93 results about "BODIPY" patented technology

The invention relates to the technical field of biological medicines, and particularly discloses a BODIPY (boron dipyrromethene)-based compound and an application of the BODIPY-based compound in photodynamic oxidation of beta-amyloid protein (Abeta). The compound takes iodo-BODIPY as a photosensitive core and is connected with 4-t-butyloxycarboryl benzene as an A beta recognition group. The introduction of iodine atoms significantly enhances the intersystem crossing ability of molecules, so that the molecules have excellent reactive oxygen species (ROS) generation ability. The compound has high ROS yield, good optical stability and biocompatibility, can specifically target A beta aggregate, realizes photodynamic oxidative degradation, and provides a novel potential tool for treatment of Alzheimer's disease.

The invention discloses an aza-BODIPY biomedical phototherapy agent taking oxajulolidine as a donor and a preparation method thereof, and relates to a medical phototherapy agent for treating brain glioma and a preparation method thereof, and the prepared compound is prepared by introducing an oxajulolidine fragment with electron donating property into a key position of an aza-BODIPY skeleton, so that the aza-BODIPY biomedical phototherapy agent is obtained. The donor-acceptor type molecular near-infrared phototherapy agent with a new structure is constructed, has good near-infrared absorption and emission performance and excellent stability, and shows a remarkable effect in the field of cancer photodynamic (PDT)-photothermal (PTT) synergistic treatment. The structural categories of the near-infrared aza-BODIPY biomolecules are enriched, and a new molecular platform is provided for expansion and application of the near-infrared aza-BODIPY biomolecules in the fields of biological imaging, tumor diagnosis and treatment, functional materials and the like.

The invention discloses a high-activity BODIPY type photosensitizer targeting double organelles as well as a preparation method and application of the high-activity BODIPY type photosensitizer, and relates to the technical field of medical photosensitizers. The high-activity BODIPY type photosensitizer is prepared by the following steps: reacting 2, 4-dimethyl pyrrole with 4-bromobutyryl chloride to obtain a compound Br-BY containing carboxyl, then reacting with morpholine to obtain a morpholine substituted compound Mor-BY, and finally reacting with N-iodosuccinimide (NIS) to obtain a single atom I substituted BODIPY compound Mor-IBY, namely the target photosensitizer. The photosensitizer prepared by the invention can target mitochondria and lysosome in cancer cells at the same time, and can be excited by visible light; the compound has good water solubility, can generate a large amount of reactive oxygen species (ROS) under irradiation of green light (520 nm), shows excellent photodynamic activity to tumor cells, and has low toxicity to normal cells.

The invention discloses an imidazolyl BODIPY derivative viscosity fluorescent probe with an aggregation-induced fluorescence enhancement (AIEE) effect and application thereof, the imidazolyl BODIPY derivative viscosity fluorescent probe is realized by the following method: taking a 2-formaldehyde BODIPY derivative (I), diphenyl ethanedione and aniline as raw materials, and carrying out Debus-Radziszewski imidazole synthesis reaction under the catalytic action of ammonium acetate, and the chemical structural formula of the imidazolyl BODIPY derivative viscosity fluorescent probe is as shown in formula (II). The preparation method is simple in reaction step, mild in reaction condition, simple and convenient to separate and purify and high in yield; the fluorescent probe has an aggregation-induced fluorescence enhancement effect, has high responsiveness to viscosity, can be used for detecting viscosity change in a solution and cells, and can provide an effective detection method for researching physiological action of viscosity in cells.

The invention discloses a near-infrared ratio type fluorescent probe for rapidly and reversibly detecting histamine (HA), a preparation method of the fluorescent probe and application of the fluorescent probe in dynamic cell imaging, and belongs to the technical field of fluorescence imaging and biosensing. The preparation method comprises the following specific steps: synthesizing aza-BODIPY molecules (1a-1d, 2a-2d) with different halogenations, and meanwhile, connecting the aza-BODIPY molecules with hydroxyl groups at 3 and 5 sites with a hydrophilic PEG (Polyethylene Glycol) fragment and halogen to obtain an HA probe HAPCyto with good water solubility; in addition, the hydroxyl aza-BODIPY molecules are continuously subjected to substitution, halogenation and hydrolysis reaction to obtain carboxyl-containing aza-BODIPY molecules, then the aza-BODIPY molecules are subjected to amidation reaction by utilizing the site, and different organic fragments are respectively connected to obtain a cell membrane targeted HA probe HAPPM, a golgi apparatus targeted HA probe HAPGA and a HaloTag HA fluorescent probe HAPHaloTag. When HA exists in a solution, the developed probe can realize rapid reversible detection of the near-infrared ratio of histamine, also shows good reversible property in mast cells, and can realize dynamic monitoring of histamine in cells.

The invention relates to the technical field of chemiluminescence probes, in particular to a synthesis method and application of a boron dipyrromethene framework near-infrared two-region chemiluminescence probe based on X-ray activation, and the chemical structural formula of the chemiluminescence probe is shown in the specification. A novel BODIPY compound which is high in quantum yield and has a strong or narrow emission band is used as a chemiluminescence substrate for a core framework, a core framework of an electron withdrawing group with longer emission wavelength, an electron donating group and two molecules with larger wavelength overlap ratio are subjected to one-time CERT effect to be efficiently combined into a single molecule, and 1,050 nm chemiluminescence which is higher than 970 nm is emitted.

The invention relates to the technical field of biomedical detection and functional organic fluorescent materials, in particular to synthesis and application of a single-molecule probe combining BODIPY (boron dipyrromethene) and a semi-cyano dye. Comprising the following steps: preparing an intermediate 1: reacting 4-hydroxybenzaldehyde with 2, 4-dimethyl pyrrole to generate BDP-OMe, and then reacting with pyridinium chlorochromate to obtain the intermediate 1; preparation of an intermediate 2: carrying out reflux reaction on 2, 3, 3-trimethyl-3H-indole and 2-bromoethanol in ethanol to obtain the intermediate 2; and synthesizing a final product: heating the intermediate 1 and the intermediate 2 in toluene to react, and performing post-treatment and column chromatography purification to obtain the probe CyB-C. The bimodal detection capability enables the probe to simultaneously distinguish the microenvironment difference between normal cells and cancer cells and monitor diseases related to viscosity abnormity.

The invention belongs to the technical field of fluorescent dyes, and particularly relates to a phenanthroline-based double-BODIPY fluorescent dye with an asymmetric structure as well as a preparation method and application of the phenanthroline-based double-BODIPY fluorescent dye. The preparation method comprises the following steps: mixing a chlorinated BODIPY derivative with 1, 10-phenanthroline-5-amino, adding palladium acetate, tri-tert-butylphosphine, potassium tert-butoxide and toluene, and carrying out a heating reflux reaction; and after the reaction is finished, cooling, reducing pressure to remove toluene, dissolving the obtained product with dichloromethane, washing, drying, concentrating, and separating and purifying through silica gel column chromatography to obtain the target dye. The unique asymmetric structure in the prepared target dye destroys the planarity and symmetry of molecules, effectively weakens the fluorescence quenching effect caused by molecular self-absorption and pi... pi accumulation, and further has relatively large Stokes shift and high solid-state luminous efficiency; good application potentials are shown in a plurality of fields such as high-performance solid-state light-emitting devices and biological probes.

The application provides a method for monitoring lipid oxidation tendency, and belongs to the technical field of fluorescent probe detection. The method utilizes the fluorescence characteristics of a BODIPY molecular probe, and through selecting a molecular probe with a specific structure, directional reaction occurs between the BODIPY molecular probe and oxygen free radicals generated by lipid oxidation at a specific pH value. The conjugated system of the BODIPY molecular probe is destroyed, the half-chlorin structure is broken, and the fluorescence color changes from red to blue-green. According to the change of the fluorescence color before and after the reaction, the visualization monitoring of the lipid oxidation tendency and spatial distribution is realized through fluorescence imaging.

The invention relates to a preparation method of a heavy-atom-free photosensitizer based on a BODIPY dye, the photosensitizer comprises a thiocarbamate light cage, not only can generate singlet oxygen (1O2) under red light irradiation, but also can release carbonyl sulfide (COS), and generates hydrogen sulfide (H2S) under physiological conditions through carbonic anhydrase catalysis. By reasonably adjusting the molecular structure, the singlet oxygen quantum yield and hydrogen sulfide release efficiency of the photosensitizer are remarkably improved. The method is the first case which is reported at present and can simultaneously activate and release the organic optical functional micromolecules of H2S and 1O2 through a single beam of red light. The strategy effectively solves the problem of dependence on oxygen in type II photodynamic therapy (PDT), and further effectively improves the effect of PDT hypoxic tumors. In in-vitro and in-vivo experiments, hydrogen sulfide gas and photodynamic synergic treatment trigger pyroptosis of cells, promote maturation of dendritic cells and stimulate antitumor immune response. Therefore, the invention provides a synergistic treatment strategy combining gas, photodynamic and immunotherapy, and has a remarkable effect in the aspect of hypoxic tumor treatment. The photosensitizer material disclosed by the invention is simple to prepare and low in cost, has a wide application prospect, and particularly provides a solution with huge potential for cancer treatment in the field of biomedicine.

The invention discloses a silver ion fluorescent probe based on pyrrolo-pyrrole aza-BODIPY as well as a preparation method and application of the silver ion fluorescent probe. The probe has a specific chemical structure, and alkynyl groups are modified at two ends of the probe. When the probe is combined with silver ions, the ultraviolet absorption spectrum of the probe has absorption peak widening and red shift within the range of 680-690nm, and meanwhile, the fluorescence emission of the probe under the excitation of 650nm is remarkably quenched, so that the specific dual-mode detection of the silver ions is realized. The probe shows high selectivity and high sensitivity on silver ions, the detection limit can reach the nanomole level, the anti-interference capability is high, and the probe can work in water or various organic solvents. The invention also provides a clear synthetic route of the fluorescent probe. The probe is suitable for rapid and sensitive detection of silver ions in environmental or biological samples.

The subject invention pertains to compositions of a probe comprising two pH-reversible forms, including the boron dipyrromethene (BODIPY) fluorescent form and the non-fluorescent leuco-BODIPY form, for use in confocal imaging methods of intracellular vesicles as well as extracellular vesicles that are present in conditioned culture medium and / or secreted by living cells, without inducing severe cytotoxicity.

This invention belongs to the field of pharmaceutical synthesis technology, and relates to meta-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods, and pharmaceutical uses, specifically meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods, and applications. The compounds of this invention, through photosensitization efficiency and in vitro and in vivo antibacterial activity tests, demonstrate good antibacterial activity and can be used to prepare novel pyridine quaternary ammonium salt-containing fluoroboron dipyrrole (BODIPY) photosensitizers, and further to prepare new antibacterial drugs.

A molecular probe for selective detection of a nitrate and / or a decomposition product of a nitrate by generating a fluorescence signal in response to an excitation in the wavelength range between 340-370 and 480-520 nm, wherein the molecular probe is selected from a triarylborane dye according to formula (7) and a BODIPY™ (boron-dipyrromethene) dye according to formula (13):

The invention belongs to the technical field of medicine synthesis, and discloses a pantothenic acid modified aza-BODIPY photosensitizer, the structural general formula of the pantothenic acid modified aza-BODIPY photosensitizer is shown as a formula IV, and n is equal to 1-6; the dashed line represents the presence or absence of a C-C bond. The synthesized pantothenic acid modified aza-BODIPY photosensitizer has good photosensitive activity and cancer cell specific uptake ability, for example, the singlet oxygen yield (phi delta = 0.61-0.69) of photosensitizer compounds 1-8 is higher than that of a reference compound, and the pantothenic acid modified aza-BODIPY photosensitizer can be further prepared into targeted photodynamic drugs for photodynamic therapy of wide non-specific tumors.

The invention belongs to the technical field of preparation of antitumor drugs, and particularly relates to an activatable BODIPY photosensitizer and a preparation method and biological application thereof, and a water-soluble photosensitive probe BDP-1 is obtained by modifying a BODIPY structure with a GSH response unit and piperazine salt. The BDP-1 can be activated by GSH (glutathione) overexpressed by tumor cells, and has good biocompatibility and tumor targeting property. By modifying different functional groups, the imaging effect is better, the water solubility is better, the phototoxicity is stronger, and an excellent PDT effect on a tumor-bearing Balb / c mouse model is shown. This is due to the specific enrichment of BDP-1 on tumor sites, and the concentration of the photosensitizer in tumor tissues is improved, so that the photodynamic therapy efficiency is improved.

The invention discloses a photopolymerization composition of a series of aza-boron-fluorine dipyrrole derivatives, and belongs to the technical field of photocuring materials. In the composition, the aza-boron-fluorine dipyrrole derivative is used as a photosensitizer, has high molar extinction coefficient, excellent light stability and wide spectral response characteristic, and can realize efficient intersystem crossing and long triplet service life. After being compounded with tris (3-chloro-4-methylphenyl) hexyl tetrabutylammonium borate (NB), the acrylate monomer polymerization can be rapidly initiated under 365 nm ultraviolet light, the curing time is within 20 seconds, and the highest double bond conversion rate can reach 75%. Wherein the brominated aza-BODIPY derivative (ADP-Br) can also be efficiently polymerized under the irradiation of 620 nm red light, and the conversion rate of double bonds can be up to 50%. The photopolymerization system disclosed by the invention is high in initiation efficiency, high in curing speed and wide in application scene, and can be applied to the fields of photocureable coatings, adhesives, photoetching materials, 3D printing and the like.

The application discloses an MMP-2 responsive targeted brain glioma synergistic diagnosis and treatment and immune activation nano probe and a preparation method and application thereof, and relates to the technical field of biological medicine. The probe is formed by assembling an Angiopep-2 targeting peptide, an MMP-2 response sequence, a chemotherapeutic drug and a photosensitizer I-BODIPY, has a hydrodynamic diameter of 10-50 nm, and has excellent biocompatibility. The probe is combined with an LRP1 receptor through the Angiopep-2 to cross the blood-brain barrier, is specifically cut by MMP-2 in a tumor microenvironment to release drugs at a fixed point, integrates the functions of chemotherapy, photothermal / photodynamic therapy and fluorescence imaging, synchronously activates immunogenic cell death and paraptosis, and reshapes an anti-tumor immune microenvironment. The probe can realize precise targeting of brain glioma, synergistic diagnosis and treatment, immune activation and tumor staging evaluation, significantly prolongs the survival period of tumor-bearing mice, and provides a new scheme for glioblastoma diagnosis and treatment.

The present application belongs to the technical field of fluorescence analysis, and relates to a fluorescent dye used for fluorescence analysis, in particular to a fluorescent dye with a meso amide substituted BODIPY structure, a preparation method and application. Especially, it relates to a meso amide substituted 1,3,5,7-tetramethyl-BODIPY compound, and anti-quenching characteristics and application in biological imaging. The compound has excellent amphiphilicity, certain anti-water quenching ability, high fluorescence quantum yield in organic solvents and water, and can be used for fluorescence labeling, biological imaging and development of new fluorescent probes. The fluorescent dye with the meso amide substituted BODIPY structure has the following skeleton structure (I):

The application discloses a novel BODIPY-based near-infrared ratio fluorescent probe for targeted detection of endoplasmic reticulum hypochlorous acid and a preparation method and application thereof. The fluorescent probe is 4-((4-(3,7-di(2-(10-butyl-10H-phenothiazine-3-yl)vinyl)-1,9-dimethyl-5H-4-(dipyrromethene difluoroboron-10-yl)phenoxy)methyl)benzenesulfonamide, which is abbreviated as PTB-BSA. The probe PTB-BSA can specifically recognize hypochlorous acid, and the color of the probe PTB-BSA solution added with hypochlorous acid rapidly changes from green to dark blue under sunlight. In addition, the fluorescence emission spectrum of the probe PTB-BSA is obviously blue-shifted, and the fluorescence emission wavelength is shifted from 752 nm to 681 nm. The linear range of the probe for hypochlorous acid is 0-60 muM, the detection limit is as low as 35 nM, and the response time is within 10 s. The probe exhibits good selectivity for hypochlorous acid, and is not affected and interfered by other anions, biological thiols and active oxygen. More importantly, the probe can also target the endoplasmic reticulum, and can realize organelle-level detection of the content of hypochlorous acid. This has very important significance for in-depth study on the action process of hypochlorous acid in a biological body.

The invention provides a cross-linked porous polymer for detecting tryptamine and a preparation method and application thereof.The cross-linked porous polymer comprises a BODIPY fluorescent component and a triphenylamine electron withdrawing component and has a pore channel structure, a large specific surface area and an extended pi conjugated system, and the BODIPY fluorescent component and the triphenylamine electron withdrawing component are connected through alkynyl. In the preparation method, the pore size distribution of the material can be regulated and controlled through a reaction solvent, so that the adsorption and enrichment capacity on a target analyte is improved, and meanwhile, the mass transfer and diffusion rate of the analyte in the material is increased. The unique extended pi conjugated skeleton structure can improve the fluorescence signal change amplitude before and after target detection, and the three-dimensional covalent cross-linked network endows the material with excellent chemical / light stability. The fluorescent sensing material organically combines three functions of adsorption enrichment, signal amplification and good stability, and realizes high-sensitivity, rapid and stable detection of tryptamine.

The invention discloses a method for constructing a near-infrared first-zone boron-dipyrromethene dye conjugate through a Knoevenagel condensation reaction and a preparation method of the near-infrared first-zone boron-dipyrromethene dye conjugate. According to the method, 5, 5-difluoro-1, 3, 7, 9-tetramethyl-10-(trifluoromethyl)-5H-4 lambda, 5 lambda-dipyrrolo [1, 2-c: 2 ', 1'-f] [1, 3, 2] diazaborocyclohexane meso-CF3-BODIPY is taken as a raw material, 5-hydroxyindole-3-formaldehyde or 3-indoleformaldehyde or 6-hydroxyindole-3-formaldehyde is taken as a reactant, acetic acid and piperidine are taken as catalysts, and 1, 4 dioxane is taken as a solvent, so that the meso-CF3-BODIPY conjugate is prepared. The method has the advantages of mild reaction conditions, easily available raw materials and excellent yield, and provides a new method for synthesizing the BODIPY conjugate.

This invention provides a method for quantitative analysis of intracellular lipid content based on the Bodipy 493 / 503 fluorescent probe, relating to the field of lipid metabolism detection technology. The method includes: (1) determining the absorption spectrum and excitation / emission spectrum of Bodipy 493 / 503 in isopropanol, and determining the maximum absorption wavelength and maximum excitation / emission wavelength of the fluorescent probe in isopropanol based on the spectral results; (2) staining the target cells with the Bodipy 493 / 503 probe after treatment with the compound, observing the changes in fluorescence signal in the field of view before and after isopropanol extraction, and taking pictures; (3) measuring the absorbance and fluorescence intensity of the isopropanol extract, analyzing the experimental results, and comparing them with the results of triglyceride content detection. This quantitative method is simple, fast, sensitive, effective, and has good experimental controllability and repeatability. The analytical results obtained are consistent with those obtained using other lipid content analysis methods, and it can be of great application in the field of research on the lipid metabolism interference effects of chemicals or environmental pollutants.

The invention discloses a polygonal anthracene functionalized BODIPY supramolecular metal ring compound as well as a preparation method and application thereof, and belongs to the technical field of supramolecular materials, the polygonal anthracene functionalized BODIPY supramolecular metal ring compound is obtained by self-assembly reaction of an anthracene functionalized BODIPY photosensitizer with a specific structure and a platinum compound; by selecting platinum compounds with different coordination included angles, triangular, quadrilateral and hexagonal supramolecular metal ring compounds are respectively prepared. Furthermore, amphiphilic polymer F127 is used for wrapping the supramolecular metal ring compound to form water-soluble nanoparticles, so that phototherapy and chemotherapy combined therapy of hypoxic tumors can be realized, and the amphiphilic polymer F127 has a wide application prospect in the aspects of biological imaging and tumor therapy.

Embodiments of the disclosure include methods and compositions related to use of compound comprising a particular peptide linked to a dye. In specific embodiments, the peptide DIRG is linked to the BODIPY dye. In specific embodiments, the compositions are utilized for treatment of neurological conditions and secondary pathologies related therewith, such as spinal cord injury and Alzheimer's Disease, as examples.

The application discloses a compound Cl-BODIPY used as a fluorescent probe for rapid nondestructive detection of food freshness, and also establishes a corresponding preparation method and detection method. The probe produces a color and fluorescent dual optical signal change through specific interaction of a recognition group with volatile biogenic amines, and provides a simple and convenient detection method for rapid detection of volatile biogenic amines. The fluorescent probe is simple to prepare, low in cost, and has the characteristics of high sensitivity, high selectivity and rapid response, can in-situ rapidly detect volatile biogenic amines produced by fish and meat food spoilage, and judges the freshness (biogenic amine content) of fish and meat through colorimetric and fluorescent dual visual signal changes, thereby providing an effective means for rapid nondestructive detection of food freshness, having great application prospect and great popularization significance.

The invention provides a ring tension-regulated near-infrared BODIPY dye as well as a preparation method and application thereof, and belongs to the technical field of organic light-emitting functional materials, the ring tension-regulated near-infrared BODIPY dye has a structure as shown in a formula (I),

The invention provides a fluorescence labeling reagent for lipoprotein subtype detection and a preparation method and application, and belongs to the technical field of biological detection.The fluorescence labeling reagent comprises a fluorescent dye and a stabilizer, the fluorescent dye is a sulfonated derivative of BODIPY 505 / 515, and the sulfonated derivative of BODIPY 505 / 515 is compounded and optimized through the fluorescent dye and the stabilizer. The binding specificity and attenuation resistance of the labeling reagent and lipoprotein are remarkably improved, and the advantages of improving the low-concentration detection precision, reducing the influence of background interference and being slightly influenced by environment temperature are achieved; compared with a traditional probe, the fluorescence labeling probe provided by the invention does not have a high-concentration quenching phenomenon, so that the upper limit of lipoprotein detection is remarkably improved, the problem of light intensity distortion caused by fluorescence attenuation and sample diffusion is solved, and rapid and high-sensitivity labeling and quantitative analysis are realized.

The invention belongs to the field of medicinal chemistry, and discloses a red-light-started light cage dihydrotetrazine compound or a preparation method and application thereof. In particular to a light cage dihydrotetrazine compound containing dipyrromethene boron (BODIPY) or anthocyanin (CYANINE) or pharmaceutically acceptable salt of the light cage dihydrotetrazine compound, a preparation method of the light cage dihydrotetrazine compound, a pharmaceutical composition containing the light cage dihydrotetrazine compound and pharmaceutical application of the light cage dihydrotetrazine compound. The compound provided by the invention can generate tetrazine under red light starting, overcomes the problems of high toxicity of short-wavelength ultraviolet light and blue light to organisms and poor tissue penetrability, provides a new tool for time-space controllable precise drug delivery and biomarker research, and has wide clinical application prospects.

This invention relates to the field of organic synthesis technology, and particularly to a dual-fluorescent probe for Bodipy and NBD, its synthesis method, and its application. The method includes: first, synthesizing NBD coumarin compound 6; then, using nitrobenzaldehyde f and dimethylpyrrole as starting materials, undergoing a four-step one-pot cascade reaction with catalytic amounts of trifluoroacetic acid, DDQ oxidation, and excess triethylamine and Lewis acid boron trifluoride diethyl ether to obtain the fluorescent compound Bodipy h; finally, subjecting the fluorescent compound Bodipy h to reduction and acylation to obtain Bodipy fluorescent probe 8; and finally, after lithium hydroxide demethylation of Bodipy fluorescent probe 8 to obtain a carboxylic acid, which is then amidated with the deBoc-protected NBD compound 6 by trifluoroacetic acid to obtain the target product, dual-fluorescent probe 9. This invention anticipates that the fluorescence of coumarin and naphthalimide, through this dual quenching process, can efficiently achieve the quenching strategy, and can be applied to the simultaneous detection of H2S and hNQO1 in vivo or in vitro.