The Activation of Fibroblast Growth Factors by Heparin: Synthesis, Structure, and Biological Activity of Heparin‐Like Oligosaccharides

No abstract is available for this paper.

• Publication year

  2001

• Venue

  ChemBioChem

• Publication date

  2001-09-03

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/1439-7633(20010903)2:9<673::AID-CBIC673>3.0.CO;2-7PMID 11828504
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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• Fibroblast growth factors as multifunctional signaling factors.

  1999cited by this paper
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• Oligosaccharides corresponding to the regular sequence of heparin: chemical synthesis and interaction with FGF-2.

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• Molecular characteristics of fibroblast growth factor-fibroblast growth factor receptor-heparin-like glycosaminoglycan complex.

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• The heparan sulfate-fibroblast growth factor family: diversity of structure and function.

  1998cited by this paper
• Structure of a heparin-linked biologically active dimer of fibroblast growth factor

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• Solution structure of acidic fibroblast growth factor bound to 1,3, 6-naphthalenetrisulfonate: a minimal model for the anti-tumoral action of suramins and suradistas.

  1998cited by this paper
• Destabilization, oligomerization and inhibition of the mitogenic activity of acidic fibroblast-growth factor by aurintricarboxylic acid.

  1997cited by this paper
• Fibroblast growth factors and their receptors.

  1997cited by this paper
• Glycosaminoglycans can influence fibroblast growth factor-2 mitogenicity without significant growth factor binding.

  1997cited by this paper
• Growth factors in the extracellular matrix

  1997cited by this paper
• Heparin-dependent fibroblast growth factor activities: effects of defined heparin oligosaccharides.

  1997cited by this paper
• NMR solution conformation of heparin-derived hexasaccharide.

  1997cited by this paper
• Heparan sulphate.

  1997cited by this paper
• Three-dimensional structure of acidic fibroblast growth factor in solution: effects of binding to a heparin functional analog.

  1996cited by this paper
• NMR solution conformation of heparin-derived tetrasaccharide.

  1996cited by this paper
• X-ray structure of native full-length human fibroblast-growth factor at 0.25-nm resolution.

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• Heparin Structure and Interactions with Basic Fibroblast Growth Factor

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• Fibroblast growth factors: at the heart of angiogenesis.

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• FGF binding and FGF receptor activation by synthetic heparan-derived di- and trisaccharides.

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• Utility of non-covalent complexes in the matrix-assisted laser desorption ionization mass spectrometry of heparin-derived oligosaccharides.

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• The ins and outs of fibroblast growth factors.

  1994cited by this paper
• 1H-NMR assignment and solution structure of human acidic fibroblast growth factor activated by inositol hexasulfate.

  1994cited by this paper
• Specific heparan sulfate saccharides mediate the activity of basic fibroblast growth factor.

  1994cited by this paper
• Heparin-induced oligomerization of FGF molecules is responsible for FGF receptor dimerization, activation, and cell proliferation.

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• N.m.r. and molecular-modelling studies of the solution conformation of heparin.

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• Preparation of affinity-fractionated, heparin-derived oligosaccharides and their effects on selected biological activities mediated by basic fibroblast growth factor.

  1993cited by this paper
• Nature of the interaction of heparin with acidic fibroblast growth factor.

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• Mitogenic activity of acidic fibroblast growth factor is enhanced by highly sulfated oligosaccharides derived from heparin and heparan sulfate

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• Heparin-Binding Proteins

  1992cited by this paper
• High-level synthesis in Escherichia coli of shortened and full-length human acidic fibroblast growth factor and purification in a form stable in aqueous solutions.

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  1992cited by this paper
• Signal transduction by receptors with tyrosine kinase activity.

  1990cited by this paper
• Conformer populations of L-iduronic acid residues in glycosaminoglycan sequences.

  1990cited by this paper
• Binding of heparin to antithrombin III: a chemical proof of the critical role played by a 3-sulfated 2-amino-2-deoxy-D-glucose residue.

  1988cited by this paper
• Synthesis of heparin fragments. A chemical synthesis of the pentasaccharide O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-4 )-O-(beta-D-glucopyranosyluronic acid)-(1-4)-O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-glu copyranosyl)-(1-4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1

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  1986cited by this paper
• Controversial glycosaminoglycan conformations

  1986cited by this paper
• Structure and biological activity of heparin.

  1985cited by this paper
• Mono- and bidimensional 500 MHz 1H-NMR spectra of a synthetic pentasaccharide corresponding to the binding sequence of heparin to antithrombin-III: evidence for conformational peculiarity of the sulfated iduronate residue.

  1985cited by this paper

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  2016cites this paper
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  2016cites this paper
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