Multifunctional biosensors based on peptide-polyelectrolyte conjugates.

A novel enzymatic platform for the sensing of H2O2 and glucose that uses L,L-diphenylalanine micro/nanostructures (FF-MNSs) as an enzyme support is shown. This platform is obtained by the self-assembly of poly(allylamine hydrochloride) (PAH), FF-MNSs, and microperoxidase-11 (MP11) anchored onto the peptide matrix, in two different crystal structures of FF-MNSs: hexagonal (P61) and orthorhombic (P22121). The electroactive area of the electrodes increases in the presence of FF-MNSs. We also demonstrate via theoretical calculations that the valence band energy of the orthorhombic structure allows it to be doped, similarly to p-type semiconductors, where PAH acts as a doping agent for the orthorhombic peptide structure, decreasing the band-gap by around 1 eV, which results in a smaller charge transfer resistance. These results are consistent with electrochemical impedance spectroscopy measurements, which further elucidate the role of the band structure of the orthorhombic FF-MNSs in the conductivity and electron transfer rates of the hybrid material. An effective communication between the electrode and the active site of a glucose oxidase enzyme through MP11-protein complexes occurs, paving the way for FF-MNSs in the orthorhombic phase for the future development of bioelectronics sensing devices.

[1]  Tommi A. White,et al.  Self‐Assembled Peptide–Polyfluorene Nanocomposites for Biodegradable Organic Electronics , 2015 .

[2]  Yongmei Yin,et al.  Peptide-based method for detection of metastatic transformation in primary tumors of breast cancer. , 2015, Analytical chemistry.

[3]  K. Bren,et al.  Biological significance and applications of heme c proteins and peptides. , 2015, Accounts of chemical research.

[4]  Ning Xia,et al.  Ferrocene-phenylalanine hydrogels for immobilization of acetylcholinesterase and detection of chlorpyrifos , 2015 .

[5]  Genxi Li,et al.  Peptide network for detection of tissue-remodeling enzyme in the prognosis of hepatocellular carcinoma. , 2015, ACS applied materials & interfaces.

[6]  A. Mulchandani,et al.  Bioelectrochemistry of heme peptide at seamless three-dimensional carbon nanotubes/graphene hybrid films for highly sensitive electrochemical biosensing. , 2015, ACS applied materials & interfaces.

[7]  S. Krishnan,et al.  Enhanced electroactivity and substrate affinity of microperoxidase-11 attached to pyrene-linkers π–π stacked on carbon nanostructure electrodes , 2015 .

[8]  Michael Gaus,et al.  Parameterization of the DFTB3 method for Br, Ca, Cl, F, I, K, and Na in organic and biological systems. , 2015, Journal of chemical theory and computation.

[9]  Genxi Li,et al.  Method to study stoichiometry of protein post-translational modification. , 2014, Analytical chemistry.

[10]  Amrit Laudari,et al.  Bioinspired peptide nanostructures for organic field-effect transistors. , 2014, ACS applied materials & interfaces.

[11]  Ehud Gazit,et al.  The physical properties of supramolecular peptide assemblies: from building block association to technological applications. , 2014, Chemical Society reviews.

[12]  W. Alves,et al.  A nonenzymatic biosensor based on gold electrodes modified with peptide self-assemblies for detecting ammonia and urea oxidation. , 2014, Langmuir : the ACS journal of surfaces and colloids.

[13]  W. Alves,et al.  The role of water and structure on the generation of reactive oxygen species in peptide/hypericin complexes , 2014, Journal of peptide science : an official publication of the European Peptide Society.

[14]  S. Grimme,et al.  Accurate Modeling of Organic Molecular Crystals by Dispersion-Corrected Density Functional Tight Binding (DFTB). , 2014, The journal of physical chemistry letters.

[15]  M. Ferreira,et al.  Amperometric glucose biosensor based on layer-by-layer films of microperoxidase-11 and liposome-encapsulated glucose oxidase. , 2014, Bioelectrochemistry.

[16]  Yizeng Liang,et al.  Ferrocenoyl phenylalanine: a new strategy toward supramolecular hydrogels with multistimuli responsive properties. , 2013, Journal of the American Chemical Society.

[17]  Y. Zhai,et al.  A SELF-CONSISTENT-CHARGE DENSITY-FUNCTIONAL TIGHT-BINDING THEORY BASED MOLECULAR DYNAMICS SIMULATION OF A ZWITTERIONIC GLYCINE IN AN EXPLICIT WATER ENVIRONMENT , 2013 .

[18]  W. Alves,et al.  The effects of water molecules on the electronic and structural properties of peptide nanotubes. , 2013, Physical chemistry chemical physics : PCCP.

[19]  Ai-Jun Wang,et al.  A study on the direct electrochemistry and electrocatalysis of microperoxidase-11 immobilized on a porous network-like gold film: Sensing of hydrogen peroxide , 2013, Microchimica Acta.

[20]  Hao Li,et al.  A general way to assay protein by coupling peptide with signal reporter via supermolecule formation. , 2013, Analytical chemistry.

[21]  M. Elstner,et al.  Parametrization and Benchmark of DFTB3 for Organic Molecules. , 2013, Journal of chemical theory and computation.

[22]  W. Alves,et al.  Micro- and nano-sized peptidic assemblies prepared via solid-vapor approach: Morphological and spectroscopic aspects , 2012 .

[23]  Byung-Wook Park,et al.  A novel glucose biosensor using bi-enzyme incorporated with peptide nanotubes. , 2012, Biosensors & bioelectronics.

[24]  Jae Hong Kim,et al.  Self-assembled light-harvesting peptide nanotubes for mimicking natural photosynthesis. , 2012, Angewandte Chemie.

[25]  W. Alves,et al.  Electrochemical determination of dopamine based on self-assembled peptide nanostructure. , 2011, ACS applied materials & interfaces.

[26]  A. B. Islam,et al.  A Mediator Free Amperometric Bienzymatic Glucose Biosensor Using Vertically Aligned Carbon Nanofibers (VACNFs) , 2011, IEEE Sensors Journal.

[27]  S. Filipek,et al.  Diphenylalanine peptide nanotube: charge transport, band gap and its relevance to potential biomedical applications , 2011 .

[28]  Michael Gaus,et al.  DFTB3: Extension of the self-consistent-charge density-functional tight-binding method (SCC-DFTB). , 2011, Journal of chemical theory and computation.

[29]  M. Hedström,et al.  Stability of diphenylalanine peptide nanotubes in solution. , 2011, Nanoscale.

[30]  Chan Beum Park,et al.  Self-assembly of semiconducting photoluminescent peptide nanowires in the vapor phase. , 2011, Angewandte Chemie.

[31]  A. S. Sigov,et al.  Temperature-driven phase transformation in self-assembled diphenylalanine peptide nanotubes , 2010 .

[32]  Bin Wang,et al.  Modifying Randles circuit for analysis of polyoxometalate layer-by-layer films. , 2010, The journal of physical chemistry. B.

[33]  Junbai Li,et al.  Self-assembly and application of diphenylalanine-based nanostructures. , 2010, Chemical Society reviews.

[34]  N. Amdursky,et al.  Strong piezoelectricity in bioinspired peptide nanotubes. , 2010, ACS nano.

[35]  Tae Hee Han,et al.  Role of Water in Directing Diphenylalanine Assembly into Nanotubes and Nanowires , 2010, Advanced materials.

[36]  Chan Beum Park,et al.  High stability of self‐assembled peptide nanowires against thermal, chemical, and proteolytic attacks , 2010, Biotechnology and bioengineering.

[37]  G. Rosenman,et al.  Self-assembled arrays of peptide nanotubes by vapour deposition. , 2009, Nature nanotechnology.

[38]  Chan Beum Park,et al.  Bio-inspired fabrication of superhydrophobic surfaces through peptide self-assembly , 2009 .

[39]  Chan Beum Park,et al.  Synthesis of diphenylalanine/polyaniline core/shell conducting nanowires by peptide self-assembly. , 2009, Angewandte Chemie.

[40]  P. Hellwig,et al.  Far infrared spectroscopy on hemoproteins : A model compound study from 1800-100 cm-1 , 2008 .

[41]  Zhihui Dai,et al.  A bienzyme channeling glucose sensor with a wide concentration range based on co-entrapment of enzymes in SBA-15 mesopores. , 2008, Biosensors & bioelectronics.

[42]  H. Marques.  Insights into porphyrin chemistry provided by the microperoxidases, the haempeptides derived from cytochrome c. , 2007, Dalton transactions.

[43]  T. Frauenheim,et al.  DFTB+, a sparse matrix-based implementation of the DFTB method. , 2007, The journal of physical chemistry. A.

[44]  L. Adler-Abramovich,et al.  Direct observation of the release of phenylalanine from diphenylalanine nanotubes. , 2006, Journal of the American Chemical Society.

[45]  L. Adler-Abramovich,et al.  Thermal and chemical stability of diphenylalanine peptide nanotubes: implications for nanotechnological applications. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[46]  David Barlam,et al.  Self-assembled peptide nanotubes are uniquely rigid bioinspired supramolecular structures. , 2005, Nano letters.

[47]  Meital Reches,et al.  Formation of Closed-Cage Nanostructures by Self-Assembly of Aromatic Dipeptides , 2004 .

[48]  G. Ragoisha,et al.  Potentiodynamic electrochemical impedance spectroscopy , 2004 .

[49]  Meital Reches,et al.  Casting Metal Nanowires Within Discrete Self-Assembled Peptide Nanotubes , 2003, Science.

[50]  T. Tatsuma,et al.  Peroxidase model electrodes: heme peptide modified electrodes as reagentless sensors for hydrogen peroxide. , 1991, Analytical chemistry.

[51]  Swatantar Kumar,et al.  State of heme in heme c systems: Cytochrome c and heme c models , 1983 .

[52]  Kevin M. Smith,et al.  Structural correlations and vinyl influences in resonance Raman spectra of protoheme complexes and proteins , 1982 .

[53]  P. Stein,et al.  Porphyrin core expansion and doming in heme proteins. New evidence from resonance Raman spectra of six-coordinate high-spin iron(III) hemes , 1979 .

[54]  H. Monkhorst,et al.  SPECIAL POINTS FOR BRILLOUIN-ZONE INTEGRATIONS , 1976 .

[55]  H. Rietveld.  A profile refinement method for nuclear and magnetic structures , 1969 .

[56]  H. Nezammahalleh,et al.  An investigation on the chemical stability and a novel strategy for long-term stabilization of diphenylalanine nanostructures in aqueous solution , 2015 .

[57]  Mario Aranda-Bustos,et al.  Development of a Bienzymatic Amperometric Glucose Biosensor Using Mesoporous Silica (MCM‐41) for Enzyme Immobilization and Its Application on Liquid Pharmaceutical Formulations , 2013 .

[58]  H. Rietveld.  Line profiles of neutron powder-diffraction peaks for structure refinement , 1967 .