Self-Assembly of Bioconjugated Amphiphilic Mesogens Having Specific Binding Moieties at Aqueous–Liquid Crystal Interfaces

New bioconjugated amphiphilic mesogens with recognition groups have been synthesized, and their self-assembly behavior has been characterized at aqueous–liquid crystal (LC) interfaces. Specifically, the rod-shaped 2,3-difluoro-4′-(4-trans-pentylcyclohexyl)biphenyl-based mesogen was conjugated with either biotin or the arginine–glycine–aspartic acid (RGD) peptide sequence through a tetraethylene glycol chain. Langmuir film measurements revealed that the two biorecognition moieties lead to very different surface pressure–area isotherms, indicating that biotin and RGD have distinct effects on self-assembled monolayers formed by these bioconjugated mesogens at aqueous surfaces. Measurements of the surface-induced orientations of LCs exhibited by biotin-conjugated mesogens mixed with the room-temperature nematic LC 4-cyano-4′-pentylbiphenyl (5CB) revealed formation of cholesteric phases (consistent with the chiral nature of biotin) and evidence of the presence of the conjugated mesogen at aqueous interfaces. P...

[1]  Jinbao Guo,et al.  Hydrogen-bonded chiral molecular switches: photo- and thermally-reversible switchable full range color in the self-organized helical superstructure , 2015 .

[2]  T. Seki.  New strategies and implications for the photoalignment of liquid crystalline polymers , 2014 .

[3]  H. Ohno,et al.  Macroscopic photocontrol of ion-transporting pathways of a nanostructured imidazolium-based photoresponsive liquid crystal. , 2014, Journal of the American Chemical Society.

[4]  M. Steinhart,et al.  Honeycombs in honeycombs: complex liquid crystal alumina composite mesostructures. , 2014, ACS nano.

[5]  D. Broer,et al.  Self-assembled dynamic 3D fingerprints in liquid-crystal coatings towards controllable friction and adhesion. , 2014, Angewandte Chemie.

[6]  Fang Zuo,et al.  An air-supported liquid crystal system for real-time reporting of host-guest inclusion events. , 2014, Chemical communications.

[7]  Soo-young Park,et al.  Liquid crystal-based proton sensitive glucose biosensor. , 2014, Analytical chemistry.

[8]  I. Aprahamian,et al.  Manipulating liquid-crystal properties using a pH activated hydrazone switch. , 2013, Angewandte Chemie.

[9]  M. Bremer,et al.  The TV in your pocket: development of liquid-crystal materials for the new millennium. , 2013, Angewandte Chemie.

[10]  C. Tschierske.  Development of structural complexity by liquid-crystal self-assembly. , 2013, Angewandte Chemie.

[11]  Reza Abbasi,et al.  Chemical and biological sensing using liquid crystals , 2013, Liquid crystals reviews.

[12]  Patrick S. Noonan,et al.  Liquid crystal reorientation induced by aptamer conformational changes. , 2013, Journal of the American Chemical Society.

[13]  N. Abbott,et al.  Influence of specific anions on the orientational ordering of thermotropic liquid crystals at aqueous interfaces. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[14]  Michael G Debije,et al.  Functional organic materials based on polymerized liquid-crystal monomers: supramolecular hydrogen-bonded systems. , 2012, Angewandte Chemie.

[15]  A. Schenning,et al.  Printable optical sensors based on H-bonded supramolecular cholesteric liquid crystal networks. , 2012, Journal of the American Chemical Society.

[16]  N. Abbott,et al.  Ordering transitions triggered by specific binding of vesicles to protein-decorated interfaces of thermotropic liquid crystals. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[17]  N. Abbott,et al.  Liquid Crystalline Materials for Biological Applications. , 2012, Chemistry of materials : a publication of the American Chemical Society.

[18]  G. Schweicher,et al.  Substrate‐Induced Crystal Plastic Phase of a Discotic Liquid Crystal , 2012, Advanced materials.

[19]  Daniel A. Beller,et al.  Pillar‐Assisted Epitaxial Assembly of Toric Focal Conic Domains of Smectic‐A Liquid Crystals , 2011, Advanced materials.

[20]  Daniel J. Welsh,et al.  Comparing dendritic and self-assembly strategies to multivalency--RGD peptide-integrin interactions. , 2011, Organic & biomolecular chemistry.

[21]  Nobuhiro Kawatsuki,et al.  Photoalignment and Photoinduced Molecular Reorientation of Photosensitive Materials , 2011 .

[22]  Takashi Kato.  From nanostructured liquid crystals to polymer-based electrolytes. , 2010, Angewandte Chemie.

[23]  Jinghuan Huang,et al.  Nanostructured interfaces with RGD arrays to control cell–matrix interaction , 2010 .

[24]  N. Abbott,et al.  Design of Biomolecular Interfaces Using Liquid Crystals Containing Oligomeric Ethylene Glycol , 2010, Advanced functional materials.

[25]  Kun-Lin Yang,et al.  Decorating Liquid Crystal Surfaces with Proteins for Real‐Time Detection of Specific Protein–Protein Binding , 2009 .

[26]  H. Ohno,et al.  Electric‐Field‐Responsive Lithium‐Ion Conductors of Propylenecarbonate‐Based Columnar Liquid Crystals , 2009 .

[27]  Masuki Kawamoto,et al.  Thermo and Photoresponsive Behavior of Liquid-Crystalline Helical Structures with the Aid of Dual Molecular Motions , 2009 .

[28]  Sheila MacNeil,et al.  Production and performance of biomaterials containing RGD peptides , 2008 .

[29]  Xinyan Bi,et al.  An Air‐Supported Liquid Crystal System for Real‐Time and Label‐Free Characterization of Phospholipases and Their Inhibitors , 2008 .

[30]  D. K. Schwartz,et al.  DNA hybridization-induced reorientation of liquid crystal anchoring at the nematic liquid crystal/aqueous interface. , 2008, Journal of the American Chemical Society.

[31]  D. Broer,et al.  Nanoporous Membranes of Hydrogen‐bridged Smectic Networks with Nanometer Transverse Pore Dimensions , 2008 .

[32]  Nicholas L. Abbott,et al.  Ordering Transitions in Thermotropic Liquid Crystals Induced by the Interfacial Assembly and Enzymatic Processing of Oligopeptide Amphiphiles , 2008 .

[33]  N. Abbott,et al.  Preparation of microscopic and planar oil-water interfaces that are decorated with prescribed densities of insoluble amphiphiles. , 2008, Journal of the American Chemical Society.

[34]  Masafumi Yoshio,et al.  Induction of columnar and smectic phases for spiropyran derivatives: effects of acidichromism and photochromism. , 2008, Chemistry, an Asian journal.

[35]  Gregory P. Crawford,et al.  Liquid-crystal materials find a new order in biomedical applications. , 2007, Nature materials.

[36]  S. Rowan,et al.  Supramolecular Interactions in the Formation of Thermotropic Liquid Crystalline Polymers , 2007 .

[37]  H. Ohno,et al.  Uniaxially Parallel Alignment of a Smectic A Liquid-Crystalline Rod−Coil Molecule and Its Lithium Salt Complexes Using Rubbed Polyimides , 2007 .

[38]  T. Hegmann,et al.  Nanoparticles in Liquid Crystals: Synthesis, Self-Assembly, Defect Formation and Potential Applications , 2007 .

[39]  C. Carman,et al.  Structural basis of integrin regulation and signaling. , 2007, Annual review of immunology.

[40]  D. K. Schwartz,et al.  Anchoring of a nematic liquid crystal on a wettability gradient. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[41]  W. R. Salaneck,et al.  Effect of interfaces on the alignment of a discotic liquid-crystalline phthalocyanine. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[42]  D. Gin,et al.  Recent Advances in the Design of Polymerizable Lyotropic Liquid‐Crystal Assemblies for Heterogeneous Catalysis and Selective Separations , 2006 .

[43]  Sean P. Palecek,et al.  Thermotropic Liquid Crystals as Substrates for Imaging the Reorganization of Matrigel by Human Embryonic Stem Cells , 2006 .

[44]  K. Binnemans.  Ionic liquid crystals. , 2005, Chemical reviews.

[45]  H. Ohno,et al.  Nano-segregated polymeric film exhibiting high ionic conductivities. , 2005, Journal of the American Chemical Society.

[46]  S. Stupp,et al.  Presentation and recognition of biotin on nanofibers formed by branched peptide amphiphiles. , 2005, Nano letters.

[47]  Takashi Kato,et al.  Functional liquid-crystalline assemblies: self-organized soft materials. , 2005, Angewandte Chemie.

[48]  N. Abbott,et al.  Biomolecular Interactions at Phospholipid-Decorated Surfaces of Liquid Crystals , 2003, Science.

[49]  Tomiki Ikeda,et al.  Photomodulation of liquid crystal orientations for photonic applications , 2003 .

[50]  N. Abbott,et al.  Surface-Driven Switching of Liquid Crystals Using Redox-Active Groups on Electrodes , 2003, Science.

[51]  C. Guymon,et al.  Physical properties of hydrogels synthesized from lyotropic liquid crystalline templates , 2003 .

[52]  N. Abbott,et al.  Effect of Surfactant Structure on the Orientation of Liquid Crystals at Aqueous−Liquid Crystal Interfaces† , 2003 .

[53]  M. Boamfa,et al.  Observation of surface and bulk phase transitions in nematic liquid crystals , 2003, Nature.

[54]  Takashi Kato.  Self-Assembly of Phase-Segregated Liquid Crystal Structures , 2002, Science.

[55]  K. Kawata.  Orientation control and fixation of discotic liquid crystal. , 2002, Chemical record.

[56]  Kiyoshi Kanie,et al.  Self-assembly of thermotropic liquid-crystalline folic acid derivatives: hydrogen-bonded complexes forming layers and columns , 2001 .

[57]  Kunihiro Ichimura,et al.  Photoalignment of Liquid-Crystal Systems. , 2000, Chemical reviews.

[58]  F. Szoka,et al.  Orientation of the pore-forming peptide GALA in POPC vesicles determined by a BODIPY-avidin/biotin binding assay. , 1999, Biophysical journal.

[59]  J. Baudry,et al.  Arch-texture in cholesteric liquid crystals , 1996 .

[60]  A. Verkman,et al.  Imaging of endosome fusion in BHK fibroblasts based on a novel fluorimetric avidin-biotin binding assay. , 1995, Biophysical journal.

[61]  J. Mann,et al.  Multilayer Formation in Thin Films of Thermotropic Liquid Crystals at the Air-Water Interface , 1994 .

[62]  H. Yokoyama,et al.  Continuous anchoring transition in liquid crystals , 1993, Nature.

[63]  B Jerome,et al.  Surface effects and anchoring in liquid crystals , 1991 .

[64]  H. Ringsdorf,et al.  Interaction between biotin lipids and streptavidin in monolayers: formation of oriented two-dimensional protein domains induced by surface recognition. , 1989, Biochemistry.

[65]  Kunihiro Ichimura,et al.  Reversible change in alignment mode of nematic liquid crystals regulated photochemically by command surfaces modified with an azobenzene monolayer , 1988 .

[66]  Erkki Ruoslahti,et al.  Cell attachment activity of fibronectin can be duplicated by small synthetic fragments of the molecule , 1984, Nature.