91 results about "Tetrazine" patented technology

The present disclosure generally relates to tetrazine-based targeting agents for bioorthogonal delivery of a payload to a targeted location in a subject for use in, for example, cancer, treatment of tumor growth, and immunotherapy.

The invention discloses a tetrazine probe synthon and a preparation method and application thereof.The preparation method comprises the following steps that under the inert atmosphere, diethyl cyanomethylphosphonate, 3-hydroxypropionitrile, 3-mercaptopropionic acid and hydrazine hydrate are mixed and then react at the room temperature, a sodium nitrite solution is added after the reaction is finished, then acid is continuously added till the reaction system reaches acidity, and a tetrazine probe synthon product is obtained; continuously reacting to obtain an intermediate; and dissolving the intermediate in a solvent in an inert atmosphere, adding triethylamine, slowly adding methanesulfonyl chloride, and reacting at room temperature to obtain the tetrazine probe synthon shown in the formula I. The invention further discloses a preparation method of the tetrazine probe synthon. The tetrazine probe synthon provided by the invention can perform series Heck reaction and HWE reaction, so that controllable combination of functional groups on two sides of a tetrazine coupling probe is realized under mild reaction conditions, and the functional groups on two sides are designed according to actual requirements to regulate and control photophysical properties of the probe. A brand new way is provided for developing a high-performance biological orthogonal fluorescent probe.

Nontoxic, targeted poly beta-amino esters (PBAEs) are synthesized by using click chemistry to attach a targeting moiety. The click chemistry uses a dienophile, such as a strained alkene ring, and a diene, such as tetrazine, to provide rapid attachment of targeting moieties to PBAE polymers and nanoparticle surfaces containing them. Targeting moieties such as aptamers, antibodies or antibody-like proteins can be quickly and safely coupled to PBAEs to provide highly specific localization of nanoparticles for gene therapy or targeted delivery of therapeutics.

The application discloses application of a divinyl tetrazine in cyclization of a linear polypeptide, and a structure formula of the divinyl tetrazine is; the linear polypeptide has at least two free mercapto groups, and the vinyl groups of the divinyl tetrazine are subjected to Michael addition reaction with corresponding mercapto groups to form a ring. The application provides a new use of the divinyl tetrazine, the divinyl tetrazine can be subjected to high-efficiency Michael addition reaction with two natural cysteine mercapto groups on the linear polypeptide through the vinyl groups, so that double-mercapto peg cyclization of the linear polypeptide is realized, and the purpose of limiting the conformation of the linear polypeptide and improving the stability of the linear polypeptide is achieved. Moreover, the divinyl tetrazine can be subjected to a reverse electron demand Diels-Alder reaction with trans-cyclooctene (TCO) after the two vinyl groups are subjected to reaction with mercapto groups, so that functional polypeptides can be modularly constructed by coupling with functional molecules modified with TCO, and related applications are realized.

The invention belongs to the technical field of organic electroluminescent functional materials and devices, and particularly relates to a triazine derivative containing pyridine and carbazole substituent groups and application of the triazine derivative. According to the invention, pyridine and carbazole are introduced to a substituent group of triazine, so that a conjugated system of the material is enhanced, and the electron transport performance and thermal stability of the compound are improved. The organic electroluminescent device prepared from the organic electronic material has the advantages of lower driving voltage, higher external quantum efficiency and longer service life.

This invention belongs to the field of semiconductor manufacturing and circuit board electroplating technology, and particularly relates to an acidic copper sulfate electroplating solution containing a tetrazine structure, its preparation method, and its application. The electroplating solution is prepared by the following method: first, anhydrous copper sulfate is dissolved in ultrapure water, and then sulfuric acid, chloride ions, inhibitors, accelerators, and synergist 3,6-bis(pyridin-3-yl)-1,2,4,5-tetrazine are added sequentially under stirring conditions, and the mixture is stirred until homogeneous. This invention also provides a method for using the above electroplating solution in TSV blind via electroplating, including pretreatment of a TSV silicon blind via substrate with a diameter of 10 µm and a depth of 30 µm, using it as a cathode, clamping it with a platinum electrode, and placing it in the copper sulfate electroplating solution for electroplating. The electroplating solution formulation of this invention has a synergistic effect, exhibits excellent filling performance in TSV blind via electroplating, and is suitable for electroplating processes of high aspect ratio microvias.

The invention discloses an ethynyl tetrazine compound and application thereof in synthesis of a dinitrogen heterocyclic compound or an isotope marker of the dinitrogen heterocyclic compound. When the ethynyl tetrazine compound is used for preparing the dinitrogen heterocyclic compound, a nitrogen heterocyclic ring structure can be introduced by taking a tetrazine group as a synthon; the diversity of substituent groups of the dinitrogen heterocyclic compound is enriched, and more structure types and activity screening objects are provided for drug research and development. Meanwhile, the synthesis path of the dinitrogen heterocyclic compound synthesized by taking the ethynyl tetrazine compound as a starting material is shorter, the reaction condition is milder, and more importantly, the ethynyl tetrazine compound can be used for preparing an isotope labeled dinitrogen heterocyclic compound, so that the ethynyl tetrazine compound has very important significance in the research and development process of new drugs.

The present invention relates to the field of nuclear medicine technology, and discloses a targeted compound bimolecular probe, comprising a component A and a component B respectively labeled with radioactive metal nuclides; component A is a molecular probe targeting fibroblast activation protein (FAP), and the molecular probe targeting fibroblast activation protein (FAP) includes a trans-cyclooctene group (TCO); component B is a molecular probe targeting integrin α v β6 molecular probe, targeting integrin α v The β6 molecular probe includes a tetrazine group (Tz); wherein the radioactivity ratio of component A to component B is (1-2): (2-1). The present invention has the following technical effects: the TCO in the FAP-targeting molecular probe and the integrin α v The Tz in the β6 molecular probe can undergo a bioorthogonal reaction, achieving a tertiary amplification effect, increasing tumor uptake, prolonging the retention time of the targeted compound bimolecular probe, improving the target / non-target ratio, and enhancing nuclear medicine diagnostic and therapeutic effects. The present invention also discloses a method for preparing and using the targeted compound bimolecular probe.

The present disclosure relates to ureido ligands targeting PSMA comprising a moiety targeting PSMA, a linker, and a pyridazine moiety. The disclosed PSMA-targeted ureido ligands are suitable for use as radiopharmaceuticals, as imaging agents (e.g., diagnostic agents), or for the treatment of prostate cancer, or as diagnostic agents.

A calix[4]arenes of the formula (1a),wherein: Y1, Y2, Y3 and Y4 are selected from hydrogen, halogen, NO2, N3, CN, CHO, COOR′, CONR″2, NR2, triazole moiety and C1-C3-alkyl group, the C1-C3-alkyl group being optionally substituted, Z is a heterocyclic moiety which is selected from the group including of imidazole, benzimidazole, benzothiazole, benzoxazole, purine, tetrazine, oxazole, pyrazole and thiazole, the heterocyclic moiety being optionally substituted, R1 and R2 are selected from hydrogen and C1-C8-alkyl, the C1-C8-alkyl group being optionally substituted, n being an integer between 1 and 4, They exhibit high cytotoxicity against cancer cells.

The application discloses a kind of single-substituted 1,2,4,5-tetrazine compounds based on five-membered heterocyclic ring and preparation method thereof.The single-substituted 1,2,4,5-tetrazine compounds based on five-membered heterocyclic ring keep high reaction rate (10 4 ~10 5 M ‑1 s ‑1 ), improve the LUMO+1 orbital energy of single-substituted tetrazine compound to improve its stability, or improve the reaction ability of tetrazine compound under the same or similar LUMO+1 orbital energy, so that the single-substituted 1,2,4,5-tetrazine compounds based on five-membered heterocyclic ring have higher stability when the reaction rate is certain, have higher reaction rate when the stability is certain, provide a new idea for breaking the limitation of orbital energy and reaction ability with trans-cyclooctene, can promote the retro Diels-Alder reaction of 1,2,4,5-tetrazine compound and trans-cyclooctene in vivo, and is of great significance to the field of medicine.

The present application belongs to the technical field of rubbers, and particularly relates to a rubber composition and a preparation method therefor, and an OTR engineering tire using same. The rubber composition disclosed in the present application comprises (in parts by mass) 100 parts of a diene rubber, 0-1.5 parts of a tetrazine compound, 0.2-1.5 parts of a pyrazolone compound, 0-30 parts of a liquid rubber, 20-100 parts of a reinforcing filler, 0-5 parts of a silane coupling agent, 2-10 parts of a vulcanization activator, and a vulcanization accelerator, a vulcanizing agent, an antioxidant, a resin and a plasticizer. Moreover, the ratios of the tetrazine compound and the liquid rubber are not zero at the same time. The present application can significantly reduce the heat generated by the OTR engineering tire, and can also improve the damage resistance of the tire.

According to the phenothiazine functional precursor, the photosensitizer and the preparation method of the phenothiazine functional precursor, halogen or thienyl is introduced into R1 and / or R2 sites of a benzophenothiazine structure to serve as heavy atoms on the basis of structure-function relationship research of benzophenothiazine site modification, generation of strong spin-orbital coupling can be promoted, and the photosensitizer has the advantages that the photosensitizer can be used as a photosensitizer; further, intersystem crossing of the phenothiazine photosensitizer from an excited singlet state (S1) to a triplet state (T1) is promoted, so that the photosensitive effects of the phenothiazine functional precursor and the corresponding phenothiazine photosensitizer are effectively improved. Besides, after the phenothiazine photosensitizer is modified by adding a tetrazine group, controllable closing and opening of phenothiazine are realized, so that the dark toxicity of phenothiazine is effectively reduced, the targeting property and the treatment effect of the photosensitizer are improved by accessing a targeting group and a drug group into the phenothiazine photosensitizer, and the phenothiazine photosensitizer has a wide application prospect.

The invention relates to a macroporous pyrene tetraketone-triazine covalent organic framework material as well as a synthesis method and application thereof, and belongs to the technical field of organic functional materials. The material is prepared from 2, 7-aminopyrene-4, 5, 9, 10-tetraketone and 4, 4 ', 4' '-(1, 3, 5-triazine-2, 4, 6-triyl) tri (benzaldehyde) through polymerization. The material has a relatively large mesoporous structure, high crystallinity and rich redox active sites. The large-size mesoporous structure is favorable for keeping relatively high ion flux of the diaphragm, the bidirectional catalytic action of pyrene tetraketone conjugated carbonyl can improve the reaction kinetics of the high-load lithium-sulfur battery, and the soft-package lithium-sulfur battery prepared under the conditions of high-activity load and poor electrolyte shows stable cycle performance and relatively high specific capacity.

The present invention relates to fibroblast activation protein (FAP) - based ligands assembled through tetrazine ligation and their use in radiotherapy and imaging. The FAP inhibitor (FAPi) ligand compounds provided herein comprises a FAP targeting moiety, a linker, an IsoF-TCO and a radiolabeled tetrazine. The FAPi targeting compounds are possessing advantageous pharmacokinetic properties and enable quick and efficient modifications of the radiopharmaceuticals allowing a fast renal excretion and reduced liver accumulation.

This application discloses a tetrazine energetic material and its preparation method and application, which belongs to the field of laser detonation and ignition technology. The energetic material includes MC2H x N 10 O y crystal; M is selected from any one of Mn, Fe, Co, Cu, Zn, Cd, and Ni; when M is selected from any one of Mn, Fe, Co, Cu, Zn, and Cd, x=8, y=7; when M is Ni, x=10, y=8. The tetrazine energetic material, as a laser detonation ignition material, generally requires lower laser detonation ignition energy than previously reported compounds and overcomes the serious ClO4 ‑ Despite the shortcomings of ion contamination and high laser ignition threshold, it has important commercial application value in the field of laser initiation and ignition.

The invention belongs to the technical field of material characterization, and provides a method for characterizing compatibility of butadiene styrene rubber and other rubbers, a tetrazine compound is added into a mixture of the butadiene styrene rubber and other rubbers, the tetrazine compound is easy to react with the butadiene styrene rubber, and the mixture forms bright yellow at 135 DEG C, so that the compatibility of the butadiene styrene rubber and other rubbers is improved. According to the characteristics that other rubber types are difficult to react with tetrazine compounds and the mixture forms dark purple under various temperature conditions, the mixture is uniformly blended in an internal mixer, then reacts for 1-2 minutes under the condition of 135-145 DEG C, is sliced after being cooled to room temperature, and is observed in morphology and color under a high-depth-of-field intelligent microscope; the method is easy to operate, instruments and equipment are low in cost, visual and rapid, the method is not limited by a formula, a theoretical basis and an experimental reference are provided for compatibility characterization and performance regulation and control of a blending system of the butadiene styrene rubber and the other rubber, and the method has guiding significance for development of high-performance rubber materials.

The invention relates to the field of antioxidants, in particular to a tetrazinone compound, application of the tetrazinone compound and an antioxidant. The structure of the tetrazinone compound provided by the invention is characterized by hydrazine, the existence of a benzene ring structure is not required in a core skeleton and an active unit, and the tetrazinone compound is a breakthrough in the structure of a traditional arylamine free radical antioxidant and is an antioxidant active material compound with a brand-new structure; the antioxidant not only has extremely efficient antioxidant efficiency on peroxidation of hydrocarbon and phospholipid biofilms, but also can reach or even exceed existing phenol or arylamine antioxidants. The tetrazinone compound provided by the invention has very strong universality when being applied to antioxidants, and can be applied to the fields of biological medicines, chemical materials and the like as an antioxidant.

The invention belongs to the technical field of organic compound preparation, and discloses a photochemical preparation method of a tetraphenylhexahydrotetrazine compound. The preparation method comprises the following steps: mixing an azobenzene compound, biborate, a carbon source and an organic solvent, wherein the carbon source comprises alkyl aldehyde or nitroalkane; and reacting under light irradiation, removing the organic solvent, and separating and purifying to obtain the compound. The tetraphenylhexahydrotetrazine compound with high yield can be prepared by taking an azobenzene compound as a raw material, taking aldehyde or nitroalkane as a carbon source, adding bis (borate), and carrying out illumination in the absence of a metal catalyst within the reaction time of less than 1 hour. Moreover, the preparation method disclosed by the invention shows wide functional group compatibility, so that various types of azobenzene compounds can be converted into tetraphenylhexahydrotetrazine compounds, and the application prospect is wide.

Described herein are nucleic acid complexes for the targeted delivery of reversibly capped mRNA complexes (procapped mRNA) which are conditionally activated in the presence of a selected cell signal. The mRNA complexes can include mRNA with is 5' capped with a selectively removable protecting group involving a click-release reaction between tetrazine and trans-cyclooctene (TCO), to achieve selective activation of mRNA within targeted cells.

The present invention provides bioorthogonal tetrazine reaction entities for use in pretargeting approaches comprising imaging, therapy and diagnostics specifically pretargeting theranostics. The present invention also provides precursors of the tetrazine reaction entities and kits comprising the tetrazine reaction entity or the precursor of the tetrazine reaction entity and a dienophile with inverse electron demand Diels-Alder cycloaddition reactivity.

The invention relates to the technical field of biological medicine, particularly discloses a novel coupling method of double-target nucleic acid molecules and application thereof, and provides a strategy method for connecting two nucleic acid chains through cyclization reaction between tetrazine and alkene or alkyne. According to the present invention, a cyclization reaction is performed between a nucleic acid chain of a tetrazine group (Strand 1) and a nucleic acid chain of an alkene or alkyne group (Strand 2), a connection unit of dihydropyridazine or pyridazine is generated between the two nucleic acid chains, and four connection modes are selected: between 5'of Strand 1 and 3 'of Strand 2, between 5' of Strand 1 and 5 'of Strand 2, and between 3' of Strand 1 and 5 'of Strand 2. Furthermore, two nucleic acid chains connected with dihydropyridazine or pyridazine are respectively combined with complementary nucleic acid chains according to complementary base pairing to prepare a double-target oligonucleotide drug.

CRISPR-Cas genome editing technology has applications in biomedical research and therapeutics that has led to an increased demand for guide RNAs. Synthesis of chemically modified single-guide RNAs (sgRNAs)>100 nt remains a bottleneck. A tetrazine ligation method is disclosed herein for the preparation of sgRNAs that overcomes this synthesis challenge. For example, a tetrazine moiety on a 3′-end of crRNA and a norbornene moiety on a 5′-end of tracrRNA permits ligation between crRNA and tracrRNA to form an sgRNA under mild conditions. Tetrazine-ligated sgRNAs allow efficient genome editing as demonstrated by reporter models and endogenous loci in human cells. A structural modification of the linker moiety permits achievement of high efficiency editing.

This application relates to additives for imparting low heat generation properties to rubber components. The additive, which is used to impart low heat generation properties to rubber components, contains a tetrazine compound or a salt thereof represented by the following general formula (1). Wherein, X... 1 and X 2 "Same" or "different" refers to a hydrogen atom, alkyl, alkylthio, aralkyl, aryl, arylthio, heterocyclic, or amino group. Each of the above groups may have more than one substituent.

The invention relates to the technical field of chemical separation, in particular to an adsorbent based on a metal organic framework material as well as a preparation method and application of the adsorbent. The adsorbent is constructed by zinc ions, 3, 6-di-4-pyridyl-1, 2, 4, 5-tetrazine ligand and polycycloalkane dicarboxylic acid ligand H2L; h2L is selected from at least one of compounds with the structural formula shown in the attached drawing of the specification. The preparation method comprises the following step of: reacting metal salt and a ligand in a mixed solvent of N, N-dimethylformamide and methanol at 100 DEG C to obtain the metal complex. The adsorbent has the ethane adsorption capacity and selectivity higher than those of ethylene under mild conditions, and can be used for adsorption processes such as a fixed bed, so that ethylene penetrates preferentially, and high-purity ethylene gas is obtained in one step. The material has the advantages of being simple and convenient to synthesize, high in stability and easy to regenerate, and an energy-saving and efficient new scheme is provided for ethane / ethylene separation.

The application discloses a tetrazine cyanine compound and a preparation method and application thereof. The skeleton of the tetrazine cyanine compound is directly connected with a BFI part of cyanine, can better affect the overall fluorescence opening multiple of the tetrazine cyanine compound by adjusting an R1 group, can also realize high-resolution imaging of a lysosome, an endoplasmic reticulum and a mitochondrial membrane by selecting a suitable R1 group and cooperating with a predetermined site molecule, can realize high fluorescence opening multiple in a near-infrared region, can significantly enhance a fluorescence emission signal from an extremely low background level after reacting with BCN, and can also have excellent light stability, wherein the fluorescence intensity of a TBCy3P addition product generated in situ is basically maintained unchanged in the whole irradiation period under continuous 100-frame laser scanning excitation, and the cell morphology is normal.

The present invention addresses the problem of providing a rubber composition with which it is possible to suppress the occurrence of cracks while also improving fuel efficiency. As a means for solving said problem, this rubber composition is characterized by including: a diene rubber (A); a heterocyclic compound (B) having at least one heterocycle selected from the group consisting of a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, and a tetrazine ring; and an anti-aging agent (C). The rubber composition is also characterized in that the anti-aging agent (C) includes at least one selected from the group consisting of phenylenediamine-based anti-aging agents (C1-1) represented by a specific structural formula and aminoquinoline-based anti-aging agents (C1-2) represented by a specific structural formula.

The present invention addresses the problem of providing a rubber composition with which it is possible to suppress the occurrence of cracks while also improving fuel efficiency. As a means for solving said problem, this rubber composition is characterized by including: a diene rubber (A); a heterocyclic compound (B) having at least one heterocycle selected from the group consisting of a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, and a tetrazine ring; and an anti-aging agent (C). The rubber composition is also characterized in that the anti-aging agent (C) includes a triphenylamine-based anti-aging agent (C1) represented by a specific structural formula.

This disclosure generally relates to tetrazine-based targeting agents for bioorthogonal delivery of payloads to targeted sites in a subject, which have applications, for example, in the treatment of cancer, tumor growth, and immunotherapy.

The application discloses a multifunctional backbone molecule for controllable and visual monitoring of drug release and a preparation method and application thereof, the multifunctional backbone molecule has a structure shown in formula I, includes a tetrazine structural unit and a phenanthrene dioxin skeleton, and fluorescence of the phenanthrene dioxin is quenched through fluorescence resonance energy transfer effect between the tetrazine and the phenanthrene dioxin parent nucleus. The multifunctional backbone molecule provided by the application can be subjected to a reverse electron demand Diels-Alder bioorthogonal bond cleavage reaction with a prodrug modified by a trans-cyclooctene, 3-isocyanopropyl or 3-isocyanopropyl-1-carbamoyl group, so that the quenching effect is destroyed, fluorescence is recovered, the prodrug is activated, controllable release and visual monitoring of the drug are realized. In addition, the multifunctional backbone molecule provided by the application can be connected with a targeting group on the phenanthrene dioxin skeleton, so that controllable release of the drug at a target site and real-time visual monitoring of the drug release are realized.