Artificial and natural sialic acid precursors influence the angiogenic capacity of human umbilical vein endothelial cells

Molecules

Volumn 18, Issue 3, 2013, Pages 2571-2586

  Bayer, Nils B ^a   Schubert, Uwe ^a   Sentürk, Zehra ^a   Rudloff, Silvia ^a   Frank, Sandra ^a   Hausmann, Heike ^a   Geyer, Hildegard ^a   Geyer, Rudolf ^a   Preissner, Klaus T ^a   Galuska, Sebastian P ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Angiogenesis; Artificial sialic acids; Glycoengineering; Mannosamine

Indexed keywords

ANGIOGENIC FACTOR; DRUG DERIVATIVE; GLYCOCONJUGATE; GLYCOPROTEIN; N ACETYLNEURAMINIC ACID;

ANGIOGENESIS; ARTICLE; BIOSYNTHESIS; CHEMISTRY; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MASS SPECTROMETRY; METABOLISM; PHYSIOLOGY; UMBILICAL VEIN ENDOTHELIAL CELL;

ANGIOGENESIS INDUCING AGENTS; BIOSYNTHETIC PATHWAYS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOCONJUGATES; GLYCOPROTEINS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; MASS SPECTROMETRY; N-ACETYLNEURAMINIC ACID; NEOVASCULARIZATION, PHYSIOLOGIC;

EID: 84875581902     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18032571     Document Type: Article

References (29)

1. Angata, T.; Varki, A. Chemical diversity in the sialic acids and related alpha-keto acids: An evolutionary perspective. Chem. Rev. 2002, 102, 439-469.
2. Schauer, R. Achievements and challenges of sialic acid research. Glycoconj. J. 2000, 17, 485-499.
3. Schauer, R. Sialic acids: Fascinating sugars in higher animals and man. Zoology (Jena) 2004, 107, 49-64.
4. Schauer, R. Sialic acids as regulators of molecular and cellular interactions. Curr. Opin. Struct. Biol. 2009, 19, 507-514.
5. McEver, R.P.; Moore, K.L.; Cummings, R.D. Leukocyte trafficking mediated by selectin-carbohydrate interactions. J. Biol. Chem. 1995, 270, 11025-11028.
6. Du, J.; Meledeo, M.A.; Wang, Z.; Khanna, H.S.; Paruchuri, V.D.; Yarema, K.J. Metabolic glycoengineering: Sialic acid and beyond. Glycobiology 2009, 19, 1382-1401.
7. Keppler, O.T.; Horstkorte, R.; Pawlita, M.; Schmidt, C.; Reutter, W. Biochemical engineering of the N-acyl side chain of sialic acid: Biological implications. Glycobiology 2001, 11, 11R-18R.
8. Keppler, O.T.; Stehling, P.; Herrmann, M.; Kayser, H.; Grunow, D.; Reutter, W.; Pawlita, M. Biosynthetic modulation of sialic acid-dependent virus-receptor interactions of two primate polyoma viruses. J. Biol. Chem. 1995, 270, 1308-1314.
9. Strilic, B.; Eglinger, J.; Krieg, M.; Zeeb, M.; Axnick, J.; Babal, P.; Muller, D.J.; Lammert, E. Electrostatic cell-surface repulsion initiates lumen formation in developing blood vessels. Curr. Biol. 2010, 20, 2003-2009.
10. Aich, U.; Campbell, C.T.; Elmouelhi, N.; Weier, C.A.; Sampathkumar, S.G.; Choi, S.S.; Yarema, K.J. Regioisomeric SCFA attachment to hexosamines separates metabolic flux from cytotoxicity and MUC1 suppression. ACS Chem. Biol. 2008, 3, 230-240.
11. Galuska, S.P.; Geyer, H.; Weinhold, B.; Kontou, M.; Rohrich, R.C.; Bernard, U.; Gerardy-Schahn, R.; Reutter, W.; Munster-Kuhnel, A.; Geyer, R. Quantification of nucleotide-activated sialic acids by a combination of reduction and fluorescent labeling. Anal. Chem. 2010, 82, 4591-4598.
12. Klein, A.; Diaz, S.; Ferreira, I.; Lamblin, G.; Roussel, P.; Manzi, A.E. New sialic acids from biological sources identified by a comprehensive and sensitive approach: Liquid chromatographyelectrospray ionization-mass spectrometry (LC-ESI-MS) of SIA quinoxalinones. Glycobiology 1997, 7, 421-432.
13. Korff, T.; Augustin, H.G. Integration of endothelial cells in multicellular spheroids prevents apoptosis and induces differentiation. J. Cell Biol. 1998, 143, 1341-1352.
14. Montesano, R.; Pepper, M.S.; Vassalli, J.D.; Orci, L. Phorbol ester induces cultured endothelial cells to invade a fibrin matrix in the presence of fibrinolytic inhibitors. J. Cell Physiol. 1987, 132, 509-516.
15. Sato, Y.; Isaji, T.; Tajiri, M.; Yoshida-Yamamoto, S.; Yoshinaka, T.; Somehara, T.; Fukuda, T.; Wada, Y.; Gu, J. An N-glycosylation site on the beta-propeller domain of the integrin alpha5 subunit plays key roles in both its function and site-specific modification by beta1,4- Nacetylglucosaminyltransferase III. J. Biol. Chem. 2009, 284, 11873-11881.
16. Isaji, T.; Sato, Y.; Fukuda, T.; Gu, J. N-Glycosylation of the I-like domain of beta1 integrin is essential for beta1 integrin expression and biological function: Identification of the minimal N-glycosylation requirement for alpha5beta1. J. Biol. Chem. 2009, 284, 12207-12216.
17. Duchesne, L.; Tissot, B.; Rudd, T.R.; Dell, A.; Fernig, D.G. N-Glycosylation of fibroblast growth factor receptor 1 regulates ligand and heparan sulfate co-receptor binding. J. Biol. Chem. 2006, 281, 27178-27189.
18. Manfredi, M.G.; Lim, S.; Claffey, K.P.; Seyfried, T.N. Gangliosides influence angiogenesis in an experimental mouse brain tumor. Cancer Res. 1999, 59, 5392-5397.
19. Ziche, M.; Morbidelli, L.; Alessandri, G.; Gullino, P.M. Angiogenesis can be stimulated or repressed in vivo by a change in GM3:GD3 ganglioside ratio. Lab. Invest. 1992, 67, 711-715.
20. Bork, K.; Gagiannis, D.; Orthmann, A.; Weidemann, W.; Kontou, M.; Reutter, W.; Horstkorte, R. Experimental approaches to interfere with the polysialylation of the neural cell adhesion molecule in vitro and in vivo. J Neurochem 2007, 103 (Suppl. 1), 65-71.
21. Horstkorte, R.; Muhlenhoff, M.; Reutter, W.; Nohring, S.; Zimmermann-Kordmann, M.; Gerardy-Schahn, R. Selective inhibition of polysialyltransferase ST8SiaII by unnatural sialic acids. Exp. Cell Res. 2004, 298, 268-274.
22. Weidemann, W.; Klukas, C.; Klein, A.; Simm, A.; Schreiber, F.; Horstkorte, R. Lessons from GNE-deficient embryonic stem cells: Sialic acid biosynthesis is involved in proliferation and gene expression. Glycobiology 2010, 20, 107-117.
23. Luchansky, S.J.; Yarema, K.J.; Takahashi, S.; Bertozzi, C.R. GlcNAc 2-epimerase can serve a catabolic role in sialic acid metabolism. J. Biol. Chem. 2003, 278, 8035-8042.
24. Campbell, C.T.; Sampathkumar, S.G.; Yarema, K.J. Metabolic oligosaccharide engineering: Perspectives, applications, and future directions. Mol. BioSyst. 2007, 3, 187-194.
25. Jaffe, E.A.; Nachman, R.L.; Becker, C.G.; Minick, C.R. Culture of human endothelial cells derived from umbilical veins. Identification by morphologic and immunologic criteria. J. Clin. Invest. 1973, 52, 2745-2756.
26. Hara, S.; Takemori, Y.; Yamaguchi, M.; Nakamura, M.; Ohkura, Y. Fluorometric high-performance liquid chromatography of N-acetyl- and N-glycolylneuraminic acids and its application to their microdetermination in human and animal sera, glycoproteins, and glycolipids. Anal. Biochem. 1987, 164, 138-145.
27. Galuska, S.P.; Geyer, H.; Mink, W.; Kaese, P.; Kuhnhardt, S.; Schafer, B.; Muhlenhoff, M.; Freiberger, F.; Gerardy-Schahn, R.; Geyer, R. Glycomic strategy for efficient linkage analysis of di-, oligo- and polysialic acids. J. Proteom. 2012, 75, 5266-5278.
28. Keppler, O.T.; Herrmann, M.; von der Lieth, C.W.; Stehling, P.; Reutter, W.; Pawlita, M. Elongation of the N-acyl side chain of sialic acids in MDCK II cells inhibits influenza A virus infection. Biochem. Biophys. Res. Commun. 1998, 253, 437-442.
29. Werner, A.; Horstkorte, R.; Glanz, D.; Biskup, K.; Blanchard, V.; Berger, M.; Bork, K. Glycoengineering the N-acyl side chain of sialic acid of human erythropoietin affects its resistance to sialidase. Biol. Chem. 2012, 393, 777-783.