Journal: Advanced healthcare materials

Article Title: Controlling the release of small, bioactive proteins via dual mechanisms with therapeutic potential

doi: 10.1002/adhm.201700713

Figure Lengend Snippet: A) Reducing-microenvironment- or light-sensitive hydrogels were formed by reacting B) an aryl-thiol end functionalized poly(ethylene glycol) macromolecular precursor (PEG-4-MPA) or a photodegradable aryl-thiol end functionalized PEG (PEG-4-PD-MPA) with a maleimide-end functionalized PEG (PEG-2-MI) and a maleimide functionalized low molecular heparin (Heparin-MI) via a Michael-type reaction in an aqueous microenvironment. Low molecular weight proteins, such as growth factors (FGF-2 in the present study), cytokines, and immunomodulatory agents, can be incorporated within the hydrogel during network formation utilizing heparin-associated receptor-ligand interactions for protein retention. C) Aryl-thiol based succinimide thioether linkages exchange with free thiols in solution leading to the formation of a relatively stable alkyl-thiol (i.e., cysteine) based succinimide thioether linkage, resulting in hydrogel degradation. D) The photolabile o-nitrobenzyl moieties undergo irreversible photoisomerization in response to cytocompatible doses of long wavelength UV or visible light, yielding ketone and amide products.

Article Snippet: 4-arm amine-functionalized poly(ethylene glycol) (PEG-4-NH 2 , M n ~ 10,000 g/mol) and linear maleimide-functionalized poly(ethylene glycol) (PEG-MI, M n ~ 5,000 g/mol) were purchased from JenKem Technology USA Inc. (Allen, TX).

Techniques: Molecular Weight

Journal: Bioactive Materials

Article Title: Chemically revised conducting polymers with inflammation resistance for intimate bioelectronic electrocoupling

doi: 10.1016/j.bioactmat.2023.02.010

Figure Lengend Snippet: (A) Schematic of surface modification of COOH-functionalized PEDOT films with YIGSR-based peptides through physical adsorption and chemical conjugation. (B) Average number of PC12 cells/cm 2 attached to the surface of COOH-functionalized PEDOT films modified with YIGSR-based peptides. Reproduced with permission . Copyright 2016, Elsevier Ltd. (C) Schematic representation of a biomimetic conducting polymer. (D) Adsorption of various proteins on poly(EDOT-PC) (black) and poly(EDOT-OH) (red). (E) Proliferation and (F) differentiation (in the presence of NGF) of PC12 cells attached to CSSSSIKVAV-conjugated poly(EDOT-MI- co -EDOT-PC) films after 24, 48 and 120 h. Scale bar: 200 μm. Reproduced with permission . Copyright 2014, Macmillan Publishers Limited.

Article Snippet: Zhu and Yu et la [ ]. synthesized a biomimetic conducting copolymer with phosphorylcholine-functionalized EDOT (EDOT-PC) and a maleimide-functionalized EDOT (EDOT-MI), and they further grafted IKVAV peptides onto the copolymer surfaces through maleimide-thiol chemistry ( C).

Techniques: Modification, Adsorption, Conjugation Assay, Polymer

Journal: Bioactive Materials

Article Title: Chemically revised conducting polymers with inflammation resistance for intimate bioelectronic electrocoupling

doi: 10.1016/j.bioactmat.2023.02.010

Figure Lengend Snippet: Hydrophilic and zwitterionic group functionalized conducting polymers, applications, and key results (Abbreviation: PC = phosphorylcholine, SB = sulfobetaine, CB = carboxybetaine, BSA = bovine serum albumin, FN = fibronectin, FNG = fibrinogen, MA = methacrylate, MI = maleimide, HQ = hydroquinone, Th = thiophene, MAA = methacrylamide, PTh-CB- co -ThAA = carboxybetaine thiophene- co -thiophene-3-acetic acid, and PThAA = poly(thiophene-3-acetic acid)).

Article Snippet: Zhu and Yu et la [ ]. synthesized a biomimetic conducting copolymer with phosphorylcholine-functionalized EDOT (EDOT-PC) and a maleimide-functionalized EDOT (EDOT-MI), and they further grafted IKVAV peptides onto the copolymer surfaces through maleimide-thiol chemistry ( C).

Techniques: In Vitro, In Vivo, Injection, Sequencing, Clinical Proteomics, Incubation, Protein Binding, Polymer, Adsorption, Control, Cell Differentiation

Journal: Bioactive Materials

Article Title: Chemically revised conducting polymers with inflammation resistance for intimate bioelectronic electrocoupling

doi: 10.1016/j.bioactmat.2023.02.010

Figure Lengend Snippet: (A) Syntheses of phosphorylcholine functionalized conducting polymers. i) Syntheses of PEDOT-PC from EDOT-OH . ii) Synthesis route for EDOT-PC from 3, 4-dimethoxythiophene. Electrochemical copolymerization of EDOT and EDOT-PC . iii) Synthesis of zwitterionic EDOTs from EDOT-SH, and electropolymerization of zwitterionic EDOTs and EDOT (B) Syntheses of sulfobetaine functionalized conducting polymers. i) Synthetic route of PEDOT-SB from 3, 4-dimethoxythiophene . ii) Synthesis of PEDOT-SB from EDOT-OH . iii) Synthetic route of PEDOT-C 4 -SB and PEDOT-C 5 -SB from EDOT-OH (C) Syntheses of carboxybetaine functionalized conducting polymers. i) Schematic illustration of the construction process of antifouling PANI. Reproduced with permission . Copyright 2018, Elsevier Ltd. ii) Synthetic routes to PCBTh homopolymer and its random copolymers: PCBTh- co -ThAA, PCBTh- co -ThMAA and PCBTh- co -ThSH . iii) Synthetic routes to obtain PCBTh and PCBTh- co BF . iv) Synthetic routes for polymer PCBTh–C 8 C 10 .

Article Snippet: Zhu and Yu et la [ ]. synthesized a biomimetic conducting copolymer with phosphorylcholine-functionalized EDOT (EDOT-PC) and a maleimide-functionalized EDOT (EDOT-MI), and they further grafted IKVAV peptides onto the copolymer surfaces through maleimide-thiol chemistry ( C).

Techniques: Polymer

Journal: Bioactive Materials

Article Title: Chemically revised conducting polymers with inflammation resistance for intimate bioelectronic electrocoupling

doi: 10.1016/j.bioactmat.2023.02.010

Figure Lengend Snippet: (A) Zwitterionic biointerfaces form different chemical structures of functionalized EDOT monomers to PEDOT copolymers. (B) Difference in cell arrangement between patterned and adjacent nonpatterned substrates. (C) Cell arrangement and differentiation between patterned and adjacent nonpatterned substrates. (D) Formation of a neuron network of PC12 cells on the PEDOT platform with cell-binding stripes of width 2 μm after differentiation for 120 h. (E) Polar plots of the lengths and orientation angles of the neurites of PC12 cells differentiated for 24 h on PEDOT copolymer films with cell-binding stripes of width 20 μm and cell-resistance stripes of width 50 μm. Control platform (F) with cell adhesive stripes of width 20/50 μm and (G) with smooth poly(EDOT-OH). Reproduced with permission . Copyright 2020, American Chemical Society.

Article Snippet: Zhu and Yu et la [ ]. synthesized a biomimetic conducting copolymer with phosphorylcholine-functionalized EDOT (EDOT-PC) and a maleimide-functionalized EDOT (EDOT-MI), and they further grafted IKVAV peptides onto the copolymer surfaces through maleimide-thiol chemistry ( C).

Techniques: Binding Assay, Control, Adhesive

Journal: Bioactive Materials

Article Title: Chemically revised conducting polymers with inflammation resistance for intimate bioelectronic electrocoupling

doi: 10.1016/j.bioactmat.2023.02.010

Figure Lengend Snippet: (A) In situ monitoring of CSSSSIKVAV (red), CSSSSGKVAV (blue) and SSSSIKVAV (black) conjugation on poly(EDOT-MI- co -EDOT-PC) films polymerized from a monomer solution containing 5 mM EDOT-MI and 5 mM EDOT-PC. (B) Conjugation of CSSSSIKVAV (red) and CSSSSGKVAV (blue) on poly(EDOT-MI- co -EDOT-PC) films. (C) Density of PC12 cells attached to poly(EDOT-MI- co -EDOT-PC) films after conjugation with the ligands CSSSSIKVAV (red) and CSSSSGKVAV (blue). (D) Selective adhesion of PC12 and NIH3T3 cells on a polystyrene culture dish (black), poly(EDOT-OH) (red) and a biomimetic PEDOT (blue). (E) Schematic representation of the device used for cell growth with applied electrical stimulation and illustration of the electrical pulse used. (F–H) Microscopy images of differentiated PC12 cells cultured in NGF-supplemented medium on (F) a PEDOT film, (G) a biomimetic PEDOT film, and (H) the biomimetic PEDOT film with applied pulsed electrical stimulation at an amplitude of 60 mV. Scale bars: 200 mm. (I–K) Corresponding neurite length distributions of (F–H). (L) Median neurite length of PC12 cells on PEDOT and biomimetic PEDOT. The biomimetic PEDOT used in (D–L) was prepared from 3 mM EDOT-MI and 7 mM EDOT-PC conjugated with IKVAV. Reproduced with permission . Copyright 2014, Macmillan Publishers Limited. (M) Schematic illustration of the PTh-CB- co -ThMAA hydrogel that consists of a conducting backbone and multifunctional zwitterionic side chains. (N) Adsorption of BSA (bottom curve) and FNG (top curve) in PBS buffer on PThCB- co -ThSH-modified SPR substrates. (O and P) Representative fluorescence microscopy images of attached bovine aortic endothelial cells (BAECs) on the (O) PThCB- co -ThMAA hydrogel and (P) PThCB- co -ThRGD hydrogel. (H) Quantitative cell density on different surfaces. (PThCB- co -ThAA = carboxybetaine thiophene- co -thiophene-3-acetic acid, PTh-CB- co -ThMAA = PThCB- co -ThAA was further modified with 2-aminoethyl methacrylamide, PCBMA = carboxybetaine methacrylate, and PThAA = poly(thiophene-3-acetic acid, PThCB- co -ThSH = cysteamine conjugated PCBTh- co -ThAA, TCPS = tissue culture polystyrene). Reproduced with permission . Copyright 2015, The Royal Society of Chemistry.

Article Snippet: Zhu and Yu et la [ ]. synthesized a biomimetic conducting copolymer with phosphorylcholine-functionalized EDOT (EDOT-PC) and a maleimide-functionalized EDOT (EDOT-MI), and they further grafted IKVAV peptides onto the copolymer surfaces through maleimide-thiol chemistry ( C).

Techniques: In Situ, Conjugation Assay, Microscopy, Cell Culture, Adsorption, Modification, Fluorescence

Journal: Bioactive Materials

Article Title: Chemically revised conducting polymers with inflammation resistance for intimate bioelectronic electrocoupling

doi: 10.1016/j.bioactmat.2023.02.010

Figure Lengend Snippet: (A) Schematic illustration of poly(EDOT-HQ)/poly(EDOT-BQ) switching and the formation/cleavage of oxime linkages on poly(EDOT-HQ) films. (B) Bright-field image of a poly(EDOT-HQ) film coated on two sets of interdigitated Au working microelectrodes (WE1, WE2) (top left); fluorescence images by two-photon excitation microscopy showing the selective immobilization and release of aminooxy-functionalized Alexa-488 dyes on poly(EDOT-HQ)-coated interdigitated Au microelectrodes. When the oxidative potential was only applied to WE1 to convert poly(EDOT-HQ) to poly(EDOT-BQ), the Alexa dyes were selectively immobilized on WE1 through oxime conjugation (top-right); when the oxidative potential was applied to both WE1 and WE2, Alexa dyes were immobilized on both electrodes (bottom-left). Alexa dyes were selectively released from WE2 by applying a reductive potential to cleave the oxime conjugate (bottom right). (C) The controlled attachment and release of NIH3T3 cells on RGD peptide-conjugated poly(EDOT-HQ- co -EDOT-PC) film compared to those nonspecifically attached to poly(EDOT-OH) controls paired on patterned ITO glass; bright-field images of PC12 cells on RGD-conjugated poly(EDOT-HQ- co -EDOT-PC) films. Reproduced with permission . Copyright 2018, John Wiley & Sons, Inc.

Article Snippet: Zhu and Yu et la [ ]. synthesized a biomimetic conducting copolymer with phosphorylcholine-functionalized EDOT (EDOT-PC) and a maleimide-functionalized EDOT (EDOT-MI), and they further grafted IKVAV peptides onto the copolymer surfaces through maleimide-thiol chemistry ( C).

Techniques: Fluorescence, Microscopy, Conjugation Assay