequently incorporated into nascent glycoproteins. To investigate whether natural and/or artificial sialic acid precursors are able to modulate the angiogenic capacity of HUVECs, a spheroid assay was performed. By this means, an increase in total capillary length has been observed when cells incorporated N-butylneuraminic acid (Neu5But) into their glycoconjugates. In contrast, the natural precursor ManNAc inhibited the growth of capillaries. Thus, sialic acid precursors may represent useful agents to modulate blood vessel formation.
- Subjects
SIALIC acids; UMBILICAL veins; ENDOTHELIAL cells; GLYCOCONJUGATES; MANNOSAMINE
- Publication
Molecules, 2013, Vol 18, Issue 3, p2571
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules18032571