30 results about "Dioxetane" patented technology

The application provides a chemical luminescence substrate with high chemical luminescence intensity, long wavelength and good stability, and a preparation method and application thereof. The chemical luminescence substrate has a structure shown in formula I. In addition, the application provides spontaneous fluorescence wavelength and intensity of the chemical luminescence probe in a physiological environment, and application of the chemical luminescence probe in in-vivo imaging. Test results show that the chemical luminescence probe provided in the application has long-wavelength spontaneous fluorescence (600 nm), can effectively penetrate skin tissue, has high spontaneous fluorescence intensity (> 10 7 p / s / cm 2 / sr), excellent thermal stability (without 1,2-dioxetane structure) and diversified detection groups (suitable for different detection models).

This invention discloses a microRNA-responsive 1,2-dioxane-based chemiluminescent compound, its dual-probe system, kit, synthesis method, and applications. The compound's core is an o-acrylate-substituted phenoxyadamantane-1,2-dioxane, with the phenolic hydroxyl group protected by an azide benzyl group. The two-component probe system constructed based on this compound comprises an azide-modified first probe and a phosphine-modified second probe, each complementary to different segments of the target microRNA. Hybridization brings the two probes closer, triggering a Staudinger reaction to remove the protecting group and activate the chemiluminescent signal. This probe system requires no enzyme amplification or nucleic acid extraction, achieves a detection limit of 1.37 fM, and a signal-to-noise ratio as high as 157-fold. It can be successfully used for real-time imaging of endogenous microRNA-21 in live cells, showing broad application prospects in early tumor screening, auxiliary diagnosis, and prognostic assessment.

The invention relates to synthesis and anti-tumor application of a nitroreductase activated camptothecin chemiluminescent prodrug. The prodrug molecule (CPT-NBz-CL) integrates three key functional units through a 2, 6-hydroxymethyl p-cresol derived self-burning group: (i) a nitrobenzene group (NBz) as a nitroreductase (NTR) specific trigger; (ii) a potent chemotherapeutic drug camptothecin (CPT) as a cytotoxic load; (iii) a Schaap type phenolic group-dioxetane structure is used as a chemiluminescence reporter group (CL), and the structure is shown as a formula (I). In order to carry out comparative research, a control molecule CL-NBz-CL which lacks a CPT load but retains a trigger and a reporter group is synchronously synthesized. The structures and optical properties of the two molecules are comprehensively characterized through analysis means such as nuclear magnetic resonance hydrogen spectrum, carbon spectrum, absorption spectrum, fluorescence spectrum and luminescent spectrum, and the molecules can verify that the molecules have specific detection capability on NTR through chemiluminescence, fluorescence spectrum, selectivity and the like in vitro.

The invention discloses a microRNA (Ribonucleic Acid) response type 1, 2-dioxetane chemiluminescent compound as well as a double-probe system, a kit, a synthesis method and application thereof. The parent nucleus of the compound is o-acrylate substituted phenoxy adamantane-1, 2-dioxetane, and a phenolic hydroxyl group is protected by an azido benzyl group. A two-component probe system constructed based on the compound comprises a first azide-modified probe and a second phosphino-modified probe, the first azide-modified probe and the second phosphino-modified probe are respectively complementary with different sections of target microRNA, the two probes are pulled close through hybridization, a schudinger reaction is triggered to remove a protecting group, and a chemiluminescence signal is activated. The probe system does not need enzyme amplification and nucleic acid extraction, the detection limit reaches 1.37 fM, the signal-to-noise ratio reaches up to 157 times, and the probe system can be successfully used for real-time imaging of living cell endogenous microRNA-21 and has wide application prospects in the fields of early tumor screening, auxiliary diagnosis and prognosis evaluation.

The application belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of a darunavir intermediate (3aS, 4S, 6aR)-4-methoxytetrahydrofuro[3,4-b]furan-2(3H)-one. The application takes 5-(methyloxy)2-(5H)-dioxetane as a raw material, and synthesizes the darunavir intermediate compound formula I {(3aS, 4S, 6aR)-4-methoxytetrahydrofuro[3,4-b]furan-2(3H)-one} through two-step reactions of condensation and radical ring closure, has a purity of greater than 98.5%, has a high yield, is a low-cost and simple-to-operate synthesis method, and is suitable for large-scale commercial production.

The invention discloses a dioxetane chemiluminescent probe suitable for a biological orthogonal catalytic reaction as well as synthesis and application of the dioxetane chemiluminescent probe. A phenolic hydroxyl group active site of the probe is protected by an allyl bio-orthogonal cleavable group, and when a ruthenium metal complex catalyst is not added, the probe is in a silence state, and a chemiluminescence signal is weak; and in the presence of the ruthenium catalyst, the protecting group can be specifically catalytically cracked and removed, so that the probe is quickly activated and converted into a luminous'on 'state, and a strong chemiluminescence signal is generated. According to the invention, efficient combination of biological orthogonal cutting reaction and chemiluminescence signal output is realized, and the prepared biological orthogonal chemiluminescence probe has an excellent on-off ratio and is suitable for high-contrast biological imaging of living cell and living body levels.

Described herein are 1,2-dioxetane dimers that are useful as chemiluminescent probes, diagnostic agents, and imaging agents. Also described herein are compositions containing such compounds and methods of using the same.

The invention provides a 1, 2-dioxetane derivative as well as a preparation method and application thereof, and belongs to the technical field of chemiluminescent substrates. The 1, 2-dioxetane derivative provided by the invention has high luminous efficiency and good stability. The result of the embodiment shows that the time required by the 1, 2-dioxetane derivative provided by the invention to reach the maximum luminescence peak value at 25 DEG C is only 5-30 minutes, and the continuous luminescence time can reach 70 minutes.

The present invention provides phenoxy-dioxetane-based chemiluminescence probes having enhanced chemiexcitation and chemical stability, in which either an adamantyl derivative equipped with a hetero -functional group or a six-member carbocyclic or heterocyclic ring having an electron-withdrawing motif is spiro fused to the dioxetane. The chemiluminescence probes disclosed are useful for both diagnostics and in vivo imaging.

The invention relates to the technical field of immunoassay, and discloses a chemiluminescence immunoassay method for high-sensitivity detection of cardiac troponin I. The chemiluminescence immunoassay method comprises the following steps: fixing an anti-cardiac troponin I capture antibody based on a solid phase carrier; a sample to be detected is in contact with the solid phase carrier coated with the capture antibody, a detection antibody is added, the detection antibody is connected with a signal marker, and the signal marker is a compound formed by loading alkaline phosphatase on a nano material or is the nano material; a chemiluminescent substrate is added, and the chemiluminescent substrate is a compound based on 1, 2-dioxetane; detecting a chemiluminescence signal so as to quantify cardiac troponin I; according to the invention, the problem of non-uniform detection of degradation fragments is solved, and the diagnosis window period is prolonged; meanwhile, extremely high detection sensitivity, signal-to-noise ratio and stability are realized, and the kit is suitable for early and accurate diagnosis of myocardial injury.

This invention relates to a class of dihydroxanthine chemiluminescent groups, their preparation methods, and applications. The dihydroxanthine chemiluminescent group developed in this invention, compared to the traditional phenolic dioxane chemiluminescent group which uses two rigid six-membered rings to fix the double bond conformation, exhibits a higher luminescence quantum yield and a longer emission wavelength. More importantly, it possesses a reactive aldehyde group, which, while maintaining high rigidity, extends the π-electron conjugated system, causing its emission wavelength to redshift to the near-infrared region. This allows it to be extended to chemiluminescence detection and in vivo imaging in small animal models.

The presently claimed and described technology provides methods for chemiluminescence-based assays employing 1,2 dioxetane compounds. In some instances, the analyte is cardiac troponin I (TNI), Thyroid-stimulating Hormone (TSH), or procalcitonin (PCT). Methods disclosed herein comprise: exposing a biological sample to a capture antibody configured to bind to at least one portion of an analyte disclosed herein generating a first reaction mixture; exposing the first reaction mixture to an enzyme-conjugated affinity molecule, forming a second reaction mixture; exposing the second reaction mixture to a substrate formulation comprising a 1,2 dioxetane compound disclosed herein; wherein the reaction between the enzyme-conjugated affinity molecule and the substrate formulation generates a chemiluminescent detection signal; recording the detection signal generated by the reaction; and comparing the recorded signal to a calibration curve to quantify the level of the analyte in the biological sample.

The present invention provides dioxetane-based chemiluminescence probes, more specifically fluorophore-tethered dioxetane-based chemiluminescence probes and compositions thereof. The chemiluminescence probes disclosed are useful for both diagnostics and in vivo imaging.

The invention designs and synthesizes a small molecule probe which has an adamantane-dioxetane structure, and when the probe encounters esterase (such as acetylesterase, butyryl esterase or capryloyl esterase), adamantane-1, 2-dioxetane is rapidly degraded into a stable methyl ester structure and adamantanone, and meanwhile, light is released, so that the probe can be used for rapidly detecting the content of the adamantane-1, 2-dioxetane. The activity level of the biological enzyme is detected by monitoring the luminous intensity change of the reaction system, and the method can be used for detecting various microorganisms. And the small-molecule probe has the characteristics of high sensitivity and strong anti-interference performance, and has a relatively good application prospect.

The invention relates to a chemiluminescence substrate solution and a chemiluminescence detection method. The chemiluminescent substrate liquid comprises a chemiluminescent substrate, fluorescein and a water-soluble polymer quaternary ammonium salt, wherein the chemiluminescent substrate is selected from a chlorinated dioxetane compound with a spiro-adamantane substituent group. The chemiluminescent substrate solution has a wider linear detection range.

The presently claimed and described technology provides methods for chemiluminescence-based assays for detecting interferon-gamma (IFN-γ) in a biological sample employing a dioxetane compound.

The invention provides an ONOO <-> specific response chemiluminescent small-molecule probe as well as a preparation method and application thereof, and relates to the technical field of application of chemiluminescent probes. The light-emitting small molecule probe is named as CL-P, and a diphenyl phosphonate structure is used as an ONOO <-> response site; schap's dioxetane emitting 550nm is used as a chemiluminescent donor molecule, and the Schap's dioxetane and the Schap's dioxetane are linked together through an ether bond to obtain the chemiluminescent material. According to the probe, specific response and detection of ONOO <-> in vitro and in cells are realized by using a biologically responsive chemiluminescence signal for the first time, lung enrichment in APAP-induced mouse liver injury and lung injury diseases is realized, and specific response imaging of high-expression ONOO <-> is realized. The probe can also realize in-vivo responsive chemiluminescence imaging of ONOO <-> molecules of other lung diseases.

The presently claimed and described technology provides methods for chemiluminescence-based assays for detecting p24 antigen in a biological sample employing 1,2 dioxetane compounds.

The present disclosure relates to a chemiluminescent substrate solution and a chemiluminescence detection method. The chemiluminescent substrate solution includes a chemiluminescent substrate, a fluorescein, and a water-soluble polymeric quaternary ammonium salt, wherein the chemiluminescent substrate is selected from chlorinated dioxetane compounds with a spiroadamantane substituent. The chemiluminescent substrate solution has a wider linear detection range.

Polymers and copolymers and compositions containing one or more such polymers and copolymers. The polymers and copolymers comprise two or more glycolaldehyde dimers of different structures as monomer units. Exemplary dimers are 2, 5-dihydroxy-1, 4-dioxane, (1, 2-hydroxyethoxy) acetaldehyde, 2-(hydroxymethyl)-1, 3-dioxolane-4-ol, 1, 1 '-oxybis (ethane-1, 2-diol), 2, 2'-oxybis (ethane-1, 1-diol), (1, 3-dioxetan-2, 4-diyl) dimethanol, and 2, 2 '-oxydiacetaldehyde. Copolymers containing two or more glycolaldehyde dimers have improved optical and mechanical properties.

The presently claimed and described technology provides methods for chemiluminescence-based assays for detecting phosphorylated tau (p-tau)217 in a biological sample employing 1,2 dioxetane compounds.

Polymer and copolymers and compositions containing one or more of such polymers and copolymers. Polymers and copolymers comprise two or more structurally different glycolaldehyde dimers as monomer units. Exemplary glycolaldehyde dimers are 2,5-dihydroxy-1,4-dioxane; (1,2-hydroxyethoxy) acetaldehyde; 2-(hydroxymethyl)-1,3-dioxolan-4-ol; 1,1′-oxydi(ethane-1,2-diol); 2,2′-oxydi(ethane-1,1-diol); (1,3-dioxetane-2,4-diyl)dimethanol; and 2,2′-oxydiacetaldehyde). Copolymers containing one or more glycolaldehyde dimers and a second monomer that is not a glycolaldehyde dimer are also provided. Copolymers exhibit improved optical and mechanical properties.

The invention belongs to the technical field of micromolecular chemiluminescent materials, and particularly relates to a hydrogen sulfide activated chemiluminescent probe as well as a preparation method and application thereof. The chemiluminescent probe disclosed by the invention is an adamantane-dioxetane chemical compound and has five types in total, and the five types are respectively marked as HS-CL, HS-CL-TCF, HS-CL-TCCH, HS-CL-QM or HS-CL-DCMC. The chemiluminescent probe can be used for detecting hydrogen sulfide, including measuring hydrogen sulfide generated by hydrolysis of beta-lactamase and beta-lactam drugs, distinguishing drug-resistant bacteria from drug-sensitive bacteria and the like.

Described herein are 1, 2-dioxetane useful as chemiluminescent probes, diagnostic agents, and imaging agents. Compositions containing such compounds and methods of use thereof are also described herein.

Described herein are 1,2-dioxetane dimers that are useful as chemiluminescent probes, diagnostic agents, and imaging agents. Also described herein are compositions containing such compounds and methods of using the same.

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a dioxetane-containing gold (III) complex as well as a preparation method and application thereof. The dioxetane-containing gold (III) complex provided by the invention can selectively release active gold in tumor cells under the condition of high-concentration GSH (glutathione), and the active gold can further react with GSH and other sulfydryl-containing molecules or proteins to inhibit the activity of the molecules or proteins and generate a strong anti-tumor effect; besides, the gold (III) complex provided by the invention can realize a good anti-tumor effect without using other prodrug activation strategies such as illumination activation or palladium-catalyzed biological orthogonal metallization reaction, and shows excellent inhibitory activity on various cancer cell lines; the compound has a wide application prospect in preparation of medicines for preventing and / or treating cancers.

The invention discloses an enzyme targeted response type glycoside oxetane chemiluminescent reagent and application thereof in the field of tumor imaging. A phenol adamantane 1, 2-dioxetane functional group is structurally modified, a specific biological enzyme response group and a benzyl fluorine bridging group are introduced, an enzyme digestion reaction is performed to leave a fluorine group to generate an ortho-quinone methyl intermediate, the ortho-quinone methyl intermediate and biological macromolecules such as serum protein are further bonded to form a compound, and then strong chemiluminescence is generated. The chemiluminescence real-time tracking specific enzyme function is realized, and the chemiluminescence real-time tracking specific enzyme function is applied to tracking of diseases with abnormal specific enzyme function, and has important application potential in the fields of tumor imaging, tumor operation excision visualization and the like.

The invention relates to a method of making a 1,2-dioxetane, the method comprising reacting a naphthalene endo peroxide (NEPO) with the double bond of an enol ether to form the 1,2-dioxetane. The 1,2-dioxetanes are of great commercial interest for a variety of applications, such as singlet oxygen detection, enzyme detection and pathogen (e.g., Salmonella spp. and Listeria spp.) detection.