271 results about "Tetrazine" patented technology

Coupling reactions, suitable for use in organic or aqueous media, are performed by contacting a 1,2,4,5-tetrazine with a dienophile. The dienophile may be covalently bonded to a protein, and the coupling reaction may be performed in biological media such as those containing cells or cell lysates. The reactions may be performed in the presence of primary amines, thiols, acetylenes, azides, phosphines, and products of Staudinger and / or Sharpless-Huisgen reactions Novel 3-substituted cyclopropene compounds and trans-cyclooctenes are exemplary dienophiles for these reactions.

The present invention comprises apparatus and methods employing a gas produced from a tetrazine-based energetic material such as that known as “BTATz” containing 3;6-BtS(1H-1,2,3,4-Tetrazol-5-ylamino)1-,2,4,5-tetrazine 3;6-BtS(1H-1,2,3,4-Tetrazol-5-ylamino)1-,2,4,5-tetrazine or salts thereof. The tetrazinebased energetic material is ignited through the use of a percussion cap, a piezoelectric crystal or a battery-supplied electric spark or by encapsulating it in a container that is then exposed to a burning flame. The gas produced upon ignition is employed a propellant such as to inflate life rafts, life vests, emergency evacuation slides, tires, air bags and other inflatable devices. The gas produced upon ignition is alternatively employed to power an engine and many other applications such as a fire suppressant.

The invention provides methods and compositions for a mutein aminoacyl-tRNA synthetase that preferentially charges a tRNA with a non-natural amino acid. Also provided are methods for incorporating the non-natural amino acids, pyridinyl-amino tetrazine amino acids, into a protein, and further conjugating a biologically active adduct to the pyridinyl-amino tetrazine.

A Diels-Alder adduct of a trans-cyclooctene with a tetrazine is provided, wherein the adduct bears a substituent labeled with a radionuclide. A method of producing a PET or other image of an organ in an animal or human includes forming the Diels-Alder adduct in the animal or human. Trans-cyclooctenes and tetrazines suitable for preparing the adducts are provided.

A composite medicine for treating solid tumor by locally putting it in the tumor is composed of the active anticancer component (tetraazine compound and its synergist chosen from taxol-type anticancer medicine, antineoplastic antibiotic and antibetabolitic medicine), and the medicinal auxiliary (biocompatible and biodegradable high-molecular polymer).

Described is a pretargeting method, and related kits, for targeted medical imaging and / or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other an E-cyclooctene which has one or more axial substituents.

Copolymers of formula (I):where each A is S, Se or C═C; each x is an integer from 1 to 4; each R1 is independently H, F, CN or a C1-C20 linear or branched aliphatic group; Ar is one or more substituted or unsubstituted aromatic units; and, n is an integer 5 or greater, can be formed into films or membranes that are useful as active layers in organic electronic device, such as PV solar cells, providing high power conversion efficiencies and good thermal stability. Such copolymers may be synthesized from monomers of formula (II):by Stille or Suzuki coupling reactions. Such monomers may be synthesized by a variation of the Pinner synthesis.

The invention discloses a novel amino acid derivative L-4-terazine-phenylalanine (3-(4-(1,2,4,5-tetrazin-3-yl) phenyl)-2-aminopropanoic acid). L-4-cyan-phenylalanine is used as an initial reactant and reacts with formamidine acetate and anhydrous hydrazine under catalysis of sulfur; then the reactants are oxidized by sodium nitrite to generate L-4-1,2,4,5-terazine-phenylalanine. The L-4-1, 2, 4, 5-terazine-phenylalanine is integrated into the biologically active peptide and protein molecules as phenylalanine / tyrosine analogue, and can be applied to on biological orthogonal field based on inverse electronic Diels-Alder reaction as a biomarker; meanwhile, the L-4-1,2,4,5-terazine-phenylalaninethe can be introduced into biologically active peptide as phenylalanine / tyrosine analogue through solid phase polypeptide synthesis method and conduct pharmacological evaluation, so as to improve drug property of certain biologically active peptide.

Described is a pretargeting method, and related kits, for targeted medical imaging and / or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other a cyclooctene or cyclooctyne.

This invention provides an electrode electrolyte for a solid polymer-type fuel cell, in which a cost problem and a problem related to recovery of catalyst metals are solved, having excellent proton conductivity, dimensional stability and heat resistance.An electrode electrolyte for a solid polymer electrolyte-type fuel cell contains a polymer, which has a polyphenylene structure as a main chain and both a sulfonic acid group and a nitrogen-containing heterocyclic group as a side chain. A side chain having the nitrogen-containing heterocyclic group has a structure represented by the following general formula (D).(In formula, Z represents at least one kind of structures selected from a group consisting of a direct bond, —O— and —S—, Y represents at least one kind of structures selected from a group consisting of —CO—, —SO2—, —SO—, —CONH—, —COO—, —(CF2)1— (1 is an integer of 1 to 10) and —C(CF3)2— and R20 represents a nitrogen-containing heterocyclic group. q represents an integer of 1 to 5 and p represents an integer of 0 to 4.)The above nitrogen-containing heterocyclic group is at least one kind of group derived from a compound selected from the group consisting of nitrogen-containing heterocyclic compounds including pyrrole, thiazole, isothiazole, oxazole, isoxazole, pyridine, imidazole, imidazoline, pyrazole, 1,3,5-triazine, pyrimidine, pyridazine, pyrazine, indole, quinoline, isoquinoline, purine, benzimidazole, benzoxazole, benzothiazole, tetrazole, tetrazine, triazole, carbazole, acridine, quinoxaline and quinazoline and derivatives thereof.

The invention discloses a new compound, N1,N4-di(3-hydroxyphenyl)-3,6-dimethyl-1,2,4,5-tetrazine-1,4-dicarbonamide shown in formula (I), and preparation and application thereof. The preparation of the compound comprises the steps of using 3,6-dimethyl-1,6-dihydro-1,2,4,5-tetrazine and bis(trichloromethyl) carbonate as raw materials to react with m-hydroxyaniline in an organic solvent in the presence of alkaline catalyst. The compound provided by the invention is applied for preparing medicines for treatment and prevention of human gastric cancer, ovarian cancer, liver cancer, breast cancer or lung cancer. According to the invention, the compound is rational in design, easy in operation, low in production cost and easy to obtain raw materials, and is suitable for industrialized application, and a new choice for screening anti-tumor medicines is provided.

Described is a pretargeting method, and related kits, for targeted medical imaging and / or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other an E-cyclooctene which has one or more axial substituents.

Copolymers of formula (I):where each A is S, Se or C═C; each x is an integer from 1 to 4; each R1 is independently H, F, CN or a C1-C20 linear or branched aliphatic group; Ar is one or more substituted or unsubstituted aromatic units; and, n is an integer 5 or greater, can be formed into films or membranes that are useful as active layers in organic electronic device, such as PV solar cells, providing high power conversion efficiencies and good thermal stability. Such copolymers may be synthesized from monomers of formula (II):by Stille or Suzuki coupling reactions. Such monomers may be synthesized by a variation of the Pinner synthesis.

The invention discloses an oxygen reduction catalyst including a pyrryl tetrazine ring and a preparation method of the oxygen reduction catalyst. Monomer (pyrryl)n-1 and 2,4,5-tetrazine (n is 1 or 2) react with a catalyst and an alkylate reagent, a pyrryl tetrazine ring polymer is obtained, the pyrryl tetrazine ring polymer is subjected to thermal treatment in an inert atmosphere, and finally the oxygen reduction catalyst easy to operate, economical, efficient, high in stability and high in catalytic activity is obtained. Industrial production is promoted.

Provided is an additive for imparting low heat build-up to a rubber component, wherein the additive includes a tetrazine compound represented by general formula (1):(wherein X1 and X2 are the same or different and represent a hydrogen atom or an alkyl, alkylthio, aralkyl, aryl, arylthio, heterocyclic, or amino group; and each of these groups may have one or more substituents), or a salt thereof.

The present invention relates to an anticancer medicine composition and belongs to the field of medicine technology. The anticancer medicine composition contains tetrazine medicine and medicinal supplementary material. The tetrazine medicinecan inhibit intracellular DNA repair function and reduce the tolerance one tumor cell on anticancer nitrosourea medicine; and the medicine supplementary material is mainly degradable biocompatible polymer. During the degrading and absorption process of the supplementary material, the anticancer medicine is released slowly to the tumor part, and this can lower the systemic toxic reaction while maintaining local effective medicine concentration. The anticancer medicine composition contains also anticancer nitrosourea medicine, and is set to the tumor part locally to enhance the treatment effect.

Coupling reactions, suitable for use in organic or aqueous media, are performed by contacting a 1,2,4,5-tetrazine with a dienophile. The dienophile may be covalently bonded to a protein, and the coupling reaction may be performed in biological media such as those containing cells or cell lysates. The reactions may be performed in the presence of primary amines, thiols, acetylenes, azides, phosphines, and products of Staudinger and / or Sharpless-Huisgen reactions Novel 3-substituted cyclopropene compounds and trans-cyclooctenes are exemplary dienophiles for these reactions.

The invention provides a prodrug activation compound, which is characterized by comprising a polypeptide fragment, and a tetrazine group and a hydrophobic group which are connected to the polypeptidefragment through chemical bonds; wherein at least one phosphorylated tyrosine exists in the amino acid of the polypeptide fragment. The prodrug activation compound provided by the invention has targeting property and specificity, can be quickly and efficiently accumulated in tumor cells and is self-assembled in situ to form a nano assembly, so that a trans-cyclooctene modified anti-tumor prodrug is efficiently and specifically activated; the prodrug activating compound and the prodrug system are good in biocompatibility and free of system toxicity. A solid-phase synthesis method is adopted inthe preparation method of the prodrug activated compound, the operation is simple, and the obtained product is high in chemical purity and high in total yield.

The invention discloses a tetrazine ring polycarbazole-based nitrogen-doped carbon-oxygen reduction catalyst and a preparation method thereof. The method comprises the steps of firstly synthesizing 3,6-bis(carbazolyl)-1,2,4,5-tetrazine (TCy) through a simple method; synthesizing a novel super-crosslinked polymer tetrazine ring polycarbazole (PTCy-1 or PTCy-2) by taking TCy as a monomer through Friedel-Crafts alkylation reaction or oxidative coupling reaction; and obtaining the tetrazine ring polycarbazole-based nitrogen-doped carbon-oxygen reduction catalyst (N / C) from the tetrazine ring polycarbazole through a direct pyrolysis method. The synthesized catalyst has excellent oxygen reduction (ORR) catalytic activity and electrochemical stability.

This invention relates to the use of temozolomide esters (4-dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylate esters) Formula 1 as potent anticancer pro-drugs for treatment of cancers by topical and transdermal applications, and to a novel process for synthesis of temozolomide esters by a direct esterification of temozolomide acid (3,4-dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid) with a halogeno-aliphatic compound in presence of a base, or with an alcohol in presence of a dehydrate agent.

The invention relates to a polypeptide comprising an amino acid having a norbornene group. Suitably said norbornene group is present as an amino acid residue of a norbornene lysine. The invention also relates to a method of producing a polypeptide comprising a norbornene group, said method comprising genetically incorporating an amino acid comprising a norbornene group into a polypeptide. The polypeptide comprising the norbornene group can be specifically labelled by inverse electron demand Diels-Alder reaction with a tetrazine compound.

Described is a pretargeting method, and related kits, for targeted medical imaging and / or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other an E-cyclooctene which has a flattened structure as a result of the position of at least two exocyclic bonds.

The invention relates to a crosslinkable organic molecule having a structure of the formula (1) and to the use thereof, wherein Ar is independently of one another, an unsaturated or aromatic carbo- or heterocyclic unit with 5 to 30 ring atoms, selected from the group consisting of naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazol, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazine-imidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, isothiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,3,4- oxatriazole, 1,2,3,4-oxatriazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazin, purine, pteridine, indolizine, benzothiadiazole, indenocarbazole, indenofluorene, spirobifluorene, and indolocarbazole; D1 is a donor group having a structure of the formula (1a); and D2 is a donor group having a structure of the formula (1b).

The present invention provides a composition for absorbing a gaseous unsaturated compound comprising a tetrazine compound incorporated in a polymeric substrate, wherein the tetrazine compound is stable to the presence of moisture. The invention further provides a method of retarding the ripening or senescence of fruit or other plant material using the composition of the present invention. Also provided are methods of removing a gaseous unsaturated compound from an environment and methods of measuring the concentration of, or indicating the presence of, a gaseous unsaturated compound.

Described herein are tetrazine derivatives and efficient synthetic methods of synthesis thereof using elimination-Heck cascade reaction. Provided herein is the synthesis of conjugated tetrazines from the tetrazine derivatives. Also provided herein are methods of use of the conjugated tetrazines as fluorogenic probes for live-cell imaging.

The invention discloses energetic ionic salts of a 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and a preparation method of the energetic ionic salts, and belongs to the technical field of energetic materials. The synthesis method comprises the following steps: reacting a silver salt of the 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide with corresponding hydrochloride of energetic cation; filtering and participating; and evaporating filtrate and removing a solvent, so as to obtain a target product. The energetic ionic salts are simple in synthesis method, and easy to industrialize. The 6 energetic ionic salts disclosed by the invention are relatively high in density (rho is 1.77-1.97g / cm<3>); the impact sensitivity is greater than 40J; the friction sensitivity is greater than or equal to 324N; the energetic ionic salts belong to insensitive explosives; and all energetic ionic salts are excellent in calculating detonation performance, and are energetic materials with potential.

The invention discloses application of an asymmetrical 1,2,4,5-tetrazine activating agent to a prodrug or rapid activation of protein in the bioorthogonal field based on an inverse electron Diels-Alder reaction. The application disclosed by the invention has the advantages that compared with a symmetrical tetrazine molecule, the asymmetrical 1,2,4,5-tetrazine activating agent has the advantages of extremely high activating efficiency and no toxicity to cells in the asymmetrical 1,2,4,5-tetrazine activating agent and the bioorthogonal reaction process, can be used for rapidly activating the prodrug, in particular to proteins taking lysine, tyrosine, serine or threonine as active residues in vitro or vivo, can be used for the aspects such as research on life course and treatment on diseases, and has an extremely wide application prospect.

The invention provides hydrogel capable of being rapidly cured based on reverse Diels-Alder reaction as well as a preparation method and application thereof. The preparation method comprises the following steps of modifying 3-(4-benzylamino)-1, 2, 4, 5-tetrazine onto four-arm polyethylene glycol to obtain four-arm polyethylene glycol modified by tetrazine, carrying out condensation reaction on hyaluronic acid and 5-norbornene-2-methylamine to obtain norbornene modified hyaluronic acid, carrying out reverse Diels-Alder reaction on tetrazine modified four-arm polyethylene glycol and norbornene modified hyaluronic acid to obtain the hydrogel capable of being quickly cured. The hydrogel capable of being rapidly cured, which is obtained on the basis of the reverse Diels-Alder reaction, is shortin curing time, good in biocompatibility and low in toxicity, a three-dimensional living environment can be provided for cells, and the adhesion and proliferation of stem cells on a three-dimensionalbracket are improved.