Nitrogen Bonded Directly To The Xanthene Ring System (e.g., Rhodols, Aminofluorans, Etc.) Patents (Class 549/225)
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Publication number: 20130196362Abstract: Provided herein are improved fluorogenic compounds and probes that can be used as reagents for measuring, detecting and/or screening peroxynitrite. The fluorogenic compounds of the invention can produce fluorescence colors, such as green, yellow, red, or far-red. Also provided herein are fluorogenic compounds for selectively staining peroxynitrite in the mitochondria of living cells. Provided also herein are methods that can be used to measure, directly or indirectly, the presence and/or amount of peroxynitrite in chemical samples and biological samples such as cells and tissues in living organisms. Also provided are high-throughput screening methods for detecting or screening peroxynitrite or compounds that can increase or decrease the level of peroxynitrite in chemical and biological samples.Type: ApplicationFiled: January 30, 2013Publication date: August 1, 2013Applicant: THE UNIVERSITY OF HONG KONGInventor: THE UNIVERSITY OF HONG KONG
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Patent number: 8445702Abstract: The present invention provides a metal chelator and methods that facilitate binding, detecting, monitoring and quantitating of zinc ions in a sample. The metal chelating moiety of the zinc-binding compound is an analog of the well-known calcium chelator, BAPTA (1,2-bis(2-aminophenoxy)ethane-N,N,N?,N?-tetraacetic acid), wherein the chelating moiety has been modified from a tetraacetic acid moiety to a tri- di- or monoacetic moiety. This change in acetic acid groups on the metal chelating moiety results in the selective bindings of zinc ions in the presence of calcium ions, both of which are present in biological fluids and intracellular cytosolic fluid and organelles.Type: GrantFiled: February 18, 2011Date of Patent: May 21, 2013Assignee: Life Technologies CorporationInventor: Kyle Gee
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Publication number: 20130053392Abstract: A carbonic anhydrase IX (CA IX) inhibitor which comprises a compound of general formula: R—NH—CX—NH—(CH2)n—Ar-Q-SO2—NH2 or a pharmaceutically-acceptable salt, derivative or prodrug thereof; wherein n=0, 1 or 2; Q is O or NH; X is O or S; and R comprises an organic substituent group.Type: ApplicationFiled: February 14, 2011Publication date: February 28, 2013Inventors: Peter Ebbesen, Claudlu T. Supuran, Andrea Scozzafava, Erik Olai Pettersen, Kaye Williams, Ludwig Dubois, Philippe Lambin
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Publication number: 20120172583Abstract: Novel linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye are provided. These linkers facilitate the efficient transfer of energy between a donor and acceptor dye in an energy transfer dye. One of these linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye has the general structure R21Z1C(O)R22R28 where R21 is a C1-5 alkyl attached to the donor dye, C(O) is a carbonyl group, Z1 is either NH, sulfur or oxygen, R22 is a substituent which includes an alkene, diene, alkyne, a five and six membered ring having at least one unsaturated bond or a fused ring structure which is attached to the carbonyl carbon, and R28 includes a functional group which attaches the linker to the acceptor dye.Type: ApplicationFiled: September 14, 2010Publication date: July 5, 2012Applicant: LIFE TECHNOLOGIES CORPORATIONInventors: Linda G. Lee, Sandra L. Spurgeon, Barnett B. Rosenblum
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Publication number: 20120121536Abstract: Glucose deprivation is an attractive strategy in cancer research and treatment. Cancer cells upregulate glucose uptake and metabolism for maintaining accelerated growth and proliferation rates. Specifically blocking these processes is likely to provide new insights to the role of glucose transport and metabolism in tumorigenesis, as well as in apoptosis. As solid tumors outgrow the surrounding vasculature, they encounter microenvironments with a limited supply of nutrients leading to a glucose deprived environment in some regions of the tumor. Cancer cells living in the glucose deprived environment undergo changes to prevent glucose deprivation-induced apoptosis. Knowing how cancer cells evade apoptosis induction is also likely to yield valuable information and knowledge of how to overcome the resistance to apoptosis induction in cancer cells.Type: ApplicationFiled: March 24, 2011Publication date: May 17, 2012Applicant: OHIO UNIVERSITYInventors: Xiaozhuo Chen, Stephen Bergmeier
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Patent number: 8114904Abstract: Provided herein are compounds or fluorogenic probes which can be used as reagents for measuring, detecting and/or screening ROS or RNS such as peroxynitrite or hypochlorite. Provided also herein are methods that can be used to measure, directly or indirectly, the amount of peroxynitrite or hypochlorite in chemical samples and biological samples such as cells and tissues in living organisms. Specifically, the methods include the steps of contacting the fluorogenic probes disclosed herein with the samples to form one or more fluorescent compounds, and measuring fluorescence properties of the fluorescent compounds. Provided also herein are high-throughput screening fluorescent methods for detecting or screening peroxynitrite or compounds that can increase or decrease the level of peroxynitrite or hypochlorite in chemical and biological samples.Type: GrantFiled: April 3, 2009Date of Patent: February 14, 2012Assignee: Versitech Limited & Morningside Ventures LimitedInventors: Dan Yang, Tao Peng
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Patent number: 7985865Abstract: A compound having the formula wherein R1, Z, and the carbonyl can be comprised by a common ring, wherein R1 comprises a chromophore that absorbs light from the visible wavelength range, and wherein n is an integer of at least 12. A solid phase change ink composition is also disclosed containing a colorant comprising a chromophore that absorbs light from the visible wavelength range and has the formula wherein R1, Z, and the carbonyl can be comprised by a common ring, and wherein n is an integer of at least 12. Also disclosed is a method of forming a colorant wherein a first compound having the formula is reacted with a second compound having the formula Z(CH2)nCH3 wherein n is an integer of at least 12 to form a third compound having the formula wherein the third compound comprises a chromophore that absorbs light from the visible wavelength range.Type: GrantFiled: December 14, 2007Date of Patent: July 26, 2011Assignee: Xerox CorporationInventors: Jeffrey H Banning, Michael B. Meinhardt, Donald R Titterington, Clifford R King
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Patent number: 7704756Abstract: Fluorogenic or chromogenic dyes are useful as reporter molecules for detecting cell entry by a specific molecule.Type: GrantFiled: January 30, 2006Date of Patent: April 27, 2010Assignee: Novartis Vaccines and Diagnostics, Inc.Inventors: Daniel J. Suich, Ronald N. Zuckermann
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Patent number: 7615377Abstract: The present invention is directed, in part, to fluorescein-based ligands for detection of metal ions, and methods of making and using the same.Type: GrantFiled: August 27, 2004Date of Patent: November 10, 2009Assignee: Massachusetts Institute of TechnologyInventors: Stephen J. Lippard, Elizabeth Marie Nolan
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Patent number: 7488820Abstract: The present invention is directed, in part, to naphthofluorescein-based ligands for detection of metal ions, and methods of making and using the same.Type: GrantFiled: January 19, 2005Date of Patent: February 10, 2009Assignee: Massachusetts Institute of TechnologyInventors: Stephen J. Lippard, Christopher J. Chang, Elizabeth M. Nolan
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Publication number: 20080214811Abstract: The invention provides a novel class of xanthene dyes, some of which are functionalized to allow their coupling to conjugation partners of interest, e.g. biomolecules, drugs, toxins and the like. Also provided are conjugates of the dyes, methods of preparing and using the dyes and their conjugates and kits including the dyes and their conjugates.Type: ApplicationFiled: February 25, 2008Publication date: September 4, 2008Applicant: Biosearch Technologies, Inc.Inventors: Mark Reddington, Matt Lyttle
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Patent number: 7083667Abstract: Disclosed herein is a colorant compound represented by the following general formula (1): wherein R1 and R2 are the same or different from each other and denote a linear alkyl group having 1 to 4 carbon atoms, R3 is an alkyl group having 1 to 6 carbon atoms, and An? is a counter anion, an ink comprising the colorant compound, and an ink tank, a recording unit, a recording apparatus and a recording process comprising or using the ink.Type: GrantFiled: February 9, 2005Date of Patent: August 1, 2006Assignee: Canon Kabushiki KaishaInventors: Yasuaki Murai, Takayuki Toyoda, Takeshi Miyazaki, Yuko Yamagishi
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Patent number: 6916925Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds arc useful, inter alia, for determining the binding and/or receptor sites of the molecules.Type: GrantFiled: July 22, 2003Date of Patent: July 12, 2005Assignee: 3M Innovative Properties Co.Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
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Publication number: 20040242902Abstract: Fluorescent phenyl xanthene dyes are described that comprise any fluorescein, rhodamine or rhodol comprising a particular C9 phenyl ring. One or both of the ortho groups on the lower C9 phenyl ring is ortho substituted with a group selected from alkyl, heteroalkyl, alkoxy, halo, haloalkyl, amino, mercapto, alkylthio, cyano, isocyano, cyanato, mercaptocyanato, nitroso, nitro, azido, sulfeno, sulfinyl, and sulfino. In one embodiment, halo and/or hydroxy groups are used. Optimal dyes contain a lower C9 phenyl ring in which both ortho groups are the same and the lower ring exhibits some form a symmetry relative to an imaginary axis running from the phenyl rings point of attachment to the remainder of the xanthene dye through a point para to the point of attachment. The phenyl xanthene dyes may be activated. Furthermore, the phenyl xanthene dyes may be conjugated to one or more substances including other dyes.Type: ApplicationFiled: May 4, 2004Publication date: December 2, 2004Inventors: Joe Y.L. Lam, Steven M. Menchen, Ruiming Zou, Scott C. Benson
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Publication number: 20040101839Abstract: A compound represented by general formula (I) below; 1Type: ApplicationFiled: December 24, 2003Publication date: May 27, 2004Inventors: Hisafumi Ikeda, Isao Saito, Fumihiko Kitagawa
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Patent number: 6635602Abstract: A process for the manufacture of mixtures of fluoran compounds by the reaction of keto acids of formula (II) with a compound of formula (III) in the presence of a dehydrating condensation agent, wherein R1 and R2 independently represent hydrogen; an alkyl of 1-18 carbon, a secondary alkyl with respect to the carbon atom bonded to the nitrogen atom of 3-13 carbon atoms, a cycloalkyl of 4-8 carbon atoms or a phenyl, both of which may be substituted by at least one substituted selected from the group consisting of halogen atoms and alkyls having 1-4 carbon atoms, an aralkyl of 7-10 carbon atoms; or R1 and R2, together with the adjacent nitrogen atom from a heterocyclic ring; R3 is hydrogen, an alkyl of 1-4 carbon atoms, an alkoxy of 1-4 carbon atoms, a phenyl; a substituted phenyl or a halogen; R4 is an alkyl group of 1-18 carbon atoms, a carboxyalkyl of 1-18 carbon atoms, a carboxycycloalkyl of 4-8 carbon atoms, an alkylamino of 1-18 carbon atoms, a cycloalkylamino of 4-8 carbon atoms, a dialkylamino or dicycloType: GrantFiled: February 26, 2001Date of Patent: October 21, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: James Philip Taylor, Michael Heneghan
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Patent number: 6630588Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds are useful, inter alia, for determining the binding and/or receptor sites of the molecules.Type: GrantFiled: February 19, 2002Date of Patent: October 7, 2003Assignee: 3M Innovative Properties CompanyInventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
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Publication number: 20030171600Abstract: A compound represented by the following formula (I): 1Type: ApplicationFiled: April 14, 2003Publication date: September 11, 2003Applicant: Daiichi Pure Chemicals Co., Ltd.Inventors: Tetsuo Nagano, Hirotatsu Kojima
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Publication number: 20030055243Abstract: Atropisomeric energy-transfer dye compounds are disclosed. A variety of molecular biology applications utilize atropisomeric xanthene fluorescent dyes as labels for substrates such as nucleotides, nucleosides, polynucleotides, polypeptides and carbohydrates. Methods include DNA sequencing, DNA fragment analysis, PCR, SNP analysis, oligonucleotide ligation, amplification, minisequencing, and primer extension.Type: ApplicationFiled: August 21, 2002Publication date: March 20, 2003Applicant: PE Corporation (NY)Inventors: Linda G. Lee, Meng C. Taing, Barnett B. Rosenblum
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Patent number: 6482938Abstract: Disclosed are compounds having two kinds of reporters that can be a donor and an acceptor for energy transfer, for example, fluorescent groups, and having a 2′, 3′-dideoxyribonucleotide residue or a 3′-deoxyribonucleotide residue. These compounds can be used as terminators for the chain terminator method. The two kinds of reporters are arranged with a distance sufficient for causing energy transfer from the donor to the acceptor. Also disclosed are methods for determining DNA sequences based on the chain terminator method wherein the chain termination reaction is performed by using the above terminators. Also disclosed are compounds having two kinds of reporters that can be a donor and an acceptor for energy transfer, which can be used as a primer or an initiator in methods for determining DNA sequences utilizing the chain terminator method, and methods for determining DNA sequences utilizing the compounds.Type: GrantFiled: September 17, 1999Date of Patent: November 19, 2002Assignees: Wako Pure Chemical Industries, Ltd., The Institute of Physical & Chemical ResearchInventors: Yoshihide Hayashizaki, Takumi Tanaka
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Publication number: 20020147348Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodamines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.Type: ApplicationFiled: April 10, 2001Publication date: October 10, 2002Inventors: Rajnish Batlaw, Patrick D. Moore
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Patent number: 6452020Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodamines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.Type: GrantFiled: April 10, 2001Date of Patent: September 17, 2002Assignee: Milliken & CompanyInventors: Rajnish Batlaw, Patrick D. Moore
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Publication number: 20020115092Abstract: Mechanically linked energy transfer labels comprising at least one donor fluorophore, at least one acceptor fluorophore, and at least one support member, wherein steric interactions between the donor fluorophore(s), the acceptor fluorophore(s), and/or the support member(s) induce non-covalent association between the fluorophores and the support member(s), thereby forming a three-dimensional macromolecular structure which mechanically links the donor fluorophore(s) and the acceptor fluorophore(s). Fluorescence resonance energy transfer (FRET) occurs from donor fluorophore to acceptor fluorophore through space. No direct connectivity with covalent bonds exists between the fluorophores. Instead, mechanical barriers hold the donor/acceptor fluorophores in place during the FRET process.Type: ApplicationFiled: November 8, 2001Publication date: August 22, 2002Applicant: The Scripps Research InstituteInventor: Julius Rebek
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Patent number: 6403812Abstract: Long wavelength, narrow emission bandwidth fluorecein dyes are provided for detecting spacially overlapping target substances. The dyes comprise 4,7-dichlorofluoresceins, and particularly 2′,4′,5′,7′-tetrachloro-4,7-dicloro-5- (and 6-) carboxyfluoresceins. Methods and kits for using the dyes in DNA analysis are provided.Type: GrantFiled: May 30, 2000Date of Patent: June 11, 2002Assignee: The Perkin-Elmer CorporationInventors: Steven M. Menchen, Linda G. Lee, Charles R. Connell, N. Davis Hershey, Vergine Chakerian, Sam L. Woo, Steven Fung
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Patent number: 6376669Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds are useful, inter alia, for determining the binding and/or receptor sites of the molecules.Type: GrantFiled: November 2, 2000Date of Patent: April 23, 2002Assignee: 3M Innovative Properties CompanyInventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
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Patent number: 6162610Abstract: Xanthan esters and acridans are substrates for horseradish peroxidase. These stable, enzymatically cleavable chemiluminescent esters are substrates for horseradish peroxidase which, together with peroxide is among the extensively used enzyme in enzyme-linked detection methods, including immunoassays, oligonucleotide detection and nucleic acid hybridization. The novel compounds are used, together with peroxide, alkali and the peroxidase, to indicate the presence and/or concentration of target compounds. The assays may be enhanced by the use of polymeric quaternary onium enhancement compounds or similar compounds selected to enhance the chemiluminescence emitted.Type: GrantFiled: September 11, 1998Date of Patent: December 19, 2000
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Patent number: 6162931Abstract: The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.Type: GrantFiled: April 12, 1996Date of Patent: December 19, 2000Assignee: Molecular Probes, Inc.Inventors: Kyle R. Gee, Martin Poot, Dieter H. Klaubert, Wei-Chuan Sun, Richard P. Haugland, Fei Mao
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Patent number: 6130101Abstract: The present invention describes xanthene dyes, including rhodamines, rhodols and fluoresceins that are substituted one or more times by a sulfonic acid or a salt of a sulfonic acid. The dyes of the invention, including chemically reactive dyes and dye-conjugates are useful as fluorescent probes, particularly in biological samples.Type: GrantFiled: September 23, 1997Date of Patent: October 10, 2000Assignee: Molecular Probes, Inc.Inventors: Fei Mao, Wai-Yee Leung, Richard P. Haugland
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Patent number: 6071853Abstract: Disclosed are a novel crystal form of the fluoran compound represented by formula (I) as characterised by specific X-ray powder diffraction pattern and melting range; process for the preparation of said novel crystal form and recording materials comprising the said crystal form.Type: GrantFiled: November 24, 1998Date of Patent: June 6, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Roy Alan Kirk, Jonathon Gawtrey, Michael Heneghan, John Whitworth, Ian Antony Dearden, James Philip Taylor, John Barry Henshall
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Patent number: 5739078Abstract: By using the fluoran compound represented by the following general formula (I); ##STR1## wherein R.sup.1 is alkyl containing 1 to 4 carbon atoms, R.sup.3 is alkyl containing 1 to 8 carbon atoms, R.sup.4 is hydrogen or alkyl containing 1 to 8 carbon atoms, or R.sup.3 and R.sup.4 may bond with each other to form a ring together with a N atom, R.sup.2 is alkyl containing 1 to 4 carbon atoms, and n denotes 0, 1 or 2, however, the substituents represented by R.sup.2 may be different with each other when n is 2, as a color former for color forming recording materials, recording materials which have excellent properties in whiteness of the background of the material under light and in photostability of color-formed images on the materials as well as in sufficient color forming capability of the material even after having exposed them to light, can be provided.Type: GrantFiled: August 22, 1996Date of Patent: April 14, 1998Assignee: Nippon Soda Co., Ltd.Inventors: Mitsuhiro Yanagita, Takehiro Sato, Shigemi Suga, Tomoya Hidaka, Toru Kawabe, Mamoru Aizawa, Shinichi Sato, Izuo Aoki
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Patent number: 5721355Abstract: Compounds useful to attach a fluorescein label to an oligonucleotide are disclosed. To create these compounds, oxygen groups on the fluorescein moiety are protected (e.g. with acyl groups). One then links a phosphoramidite to the fluorescein moiety via an amide or thiourea linkage to an active site on the fluorescein ring. The resulting compound can then be directly linked to an oligonucleotide as it is being formed in an automated synthesizer and then deprotected using the same deprotection conditions as are used to deprotect the oligonucleotides. Such compounds are, inter alia, useful to create labelled primers for DNA sequencing.Type: GrantFiled: June 25, 1996Date of Patent: February 24, 1998Assignee: Pharmacia Biotech Inc.Inventor: Charles K. Brush
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Patent number: 5654442Abstract: Long wavelength, narrow emission bandwidth fluorecein dyes are provided for detecting spacially overlapping target substances. The dyes comprise 4,7-dichlorofluoresceins, and particularly 2',4',5',7'-tetrachloro-4,7-dichloro-5- (and 6-) carboxyfluoresceins. Methods and kits for using the dyes in DNA analysis are provided.Type: GrantFiled: March 8, 1995Date of Patent: August 5, 1997Assignee: The Perkin-Elmer CorporationInventors: Steven M. Menchen, Linda G. Lee, Charles R. Connell, N. Davis Hershey, Vergine Chakerian, Sam L. Woo, Steven Fung
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Patent number: 5583236Abstract: Compounds useful to attach a fluorescein label to an oligonucleotide are disclosed. To create these compounds, oxygen groups on the fluorescein moiety are protected (e.g. with acyl groups). One then links a phosphoramidite to the fluorescein moiety via an amide or thiourea linkage to an active site on the fluorescein ring. The resulting compound can then be directly linked to an oligonucleotide as it is being formed in an automated synthesizer and then deprotected using the same deprotection conditions as are used to deprotect the oligonucleotides. Such compounds are, inter alia, useful to create labelled primers for DNA sequencing.Type: GrantFiled: December 2, 1994Date of Patent: December 10, 1996Assignee: Pharmacia Biotech Inc.Inventor: Charles K. Brush
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Patent number: 5395948Abstract: The invention relates to fluoran colour formers having improved fastness to sublimation and migration stability, to their preparation, to pressure-sensitive and heat-sensitive recording materials containing said compounds and to their preparation. The fluorans have the formula (I) as defined in claim 1.Type: GrantFiled: March 10, 1993Date of Patent: March 7, 1995Assignee: Ciba-Geigy CorporationInventor: Rudolf Zink
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Patent number: 5380629Abstract: This invention provides a process for preparing a bleach accelerator silver salt dispersion by precipitating a salt of a bleach accelerating compound and a silver salt wherein the vAg is maintained at a predetermined level during the precipitation. This invention further provides a photographic element containing a dispersion of grains of a bleach accelerator silver salt wherein the grains are isomorphic or derived from needle or platelet isomorphic crystals.Type: GrantFiled: March 30, 1993Date of Patent: January 10, 1995Assignee: Eastman Kodak CompanyInventor: Benjamin T. Chen
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Patent number: 5372949Abstract: The present invention is directed to a fluorescence polarization immunoassay for determining the 3-methoxy-4-hydroxyphenylglycol content in body fluids, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for preparing them. The assay is conducted by measuring the degree of polarization of plane polarized light that has been passed through a sample containing antiserum and tracer.Type: GrantFiled: September 3, 1992Date of Patent: December 13, 1994Assignee: Abbott LaboratoriesInventors: Christine H. Zeitvogel, Maciej B. Adamczyk, David A. Betebenner, Kenward S. Vaughan
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Patent number: 5371241Abstract: Compounds useful for attaching a fluorescein label to an oligonucleotide are disclosed. The compounds are fluorescein-linked phosphoramidites where the hydroxyl groups on the fluorescein moiety are protected by isobutyryl groups.Type: GrantFiled: July 19, 1991Date of Patent: December 6, 1994Assignee: Pharmacia P-L Biochemicals Inc.Inventor: Charles K. Brush
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Patent number: 5315015Abstract: Compounds of the formula ##STR1## wherein F is a fluorescing compound; Y is --NH-- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.Type: GrantFiled: November 10, 1992Date of Patent: May 24, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Raymond A. Hui, Kathryn S. Schwenzer
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Patent number: 5310916Abstract: Trifunctional agents useful as inhibitors of A.sub.1 -Adenosine receptors may be formulated into pharmaceutical compositions. These agents are represented by formula (I): ##STR1## wherein X is CH or N, R is an isothiocyanate group, an amino group or --NHCO.sub.2 C(CH.sub.3).sub.3 and R.sup.1 is hydrogen, carboxyl, lower alkoxycarbonyl, aminocarbonyl, ##STR2## lower alkyl, optionally substituted with: --OH, --COOH, lower ester of COOH, carboxamide, NHCOCH.sub.3, NHCOCH.sub.2 Br, halo, dimethylamino, triethylammonium, NHCONH.sub.2, SO.sub.2 NH.sub.2, --SO.sub.3 H, or a reporter group, particularly a spectroscopic reporter group such as a fluorescent dye, photoaffinity probe, or spin label probe, coupled through an amide, sulfonamide, amine or thiourea linkage, biotinylamino- (optionally containing an .epsilon.-aminocaproyl spacer chain or similar spacer chain) or; R.sup.1 is CONH--R.sup.2 or NHCSNH--R.sup.2, wherein R.sup.Type: GrantFiled: August 24, 1990Date of Patent: May 10, 1994Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Kenneth A. Jacobson, Gary L. Stiles, Daniel L. Boring
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Patent number: 5250708Abstract: A poly(oxyalkylene) substituted xanthene colorant is providing having the following structure: ##STR1## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of from 3 to 400 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol;R.sub.1 and R.sub.2 are independently selected from H, C1-C8 alkyl, aryl and Y, provided that if either R.sub.1 or R.sub.2 are Y, the other is not H;R.sub.3 and R.sub.4 are independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, Cl, Br and I;X is selected from H, SO.sub.3 --, CO.sub.2 -- and COOR.sub.5, where R.sub.5 is C1-C4 alkyl or aryl; andeach Z is independently selected from SO.sub.3 --, CO.sub.2 --, COOR.sub.6, Cl, and OH, where R.sub.6 is C1-C4 alkyl or aryl, and n is 0, 1, 2 or 3.The colorant is synthesized using a novel poly(oxyalkylene) substituted aminophenol intermediate.Type: GrantFiled: August 13, 1991Date of Patent: October 5, 1993Assignee: Milliken Research CorporationInventor: Carey N. Barry, Jr.
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Patent number: 5248791Abstract: A fluorescence polarization immunoassay (FPIA) for detecting the presence of one or more amphetamine-class analytes in a test sample is provided. The immunoassay uses competition between the analyte and a fluorescently labeled tracer for the binding site on an antibody specific for phenethylamine derivatives. The concentration of amphetamine-class analyte in the sample determines the amount of tracer that binds to the antibody. The amount of tracer/antibody complex formed can be quantitatively measured and is inversely proportional to the quantity of analyte in the test sample. The invention relates to tracers, to immunogens used to elicit antibodies for use as assay reagents, and to assay kits incorporating these tracers and assay reagents.Type: GrantFiled: January 14, 1992Date of Patent: September 28, 1993Assignee: Abbott LaboratoriesInventors: Paul J. Brynes, Donald D. Johnson, Cynthia M. Molina, Charles A. Flentge, Patrick F. Jonas
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Patent number: 5194632Abstract: Disclosed are a novel fluoran compound represented by the formula (I): ##STR1## and a heat-sensitive recording paper which is obtained by using the fluoran compound as a chromogenic compound and is excellent in preserving stability.Type: GrantFiled: July 31, 1990Date of Patent: March 16, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5166350Abstract: A process for the preparation of a fluoran compound of the formula ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, halogen, lower alkyl or lower alkoxy,R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or --NX.sub.3 X.sub.4, or (R.sub.1 and R.sub.2) or (R.sub.3 and R.sub.4) each pair together with the carbon atoms to which they are attached, form a fused benzene nucleus,X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are each independently hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by cyano, halogen, hydroxy, tetrahydrofuryl or lower alkoxy, or are cycloalkyl, aryl or aralkyl or (X.sub.1 and X.sub.2) or (X.sub.3 and X.sub.Type: GrantFiled: September 30, 1991Date of Patent: November 24, 1992Assignee: Ciba-Geigy CorporationInventors: Davor Bedekovic, Jerry L. Pool, Brian J. Williams, Robert Garner, John B. Henshall
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Patent number: 5145791Abstract: The present invention is directed to a fluoroescence polarization immunoassay for determining the 3-methoxy-4-hydroxyphenylglycol content in body fluids, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for preparing them. The assay is conducted by measuring the degree of polarization of plane polarized light that has been passed through a sample containing antiserum and tracer.Type: GrantFiled: September 30, 1991Date of Patent: September 8, 1992Assignee: Abbott LaboratoriesInventors: Christine H. Zeitvogel, Maciej B. Adamczyk, David A. Betebenner, Kenward S. Vaughan
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Patent number: 5055594Abstract: A fluorogenic substrate for tryptophanase useful for identifying an unknown microorganism is a fluorescent dye linked to an amino acid by a carbamate or thiocarbamate group. In preferred substrates, the dye is fluorescein or 7-amino-4-methyl coumarin and the amino acid linked thereto is cysteine, threonine or serine.Type: GrantFiled: July 19, 1990Date of Patent: October 8, 1991Assignee: Becton, Dickinson and CompanyInventor: Patrick D. Mize
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Patent number: 5049673Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.Type: GrantFiled: October 30, 1987Date of Patent: September 17, 1991Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Akwasi Minta
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Patent number: 5041560Abstract: A novel fluoran compound represented by the formula (I): ##STR1## is disclosed. By using the novel fluoran compound (I) as a chromogenic substance, a pressure-sensitive record material is provided which can develop an image of a clear vermilion color when it contacts a developer of an acidic substance.Type: GrantFiled: July 10, 1989Date of Patent: August 20, 1991Assignee: Hodogaya Chemical Co., Ltd.Inventors: Masahiko Yamaguchi, Katsumasa Kikkawa, Michihiro Gonda
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Patent number: 5017710Abstract: Fluoran compounds represented by the general formula (I) ##STR1## (where R is an alkyl group having 9 to 12 carbon atoms) and coloring recording materials containing the said compounds as coloring components, and benzoic acid derivatives represented by the general formula (II) ##STR2## (where R is an alkyl group having 9 to 12 carbon atoms).Type: GrantFiled: October 24, 1989Date of Patent: May 21, 1991Assignee: Nippon Soda Co., Ltd.Inventors: Tetsuo Igaki, Akio Kaneko, Sumio Manaka, Kimiaki Kinoshita
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Patent number: 4996316Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.Type: GrantFiled: December 24, 1988Date of Patent: February 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4977278Abstract: Salts of esterified rhodamine dyes are prepared in granular form by precipitating the rhodamine dyes with sodium chloride from an aqueous medium containing a water-miscible solvent by adding the sodium chloride at 80.degree.-100.degree. C., which precipitates the dyes in liquid form from the aqueous medium, then stirring the liquid dyes to convert them into a droplet form and then chilling the droplets by direct cooling to below 65.degree. C.Type: GrantFiled: September 8, 1989Date of Patent: December 11, 1990Assignee: BASF AktiengesellschaftInventor: Karl Schmeidl