Why Is the Sensory Response of Organic Probes within a Polymer Film Different in Solution and in the Solid-State? Evidence and Application to the Detection of Amino Acids in Human Chronic Wounds

We anchored a colourimetric probe, comprising a complex containing copper (Cu(II)) and a dye, to a polymer matrix obtaining film-shaped chemosensors with induced selectivity toward glycine. This sensory material is exploited in the selectivity detection of glycine in complex mixtures of amino acids mimicking elastin, collagen and epidermis, and also in following the protease activity in a beefsteak and chronic human wounds. We use the term inducing because the probe in solution is not selective toward any amino acid and we get selectivity toward glycine using the solid-state. Overall, we found that the chemical behaviour of a chemical probe can be entirely changed by changing its chemical environment. Regarding its behaviour in solution, this change has been achieved by isolating the probe by anchoring the motifs in a polymer matrix, in an amorphous state, avoiding the interaction of one sensory motif with another. Moreover, this selectivity change can be further tuned because of the effectiveness of the transport of targets both by the physical nature of the interface of the polymer matrix/solution, where the target chemicals are dissolved, for instance, and inside the matrix where the recognition takes place. The interest in chronic human wounds is related to the fact that our methods are rapid and inexpensive, and also considering that the protease activity can correlate with the evolution of chronic wounds.

[1]  F. García,et al.  Functional aromatic polyamides for the preparation of coated fibres as smart labels for the visual detection of biogenic amine vapours and fish spoilage , 2020 .

[2]  Wenbo Cao,et al.  A Label-Free Fluorescent Aptasensor for Detection of Staphylococcal Enterotoxin A Based on Aptamer-Functionalized Silver Nanoclusters , 2020, Polymers.

[3]  S. Ibeas,et al.  Polymeric chemosensor for the colorimetric determination of the total polyphenol index (TPI) in wines , 2019 .

[4]  B. Chiang,et al.  Exploration of Chitinous Scaffold-Based Interfaces for Glucose Sensing Assemblies , 2019, Polymers.

[5]  U. Günther,et al.  Detecting acetylated aminoacids in blood serum using hyperpolarized 13C-1Η-2D-NMR. , 2019, Journal of magnetic resonance.

[6]  B. Rivas,et al.  Polymer films containing chemically anchored diazonium salts with long-term stability as colorimetric sensors. , 2019, Journal of hazardous materials.

[7]  Q. Zheng,et al.  Ferrocene-Modified Polyelectrolyte Film-Coated Electrode and Its Application in Glucose Detection , 2019, Polymers.

[8]  Xiaomeng Lv,et al.  Fabrication of Carbohydrate Chips Based on Polydopamine for Real-Time Determination of Carbohydrate–Lectin Interactions by QCM Biosensor , 2018, Polymers.

[9]  R. Quesada,et al.  Polymeric chemosensor for the detection and quantification of chloride in human sweat. Application to the diagnosis of cystic fibrosis. , 2018, Journal of materials chemistry. B.

[10]  José Miguel García Pérez,et al.  Synthesis of a polymeric sensor containing an occluded pyrylium salt and its application in the colorimetric detection of trimethylamine vapors , 2018 .

[11]  A. Mir,et al.  Adsorption of direct yellow 12 from aqueous solutions by an iron oxide-gelatin nanoadsorbent; kinetic, isotherm and mechanism analysis , 2018 .

[12]  Marcia Nusgart,et al.  An Economic Evaluation of the Impact, Cost, and Medicare Policy Implications of Chronic Nonhealing Wounds. , 2018, Value in health : the journal of the International Society for Pharmacoeconomics and Outcomes Research.

[13]  Youhong Tang,et al.  Hydrogel Based Sensors for Biomedical Applications: An Updated Review , 2017, Polymers.

[14]  J. Reglero,et al.  Direct visual detection and quantification of mercury in fresh fish meat using facilely prepared polymeric sensory labels , 2017 .

[15]  J. Dumville,et al.  Protease-modulating matrix treatments for healing venous leg ulcers. , 2016, The Cochrane database of systematic reviews.

[16]  R. Bonomo,et al.  An EPR and voltammetric study of simple and mixed copper(II) complexes with l- or d-glutamate and l-arginate in aqueous solution , 2016 .

[17]  Xue Sun,et al.  Highly effective removal of Cu(II) by a novel 3-aminopropyltriethoxysilane functionalized polyethyleneimine/sodium alginate porous membrane adsorbent , 2016 .

[18]  P. G. Fernández Revisión del tratamiento de las úlceras venosas: terapia compresiva , 2015 .

[19]  A. Chatterjee,et al.  Multi-resistance kinetic models for biosorption of Cd by raw and immobilized citrus peels in batch and packed-bed columns , 2014 .

[20]  M. Valko,et al.  EPR Spectroscopy of a Clinically Active (1:2) Copper(II)-Histidine Complex Used in the Treatment of Menkes Disease: A Fourier Transform Analysis of a Fluid CW-EPR Spectrum , 2014, Molecules.

[21]  S. Ibeas,et al.  Solid sensory polymer substrates for the quantification of iron in blood, wine and water by a scalable RGB technique , 2013 .

[22]  Andrew Scobell,et al.  How China Sees America , 2012 .

[23]  José M. García,et al.  An Organic/Inorganic Hybrid Membrane as a Solid “Turn-On” Fluorescent Chemosensor for Coenzyme A (CoA), Cysteine (Cys), and Glutathione (GSH) in Aqueous Media , 2012, Sensors.

[24]  N. E. Dávila-Guzmán,et al.  Equilibrium and kinetic studies of ferulic acid adsorption by Amberlite XAD-16 , 2012 .

[25]  Xiaoyan Song,et al.  Studies on the removal of tetracycline by multi-walled carbon nanotubes , 2011 .

[26]  Xianfeng Zhou,et al.  A series of naphthalimide derivatives as intra and extracellular pH sensors. , 2010, Biomaterials.

[27]  M. Doğan,et al.  Adsorption of methylene blue onto hazelnut shell: Kinetics, mechanism and activation parameters. , 2009, Journal of hazardous materials.

[28]  J Posnett,et al.  The resource impact of wounds on health-care providers in Europe. , 2009, Journal of wound care.

[29]  Abdul Latif Ahmad,et al.  Adsorption isotherm, kinetic modeling and mechanism of 2,4,6-trichlorophenol on coconut husk-based activated carbon , 2008 .

[30]  M. Estrader,et al.  Synthesis, characterization and magnetic properties of six new copper(II) complexes with aminoacids as bridging ligand, exhibiting ferromagnetic coupling , 2008 .

[31]  R. Goyal,et al.  Anion recognition using newly synthesized hydrogen bonding disubstituted phenylhydrazone-based receptors: poly(vinyl chloride)-based sensor for acetate. , 2008, Talanta.

[32]  N. A. Ochoa,et al.  Kinetic sorption of Cr(VI) into solvent impregnated porous microspheres , 2008 .

[33]  Eric V. Anslyn,et al.  Indicator-displacement assays , 2006 .

[34]  M. de Frutos,et al.  On‐capillary derivatization and analysis of amino acids in human plasma by capillary electrophoresis with laser‐induced fluorescence detection: Application to diagnosis of aminoacidopathies , 2006, Electrophoresis.

[35]  E. Anslyn,et al.  Pattern-based discrimination of enantiomeric and structurally similar amino acids: an optical mimic of the mammalian taste response. , 2006, Journal of the American Chemical Society.

[36]  G. Mckay,et al.  Sorption of cadmium, copper, and zinc ions onto bone char using Crank diffusion model. , 2005, Chemosphere.

[37]  D. Dorsky,et al.  Enhancement of implantable glucose sensor function in vivo using gene transfer-induced neovascularization. , 2005, Biomaterials.

[38]  V. Ramamurthi,et al.  Modeling the mechanism involved during the sorption of methylene blue onto fly ash. , 2005, Journal of colloid and interface science.

[39]  J. Eastoe,et al.  The amino-acid composition of human hard tissue collagens in osteogenesis imperfecta and dentinogenesis imperfecta , 1973, Calcified Tissue Research.

[40]  P. Dubot,et al.  Interaction of S-histidine, an amino acid, with copper and gold surfaces, a comparison based on RAIRS analyses , 2004 .

[41]  S. Azizian Kinetic models of sorption: a theoretical analysis. , 2004, Journal of colloid and interface science.

[42]  L. Téot World Union of Wound Healing Societies , 2003, The international journal of lower extremity wounds.

[43]  J. Retama,et al.  Microstructural modifications induced by the entrapped glucose oxidase in cross-linked polyacrylamide microgels used as glucose sensors. , 2003, Biomaterials.

[44]  C. Dambmann,et al.  Improved Method for Determining Food Protein Degree of Hydrolysis , 2001 .

[45]  M. Dreux,et al.  HPLC-CLND for the analysis of underivatized amino acids , 2001 .

[46]  A. Magrì,et al.  Copper(II) complexes with l-lysine and l-ornithine: is the side-chain involved in the coordination?: A thermodynamic and spectroscopic study , 2000 .

[47]  J. Jansen,et al.  Biocompatibility evaluation of sol-gel coatings for subcutaneously implantable glucose sensors. , 2000, Biomaterials.

[48]  Aubaid Ah,et al.  Detection of sugars and aminoacids in antigens of Trichophyton mentagrophytes var. erinacei. , 1999 .

[49]  Aubaid,et al.  Detection of sugars and aminoacids in antigens of Trichophyton mentagrophytes var. erinacei , 1999, Mycoses.

[50]  Shu-Pao Wu,et al.  SPECTROSCOPIC AND ELECTRONIC PROPERTIES OF MIXED LIGAND AMINOACIDATOCOPPER(II) COMPLEXES MOLECULAR STRUCTURE OF CU(4,7-DIMETHYL-1,10-PHENANTHROLINE)(L -PHENYLALANINATO)(CLO4) , 1999 .

[51]  Y. Ho,et al.  Pseudo-second order model for sorption processes , 1999 .

[52]  Y. Marcus The properties of solvents , 1998 .

[53]  M. R. Udupa,et al.  Synthesis and characterization of copper (II) complexes of adenine and aminoacids , 1997, Proceedings / Indian Academy of Sciences.

[54]  E. B. Paniago,et al.  Copper(II) mixed ligands complexes of hydroxamic acids with glycine, histamine and histidine , 1997 .

[55]  L. Signor,et al.  Ascorbate Oxidation Catalyzed by Bis(histidine)copper(II) , 1996 .

[56]  G. Mukherjee,et al.  Metal ion interaction with penicillins: Part VIII. Equilibrium study of mixed ligand complex formation of Co(II), Ni(II), Cu(II) and Zn(II) with ampicillin and some amino acids , 1996, Proceedings / Indian Academy of Sciences.

[57]  J. Muzart,et al.  Enantioselective Allylic Oxidation in the Presence of the Cu(I)/Cu(II)- Proline Catalytic System. , 1995 .

[58]  J. Muzart,et al.  Enantioselective allylic oxidation in the presence of the catalytic system , 1995 .

[59]  X. Solans,et al.  Mixed chelate complexes. III. Structures of ( L -alaninato)(aqua)(2,2'-bipyridine)copper(II) nitrate monohydrate and aqua(2,2'-bipyridine)( L -tyrosinato)copper(II) chloride trihydrate , 1992 .

[60]  B. Tighe,et al.  Polymer membranes in clinical sensor applications. III. Hydrogels as reactive matrix membranes in fibre optic sensors. , 1992, Biomaterials.

[61]  J. Kiernan,et al.  Chromoxane cyanine R. II. Staining of animal tissues by the dye and its iron complexes , 1984, Journal of microscopy.

[62]  Michael H. Abraham,et al.  Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, .pi.*, .alpha., and .beta., and some methods for simplifying the generalized solvatochromic equation , 1983 .

[63]  Peter Lindroth,et al.  High performance liquid chromatographic determination of subpicomole amounts of amino acids by precolumn fluorescence derivatization with o-phthaldialdehyde , 1979 .

[64]  R. Taft,et al.  The solvatochromic comparison method. 6. The .pi.* scale of solvent polarities , 1977 .

[65]  Robert W. Taft,et al.  THE SOLVATOCHROMIC COMPARISON METHOD. 6. THE Π* SCALE OF SOLVENT POLARITIES , 1977 .

[66]  R. Taft,et al.  The solvatochromic comparison method. 2. The .alpha.-scale of solvent hydrogen-bond donor (HBD) acidities , 1976 .

[67]  R. Taft,et al.  THE SOLVATOCHROMIC COMPARISON METHOD. I. THE β-SCALE OF SOLVENT HYDROGEN-BOND ACCEPTOR (HBA) BASICITIES , 1976 .

[68]  R. Taft,et al.  The solvatochromic comparison method. I. The .beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities , 1976 .

[69]  F. Keeley,et al.  Amino acid composition and calcification of human aortic elastin. , 1974, Atherosclerosis.

[70]  A. Saifer Rapid screening methods for the detection of inherited and acquired aminoacidopathies. , 1971, Advances in clinical chemistry.

[71]  B. Cohen,et al.  Screening method for detection of specific aminoacidemias. , 1969, Clinica chimica acta; international journal of clinical chemistry.

[72]  M. E. Thomas,et al.  The detection of β-alanine in biological fluids , 1968 .

[73]  M. Belle,et al.  A new simple screening method for detecting pathological amino-acidemias with collection of blood on paper , 1967 .

[74]  J. Eastoe The amino acid composition of proteins from the oral tissues—I: A comparison of human oral epithelium, epidermis and nail proteins , 1963 .

[75]  D. Reichenberg Properties of Ion-Exchange Resins in Relation to their Structure. III. Kinetics of Exchange , 1953 .

[76]  A. Adamson,et al.  The exchange adsorption of ions from aqueous solutions by organic zeolites; kinetics. , 1947, Journal of the American Chemical Society.

[77]  A. Adamson,et al.  The exchange adsorption of ions from aqueous solutions by organic zeolites; ion-exchange equilibria. , 1947, Journal of the American Chemical Society.