1106 results about "Phenylboronic acid" patented technology

The invention discloses materials that adsorb readily to the surfaces of body tissues in situ and provide a steric barrier between such tissues, so that tissue adhesions, which typically form following surgical procedures, are minimized. These materials contain a polymer of hydrophilic molecules such as polyethylene glycol (PEG) bound to a polymer that spontaneously adsorbs to biological tissue such as phenylboronic acid (PBA). The PEG-PBA co-polymer can be formed in a variety of geometries. The materials can also be used to coat prosthetics and other implants.

The invention discloses a molecularly imprinted polymer specially combined with a specified glycoprotein. Substituted phenylboronic acid containing double bonds is used as a functional monomer. Under the alkali condition, the specified glycoprotein serving as a template (imprinting molecule) and the substituted phenylboronic acid (functional monomer) containing the double bonds form a complex; the complex is mixed with a cross linker, an initiator and a pore forming agent; copolymerization reaction between the functional monomer and the cross linker and in the cross linker is initiated under the irradiation of ultraviolet light to form a polymer; and the template modules (specified glycoprotein) in the polymer are removed by extraction of an acidic solution, and thus the molecularly imprinted polymer containing a phenylboronic acid site reversibly combined with the glycosyl of the glycoprotein and a cavity complementary with the shape of the template modules is obtained. The molecularly imprinted polymer specially combined with the specified glycoprotein has the advantages of high specificity, strong anti-interference capacity, wide practical sample range, good repeatability, simplicity in preparation and the like, and can be directly used for detecting antigens to be detected in a complex biological system of serum, saliva and the like. The invention discloses a preparation method for the molecularly imprinted polymer.

The invention discloses a dynamic polymer material. The dynamic polymer material comprises a product obtained through reaction of the following components: at least one polyol compound containing two or more 1,2-diol motifs or 1,3-diol motifs as well as at least one phenylboronic acid compound containing two or more phenylboronic acid motifs provided with aminomethyl groups in ortho-positions. Dynamic reversible phenylborate bonds are formed through the reaction of the components and then constitute a dynamic cross-linked polymer. The polymer material has reusability and recoverability because of the dynamic reversibility of the special phenylborate bonds; besides, when the polymer material adopting a specific formula receives external force, dynamic bonds break preferentially to have energy dissipation and stress elimination functions, so that the material has good toughness. The material has broad application prospect in the fields of military space equipment, functional paint and coatings, biomimetic materials, biomedical materials and the like.

The present invention is related to glucose sensors that are capable of detecting the concentration or level of glucose in a solution or fluid having either low or high ionic strength. The glucose sensors of the present invention comprise a polymerized crystalline colloidal array (PCCA) and a molecular recognition component capable of responding to glucose. The molecular recognition component may be a boronic acid, such as a phenylboronic acid, glucose oxidase, a combination of phenylboronic acid and poly(ethylene)glycol or crown ether, or another component capable of detecting glucose in various fluids and solutions. The glucose sensors of the present invention may be useful in the development of noninvasive or minimally invasive in vivo glucose sensors for patients having diabetes mellitus.

The invention provides a copolymer with a structure of a formula (I), a preparation method thereof, glucose sensitive micelle containing the same, glucose sensitive medicine-carrying micelle containing the same and a preparation method of the glucose sensitive medicine-carrying micelle. The copolymer provided by the invention comprises a polyethylene glycol monomethyl ether hydrophilic chain segment and a polyglutamic acid hydrophobic chain segment, wherein the polyglutamic acid hydrophobic chain segment takes polyglutamic acid as a main chain and the branch chain contains phenylboric acid groups. In the copolymer, both polyethylene glycol monomethyl ether and the polyglutamic acid have good biocompatibility, the polyglutamic acid has good biodegradability, the carboxyl group has pH sensitivity, and the phenylboric acid group has glucose sensitivity. The copolymer provided by the invention has good biocompatibility, biodegradability, glucose sensitivity and pH sensitivity.

The present invention relates to a new phenylboronic-acid-functionalized graphene oxide composite nano material and preparation and application thereof. The material is prepared by immobilization of polydopamine-packed magnetic nanoparticles onto polyethyleneimine-modified graphene oxide and further introduction of phenylboronic acid monomers with carboxyl by amino of polyethyleneimine, and finally the material is used for enrichment of glycoproteins. The specific process is as follows: firstly, Fe3O4 magnetic nanoparticles are prepared by a solvothermal method, and auto polymerization of polydopamine can be performed on surface of the Fe3O4 magnetic nanoparticles under alkaline conditions; the magnetic graphene oxide composite nano material can be prepared by hydrogen bond and PI-PI interaction between the polydopamine and graphene oxide, then the positively charged polyethyleneimine is immobilized onto the surface of the negatively charged magnetic graphene oxide by electrostatic self-assembly; and finally the phenylboronic-acid-functionalized magnetic graphene oxide composite nano material can be prepared by introduction of the phenylboronic acid monomers by amidation reaction, and the phenylboronic-acid-functionalized magnetic graphene oxide composite nano material is successively used in the enrichment of the glycoproteins in bioanalysis.

The invention discloses a method for preparing crisaborole and an intermediate for preparing crisaborole. The method comprises the following steps: (1) enabling components such as 2-halogen-5-(4-cyanphenoxy) benzyl acetate and bis(pinacolato)diboron to react in the presence of an organic solvent and a palladium catalyst under an alkali condition so as to obtain components such as 2-acetoxyl methyl-4-(4-cyan phenoxy) phenylboronic acid pinacol ester; (2) enabling components such as the 2-acetoxyl methyl-4-(4-cyan phenoxy) phenylboronic acid pinacol ester to react in a solvent under an acid oralkali condition, thereby obtaining crisaborole. The method is gentle in reaction condition, easy to operate, high in reaction yield, simple in aftertreatment, relatively low in cost and applicable toindustrial production.

The invention discloses a phenyloboricacid-modified cationic polymer, the structural formula is that (see lower right): wherein R is H or alkyl group containing one to ten carbons or substitution alkyl group containing nitrogen, oxygen, sulfur, chlorine, bromine or iodine; P is cationic polymer, the molecular weight Mw of P is from 400 to 500000, and n is more than or equal to 1 and less than or equal to 20. The preparation method is that: the phenyloboricacid with active groups and the cationic polymer are dissolved in methyl alcohol in N, N-dimethyl fomamide, and are reacted for 2-48 hours at the temperature of 20-60 DEG C for obtaining the phenyloboricacid-modified cationic polymer. The cationic polymer utilizes functional groups such as hydroxide radical and amino-group and the like in biomacromolecules such as phenyloboricacid group energy, protein, amylase, nucleic acid and the like to form reversible covalent-binding property, and improves the capacity of gene combination and cell carrying of carrier materials, so as to realize high-efficiency transfection of genes.

The invention provides one-pot synthesis phenylboronic acid polymer magnetic nano composite material and a preparation method and an application thereof. The preparation method comprises the following steps: dispersing ferroferric oxide nanoparticles in the alcohol containing a silane precursor and a catalyst through using a one-pot method, performing sol-gel reaction, and then continuously adding a phenylboronic acid type functional monomer, a cross-linking agent and an initiator to perform free radical polymerization in order to make synthesis phenylboronic acid polymer magnetic nano composite material. The synthesis method is simple, effective, high in yield and less in reagent consumption. The phenylboronic acid polymer magnetic nano composite material prepared has the advantages of good core-shell morphology, good magnetic field induction, strong specificity, high adsorption capacity, and good use value and application prospect in the fields such as proteomics and the like.

The invention discloses a method for enriching glycopeptide by a phenylboronic acid material. The glycopeptide is selectively enriched through optimizing the kind and concentration of an organic solvent, the kind and concentration of a buffer salt, the enrichment temperature and other parameters with phenylboronic acid modified silicon spheres as an enrichment material. The method has the characteristics of high selectivity, high adsorption amount, simple and controllable operation and the like, and is suitable for the selective enrichment of glycopeptides in a biological sample.

The invention discloses preparation and application of a pH glucose dual sensitive hydrogel. The hydrogel is formed by crosslinking of phenylboronic acid modified chitosan and an active functional group equipped crosslinking agent through imine bond and phenylboronic acid ester two dynamic covalent bonds, and has injectability and self-repairing performance. The imine bond is stable under normal physiological pH value, can hydrolyze under slightly acidic pH value, and is sensitive to the pH value change. Phenylboronic acid ester can undergo competing reaction in the presence of glucose, so that hydrogel can have network structure change so as to have glucose responsiveness. By regulating the structure, composition and functional groups of phenylboronic acid modified chitosan and the crosslinking agent, the rheological properties of the hydrogel can be adjusted, and activity release of the hydrogel to a substrate can be controlled. The system can be used as a drug carrier to convey various antitumor and diabetes drugs, also can be applied as a tissue engineering scaffold material to cell encapsulation and culture, thus realizing synergic treatment on the drug and cell level.

The invention relates to a Pd @MIL-101 composite and a preparation method and application thereof. According to the adopted technical scheme, palladium chloride is added to methyl alcohol while sodium chloride is added, ultrasonic dispersion is conducted, stirring is conducted for 10-20 hours, and sodium tetrachloropalladate is obtained; a sodium tetrachloropalladate solution is dropwise added into MIL-101 crystals slowly, pd<2+>@MIL-101 is obtained; a methanol solution of asaturated sodium borohydride is added to the pd<2+>@MIL-101, reduction is conducted under the condition of ice-water bath, and the Pd @MIL-101 composite is obtained. The synthesized Pd @MIL-101 composite has special selectivity catalytic activity for phenylboronic acid and 1,4-dibromo-benzene in a suzuki reaction, and the yield of an intermediate product 4-bromobiphenyl is effectively raised.

The invention discloses a palladium nano-composite catalyst loaded by N-doped three-dimensional graphene and a preparing method and application thereof. The method includes the steps that a formaldehyde solution and a nitrogen source are added into an oxidized graphene solution, a N-doped three-dimensional graphene composite material is prepared through a hydrothermal method, then a H2PdCl4 solution and a reducing agent are added to obtain the palladium nano-composite catalyst loaded by N-doped three-dimensional graphene, a carrier of the catalyst is graphene of a N-doped three-dimensional structure, loaded active ingredients are palladium nano particles, the loading capacity of the Pd nano particles accounts for 5-15% of the total mass of the catalyst, and the particle size is 5-10 nm. The palladium nano-composite catalyst loaded by N-doped three-dimensional graphene is applied to a Suzuki reaction of halogeno benzene and phenylboronic acid and shows high catalytic activity and high reusability.

The invention relates to the technical field of functional inorganic materials and analysis, and in particular relates to a preparation method of an organic phenylboronic acid-rich polyethyleneimine modified silicon dioxide microsphere. The preparation method comprises the following steps: (1) fixing polyethyleneimine molecules on the surface of the silicon dioxide microsphere; and (2) performing organic phenylboronic acid functional modification on the polyethyleneimine modified silicon dioxide microsphere. The silicon dioxide microsphere modified by the preparation method can perform enrichment and separation on the low-concentration cis-form dyhydroxyl compounds, so as to contribute to solving the problems of low abundance and more detection interference matters of cis-form dyhydroxyl compounds in the practical separated samples.

The invention relates to preparation and applications of mesoporous silica / insulin nanoparticles modified by phenylboronic acid, for effectively solving the problem that the traditional drug carriers release medicines unidirectionally. The technical scheme is as follows: the preparation comprises the following steps: firstly, synthesizing mesoporous silica nanoparticles, modifying amino groups on the surfaces of the mesoporous silica nanoparticles, loading medicine insulin in the mesoporous structure through physical absorption, and further modifying with phenylboronic acid and polysaccharide, thus obtaining the mesoporous silica / insulin nanoparticles modified by phenylboronic acid. The preparation and applications have the advantages that the synthesis process is simple, the prepared nanoparticles have the good biocompatibility, and the releasing valve of medicines can be repeatedly opened and closed, so that the sustained-release effect is achieved on the release of medicines; the mesoporous silica / insulin nanoparticles have a long-time circulation in the body, so that the administration times can be reduced, and thus the mesoporous silica / insulin nanoparticles belong to an innovation in diabetes treatment medicines.

The invention discloses a preparation method of LCZ696 intermediate and relates to the technical field of preparation of an aromatic nucleus compound containing 2 benzene rings and 1 chiral center. The preparation method includes the steps of S1, allowing benzyl magnesium bromide to react with methyl oxalyl chloride to obtain a compound as shown in formula I; S2, allowing the compound as shown in formula I to have a bromination reaction with a bromination reagent to generate a compound as shown in formula II; S3, coupling the compound as shown in formula II with phenylboronic acid to obtain a compound as shown in formula III; S4, performing reductive ammoniation on the compound as shown in formula III to obtain a compound as shown in formula IV; S5, applying Boc to the compound as shown in formula IV to obtain a compound as shown in formula V; S6, performing ester group reduction on the compound as shown in formula V to obtain a compound as shown in formula VI. The preparation method has the advantages that overall raw material consumption is lowered, and product productivity and market competiveness are increased; by the overall process optimization, the reaction of each step can be performed and controlled easily, the use of heavy metal catalysts is reduced and avoided, and accordingly the quality index of the final product is increased, and an economic and environment-friendly process route is developed.

The invention belongs to the technical fields of polymer materials and analysis, relates to a monodispersed organic and inorganic hybrid microsphere particle with core-shell structure and preparation and application thereof. Inorganic silica particles as the core are modified by a silanizing agent, and then 3-acetylaminophenylboronic acid and polyene cross-linking monomer coat on the click nuclear surface through a mercaptan-alkene click chemistry technology to form organic and inorganic hybrid nano / micron particles with core-shell structure, smooth surface and boric acid functional groups. According o the invention, introduction of the phenyl boronic acid functional group to the material surface by a mercaptan-alkene method not only overcomes the shortcomings of complex procedure and low reaction efficiency in a post modification method but also allows stable polymerization of APBA, increases surface bonding amount of boric acid and hydrophilic property of the material, and reduces the nonspecific adsorption of proteins. The microsphere particles of the invention can be used in separation or enrichment of glycoprotein with 1,2-cis diol structure, and has good practical value and application prospect in the field of proteomics.

Disclosed is a mucoadhesive nanoparticle delivery system for delivering an immunosuppressant, such as cyclosporine A, to a mucosal site for treatment of a disease or condition involving inflammation or excess immune activity. The system comprises nanoparticles formed from a plurality of linear amphiphilic block copolymers, each having a hydrophobic block comprising polylactide (PLA) and a hydrophilic block comprising dextran. The nanoparticles are surface-functionalized with a mucosal targeting moiety, such as a phenylboronic acid derivative, for targeted delivery and enhanced retention at the mucosal site. Pharmaceutical compositions, methods, and uses thereof comprising the mucoadhesive nanoparticle delivery system are disclosed. The compositions can be administered in an effective amount for treating the disease or condition while substantially preserving or restoring the function and / or integrity of the mucosal lining. The composition may be formulated as an aqueous suspension for administration to an anterior surface of the eye in the treatment of dry eye syndrome.

The invention discloses a preparation method of hyaluronic acid-based double-crosslinked hydrogel, which comprises the following steps: respectively modifying hyaluronic acid to obtain furan- and dopamine-modified hyaluronic acid and furan- and phenylboronic acid-modified hyaluronic acid, blending the two modified hyaluronic acids with maleimide-terminated four-arm polyethylene glycol to generatedouble crosslinking, wherein the vicinal diol structures of phenylboronic acid and dopamine can spontaneously form phenylboronic acid ester under the condition that the pH value is 7.4 and the hydrogel has injectability and adhesion, producing single cross-linked hydrogel, and making the furan group and maleimide undergo a Diels-Alder reaction in subsequent time to form secondary cross-linking, sothat the mechanical property of the hydrogel is enhanced and the double cross-linked hydrogel is obtained. By adopting a double-crosslinking mode of click chemistry and phenylboronic acid ester, theobtained product has good mechanical properties, injectability, hyaluronidase degradation resistance and excellent biocompatibility, and the two crosslinking modes are mild and rapid and can encapsulate cells for injection.

The invention discloses a preparation method of an SERS substrate of Au@Ag nanoparticles. According to the method, gold nanoparticles are prepared by reducing chloroauric acid with sodium citrate, thegold nanoparticles are modified with 4-sulfydryl aniline to link silver ions, and a certain proportion of ascorbic acid and sodium hydroxide are added to reduce a silver shell. Meanwhile, the form size of the core-shell structure is controllable, plasma resonance is realized through high coupling of the structure, and the so-called hotspots are formed in the core-shell structure, so that 4-sulfydryl aniline serving as an internal standard molecule has very high Raman signals. The Au@Ag core-shell structure is modified with 4-sulfydryl phenylboronic acid to capture glucose molecules, so that qualitative and quantitative detection of glucose is realized. The method has the advantages as follows: the internal standard substance is used for signal comparison, interference of complex substances in samples (such as urine) can be avoided, the detection sensitivity is improved, the preparation cost is low, and qualitative and quantitative detection of glucose is really realized.

The invention provides an inflammatory microenvironment responsive smart drug-loaded hydrogel and a preparation method and application thereof. The preparation method for the inflammatory microenvironment responsive smart drug-loaded hydrogel comprises the following steps: a functional polymer containing ortho-hydroxyl reacts with phenylboronic acid containing amino or carboxyl to prepare a phenylboronic acid polymer; an amphiphilic drug carrier is prepared; the prepared amphiphilic drug carrier and a hydrophobic drug are dissolved with a good solvent, and then, water is added thereinto understirring to prepare a drug-loaded micellar solution; and the hydrophilic drug and the prepared phenylboronic acid polymer are dissolved in the prepared drug-loaded micellar solution, and then, the pHvalue of a mixed solution is regulated to 8-9 to prepare the smart drug-loaded hydrogel. The hydrogel responsively releases drugs through pH and reactive oxygen, and has the advantages that the preparation components are few and the synthesis operation is simple.

The invention provides a hydrophilic phenylboric acid functional porous integral material, which is a cross-linked framework structured hydrophilic phenylboric acid functional porous integral material with penetrated transparent ducts, is formed by 4-(-3-butenyl sulfone) phenylboric acid and crosslinker N,N-bisacrylamide under initiation of a free radical reaction initiator, and can perform a covalent interaction with dihydroxyl compound under a neutral pH condition. The hydrophilic phenylboric acid functional porous integral material can be used for specifically identifying, separating, enriching or immobilizing the dihydroxyl compounds. The invention also discloses a method for preparing the hydrophilic phenylboric acid functional porous integral material.

The invention belongs to the technical field of electron transport materials and discloses an organic micro-molecular electron transport material and preparation thereof, and an n-doped electron transport layer and application thereof. The organic micro-molecular electron transport material has a structure shown as the formula I. The preparation method of the organic micro-molecular electron transport material comprises (1) subjecting 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-bromo-phenylboronic acid to coupling reaction, and then performing subsequent processing to obtain a bromine-containing intermediate; (2) subjecting the bromine-containing intermediate and bis-(pinacolato)-diboron to Suzuki reaction and then performing subsequent processing to obtain a borate intermediate; (3) subjecting the borate intermediate and 3-bromo-1, 10-phenanthroline to coupling reaction and performing subsequent processing to obtain the organic micro-molecular electron transport material. The organic micro-molecular electron transport material is simple in structure and high in thermostability and topographic stability; when n-doped, the organic micro-molecular electron transport material can beprepared into the n-doped electron transport layer, which achieves high luminous efficiency and stability when applied to organic electroluminescence devices.

The invention relates to a preparation method and application of a polymer retention filter aid containing a phenylboronic acid functional group and belongs to the technical field of papermaking. The preparation method is characterized by comprising the following steps of: mixing; carrying out coupling reaction; and separating to obtain the polymer retention filter aid containing the phenylboronic acid functional group. Compared with the existing general polymer retention filter aid, the retention filter aid applicable to the field of papermaking industry has the advantages that the retention effect is greatly improved, and the residual rate of fine filters and fillers in mother liquor can be greatly reduced under relatively small dosage; and with the use of the polymer retention filter aid, the load of papermaking wastewater treatment can also be effectively reduced.

The invention relates to a mono-dispersed core-shell structure polymer nano particle, preparation and applications thereof. At first, monoene functional monomers and polyene crosslinking monomers are polymerized to generate polymer particles taken as the cores of the polymer microsphere, and then 3-acrylamino phenylboronic acid (APBA) and polyene crosslinking monomers are covered on the surface of the cores through a reversible addition-fragmentation chain transfer (RAFT) polymerization technology so as to obtain smooth core-shell polymer nano particles containing boronic acid functional groups. Phenylboronic acid functional groups are introduced to the material surface through a RAFT method, thus the defects existing in the conventional post modification method such as tedious steps, low reaction efficiency, and unstable morphology of direct polymerized products are avoided, moreover, the APBA can be more stably polymerized, and the bonding amount of boronic acid on the surface is increased at the same time. The polymer nano particle can be used to separate or enrich glycoprotein in a 1,2-cis-diol structure, and has a very good practical value and application prospect in fields like proteomics, etc.

The invention discloses a glucose responsive gold nanoparticle and a preparation method and an application thereof. The method adopts the reversible addition-fragmentation chain transfer polymerization method to prepare isopropyl acrylamide-acrylyl sulfourea amino phenylboronic acid copolymer that which is modified to the surface of the gold nanoparticle to obtain the gold nanoparticle covered by the copolymer. The gold nanoparticle obtained through the method in disclosed by the invention can generate response with the glucose molecule in a solution; the developing system dispersed by the gold nanoparticle is driven through by the glucose molecule to change the colour of the gold nanoparticle solution at high temperature, so as to realize visual identification and detection for the glucose. The method in disclosed by the invention can be widely used for the field of nanometre bioanalysis.

The invention relates to compositions comprising enzymes and enzyme stabilizing agents. This is achieved by using an enzyme-stabilizing component which comprises a calcium compound with a bidentate ligand and a phenylboronic acid derivative. Enzyme-containing compositions comprising such an enzyme-stabilizing component are advantageously stable in storage.

Methods for enhancing cellular uptake of cargo molecules by boronating the cargo molecule, particularly with one or more phenylboronic acid groups. Cellular uptake includes at least partial uptake into the cytosol. Boronation includes ligating, crosslinking or otherwise bonding one or more phenylboronic acids substituted to contain a reactive group to a cargo molecule. Boronation also includes ligating, crosslinking or otherwise bonding a phenylboronated oligopeptide to a cargo molecule. The phenylboronate groups are optionally conjugated to the cargo molecule via linking moieties that can be selectively cleaved, such cleavable linkers can allow the phenylboronate groups to be removed from the cargo molecule after the boronated cargo molecule is introduced into the cell. The invention includes certain phenylboronates which are boronation reagents, certain boronated oligopeptides and certain boronated peptides and proteins. The invention also includes kits for enhancing cellular uptake of cargo molecules by boronation with one or more phenylboronates or boronated oligopeptides.

The invention discloses a metal organic frame / graphene carried palladium nano-composite catalyst and a preparing method and application thereof. Firstly, anhydrous zirconium tetrachloride, terephthalic acid and N,N-diamide are added in a graphene oxide solution to prepare a metal organic frame / graphene composite; secondly, normal hexane, an H2PdCl4 solution and a reducing agent are added to obtain the metal organic frame / graphene carried palladium nano-composite catalyst, wherein a carrier of the catalyst is composed of the metal organic frame and graphene, palladium nano-particles serve as carried active components, the carrying quantity of the palladium nano-particles accounts for 1-10% of the total mass of the catalyst, and the particle size ranges from 10 nm to 20 nm. The metal organic frame / graphene carried palladium nano-composite catalyst shows high catalytic activity and good reuse performance when applied to a Suzuki reaction of halogeno benzene and phenylboronic acid.

The invention discloses a bio-based self-repair gel based on a boric acid ester bond. The preparation method of the bio-based self-repair gel includes the steps of: (1) taking 3-aminobenzeneboronic acid as the functional group, and modifying a biomacromolecule containing carboxyl to obtain a benzeneboronic acid based biomacromolecule; (2) modifying guar gum with a quaternary ammonium salt to obtain cationic guar gum; and (3) mixing the benzeneboronic acid based biomacromolecule prepared by step (1) with the cationic guar gum prepared by step (2), and utilizing the reversible ester bond formedbetween benzeneboronic acid and guar gum and the electrostatic interaction of positive and negative charges to prepare the bio-based self-repair gel with a double cross-linked network structure. The bio-based self-repair gel provided by the invention has excellent biocompatibility, biodegradability and self-repairability, and has broad application prospects in biomedicine, functional devices, sensing and other fields.