An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

• (hydroxymethyl)furan and benzoylated galactose imidate, is nontoxic and antagonizes cell physiological processes in vitro that are important for the dissemination and growth of tumor cells in vivo. Keywords: angiogenesis; biomimetic synthesis; carbohydrates; in silico blind docking; melanoma cells

• upon binding of cells to fibronectin or fibrinogen. However, GSF, which inhibits cell adhesion to both ECM-proteins, inhibits the cleavage of the MMP-2 pro-sequence. A GSF–αvβ3 interaction could directly or allosterically inhibit binding of pro-MMP-2 to the integrin, and our in silico blind-docking

• , 2H, CH2OSO3), 7.65 (s, 1H, H5), 7.68 (s, 1H, H2); 13C NMR (63 MHz, DMSO-d6) δ 58.4, 60.5, 60.6 (CH2OSO3, CH2OGal, C6´), 68.2, 70.6, 73.4, 75.2 (C2´, C3´, C4´, C5´), 102.6 (C1´), 121.3, 121.7 (C3, C4), 141.49, 141.52 (C2, C5). In silico blind-docking and molecular dynamics simulations A flexible