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Synthetic multivalent ligands as probes of signal transduction
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An excellent review summarizing the most relevant examples of multivalent interactions from the mechanistic and biological points of view.
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Kiessling L.L., Gestwicki J.E., and Strong L.E. Synthetic multivalent ligands as probes of signal transduction. Angew Chem Int Ed 45 (2006) 2348-2368. An excellent review summarizing the most relevant examples of multivalent interactions from the mechanistic and biological points of view.
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Kiessling, L.L.1
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33846809157
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Dependence of effective molarity on linker length for an intramolecular protein-ligand system
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This paper brings into play thermodynamic clues of the design and study of multivalent protein ligands.
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Krishnamurthy V.M., Semetey V., Paul J.B., Shen N., and Whitesides G.B. Dependence of effective molarity on linker length for an intramolecular protein-ligand system. J Am Chem Soc 129 (2007) 1312-1320. This paper brings into play thermodynamic clues of the design and study of multivalent protein ligands.
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Krishnamurthy, V.M.1
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9
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33645827371
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Targeting protein-protein interactions by rational design: mimicry of protein surfaces
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The authors present an excellent account on protein surface binding by small multivalent supramolecular scaffolds and by mimics of secondary peptide structures.
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Fletcher S., and Hamilton A.D. Targeting protein-protein interactions by rational design: mimicry of protein surfaces. J R Soc Interface 3 (2006) 215-233. The authors present an excellent account on protein surface binding by small multivalent supramolecular scaffolds and by mimics of secondary peptide structures.
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Fletcher, S.1
Hamilton, A.D.2
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50 activity.
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Zhou, H.1
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Hamilton, A.D.8
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11
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13744258759
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Transglutaminase surface recognition by peptidocalix[4]arene diversomers
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Francese S., Cozzolinoc A., Caputo I., Esposito C., Martino M., Gaeta C., Troisi F., and Neri P. Transglutaminase surface recognition by peptidocalix[4]arene diversomers. Tetrahedron Lett 46 (2005) 1611-1615
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Francese, S.1
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A synthetic divalent Cholera toxin glycocalix[4]arene ligand having higher affinity than natural GM1 oligosaccharide
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Arosio D., Fontanella M., Baldini L., Mauri L., Bernardi A., Casnati A., Sansone F., and Ungaro R. A synthetic divalent Cholera toxin glycocalix[4]arene ligand having higher affinity than natural GM1 oligosaccharide. J Am Chem Soc 127 (2005) 3660-3661
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48649102319
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Calix[n]arene-based glycoclusters: bioactivity of thiourea-linked galactose/lactose moieties as inhibitors of binding of medically relevant lectins to a glycoprotein and cell-surface glycoconjugates and selectivity among human adhesion/growth-regulatory galectins
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The interaction of 14 calix[n]arenes endowed with a number of galactose or lactose derivatives with lectins - either bio-hazardous or acting as factors in tumor progression - is thoroughly studied. Interestingly, a preference for lactose over galactose epitopes, glycoside cluster effects, and a dependence of selective lectin inhibition on shape and valency of the glycoclusters are revealed.
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André S., Sansone F., Kaltner H., Casnati A., Kopitz J., Gabius H.-J., and Ungaro R. Calix[n]arene-based glycoclusters: bioactivity of thiourea-linked galactose/lactose moieties as inhibitors of binding of medically relevant lectins to a glycoprotein and cell-surface glycoconjugates and selectivity among human adhesion/growth-regulatory galectins. ChemBioChem 9 (2008) 1649-1661. The interaction of 14 calix[n]arenes endowed with a number of galactose or lactose derivatives with lectins - either bio-hazardous or acting as factors in tumor progression - is thoroughly studied. Interestingly, a preference for lactose over galactose epitopes, glycoside cluster effects, and a dependence of selective lectin inhibition on shape and valency of the glycoclusters are revealed.
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André, S.1
Sansone, F.2
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Casnati, A.4
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Ungaro, R.7
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Side chain elongation causes a change in enthalpy driven entropy binding in the molecular recognition of tetraanionic peptides
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Salvatella X., Peczuh M.W., Gairí M., Jain R.K., Sánchez-Quesada J., de Mendoza J., Hamilton A.D., and Giralt E. Side chain elongation causes a change in enthalpy driven entropy binding in the molecular recognition of tetraanionic peptides. Chem Commun (2000) 1399-1400
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Salvatella, X.1
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de Mendoza, J.6
Hamilton, A.D.7
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De novo protein surface design: use of cation-π interactions to enhance binding between an alfa-helical peptide and a cationic molecule in 50% aqueous solution
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Orner B.P., Salvatella X., Sánchez-Quesada J., de Mendoza J., Giralt E., and Hamilton A.D. De novo protein surface design: use of cation-π interactions to enhance binding between an alfa-helical peptide and a cationic molecule in 50% aqueous solution. Angew Chem Int Ed 41 (2002) 117-119
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Orner, B.P.1
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de Mendoza, J.4
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Hamilton, A.D.6
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16
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0345862318
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A tetraguanidinium ligand binds to the surface of the tetramerization domain of protein P53
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This paper shows how the rational design serves to target a well-defined sequence in the tetramerization domain of p53 by multivalent ligands.
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Salvatella X., Martinell M., Gairí M., Mateu M.G., Feliz M., Hamilton A.D., de Mendoza J., and Giralt E. A tetraguanidinium ligand binds to the surface of the tetramerization domain of protein P53. Angew Chem Int Ed 43 (2004) 196-198. This paper shows how the rational design serves to target a well-defined sequence in the tetramerization domain of p53 by multivalent ligands.
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Salvatella, X.1
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de Mendoza, J.7
Giralt, E.8
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Gordo S, Martos V, Santos E, Menéndez M, Bo C, Giralt E, de Mendoza J: Stability and structural recovery of the tetramerization domain of p53-R337H mutant induced by a designed templating ligand. Proc Natl Acad Sci USA 2008, 105:in press.
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18
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1842640105
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Macrocyclic proteoglycan mimics. Potent inhibition of cell adhesion by a bundle of chondroitin sulfate chains assembled on the calix[4]resorcarene platform
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Tomiteta N., Sando S., Sera T., and Aoyama Y. Macrocyclic proteoglycan mimics. Potent inhibition of cell adhesion by a bundle of chondroitin sulfate chains assembled on the calix[4]resorcarene platform. Bioorg Med Chem Lett 14 (2004) 2087-2090
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Mecca T., Consoli G.M.L., Geraci C., LaSpina R., and Cunsolo F. Polycationic calix[8]arenes able to recognize and neutralize heparin. Org Biomol Chem 4 (2006) 3763-3768
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This review is worthwhile reading and a good complement to Ref. [9].
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Hershberger S., Lee S.-G., and Chmielewski J. Scaffolds for inhibiting protein-protein interactions. Curr Top Med Chem 7 (2007) 928-942. This review is worthwhile reading and a good complement to Ref. [9].
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Hershberger, S.1
Lee, S.-G.2
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22
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33846065829
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Protein recognition and denaturation by self-assembling fragments on a DNA quadruplex scaffold
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This is an interesting attempt to substitute porphyrins scaffolds by naturally occurring selfassembling DNA motifs. It is inspired in previous studies that design porphyrin ligands to bind to telomerase-binding G-quartets.
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Tagore D.M., Sprinz K.I., Fletcher S., Jayawickramarajah J., and Hamilton A.D. Protein recognition and denaturation by self-assembling fragments on a DNA quadruplex scaffold. Angew Chem Int Ed 46 (2007) 223-225. This is an interesting attempt to substitute porphyrins scaffolds by naturally occurring selfassembling DNA motifs. It is inspired in previous studies that design porphyrin ligands to bind to telomerase-binding G-quartets.
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Angew Chem Int Ed
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Tagore, D.M.1
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In this example negatively charged dendrimer-like molecules recognize histones through ionic interactions with the positively charged histone surface. However, the cyclophane scaffold also contributes to approach molecules to the interaction site, and thus the scaffold is not limited to a structural function.
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Hayashida O., and Uchiyama M. Multivalent macrocyclic hosts: histone surface recognition, guest binding, and delivery by cyclophane-based resorcinarene oligomers. J Org Chem 72 (2007) 610-616. In this example negatively charged dendrimer-like molecules recognize histones through ionic interactions with the positively charged histone surface. However, the cyclophane scaffold also contributes to approach molecules to the interaction site, and thus the scaffold is not limited to a structural function.
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J Org Chem
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A good and brief review on the latest progress in the field.
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•], this paper constitutes a thorough update on glycodendrimers since 2000 from the chemist point of view.
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•], this paper constitutes a thorough update on glycodendrimers since 2000 from the chemist point of view.
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Strong inhibition of Cholera toxin by multivalent GM1 derivatives
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GM1-oligosaccharide (GM1os), an optimal ligand for CT, was linked to dendritic structures endowed with long arms by using highly efficient 'click chemistry' coupling. Very large multivalency effects were observed, the best structure showing unprecedented 380 000-fold more potent ligand for the toxin than for a monovalent GM1os reference.
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Pukin A.V., Branderhorst H.M., Sisu C., Weijers C.A.G.M., Gilbert M., Liskamp R.M.J., Visser G.M., Zuilhof H., and Pieters R.J. Strong inhibition of Cholera toxin by multivalent GM1 derivatives. ChemBioChem 8 (2007) 1500-1503. GM1-oligosaccharide (GM1os), an optimal ligand for CT, was linked to dendritic structures endowed with long arms by using highly efficient 'click chemistry' coupling. Very large multivalency effects were observed, the best structure showing unprecedented 380 000-fold more potent ligand for the toxin than for a monovalent GM1os reference.
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ChemBioChem
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