Synthesis and biological evaluation of polysulfated oligosaccharide glycosides as inhibitors of angiogenesis and tumor growth
A series of polysulfated penta- and tetrasaccharide glycosides containing α(1→3)/α(1→2)-linked mannose residues were synthesized as heparan sulfate (HS) mimetics and evaluated for their ability to inhibit angiogenesis. The compounds bound tightly to angiogenic growth factors (FGF-1, FGF-2, and VEGF)...
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| Main Authors: | , , , , , , , , , , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
25 February 2010
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| In: |
Journal of medicinal chemistry
Year: 2010, Volume: 53, Issue: 4, Pages: 1686-1699 |
| ISSN: | 1520-4804 |
| DOI: | 10.1021/jm901449m |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/jm901449m
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| Author Notes: | Ken D. Johnstone, Tomislav Karoli, Ligong Liu, Keith Dredge, Elizabeth Copeman, Cai Ping Li, Kat Davis, Edward Hammond, Ian Bytheway, Edmund Kostewicz, Francis C. K. Chiu, David M. Shackleford, Susan A. Charman, William N. Charman, Job Harenberg, Thomas J. Gonda, and Vito Ferro |
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| 245 | 1 | 0 | |a Synthesis and biological evaluation of polysulfated oligosaccharide glycosides as inhibitors of angiogenesis and tumor growth |c Ken D. Johnstone, Tomislav Karoli, Ligong Liu, Keith Dredge, Elizabeth Copeman, Cai Ping Li, Kat Davis, Edward Hammond, Ian Bytheway, Edmund Kostewicz, Francis C. K. Chiu, David M. Shackleford, Susan A. Charman, William N. Charman, Job Harenberg, Thomas J. Gonda, and Vito Ferro |
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| 520 | |a A series of polysulfated penta- and tetrasaccharide glycosides containing α(1→3)/α(1→2)-linked mannose residues were synthesized as heparan sulfate (HS) mimetics and evaluated for their ability to inhibit angiogenesis. The compounds bound tightly to angiogenic growth factors (FGF-1, FGF-2, and VEGF) and strongly inhibited heparanase activity. In addition, the compounds exhibited potent activity in cell-based and ex vivo assays indicative of angiogenesis, with tetrasaccharides exhibiting activity comparable to that of pentasaccharides. Selected compounds also showed good antitumor activity in vivo in a mouse melanoma (solid tumor) model resistant to the phase III HS mimetic 1 (muparfostat, formerly known as PI-88). The lipophilic modifications also resulted in reduced anticoagulant activity, a common side effect of HS mimetics, and conferred a reasonable pharmacokinetic profile in the rat, as exemplified by the sulfated octyl tetrasaccharide 5. The data support the further investigation of this class of compounds as potential antiangiogenic, anticancer therapeutics. | ||
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| 700 | 1 | |a Copeman, Elizabeth |e VerfasserIn |4 aut | |
| 700 | 1 | |a Li, Cai Ping |e VerfasserIn |4 aut | |
| 700 | 1 | |a Davis, Kat |e VerfasserIn |4 aut | |
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