Morphological control of self-assembled multivalent (SAMul) heparin binding in highly competitive media.

Tuning molecular structures of self-assembling multivalent (SAMul) dendritic cationic lipopeptides controls the self-assembled morphology. In buffer, spherical micelles formed by higher generation systems bind polyanionic heparin better than worm-like micelles formed by lower generation systems. In human serum, the binding of spherical micelles to heparin is adversely affected, while worm-like micelles maintain their relative binding ability.

[1]  K. Ahn,et al.  Molecular interactions between charged macromolecules: colorimetric detection and quantification of heparin with a polydiacetylene liposome. , 2013, Journal of materials chemistry. B.

[2]  Sabrina Pricl,et al.  Emergence of highly-ordered hierarchical nanoscale aggregates on electrostatic binding of self-assembled multivalent (SAMul) cationic micelles with polyanionic heparin. , 2017, Journal of materials chemistry. B.

[3]  U Kragh-Hansen,et al.  Molecular aspects of ligand binding to serum albumin. , 1981, Pharmacological reviews.

[4]  David K. Smith,et al.  Nanoscale self-assembled multivalent (SAMul) heparin binders in highly competitive, biologically relevant, aqueous media , 2014 .

[5]  Q. Ping,et al.  Heparin modification enhances the delivery and tumor targeting of paclitaxel-loaded N-octyl-N-trimethyl chitosan micelles. , 2016, International journal of pharmaceutics.

[6]  S. P. Moulik,et al.  Biocompatible microemulsions and their prospective uses in drug delivery. , 2008, Journal of pharmaceutical sciences.

[7]  Young Ha Kim,et al.  Accelerated Micellization and Aggregation of Pluronic Micelles by Interaction with Heparin , 2010, Journal of biomaterials science. Polymer edition.

[8]  Anna Barnard,et al.  Self-assembled multivalency: dynamic ligand arrays for high-affinity binding. , 2012, Angewandte Chemie.

[9]  Karl Fischer,et al.  Temperature triggered self-assembly of polypeptides into multivalent spherical micelles. , 2008, Journal of the American Chemical Society.

[10]  V. Percec,et al.  From structure to function via complex supramolecular dendrimer systems. , 2015, Chemical Society reviews.

[11]  P. Linse,et al.  Monte Carlo Simulations of Polyelectrolytes at Charged Micelles. 2. Effects of Linear Charge Density , 1996 .

[12]  David K. Smith,et al.  Heparin versus DNA: Chiral Preferences in Polyanion Binding to Self-Assembled Multivalent (SAMul) Nanostructures. , 2015, Journal of the American Chemical Society.

[13]  O. Rojas,et al.  Effect of PEG-PDMAEMA Block Copolymer Architecture on Polyelectrolyte Complex Formation with Heparin. , 2016, Biomacromolecules.

[14]  Kinam Park,et al.  Overcoming the barriers in micellar drug delivery: loading efficiency, in vivo stability, and micelle–cell interaction , 2010, Expert opinion on drug delivery.

[15]  W. DeGrado,et al.  De Novo Design of Self-Assembling Foldamers That Inhibit Heparin–Protein Interactions , 2014, ACS chemical biology.

[16]  R. Haag,et al.  Degradable self-assembling dendrons for gene delivery: experimental and theoretical insights into the barriers to cellular uptake. , 2011, Journal of the American Chemical Society.

[17]  J. Engberts,et al.  The use of Nile Red to monitor the aggregation behavior in ternary surfactant–water–organic solvent systems , 2005 .

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

[19]  Enzo Terreno,et al.  The extraordinary ligand binding properties of human serum albumin , 2005, IUBMB life.

[20]  Yongju Kim,et al.  Switching of carbohydrate nanofibers for regulating cell proliferation. , 2016, Soft matter.

[21]  S. Tenjarla.  Microemulsions: an overview and pharmaceutical applications. , 1999, Critical reviews in therapeutic drug carrier systems.

[22]  B. Nilsson,et al.  Development and characterization of an innovative heparin coating to stabilize and protect liposomes against adverse immune reactions. , 2016, Colloids and surfaces. B, Biointerfaces.

[23]  David K. Smith,et al.  Heparin sensing and binding - taking supramolecular chemistry towards clinical applications. , 2013, Chemical Society reviews.

[24]  B. Ninham,et al.  Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers , 1976 .

[25]  Christina Graf,et al.  Multivalency as a chemical organization and action principle. , 2012, Angewandte Chemie.

[26]  E. Laurini,et al.  Chiral recognition at self-assembled multivalent (SAMul) nanoscale interfaces - enantioselectivity in polyanion binding. , 2016, Chemical communications.

[27]  J. Borreguero,et al.  Surfactant-Mediated Polyelectrolyte Self-Assembly in a Polyelectrolyte–Surfactant Complex , 2015 .

[28]  J. Courtois,et al.  Probing oppositely charged surfactant and copolymer interactions by isothermal titration microcalorimetry. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[29]  M. Otagiri,et al.  Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. , 2002, Biological & pharmaceutical bulletin.

[30]  Samuel I Stupp,et al.  Heparin binding nanostructures to promote growth of blood vessels. , 2006, Nano letters.

[31]  J. Lehn,et al.  Multivalency by self-assembly: binding of concanavalin A to metallosupramolecular architectures decorated with multiple carbohydrate groups. , 2014, Chemistry.

[32]  K. Tam,et al.  Interaction between polyelectrolyte and oppositely charged surfactant: Effect of charge density , 2004 .

[33]  John F. Trant,et al.  Synthesis, self-assembly, and immunological activity of α-galactose-functionalized dendron-lipid amphiphiles. , 2016, Nanoscale.

[34]  Zdeněk Tošner,et al.  Thermodynamic and Kinetic Aspects of Coassembly of PEO–PMAA Block Copolymer and DPCl Surfactants into Ordered Nanoparticles in Aqueous Solutions Studied by ITC, NMR, and Time-Resolved SAXS Techniques , 2013 .

[35]  G. O’Toole,et al.  Synthesis of Bioinspired Carbohydrate Amphiphiles that Promote and Inhibit Biofilms. , 2014, Chemical science.

[36]  N. Wagner,et al.  Universal binding behavior for ionic alkyl surfactants with oppositely charged polyelectrolytes. , 2013, Journal of the American Chemical Society.

[37]  Egbert J Boekema,et al.  Light-responsive capture and release of DNA in a ternary supramolecular complex. , 2011, Angewandte Chemie.

[38]  Yang Wang,et al.  Adaptive amphiphilic dendrimer-based nanoassemblies as robust and versatile siRNA delivery systems. , 2014, Angewandte Chemie.

[39]  Nathan T. Ross,et al.  Multivalent protein binding and precipitation by self-assembling molecules on a DNA pentaplex scaffold. , 2009, Journal of the American Chemical Society.

[40]  Maurizio Fermeglia,et al.  A simple new competition assay for heparin binding in serum applied to multivalent PAMAM dendrimers. , 2013, Chemical communications.

[41]  Sabrina Pricl,et al.  Self-assembled multivalent RGD-peptide arrays--morphological control and integrin binding. , 2013, Organic & biomolecular chemistry.

[42]  David K Smith,et al.  Self-assembling ligands for multivalent nanoscale heparin binding. , 2011, Angewandte Chemie.

[43]  G. Whitesides,et al.  The agglutination of erythrocytes by influenza virus is strongly inhibited by liposomes incorporating an analog of sialyl gangliosides , 1992 .

[44]  K. Tam,et al.  New Insights on the Interaction Mechanism within Oppositely Charged Polymer/Surfactant Systems , 2002 .

[45]  U. Natarajan,et al.  Molecular Dynamics Simulations of Adsorption of Poly(acrylic acid) and Poly(methacrylic acid) on Dodecyltrimethylammonium Chloride Micelle in Water: Effect of Charge Density. , 2015, The journal of physical chemistry. B.

[46]  J. Sakamoto,et al.  Emergent Molecular Recognition through Self-Assembly: Unexpected Selectivity for Hyaluronic Acid among Glycosaminoglycans. , 2016, Angewandte Chemie.

[47]  Maurizio Fermeglia,et al.  Mallard blue: a high-affinity selective heparin sensor that operates in highly competitive media. , 2013, Journal of the American Chemical Society.

[48]  Yue Zhao,et al.  A polyion complex micelle with heparin for growth factor delivery and uptake into cells. , 2013, Journal of materials chemistry. B.

[49]  N. Lu,et al.  A low-molecular-weight heparin-coated doxorubicin-liposome for the prevention of melanoma metastasis , 2015, Journal of drug targeting.

[50]  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.

[51]  J. Chapel,et al.  Evidence of a two-step process and pathway dependency in the thermodynamics of poly(diallyldimethylammonium chloride)/poly(sodium acrylate) complexation. , 2014, Soft matter.

[52]  L. Brunsveld,et al.  Supramolecular chemical biology; bioactive synthetic self-assemblies. , 2013, Organic & biomolecular chemistry.

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