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PubMed2006

Biomimetic nanofibrous scaffolds: preparation and characterization of chitin/silk fibroin blend nanofibers.

Electrospinning of chitin/silk fibroin (SF) blend solutions in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was investigated to fabricate a biomimetic nanostructured scaffolds for tissue engineering. The morphology of the electrospun chitin/SF blend nanofibers was investigated with a field emission scanning electron microscope (FE-SEM). The average diameters of chitin/SF blend fibers decreased from 920 to 340nm, with the increase of chitin content in blend compositions. The miscibility of chitin/SF blend fibers was examined by solution viscosity measurement. The chitin and SF were immiscible in the as-spun nanofibrous structure. The dimensional stability of chitin/SF blend nanofibers, with or without water vapor after-treatment, was conducted by immersing in water. As-spun SF-rich blend nanofibrous matrices were lost their fibrous structure after the water immersion for 24h, and then changed into membrane-like structure. On the contrary, nanofibrous structures of water vapor-treated SF-rich blends were almost maintained. To assay the cytocompatibility and cell behavior on the chitin/SF blend nanofibrous scaffolds, cell attachment and spreading of normal human epidermal keratinocyte and fibroblasts seeded on the scaffolds were studied. Our results indicate that chitin/SF blend nanofibrous matrix, particularly the one that contained 75% chitin and 25% SF, could be a potential candidate for tissue engineering scaffolds because it has both biomimetic three-dimensional structure and an excellent cell attachment and spreading for NHEK and NHEF.

Adolescent↗

PubMed2005

Bone matrix like assemblies of collagen: from liquid crystals to gels and biomimetic materials.

Skeletal tissues associate in close interaction, a dense organic matrix and a mineral network. In bone, the major structural protein is type I collagen, associated with inorganic crystals of hydroxyapatite. The three-dimensional arrangement of collagen fibrils in compact bone forms regularly ordered networks and a parallel was evidenced between these structures and molecular assemblies described in liquid crystals. Similar structures are now obtained in vitro. Indeed, when purified type I collagen is highly concentrated in an acid soluble state, the protein spontaneously assembles into ordered liquid crystalline phases. After a sol/gel transition triggered by pH increase, biomimetic materials are formed which resemble the exact compact bone matrix architecture over distances reaching centimetres and more. The properties of these highly ordered materials will be reviewed recalling their supramolecular arrangement and the corresponding patterns when visualised in polarised light microscopy (birefringence) and transmission electron microscopy (TEM). The association of inorganic phases (amorphous silica) to form chiral hybrid materials will also be described so as the behaviour of cells (fibroblast adhesion and migration) when seeded on these dense biomimetic matrices.

Biomimetic Materials↗

PubMed2003

Towards biomimetic scaffolds: anhydrous scaffold fabrication from biodegradable amine-reactive diblock copolymers.

The development of biomimetic materials and their processing into three-dimensional cell carrying scaffolds is one promising tissue engineering strategy to improve cell adhesion, growth and differentiation on polymeric constructs developing mature and viable tissue. This study was concerned with the fabrication of scaffolds made from amine-reactive diblock copolymers, N-succinimidyl tartrate monoamine poly(ethylene glycol)-block-poly(D,L-lactic acid), which are able to suppress unspecific protein adsorption and to covalently bind proteins or peptides. An appropriate technique for their processing had to be both anhydrous, to avoid hydrolysis of the active ester, and suitable for the generation of interconnected porous structures. Attempts to fabricate scaffolds utilizing hard paraffin microparticles as hexane-extractable porogens failed. Consequently, a technique was developed involving lipid microparticles, which served as biocompatible porogens on which the scaffold forming polymer was precipitated in the porogen extraction media (n-hexane). Porogen melting during the extraction and polymer precipitation step led to an interconnected network of pores. Suitable lipid mixtures and their melting points, extraction conditions (temperature and time) and a low-toxic polymer solvent system were determined for their use in processing diblock copolymers of different molecular weights (22 and 42 kDa) into highly porous off-the-shelf cell carriers ready for easy surface modification towards biomimetic scaffolds. Insulin was employed to demonstrate the principal of instant protein coupling to a prefabricated scaffold.

Biocompatible Materials↗

PubMedDate not supplied

Human microvascular endothelial cell growth and migration on biomimetic surfactant polymers.

Successful engineering of a tissue-incorporated vascular prosthesis requires cells to proliferate and migrate on the scaffold. Here, we report on a series of "ECM-like" biomimetic surfactant polymers that exhibit quantitative control over the proliferation and migrational properties of human microvascular endothelial cells (HMVEC). The biomimetic polymers consist of a poly(vinyl amine) (PVAm) backbone with hexanal branches and varying ratios of cell binding peptide (RGD) to carbohydrate (maltose). Proliferation and migration behavior of HMVEC was investigated using polymers containing RGD: maltose ratios of 100:0, 75:25 and 50:50, and compared with fibronectin (FN) coated glass (1 microg/cm2). A radial Teflon fence migration assay was used to examine HMVEC migration at 12 h intervals over a 48 h period. Migration was quantified using an inverted optical microscope, and HMVEC were examined by confocal microscopy for actin and focal adhesion organization/ arrangement. Over the range of RGD ligand density studied (approximately 0.19-0.6 peptides/nm2), our results show HMVEC migration decreases with increasing RGD density in the polymer. HMVEC were least motile on the 100% RGD polymer (approximately 0.38-0.6 peptides/nm2) with an average migration of 0.20 mm2/h in area covered, whereas HMVEC showed the fastest migration of 0.48+/-0.06 mm2/h on the 50% RGD surface ( approximately 0.19-0.30 peptides/nm2). In contrast, cell proliferation increased with increasing surface peptide density; proliferation on the 50% RGD surface was 1.5%+/-0.06/h compared with 2.2%+/-0.07/h on the 100% RGD surface. Our results show that surface peptide density affects cellular functions such as growth and migration, with the highest peptide density supporting the most proliferation but the slowest migration.

Biomimetic Materials↗

PubMed2006

Construction of a biomimetic surface on microfluidic chips for biofouling resistance.

A biomimetic surface has been formed on the poly(methyl methacrylate) (PMMA) microfluidic chips for biofouling resistance on the basis of a simple modification. Accordingly, an amphiphilic phospholipid copolymer of 2-methacryloyloxyethyl phosphorylcholine and n-butyl methacrylate (PMB) was developed to introduce the phosphorylcholine functional groups onto the PMMA surface via the anchoring of hydrophobic n-butyl methacrylate units. The 2-methacryloyloxyethyl phosphorylcholine segments could form hydrophilic domains, considered to be located on the surface, to provide a biocompatible surface. X-ray photoelectron spectroscopy and Fourier transform infrared spectra confirmed the success of surface functionalization. The PMB-modified microchips containing phosphorylcholine moieties exhibited more stable electroosmotic mobility compared with the untreated one. In addition to being characterized for minimized nonspecific adhesion of serum proteins and plasma platelets, the PMB-functionalized microchannels have been exemplified by electrophoresis of proteins. This one-step procedure offers an effective approach for a biomimetic surface design on microfluidic chips, which is promising in high-throughput and complex biological analysis.

Biomimetics↗

PubMedDate not supplied

Biomimetic cooperative interactions of dried cross-linked poly(N-6-aminohexylacrylamide) with binary mixtures of solvent vapors.

Biomimetic cooperativity of hydration effect and effect of ethanol favorable for binding of bad organic sorbates were observed for their vapor sorption by cross-linked poly(N-6-aminohexylacrylamide) (PNAHAA) in the absence of liquid phase. The vapor sorption isotherms were determined for these systems by the static method of gas chromatographic headspace analysis at 298 K. The hydration above 0.09-0.13 g of H(2)O/(g of polymer) gives a cooperative increase in the PNAHAA binding affinity for benzene, cyclohexane, dioxane, and propanols up to a level which does not change by further hydration, indicating the polymer antiplasticization. Bad sorbates (dioxane, benzene) were observed to have a biomimetic cooperative influence on the binding of ethanol by the dried PNAHAA. This cooperativity does not occur in ternary systems with good nonhydroxylic sorbate acetonitrile.

Acetonitriles↗

PubMedDate not supplied

Biomimetic gel exhibiting self-beating motion in ATP solution.

Biomimetic material systems using stimuli-responsive polymers and gels have been widely studied for applications to artificial muscles, drug delivery systems, biosensors, etc. In almost all cases, however, the action is driven by on-off switching of external signals. In contrast, here we show a novel biomimetic gel to exhibit autonomous self-beating motion in ATP solution under constant condition, similar to heart muscle. An anionic polymer gel with phosphoric groups, in which creatine kinase was immobilized, was prepared. When the gel was immersed in the ATP solution, the enzymatic reaction occurs in the gel and the concentration of calcium ion changes periodically. Since the chelates between phosphoric groups and the divalent calcium ion, which acts a physical crosslinking point, are formed and dissociated periodically, the gel repeats swelling and deswelling autonomously.

Adenosine Triphosphate↗

PubMed2006

Removal of formaldehyde by hydroxyapatite layer biomimetically deposited on polyamide film.

Some harmful volatile organic compounds (VOCs), such as formaldehyde, are regulated atmospheric pollutants. Therefore, development of a material to remove these VOCs is required. We focused on hydroxyapatite, which had been biomimetically coated on a polyamide film, as an adsorbent and found that formaldehyde was successfully removed by this adsorbent. The amount of formaldehyde adsorbed increased with the area of the polyamide film occupied by hydroxyapatite. The amount of adsorbed formaldehyde and its rate of adsorption were larger for hydroxyapatite deposited on polyamide film than for the commercially available calcined hydroxyapatite powder. This high adsorption ability is achieved by the use of nanosized particles of hydroxyapatite with low crystallinity and containing a large number of active surface sites. Therefore, hydroxyapatite biomimetically coated on organic substrates can become a candidate material for removing harmful VOCs such as formaldehyde.

Adsorption↗

PubMed2006

Oligomerization of humic phenolic monomers by oxidative coupling under biomimetic catalysis.

Three humic phenolic monomers, catechol (CAT), caffeic acid (CAFF), and p-coumaric acid (COUM), were subjected to oxidative coupling catalyzed by biomimetic water-soluble iron-porphyrin (Fe(TDCPPS)CI) in either separate or mixed solution, and the reaction products were characterized by gas chromatography-mass spectrometry (GC-MS) and electrospray-mass spectrometry (ESI-MS). The GC-MS analysis proved the formation of C-C and C-O dimers, whereas the ESI-MS/MS analysis also suggested trimerization for all the monomers and tetramerization for CAT. On the basis of mass spectra, molecular structures were assigned to the observed oligomers. In the phenolic separate solutions, dimers represented about 65%, 44%, and 30% of reaction products for CAT, CAFF, and COUM, respectively, whereas trimers were from 4 to 5%. A relevant part of the products were unidentified oligomers and several degradation compounds, mostly aromatic aldehydes and alcohols and aromatic or aliphatic carboxylic acids. When all three humic phenolic monomers underwent the catalyzed coupling reaction in one mixed solution, 14% of the reaction products were identified as C-C dimers of CAT. Although no other C-O dimers of CAT, nor any dimers of COUM and CAFF, could be identified, some other structurally unknown oligomers were present among the reaction products of the mixed solution. However, no oligomers larger than tetramers were formed in either separate or mixed solutions. This work indicates the essential role of biomimetic metal-porphyrins in catalyzing the oxidative coupling of humic phenolic monomers in aqueous media, thereby promoting the polymerization of natural organic matter.

Biomimetics↗

PubMed2003

Biomimetic entry to the sarpagan family of indole alkaloids: total synthesis of +-geissoschizine and +-N-methylvellosimine.

A concise synthesis of (+)-geissoschizine (1), a biosynthetic precursor of a variety of monoterpenoid indole alkaloids, from d-tryptophan (19) was performed as a critical prelude to achieving the first biomimetic, enantioselective synthesis of the sarpagine alkaloid (+)-N(a)-methylvellosimine (5). The approach to (+)-geissoschizine was designed to address the dual problems of stereocontrolled formation of the E-ethylidene moiety and the correct relative configuration at C(3) and C(15). Key steps in the synthesis involve a vinylogous Mannich reaction to prepare the carboline 22, which has the absolute stereochemistry at C(3) corresponding to that in 1 and 5, and an intramolecular Michael addition that leads to the tetracyclic corynantheane derivative 24, which possesses the correct stereochemical relationship between C(3) and C(15). Compound 24 was then transformed into 27, the pivotal intermediate in the syntheses of 1 and 5, by a sequence that allowed the stereospecific introduction of the E-ethylidene moiety. Selective reduction of the lactam in 27 followed by removal of the C(5) carboxyl group by radical decarbonylation gave deformylgeissoschizine (2) that was converted into (+)-geissoschizine (1) by formylation. The common intermediate 27 was then converted via a straightforward sequence of reactions into the alpha-amino nitrile 39. The derived silyl enol ether 40 underwent ionization upon exposure to BF(3).OEt(2) to give the intermediate iminium ion 41 that then cyclized in a biomimetically inspired intramolecular Mannich reaction to deliver (+)-N(a)-methylvellosimine (5). This transformation provides experimental support for the involvement of such a cyclization as one of the key steps in the biosynthesis of the sarpagine and ajmaline alkaloids.

Biomimetic Materials↗

PubMed2004

Modular domain structure: a biomimetic strategy for advanced polymeric materials.

A long lasting challenge in polymer science is to design polymers that combine desired mechanical properties such as tensile strength, fracture toughness, and elasticity into one structure. A novel biomimetic modular polymer design is reported here to address this challenge. Following the molecular mechanism used in nature, modular polymers containing multiple loops were constructed by using precise and strong hydrogen bonding units. Single-molecule force-extension experiments revealed the sequential unfolding of loops as a chain is stretched. The excellent correlation between the single-molecule and the bulk properties successfully demonstrates our biomimetic concept of using modular domain structure to achieve advanced polymer properties.

Biomimetic Materials↗

PubMed2005

Bifunctional small molecules are biomimetic catalysts for silica synthesis at neutral pH.

Silicatein is an enzyme isolated from the biosilica produced by the marine demosponge, Tethya aurantia. Once isolated from the sponge, silicatein can be used in vitro to catalyze the hydrolysis and direct polycondensation of a wide variety of alkoxide, ionic, and organometallic precursors to the corresponding chalcogens at standard temperature and pressure and neutral pH. On the basis of these results, an array of small molecules that mimic the unique physiochemical environment found in the enzyme active site was investigated for catalytic activity in the formation of silica from silicon alkoxides at neutral pH. The most successful of these biomimetic catalysts (cysteamine) was used to encapsulate firefly luciferase, green and blue fluorescent proteins (GFP, BFP), and Escherichia coli cells expressing GFP in silica matrixes. The benign conditions required for the catalysis of synthesis of these silica composites does not impair the activities of the encapsulated enzyme, fluorescent proteins, or live cells as shown by fluorescence measurements. In conjunction with microcontact printing, this biomimetically catalyzed encapsulation method has been used to produce patterned functional arrays of silica nanoparticulate composite materials.

Animals↗

PubMed2005

Biomimetic synthesis of trans,syn,trans-fused polyoxepanes: remarkable substituent effects on the endo-regioselective oxacyclization of polyepoxides.

The biogenesis of trans,syn,trans-fused polycyclic ether substructures of neurotoxic natural products of the brevetoxin-ciguatoxin family may involve regio- and stereoselective oxacyclizations of polyepoxides. We report that a biomimetic Lewis acid-promoted cyclization of 1 to 2 proceeds with endo-regioselectivity and anti-stereospecificity at each position of nucleophilic addition (C3, C7, C11, and C15 in 1) when the tandem cyclization cascade is terminated by a carbonyl oxygen nucleophile. In contrast to expectations from earlier reports with simpler epoxide substrates, alkyl substituents are not required at internal epoxide positions corresponding to C7 and C11 in polyepoxide 1. Furthermore, we report that trimethylsilyl serves as a removable regioselectivity-directing substituent at positions corresponding to C3 of 1. These results greatly expand the potential applications of this biomimetic oxacyclization cascade to the synthesis of fused polycyclic ether natural products.

Biomimetic Materials↗

PubMed2005

Biomimetic anchor for surface-initiated polymerization from metal substrates.

In this paper, we demonstrate the first use of a catecholic initiator for surface-initiated polymerization (SIP) from metal surfaces to create antifouling polymer coatings. A new bifunctional initiator inspired by mussel adhesive proteins was synthesized, which strongly adsorbs to Ti and 316L stainless steel (SS) substrates, providing an anchor for surface immobilization of grafted polymers. Surface-initiated atom transfer radical polymerization (SI-ATRP) was performed through the adsorbed biomimetic initiator to polymerize methyl methacrylate macromonomers with oligo(ethylene glycol) (OEG) side chains. X-ray photoelectron spectroscopy, surface FT-IR, and contact angle analysis confirmed the sequential grafting of initiator and polymer, and ellipsometry indicated the formation of polymer coatings of up to 100 nm thickness. Cell adhesion experiments performed with 3T3-Swiss albino fibroblasts showed substantially reduced cell adhesion onto polymer grafted Ti and 316L SS substrates as compared to the unmodified metals. Moreover, micropatterning of grafted polymer coatings on Ti surfaces was demonstrated by combining SI-ATRP and molecular assembly patterning by lift-off (MAPL), creating cell-adhesive and cell-resistant regions for potential use as cell arrays. Due to the ability of catechols to bind to a large variety of inorganic surfaces, this biomimetic anchoring strategy is expected to be a highly versatile tool for polymer thin film surface modification for biomedical and other applications.

Animals↗

PubMed2006

What factors influence the ratio of C-H hydroxylation versus C=C epoxidation by a nonheme cytochrome P450 biomimetic?

Density functional calculations on a nonheme biomimetic (Fe=O(TMCS+) have been performed and its catalytic properties versus propene investigated. Our studies show that this catalyst is able to chemoselectively hydroxylate C=H bonds even in the presence of C=C double bonds. This phenomenon has been analyzed and found to occur due to Pauli repusions between protons on the TMCS ligand with protons attached to the approaching substrate. The geometries of the rate determining transition states indicate that the steric hindrance is larger in the epoxidation transition states than in the hydroxylation ones with much shorter distances; hence the hydroxylation pathway is favored over the epoxidation. Although, the reactant experiences close lying triplet and quintet spin states, the dominant reaction mechanism takes place on the quintet spin state surface; i.e., Fe=O(TMCS)+ reacts via single-state reactivity. Our calculations show that this spin state selectivity is the result of geometric orientation of the transition state structures, whereby the triplet ones are destabilized by electrostatic repulsions between the substrate and the ligand while the quintet spin transition states are aligned along the ideal axis. The reactivity patterns and geometries are compared with oxoiron species of dioxygenase and monoxygenase enzymes. Thus, Fe=O(TMCS)+ shows some similarities with P450 enzyme reactivity: it chemoselectively hydroxylates C=H bonds even in the presence of a C=C double bond and therefore is an acceptable P450 biomimetic. However, the absolute barriers of substrate oxidation by Fe=O(TMCS)+ are higher than the ones obtained with heme enzymes, but the chemoselectivity is lesser affected by external perturbations such as hydrogen bonding of a methanol molecule toward the thiolate sulfur or a dielectric constant. This is the first oxoiron complex whereby we calculated a chemoselective hydroxylation over epoxidation in the gas phase.

Algorithms↗

PubMed2004

Loosely packed self-assembled monolayer of N-hexadecyl-3,6-di(p-mercaptophenylacetylene)carbazole on gold and its application in biomimetic membrane research.

Dithiols of N-hexadecyl-3,6-di(p-mercaptophenylacetylene)carbazole (HDMC) have been synthesized and employed to form self-assembled monolayers (SAMs) on gold. One characteristic of the HDMC molecule is its peculiar molecular structure consisting of a large and rigid headgroup and a small and flexible alkyl-chain tail. HDMC adsorbates can attach to gold substrates by a strong Au-S bond with weak van der Waals interactions between the alkyl-chain tails, leading to a loosely packed hydrophobic SAM. In this way we can couple hybrid bilayer membranes (HBMs) to gold surfaces with more likeness to a cell bilayer than the conventional HBMs based on densely packed long-chain alkanethiol SAMs. The insulating properties and stability of the HDMC monolayer as well as the HDMC/lipid bilayer on gold have been investigated by electrochemical techniques including cyclic voltammetry and impedance spectroscopy. To test whether the quality of the bilayer is sufficiently high for biomimetic research, we incorporated the pore-forming protein alpha-hemolysin) and the horseradish peroxidase into the bilayers, respectively. Experimental results demonstrated that this type of loosely packed hydrophobic SAM has great potential in biomimetic bilayer research and biosensor application.

Biomimetic Materials↗

PubMed2006

Biomimetic design of microfluidic manifolds based on a generalised Murray's law.

The relationship governing the optimum ratio between the diameters of the parent and daughter branches in vascular systems was first discovered by Murray using the principle of minimum work. This relationship is now known as Murray's law and states that the cube of the diameter of the parent vessel must equal the sum of the cubes of the daughter vessels. For symmetric bifurcations, an important consequence of this geometric rule is that the tangential shear stress at the wall remains constant throughout the vascular network. In the present paper, we extend this important hydrodynamic concept to arbitrary cross-sections and provide a framework for constructing a simple but elegant biomimetic design rule for hierarchical microfluidic networks. The paper focuses specifically on constant-depth rectangular and trapezoidal channels often employed in lab-on-a-chip systems. To validate our biomimetic design rule and demonstrate the application of Murray's law to microfluidic manifolds, a comprehensive series of computational fluid dynamics simulations have been performed. The numerical predictions are shown to be in very good agreement with the theoretical analysis, confirming that the generalised version of Murray's law can be successfully applied to the design of constant-depth microfluidic devices.

Biomimetics↗

PubMed2004

Computer-aided tissue engineering: application to biomimetic modelling and design of tissue scaffolds.

Computer-aided tissue engineering (CATE) enables many novel approaches in modelling, design and fabrication of complex tissue substitutes with enhanced functionality and improved cell-matrix interactions. Central to CATE is its bio-tissue informatics model that represents tissue biological, biomechanical and biochemical information that serves as a central repository to interface design, simulation and tissue fabrication. The present paper discusses the application of a CATE approach to the biomimetic design of bone tissue scaffold. A general CATE-based process for biomimetic modelling, anatomic reconstruction, computer-assisted-design of tissue scaffold, quantitative-computed-tomography characterization, finite element analysis and freeform extruding deposition for fabrication of scaffold is presented.

Biocompatible Materials↗