Nitrogen Bonded Directly To The Xanthene Ring System (e.g., Rhodols, Aminofluorans, Etc.) Patents (Class 549/225)
  • Publication number: 20130196362
    Abstract: 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: Application
    Filed: January 30, 2013
    Publication date: August 1, 2013
    Applicant: THE UNIVERSITY OF HONG KONG
    Inventor: THE UNIVERSITY OF HONG KONG
  • Patent number: 8445702
    Abstract: 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: Grant
    Filed: February 18, 2011
    Date of Patent: May 21, 2013
    Assignee: Life Technologies Corporation
    Inventor: Kyle Gee
  • Publication number: 20130053392
    Abstract: 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: Application
    Filed: February 14, 2011
    Publication date: February 28, 2013
    Inventors: Peter Ebbesen, Claudlu T. Supuran, Andrea Scozzafava, Erik Olai Pettersen, Kaye Williams, Ludwig Dubois, Philippe Lambin
  • Publication number: 20120172583
    Abstract: 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: Application
    Filed: September 14, 2010
    Publication date: July 5, 2012
    Applicant: LIFE TECHNOLOGIES CORPORATION
    Inventors: Linda G. Lee, Sandra L. Spurgeon, Barnett B. Rosenblum
  • Publication number: 20120121536
    Abstract: 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: Application
    Filed: March 24, 2011
    Publication date: May 17, 2012
    Applicant: OHIO UNIVERSITY
    Inventors: Xiaozhuo Chen, Stephen Bergmeier
  • Patent number: 8114904
    Abstract: 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: Grant
    Filed: April 3, 2009
    Date of Patent: February 14, 2012
    Assignee: Versitech Limited & Morningside Ventures Limited
    Inventors: Dan Yang, Tao Peng
  • Patent number: 7985865
    Abstract: 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: Grant
    Filed: December 14, 2007
    Date of Patent: July 26, 2011
    Assignee: Xerox Corporation
    Inventors: Jeffrey H Banning, Michael B. Meinhardt, Donald R Titterington, Clifford R King
  • Patent number: 7704756
    Abstract: Fluorogenic or chromogenic dyes are useful as reporter molecules for detecting cell entry by a specific molecule.
    Type: Grant
    Filed: January 30, 2006
    Date of Patent: April 27, 2010
    Assignee: Novartis Vaccines and Diagnostics, Inc.
    Inventors: Daniel J. Suich, Ronald N. Zuckermann
  • Patent number: 7615377
    Abstract: 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: Grant
    Filed: August 27, 2004
    Date of Patent: November 10, 2009
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen J. Lippard, Elizabeth Marie Nolan
  • Patent number: 7488820
    Abstract: 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: Grant
    Filed: January 19, 2005
    Date of Patent: February 10, 2009
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen J. Lippard, Christopher J. Chang, Elizabeth M. Nolan
  • Publication number: 20080214811
    Abstract: 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: Application
    Filed: February 25, 2008
    Publication date: September 4, 2008
    Applicant: Biosearch Technologies, Inc.
    Inventors: Mark Reddington, Matt Lyttle
  • Patent number: 7083667
    Abstract: 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: Grant
    Filed: February 9, 2005
    Date of Patent: August 1, 2006
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yasuaki Murai, Takayuki Toyoda, Takeshi Miyazaki, Yuko Yamagishi
  • Patent number: 6916925
    Abstract: 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: Grant
    Filed: July 22, 2003
    Date of Patent: July 12, 2005
    Assignee: 3M Innovative Properties Co.
    Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
  • Publication number: 20040242902
    Abstract: 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: Application
    Filed: May 4, 2004
    Publication date: December 2, 2004
    Inventors: Joe Y.L. Lam, Steven M. Menchen, Ruiming Zou, Scott C. Benson
  • Publication number: 20040101839
    Abstract: A compound represented by general formula (I) below; 1
    Type: Application
    Filed: December 24, 2003
    Publication date: May 27, 2004
    Inventors: Hisafumi Ikeda, Isao Saito, Fumihiko Kitagawa
  • Patent number: 6635602
    Abstract: 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 dicyclo
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: October 21, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: James Philip Taylor, Michael Heneghan
  • Patent number: 6630588
    Abstract: 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: Grant
    Filed: February 19, 2002
    Date of Patent: October 7, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
  • Publication number: 20030171600
    Abstract: A compound represented by the following formula (I): 1
    Type: Application
    Filed: April 14, 2003
    Publication date: September 11, 2003
    Applicant: Daiichi Pure Chemicals Co., Ltd.
    Inventors: Tetsuo Nagano, Hirotatsu Kojima
  • Publication number: 20030055243
    Abstract: 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: Application
    Filed: August 21, 2002
    Publication date: March 20, 2003
    Applicant: PE Corporation (NY)
    Inventors: Linda G. Lee, Meng C. Taing, Barnett B. Rosenblum
  • Patent number: 6482938
    Abstract: 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: Grant
    Filed: September 17, 1999
    Date of Patent: November 19, 2002
    Assignees: Wako Pure Chemical Industries, Ltd., The Institute of Physical & Chemical Research
    Inventors: Yoshihide Hayashizaki, Takumi Tanaka
  • Publication number: 20020147348
    Abstract: 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: Application
    Filed: April 10, 2001
    Publication date: October 10, 2002
    Inventors: Rajnish Batlaw, Patrick D. Moore
  • Patent number: 6452020
    Abstract: 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: Grant
    Filed: April 10, 2001
    Date of Patent: September 17, 2002
    Assignee: Milliken & Company
    Inventors: Rajnish Batlaw, Patrick D. Moore
  • Publication number: 20020115092
    Abstract: 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: Application
    Filed: November 8, 2001
    Publication date: August 22, 2002
    Applicant: The Scripps Research Institute
    Inventor: Julius Rebek
  • Patent number: 6403812
    Abstract: 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: Grant
    Filed: May 30, 2000
    Date of Patent: June 11, 2002
    Assignee: The Perkin-Elmer Corporation
    Inventors: Steven M. Menchen, Linda G. Lee, Charles R. Connell, N. Davis Hershey, Vergine Chakerian, Sam L. Woo, Steven Fung
  • Patent number: 6376669
    Abstract: 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: Grant
    Filed: November 2, 2000
    Date of Patent: April 23, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
  • Patent number: 6162610
    Abstract: 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: Grant
    Filed: September 11, 1998
    Date of Patent: December 19, 2000
  • Patent number: 6162931
    Abstract: 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: Grant
    Filed: April 12, 1996
    Date of Patent: December 19, 2000
    Assignee: Molecular Probes, Inc.
    Inventors: Kyle R. Gee, Martin Poot, Dieter H. Klaubert, Wei-Chuan Sun, Richard P. Haugland, Fei Mao
  • Patent number: 6130101
    Abstract: 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: Grant
    Filed: September 23, 1997
    Date of Patent: October 10, 2000
    Assignee: Molecular Probes, Inc.
    Inventors: Fei Mao, Wai-Yee Leung, Richard P. Haugland
  • Patent number: 6071853
    Abstract: 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: Grant
    Filed: November 24, 1998
    Date of Patent: June 6, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Roy Alan Kirk, Jonathon Gawtrey, Michael Heneghan, John Whitworth, Ian Antony Dearden, James Philip Taylor, John Barry Henshall
  • Patent number: 5739078
    Abstract: 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: Grant
    Filed: August 22, 1996
    Date of Patent: April 14, 1998
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Mitsuhiro Yanagita, Takehiro Sato, Shigemi Suga, Tomoya Hidaka, Toru Kawabe, Mamoru Aizawa, Shinichi Sato, Izuo Aoki
  • Patent number: 5721355
    Abstract: 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: Grant
    Filed: June 25, 1996
    Date of Patent: February 24, 1998
    Assignee: Pharmacia Biotech Inc.
    Inventor: Charles K. Brush
  • Patent number: 5654442
    Abstract: 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: Grant
    Filed: March 8, 1995
    Date of Patent: August 5, 1997
    Assignee: The Perkin-Elmer Corporation
    Inventors: Steven M. Menchen, Linda G. Lee, Charles R. Connell, N. Davis Hershey, Vergine Chakerian, Sam L. Woo, Steven Fung
  • Patent number: 5583236
    Abstract: 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: Grant
    Filed: December 2, 1994
    Date of Patent: December 10, 1996
    Assignee: Pharmacia Biotech Inc.
    Inventor: Charles K. Brush
  • Patent number: 5395948
    Abstract: 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: Grant
    Filed: March 10, 1993
    Date of Patent: March 7, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 5380629
    Abstract: 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: Grant
    Filed: March 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Eastman Kodak Company
    Inventor: Benjamin T. Chen
  • Patent number: 5372949
    Abstract: 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: Grant
    Filed: September 3, 1992
    Date of Patent: December 13, 1994
    Assignee: Abbott Laboratories
    Inventors: Christine H. Zeitvogel, Maciej B. Adamczyk, David A. Betebenner, Kenward S. Vaughan
  • Patent number: 5371241
    Abstract: 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: Grant
    Filed: July 19, 1991
    Date of Patent: December 6, 1994
    Assignee: Pharmacia P-L Biochemicals Inc.
    Inventor: Charles K. Brush
  • Patent number: 5315015
    Abstract: 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: Grant
    Filed: November 10, 1992
    Date of Patent: May 24, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Raymond A. Hui, Kathryn S. Schwenzer
  • Patent number: 5310916
    Abstract: 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: Grant
    Filed: August 24, 1990
    Date of Patent: May 10, 1994
    Assignee: The United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Kenneth A. Jacobson, Gary L. Stiles, Daniel L. Boring
  • Patent number: 5250708
    Abstract: 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: Grant
    Filed: August 13, 1991
    Date of Patent: October 5, 1993
    Assignee: Milliken Research Corporation
    Inventor: Carey N. Barry, Jr.
  • Patent number: 5248791
    Abstract: 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: Grant
    Filed: January 14, 1992
    Date of Patent: September 28, 1993
    Assignee: Abbott Laboratories
    Inventors: Paul J. Brynes, Donald D. Johnson, Cynthia M. Molina, Charles A. Flentge, Patrick F. Jonas
  • Patent number: 5194632
    Abstract: 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: Grant
    Filed: July 31, 1990
    Date of Patent: March 16, 1993
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5166350
    Abstract: 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: Grant
    Filed: September 30, 1991
    Date of Patent: November 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Davor Bedekovic, Jerry L. Pool, Brian J. Williams, Robert Garner, John B. Henshall
  • Patent number: 5145791
    Abstract: 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: Grant
    Filed: September 30, 1991
    Date of Patent: September 8, 1992
    Assignee: Abbott Laboratories
    Inventors: Christine H. Zeitvogel, Maciej B. Adamczyk, David A. Betebenner, Kenward S. Vaughan
  • Patent number: 5055594
    Abstract: 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: Grant
    Filed: July 19, 1990
    Date of Patent: October 8, 1991
    Assignee: Becton, Dickinson and Company
    Inventor: Patrick D. Mize
  • Patent number: 5049673
    Abstract: 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: Grant
    Filed: October 30, 1987
    Date of Patent: September 17, 1991
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Akwasi Minta
  • Patent number: 5041560
    Abstract: 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: Grant
    Filed: July 10, 1989
    Date of Patent: August 20, 1991
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Masahiko Yamaguchi, Katsumasa Kikkawa, Michihiro Gonda
  • Patent number: 5017710
    Abstract: 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: Grant
    Filed: October 24, 1989
    Date of Patent: May 21, 1991
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Tetsuo Igaki, Akio Kaneko, Sumio Manaka, Kimiaki Kinoshita
  • Patent number: 4996316
    Abstract: 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: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4977278
    Abstract: 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: Grant
    Filed: September 8, 1989
    Date of Patent: December 11, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl