Combining supramolecular chemistry with biology.

Supramolecular chemistry has primarily found its inspiration in biological molecules, such as proteins and lipids, and their interactions. Currently the supramolecular assembly of designed compounds can be controlled to great extent. This provides the opportunity to combine these synthetic supramolecular elements with biomolecules for the study of biological phenomena. This tutorial review focuses on the possibilities of the marriage of synthetic supramolecular architectures and biological systems. It highlights that synthetic supramolecular elements are for example ideal platforms for the recognition and modulation of proteins and cells. The unique features of synthetic supramolecular systems with control over size, shape, valency, and interaction strength allow the generation of structures fitting the demands to approach the biological problems at hand. Supramolecular chemistry has come full circle, studying the biology and its molecules which initially inspired its conception.

[1]  Jean-Marie Lehn,et al.  Toward complex matter: Supramolecular chemistry and self-organization , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[2]  A. Hamilton,et al.  Peptide and protein recognition by designed molecules. , 2000, Chemical reviews.

[3]  Kimoon Kim,et al.  Noncovalent immobilization of proteins on a solid surface by cucurbit[7]uril-ferrocenemethylammonium pair, a potential replacement of biotin-avidin pair. , 2007, Journal of the American Chemical Society.

[4]  C. Blum,et al.  Modulation of protein dimerization by a supramolecular host-guest system. , 2009, Chemistry.

[5]  R. Read,et al.  Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands , 2000, Nature.

[6]  Julián Valero,et al.  Binding to protein surfaces by supramolecular multivalent scaffolds. , 2008, Current opinion in chemical biology.

[7]  K. Kudo,et al.  Supramolecular control of split-GFP reassembly by conjugation of beta-cyclodextrin and coumarin units. , 2008, Journal of the American Chemical Society.

[8]  Jurriaan Huskens,et al.  Nanometer arrays of functional light harvesting antenna complexes by nanoimprint lithography and host-guest interactions. , 2008, Journal of the American Chemical Society.

[9]  H. Ringsdorf,et al.  Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes , 1988 .

[10]  M. Fujita,et al.  Folding of an Ala-Ala-Ala Tripeptide into a β-Turn via Hydrophobic Encapsulation , 2006 .

[11]  Jay X. Tang,et al.  Hierarchical self-assembly of F-actin and cationic lipid complexes: stacked three-layer tubule networks. , 2000, Science.

[12]  L. Brunsveld,et al.  A synthetic supramolecular construct modulating protein assembly in cells. , 2007, Angewandte Chemie.

[13]  Alshakim Nelson,et al.  A self-assembled multivalent pseudopolyrotaxane for binding galectin-1. , 2004, Journal of the American Chemical Society.

[14]  Michael G. Fehlings,et al.  Self-Assembling Nanofibers Inhibit Glial Scar Formation and Promote Axon Elongation after Spinal Cord Injury , 2008, The Journal of Neuroscience.

[15]  Christopher L. McClendon,et al.  Reaching for high-hanging fruit in drug discovery at protein–protein interfaces , 2007, Nature.

[16]  Adam R. Urbach,et al.  Sequence-specific recognition and cooperative dimerization of N-terminal aromatic peptides in aqueous solution by a synthetic host. , 2006, Journal of the American Chemical Society.

[17]  S. Stupp,et al.  Light-triggered bioactivity in three dimensions. , 2009, Angewandte Chemie.

[18]  Faisal A. Aldaye,et al.  Assembling Materials with DNA as the Guide , 2008, Science.

[19]  K. Imoto,et al.  Stability of the dimerization domain effects the cooperative DNA binding of short peptides. , 1999, Biochemistry.

[20]  Krista L. Niece,et al.  Selective Differentiation of Neural Progenitor Cells by High-Epitope Density Nanofibers , 2004, Science.

[21]  H. Nguyen,et al.  Protein Dimerization Induced by Supramolecular Interactions with Cucurbit[8]uril. , 2010, Angewandte Chemie.

[22]  Samuel I Stupp,et al.  Molecular self-assembly into one-dimensional nanostructures. , 2008, Accounts of chemical research.

[23]  Joel H Collier,et al.  Modular self-assembling biomaterials for directing cellular responses. , 2008, Soft matter.

[24]  A. Murakami,et al.  Arranging quaternary structure of peptides by cyclodextrin-guest inclusion complex: sequence-specific DNA binding by a peptide dimer with artificial dimerization module , 1993 .

[25]  M. Fujita,et al.  Saccharide-coated M12L24 molecular spheres that form aggregates by multi-interaction with proteins. , 2007, Journal of the American Chemical Society.

[26]  J. Lehn,et al.  Supramolecular Chemistry: Receptors, Catalysts, and Carriers , 1985, Science.

[27]  J. F. Stoddart,et al.  Multivalent interactions between lectins and supramolecular complexes: Galectin-1 and self-assembled pseudopolyrotaxanes. , 2007, Chemistry & biology.

[28]  Zhiwei Yang,et al.  Very Strong Binding of Lithocholic Acid to β-Cyclodextrin , 1997 .

[29]  Y. Lim,et al.  Carbohydrate-coated supramolecular structures: transformation of nanofibers into spherical micelles triggered by guest encapsulation. , 2007, Journal of the American Chemical Society.

[30]  D. Reinhoudt,et al.  Supramolecular chemistry in water. , 2007, Angewandte Chemie.

[31]  Myongsoo Lee,et al.  Controlled self-assembly of carbohydrate conjugate rod-coil amphiphiles for supramolecular multivalent ligands. , 2005, Journal of the American Chemical Society.

[32]  M. C. Feiters,et al.  Beta-cyclodextrin-appended giant amphiphile: aggregation to vesicle polymersomes and immobilisation of enzymes. , 2008, Chemistry.

[33]  Adam R. Urbach,et al.  Multivalent recognition of peptides by modular self-assembled receptors. , 2009, Journal of the American Chemical Society.

[34]  Yong Chen,et al.  Cooperative binding and multiple recognition by bridged bis(beta-cyclodextrin)s with functional linkers. , 2006, Accounts of chemical research.

[35]  T. Schrader,et al.  A mechanism of efficient G6PD inhibition by a molecular clip. , 2009, Angewandte Chemie.

[36]  J. Voskuhl,et al.  Molecular recognition of bilayer vesicles. , 2009, Chemical Society reviews.

[37]  Y. Lim,et al.  Recent advances in functional supramolecular nanostructures assembled from bioactive building blocks. , 2009, Chemical Society reviews.

[38]  Lanti Yang,et al.  Strong and Reversible Monovalent Supramolecular Protein Immobilization , 2010, Chembiochem : a European journal of chemical biology.

[39]  Neel S. Joshi,et al.  An affinity-based method for the purification of fluorescently-labeled biomolecules. , 2006, Bioconjugate chemistry.

[40]  George M Whitesides,et al.  Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors. , 1998, Angewandte Chemie.

[41]  L. Brunsveld,et al.  A supramolecular polymer as a self-assembling polyvalent scaffold. , 2009, Angewandte Chemie.

[42]  E. Giralt,et al.  Stability and structural recovery of the tetramerization domain of p53-R337H mutant induced by a designed templating ligand , 2008, Proceedings of the National Academy of Sciences.

[43]  E. W. Meijer,et al.  Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering , 2007 .

[44]  Lyle Isaacs,et al.  The cucurbit[n]uril family: prime components for self-sorting systems. , 2005, Journal of the American Chemical Society.

[45]  H. Schneider,et al.  Host-guest chemistry. 14. Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. A general equation measuring hydrophobic binding contributions , 1988 .