Rhodamines Patents (Class 549/227)
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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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Patent number: 6825166Abstract: A molecular conjugate is provided having the formula: wherein n is the conjugation number, P is a moiety of a carrier molecule such as a protein, R1 is a moiety of a biologically active molecule or its analogs, derivatives, salts or secondary amines, Z is —O— or —NH—, and Y is a straight or branched alkyl having 1 to 20 carbons optionally substituted with one or more phenyl, a cycloalkyl optionally substituted with one or more alkyl or phenyl, or an aromatic group optionally substituted with one or more alkyl, electron-withdrawing or electron-donating groups. Compounds and methods useful in producing such molecular conjugates are also provided, as well as methods of concentrating biologically active molecules in selected target cells of a patient that comprise administering to the patient a selected dose of such molecular conjugates.Type: GrantFiled: March 25, 2002Date of Patent: November 30, 2004Assignee: Tapestry Pharmaceuticals, Inc.Inventors: James D. McChesney, Madhavi C. Chander, Teruna J. Siahaan, Christine R. Xu, Sterling K. Ainsworth
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Patent number: 6756231Abstract: A compound represented by the following formula (I) or (II): wherein, in the formula (I), R1, R2, R3, and R4 independently represent methyl group or ethyl group; and in the formula (II), R5, R6, R7, and R8 independently represent methyl group or ethyl group and X− represents an anion, and a reagent for measurement of nitric oxide which comprises said compound.Type: GrantFiled: August 18, 2000Date of Patent: June 29, 2004Assignees: Daiichi Pure Chemicals Co., Ltd.Inventors: Tetsuo Nagano, Hirotatsu Kojima, Kazuya Kikuchi
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Patent number: 6713622Abstract: A set of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structures wherein R1-R6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group, or, when taken together, R1 and R6 is benzo, or, when taken together, R4 and R5 is benzo; R7-R10, R12-R16 and R18 may be hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group; R11 and R17 may be hydrogen, lower alkyl, lower alkene, lower alkyne, phenyl, aryl, linking group; Y1-Y4 are hydrogen, lower alkyl, or cycloalkyl, or, when taken together, Y1 and R2, Y2 and R1 Y3 and R3, and/or Y4 and R4 is propano, ethano, or substituted forms thereof, and X1-X3 taken separately are hydrogen, chlorine, fluorine, lower alkyl, carboxylate, sulfonate, hydroxymethyl, and linking group, or any combinations thereof In another aspect, the invention includes reagType: GrantFiled: May 25, 2000Date of Patent: March 30, 2004Assignee: Applera CorporationInventor: Ronald J. Graham
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Publication number: 20030212126Abstract: Novel compounds of the formula (I) wherein: one of R1, R2, R3, R4, and (R10)n represents an halogen atom and each of the remaining R1, R2, R3, R4, and each of the remaining R10 group is independently selected in the group constituted by hydrogen, halogen atoms, an amino, acylamino, dialkylamino, cycloalkylamino, azacycloalkyl, alkylcycloalkylamino, aroylamino, diarylamino, arylalkylamino, aralkylamino, alkylaralkylamino, arylaralkylamino, hydroxy, alkoxy, aryloxy, aralkyloxy, mercapto, alkylthio, arylthio, aralkylthio, carboxyl, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, cyano, hydroxysulfonyl, amidosulfonyl, dialkylamidosulfonyl, arylalkylamidosulfonyl, formyl, acyl, aroyl, alkyl, alkylene, alkenyl, aryl, aralkyl, vinyl, alkynyl group and by the corresponding substituted groups; —m=0-1; n=1-4, A is nil, O, or NH; R9 represents an alkylene group; —Z is H, amino, dialkylamino, or trialkylamino salt; X—is an anion; R5, R6, R7 aType: ApplicationFiled: May 30, 2003Publication date: November 13, 2003Inventors: Abdelkrim Habi, Denis Gravel, Luc Villenueve, Hongsheng Su, Marc Vaillancourt
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Patent number: 6630578Abstract: Novel dendritic molecules are provided which respond immediately by emission of light when stimulated with light or electric energy, and are useful, for example, as switching material of memory. The dendritic molecules have a core, a branch structure composed of Unit 1 represented by the following formula: wherein, ring A stands for a homo or heterocyclic six membered ring, optionally other branched structures, and surface functional groups as essential constituents.Type: GrantFiled: November 20, 2001Date of Patent: October 7, 2003Assignee: Communications Research Laboratory, Independent Administrative InstitutionInventors: Hideki Miki, Tatsuo Nakahama, Shiyoshi Yokoyama, Shinro Mashiko
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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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Patent number: 6608213Abstract: This invention provides a precursor compound of a novel fluorescence-labeled probe for DNA, prepared by covalent binding of a fluorescent substance such as fluorescein isothiocyanate, wherein a conjugating group was bounded, with aminoalkylate phenylamine. This invention also provides a novel fluorescence-labeled probe for DNA by diazotizing amino group of phenylamine contained in the precursor compound. Furthermore, a fluorescence labeled plasmid can be produced by conjugating the fluorescence-labeled probe and purine ring of guanine contained in the DNA plasmid through diazonium group.Type: GrantFiled: March 22, 2001Date of Patent: August 19, 2003Assignee: Tokyo Institute of TechnologyInventors: Toshinori Sato, Yoshio Okahata
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Publication number: 20030096192Abstract: Optical data carrier comprising a preferably transparent substrate which may, if desired, have previously been coated with one or more reflection layers and to whose surface a light-writeable information layer, if desired one or more reflection layers and, if desired, a protective layer or a further substrate or a covering layer have been applied, which can be written on or read by means of blue or red light, preferably laser light, where the information layer comprises a light-absorbent compound and, if desired, a binder, characterized in that at least one xanthene dye which contains at least two anionic groups and has at least one cation containing at least one conjugated &pgr; system having at least 6 &pgr; electrons as counterion, where the cation must not be benzyltrimethylammonium, benzyltriethylammonium, tetraphenylphosphonium, butyltriphenylphosphonium or ethyltriphenylphosphonium, is used as light-absorbent compound.Type: ApplicationFiled: March 20, 2002Publication date: May 22, 2003Inventors: Horst Berneth, Friedrich-Karl Bruder, Wilfried Haese, Rainer Hagen, Karin Hassenruck, Serguei Kostromine, Peter Landenberger, Rafael Oser, Thomas Sommermann, Josef-Walter Stawitz, Thomas Bieringer
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Patent number: 6566030Abstract: A method of imaging acids in chemically amplified photoresists involves exposing to radiation a chemically amplified photoresist comprising a pH-dependent fluorophore. Upon exposure to radiation, such as deep-UV radiation, the chemically amplified photoresist produces an acid, which is then visualized by the fluorescence of the pH-dependent fluorophore. An image is generated from the fluorescence of the pH-dependent fluorophore, thus providing a map of the location of the acid in the photoresist. The images are able to be visualized prior to a post-exposure bake of the resist composition. Chemically amplified photoresists comprising pH-dependent fluorophores are useful in the practice of the present invention. The method finds particular use in examining the efficiency of photoacid generators in chemically amplified photoresists, in that it allows the practitioner the ability to directly determine the amount of acid generated within the photoresist.Type: GrantFiled: October 31, 2001Date of Patent: May 20, 2003Assignees: Yale University, Wisconsin Alumni Research FoundationInventors: Robert David Grober, Scott Josef Bukofsky, Paul Michael Dentinger, James Welch Taylor
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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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Patent number: 6455271Abstract: Novel screening methods for identifying antimicrobial agents involving use of membrane potential indicator dyes are provided.Type: GrantFiled: July 27, 2000Date of Patent: September 24, 2002Assignee: XOMA Technology, LtdInventors: Roger G. Little, II, Susan Abrahamson, Peter Wong
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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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Publication number: 20020042019Abstract: A method of imaging acids in chemically amplified photoresists involves exposing to radiation a chemically amplified photoresist comprising a pH-dependent fluorophore. Upon exposure to radiation, such as deep-UV radiation, the chemically amplified photoresist produces an acid, which is then visualized by the fluorescence of the pH-dependent fluorophore. An image is generated from the fluorescence of the pH-dependent fluorophore, thus providing a map of the location of the acid in the photoresist. The images are able to be visualized prior to a post-exposure bake of the resist composition. Chemically amplified photoresists comprising pH-dependent fluorophores are useful in the practice of the present invention. The method finds particular use in examining the efficiency of photoacid generators in chemically amplified photoresists, in that it allows the practitioner the ability to directly determine the amount of acid generated within the photoresist.Type: ApplicationFiled: October 31, 2001Publication date: April 11, 2002Inventors: Robert David Grober, Scott Josef Bukofsky, Paul Michael Dentinger, James Welch Taylor
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Patent number: 6342611Abstract: The present invention relates to novel fluorescent dyes, novel fluorogenic and fluorescent reporter molecules and new enzyme assay processes that can be used to detect the activity of caspases and other enzymes involved in apoptosis in whole cells, cell lines and tissue samples derived from any living organism or organ. The reporter molecules and assay processes can be used in drug screening procedures to identify compounds which act as inhibitors or inducers of the caspase cascade in whole cells or tissues. The reagents and assays described herein are also useful for determining the chemosensitivity of human cancer cells to treatment with chemotherapeutic drugs. The present invention also relates to novel fluorogenic and fluorescent reporter molecules and new enzyme assay processes that can be used to detect the activity of type 2 methionine aminopeptidase, dipeptidyl peptidase IV, calpain, aminopeptidase, HIV protease, adenovirus protease, HSV-1 protease, HCMV protease and HCV protease.Type: GrantFiled: October 9, 1998Date of Patent: January 29, 2002Assignee: Cytovia, Inc.Inventors: Eckard Weber, Sui Xiong Cai, John F. W. Keana, John A. Drewe, Han-Zhong Zhang
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Patent number: 6248904Abstract: The present invention relates to novel fluorescent dyes, novel fluorogenic and fluorescent reporter molecules and new enzyme assay processes that can be used to detect the activity of caspases and other enzymes involved in apoptosis in whole cells, cell lines and tissue samples derived from any living organism or organ. The reporter molecules and assay processes can be used in drug screening procedures to identify compounds which act as inhibitors or inducers of the caspase cascade in whole cells or tissues. The reagents and assays described herein are also useful for determining the chemosensitivity of human cancer cells to treatment with chemotherapeutic drugs. The present invention also relates to novel fluorogenic and fluorescent reporter molecules and new enzyme assay processes that can be used to detect the activity of type 2 methionine aminopeptidase, HIV protease, adenovirus protease, HSV-1 protease, HCMV protease and HCV protease.Type: GrantFiled: July 21, 1999Date of Patent: June 19, 2001Assignee: Cytovia, Inc.Inventors: Han-Zhong Zhang, Sui Xiong Cai
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Publication number: 20010001800Abstract: A compound represented by the following general formula: 1Type: ApplicationFiled: December 29, 2000Publication date: May 24, 2001Inventors: Tetsuo Nagano, Hirotatsu Kojima
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Patent number: 6201134Abstract: A compound represented by the following general formula: wherein R1 and R2 represent amino groups present at adjacent positions each other on the phenyl ring; R3, R4, R5 and R6 independently represent a C1-6 alkyl group; R7, R8, R9 and R10 independently represent a hydrogen atom, a C1-6 alkyl group, an allyl group, or a halogen atom; R11 represents a hydrogen atom or a C1-18 alkyl group; and X− represents an anion, and an agent for nitric oxide measurement comprising said compound. The compound efficiently reacts with nitric oxide to give a fluorescent compound that emits strong fluorescence by irradiation with excitation light of a long wavelength. This fluorescent compound is characterized in that said compound is detectable in a fluorescence wavelength range hardly influenced by autofluorescence of cells, and its fluorescence intensity is not attenuated under an acidic condition.Type: GrantFiled: April 3, 2000Date of Patent: March 13, 2001Assignee: Tetsuo NaganoInventors: Tetsuo Nagano, Hirotatsu Kojima
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Patent number: 6187913Abstract: A double- or single-stranded oligonucleotide comprising one or more respectively inter- or intra-oligonucleotide covalent cross-linkages, wherein the or each covalent linkage consists of an amide bond between a primary amine group of one strand and a carboxyl group of the other strand or the same strand, respectively, said primary amine group being directly substituted in the 2′ position of the strand nucleotide monosaccharide ring, and said carboxyl group being carried by an aliphatic spacer group substituted on a nucleotide or nucleotide analog of the other strand or the same strand, respectively. A method for preparing such oligonucleotides, and nucleotide or non-nucleotide synthons useful for preparing an oligonucleotide of the above kind, are also disclosed.Type: GrantFiled: December 23, 1997Date of Patent: February 13, 2001Assignee: GensetInventors: Marta Blumenfeld, Irena Merenkova
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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: 6143516Abstract: Novel screening methods for identifying antimicrobial agents involving use of membrane potential indicator dyes are provided.Type: GrantFiled: September 24, 1999Date of Patent: November 7, 2000Assignee: XOMA Technology Ltd.Inventors: Roger G. Little, II, Susan Abrahamson, Peter Wong
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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: 6080852Abstract: A set of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structures ##STR1## wherein R.sub.1 -R.sub.6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrite, lower alkoxy, linking group, or, when taken together, R.sub.1 and R.sub.6 is benzo, or, when taken together, R.sub.4 and R.sub.5 is benzo; R.sub.7 -R.sub.10, R.sub.12 -R.sub.16 and R.sub.18 may be hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrite, lower alkoxy, linking group; R.sub.11 and R.sub.17 may be hydrogen, lower alkyl, lower alkene, lower alkyne, phenyl, aryl, linking group; Y.sub.1 -Y.sub.4 are hydrogen, lower alkyl, or cycloalkyl, or, when taken together, Y.sub.1 and R.sub.2, Y.sub.2 and R.sub.1 Y.sub.3 and R.sub.3, and/or Y.sub.4 and R.sub.4 is propano, ethano, or substituted forms thereof, and X.sub.1 -X.sub.Type: GrantFiled: March 27, 1999Date of Patent: June 27, 2000Assignee: The Perkin-Elmer CorporationInventors: Linda Lee, Scott C. Benson, Barnett B. Rosenblum, Sandra L. Spurgeon
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Patent number: 6017712Abstract: A class of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structure ##STR1## wherein R.sub.1 -R.sub.6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group, or combinations thereof, or, when taken together, R.sub.1 and R.sub.6 is benzo, or, when taken together, R.sub.4 and R.sub.5 is benzo; Y.sub.1 -Y.sub.4 are hydrogen or lower alkyl, or, when taken together, Y.sub.1 and R.sub.2, Y.sub.2 and R.sub.1 Y.sub.3 and R.sub.3, or Y.sub.4 and R.sub.4 is propano, ethano, or substituted forms thereof; and X.sub.1 -X.sub.3 taken separately are selected from the group consisting of hydrogen, chlorine, fluorine, lower alkyl, carboxylate, sulfonic acid, --CH.sub.2 OH, and linking group. In another aspect, the invention includes reagents labeled with the 4,7-chlororhodamine dye compounds, including deoxynucleotides, dideoxynucleotides, and polynucleotides.Type: GrantFiled: November 12, 1998Date of Patent: January 25, 2000Inventors: Linda Lee, Scott C. Benson, Barnett B. Rosenblum, Sandra L. Spurgeon, Jonathan M. Cassel, Ronald J. Graham
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Patent number: 5998632Abstract: Disclosed are the Rhodamine B esters of hydroxy C.sub.2 -C.sub.6 lower alkyl acrylates. Specifically, the hydroxy lower alkyl radical is a linear hydroxy lower alkyl radical having the hydroxy group attached to the terminal carbon atom. Also shown are copolymers of diallyldimetyl ammonium chloride which contains from 0.01-2 mole percent of these Rhodamine B esters and their use in treating industrial waters.Type: GrantFiled: June 12, 1998Date of Patent: December 7, 1999Assignee: Nalco Chemical CompanyInventors: William J. Ward, Jeffrey R. Cramm, Peter E. Reed, Brian S. Johnson
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Patent number: 5981779Abstract: The present invention disclose to non-radioactive vitamin D compounds of formula (1) and methods to assay for the presence of vitamin D, vitamin D analogs and their metabolites which may be present in milk, blood or other biological fluids. The assay methods employed in this invention may be enzyme linked immununoassays (ELISAs) (with biotin containing compounds) and fluorimetric and chemiluminometric assays (with fluorescein or chemiluminiscence containing compounds).Type: GrantFiled: June 10, 1998Date of Patent: November 9, 1999Assignee: A and D Assay, IncorporatedInventors: Michael F. Holick, Rahul Ray
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Patent number: 5846737Abstract: The invention describes useful conjugates of sulforhodamine, wherein the conjugated substance and the fluorophore are separated by an alkanoic acid spacer that is attached to the fluorophore via a sulfonamide bond. The increased length of the covalent linkage due to the spacer results in dye-conjugates having a number of surprisingly advantageous properties relative to previous sulforhodamine-labeled conjugates, including increased fluorescence.Type: GrantFiled: July 26, 1996Date of Patent: December 8, 1998Assignee: Molecular Probes, Inc.Inventor: Hee Chol Kang
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Patent number: 5847162Abstract: A class of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structure ##STR1## wherein R.sub.1 -R.sub.6 are hydrogen, fluorine, chlorine, lower alkyl lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, lining group, or combinations thereof or, when taken together, R.sub.1 and R.sub.6 is benzo, or, when taken together, R.sub.4 and R.sub.5 is benzo; Y.sub.1 -Y.sub.4 are hydrogen or lower alkyl or, when taken together, Y.sub.1 and R.sub.2 is propano and Y.sub.2 and R.sub.1 is propano, or, when taken together, Y.sub.3 and R.sub.3 is propano and Y.sub.4 and R.sub.4 is propano; and X.sub.1 -X.sub.3 taken separately are selected from the group consisting of hydrogen, chlorine, fluorine, lower alkyl carboxylate, sulfonic acid, --CH.sub.2 OH, and linking group. In another aspect, the invention includes reagents labeled with the 4,7-dichlororhodamine dye compounds, including deoxynucleotides, dideoxynucleotides, and polynucleotides.Type: GrantFiled: June 27, 1996Date of Patent: December 8, 1998Assignee: The Perkin Elmer CorporationInventors: Linda Lee, Scott C. Benson, Barnett B. Rosenblum, Sandra L. Spurgeon
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Patent number: 5808103Abstract: Disclosed are the Rhodamine B esters of hydroxy C.sub.2 -C.sub.6 lower alkyl acrylates. Specifically, the hydroxy lower alkyl radical is a linear hydroxy lower alkyl radical having the hydroxy group attached to the terminal carbon atom. Also shown are copolymers of diallyldimetyl ammonium chloride which contains from 0.01-2 mole percent of these Rhodamine B esters and their use in treating industrial waters.Type: GrantFiled: November 21, 1997Date of Patent: September 15, 1998Assignee: Nalco Chemical CompanyInventors: William J. Ward, Jeffrey R. Cramm, Peter E. Reed, Brian S. Johnson
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Patent number: 5777133Abstract: Compounds having the formula: ##STR1## wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C.sub.1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (eg., m-phenylene), produced by reacting a compound having the formula: ##STR2## with an R-ylating agent (e.g., R.sub.2 SO.sub.4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: ##STR3## are produced by reacting a compound having the formula: ##STR4## wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formula ##STR5## are produced by reacting a compound of the formula ##STR6## with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups.Type: GrantFiled: January 28, 1997Date of Patent: July 7, 1998
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Patent number: 5773460Abstract: The present invention relates to novel photoactivable rhodamine derivatives for enhancing high quantum-yield production and singlet oxygen generation upon irradiation with light while maintaining desirable differential retention of rhodamine between normal and cancer cells. Representative derivatives are2-(4,5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid methyl ester hydrochloride; 2-(4, 5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid ethyl ester hydrochloride; 2-(4,5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid octyl ester hydrochloride; 2-(4,5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid n-butyl ester hydrochloride; 2-(6-ethyl amino-3-ethyl imino-3H-xanthen-9-yl)-benzoic acid n-butyl ester hydrochloride; and photoactivable derivatives thereof.Type: GrantFiled: July 1, 1996Date of Patent: June 30, 1998Assignee: Universite De MontrealInventors: Louis Gaboury, Luc Villeneuve, Richard Giasson, Tiechao Li, Ajay Kumar Gupta
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Patent number: 5741662Abstract: The present invention provides specific binding solid phase assay methods and kits for the detection of the presence or absence of a microorganism by directly staining the microorganism and specifically capturing the stained microorganism on a solid support. The methods find particular utility in the detection of Candida. The methods may simultaneously detect the presence or absence of multiple microorganisms.Type: GrantFiled: December 18, 1995Date of Patent: April 21, 1998Assignee: Quidel CorporationInventors: Randall D. Madsen, Lorraine S. Bautista, Jan W. Pawlak, Allan D. Pronovost
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Patent number: 5714342Abstract: The present invention provides for novel reagents whose fluorescence increases in the presence of particular proteases. The reagents comprise a characteristically folded peptide backbone each end of which is conjugated to a fluorophore. When the folded peptide is cleaved, as by digestion with a protease, the fluorophores provide a high intensity fluorescent signal at a visible wavelength. Because of their high fluorescence signal in the visible wavelengths, these protease indicators are particularly well suited for detection of protease activity in biological samples, in particular in frozen tissue sections. Thus this invention also provides for methods of detecting protease activity in situ in frozen sections.Type: GrantFiled: October 27, 1995Date of Patent: February 3, 1998Assignee: OncoImmunin, Inc.Inventors: Akira Komoriya, Beverly S. Packard
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Patent number: 5616729Abstract: Triggerable dioxetanes with a fluorescent substituent bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are carbon containing groups and wherein one of R.sub.1, R.sub.2 and R.sub.3 is a tethered fluorescent substitutent. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.Type: GrantFiled: December 27, 1988Date of Patent: April 1, 1997Assignee: Board of Governors of Wayne State UniversityInventors: Arthur P. Schaap, Hashem Akhavan-Tafti
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Patent number: 5576436Abstract: Conjugates of fluorescent labels with specific, selective, and high affinity ligands for receptors have been synthesized and used to directly measure binding to receptors.Type: GrantFiled: March 2, 1994Date of Patent: November 19, 1996Assignee: Pharmaceutical Discovery CorporationInventors: R. Tyler McCabe, Christopher A. Rhodes, Bruce F. DeCosta
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Novel rhodamine derivatives for photodynamic therapy of cancer and in vitro purging of the leukemias
Patent number: 5556992Abstract: The present invention relates to novel photoactivable rhodamine derivatives for enhancing high quantum-yield production and singlet oxygen generation upon irradiation with light while maintaining desirable differential retention of rhodamine between normal and cancer cells, said derivatives are selected from the group consisting of 4,5-dibromorhodamine 123 (2-(4,5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid methyl ester hydrochloride); 4, 5-dibromorhodamine 123 (2-(4,5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid ethyl ester hydrochloride); 4, 5-dibromorhodamine 123 (2-(4,5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid octhyl ester hydrochloride); 4,5-dibromorhodamine 110 n-butyl ester (2-(4,5-dibromo-6-amino-3-imino-3H-xanthen-9-yl)-benzoic acid n-butyl ester hydrochloride); Rhodamine B n-butyl ester (2-(6-ethyl amino-3-ethyl imino-3H-xanthen-9-yl)-benzoic acid n-butyl ester hydrochloride); and photoactivable derivatives thereof; whereby photoactivation of the derivatives induces cType: GrantFiled: September 2, 1994Date of Patent: September 17, 1996Assignee: Universite de MontrealInventors: Louis Gaboury, Luc Villeneuve, Richard Giasson, Tiechao Li, Ajay K. Gupta -
Patent number: 5516864Abstract: This invention describes novel sensors for ions that are based on the combination of xanthylium-based dyes with metal-binding N,N'-diaryldiaza crown ethers. These sensors are primarily useful for detection and quantitation of alkali-metal ions in aqueous solution. Binding of the ion results in a change in the fluorescence properties of the indicating dye that can be correlated with the ion concentration. Methods are provided for attaching reactive groups on these sensors for conjugation to dyes, lipids and polymers and for enhancing entry of the indicators into living cells.Type: GrantFiled: January 19, 1995Date of Patent: May 14, 1996Assignee: Molecular Probes, Inc.Inventors: Michael A. Kuhn, Richard P. Haugland
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Patent number: 5459268Abstract: The dyes of the present invention are fluorescent substituted 3',6'-diaminoxanthenes and their reduced analogs 3',6'-diaminodihydroxanthenes, which are oxidized to the fluorescent form of the dye in situ. In their oxidized form, the dyes selectively localize within mitochondria. The dyes of the present invention include an alkylating group that is covalently attached that allows their retention in mitochondria even after cell death, fixation, and permeabilization.Type: GrantFiled: October 25, 1993Date of Patent: October 17, 1995Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, Mohammad N. Malekzadeh, Yu-zhong Zhang
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Patent number: 5453517Abstract: The invention relates to fluorescent and/or reactive derivatives of 1,2-bis-(2-aminophenoxyethane)-N,N,N',N'-tetraacetic acid (BAPTA) according to the formula: ##STR1## where at least one of W and X is a functional group, with or without a spacer, that terminates in an alcohol or phenol, a thiol, a haloacetamide, an alkyl halide, an amine or aniline, a carboxylic acid, an anhydride, an isocyanate, an isothiocyanate, a maleimide, or an activated ester. The BAPTA-like molecule may be further substituted, one or more times, by additional functional groups with or without spacers or by CH.sub.3, NO.sub.2, CF.sub.3, F, Cl, Br, I, or carboxylic acid derivatives or pharmaceutically acceptable salts thereof, or by indolyl or benzofuran fluorophores. The functional groups allow for subsequent covalent attachment of one or more oxygen heterocycle fluorophores (e.g. fluorescein, coumarin, rhodamine); or polymolecular assemblies (e.g.Type: GrantFiled: February 25, 1992Date of Patent: September 26, 1995Assignee: Molecular Probes, Inc.Inventors: Michael A. Kuhn, Richard P. Haugland
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Patent number: 5410053Abstract: There are described rhodamine derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, or R.sup.2 is paired off with R.sup.5 or R.sup.4 with R.sup.6 to form 1,3-propylene, which can be substituted,R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are each hydrogen or methyl,R.sup.9 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or a radical of the formula (C.sub.2 H.sub.4 O--).sub.n H, where n is 2 or 3, andAn.sup..crclbar. is the equivalent of an anion derived from an addition or condensation polymer that contains acid groups, novel cyclic rhodamine dyes, and the use of the novel rhodamine derivatives and cyclic rhodamine dyes for dyeing polyacrylonitrile fibers, for incorporation into polymers or for preparing inks.Type: GrantFiled: March 16, 1994Date of Patent: April 25, 1995Assignee: BASF AktiengesellschaftInventors: Erwin Hahn, Claudia Kraeh, Udo Mayer, Bernhard Albert, Walter Denzinger
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Patent number: 5405975Abstract: This invention describes novel sensors for ions that are based on the combination of xanthylium-based dyes with metal-binding N,N'-diaryldiaza crown ethers. These sensors are primarily useful for detection and quantitation of alkali-metal ions in aqueous solution. Binding of the ion results in a change in the fluorescence properties of the indicating dye that can be correlated with the ion concentration. Methods are provided for attaching reactive groups on these sensors for conjugation to dyes, lipids and polymers and for enhancing entry of the indicators into living cells.Type: GrantFiled: March 29, 1993Date of Patent: April 11, 1995Assignee: Molecular Probes, Inc.Inventors: Michael A. Kuhn, Richard P. Haugland
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Patent number: 5331097Abstract: A diamino-xanthene colorant is provided having the following structure: ##STR1## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of at least 3 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-C4 alkyl, C1-C4 alkoxy, Cl, Br and I;X is selected from H, SO.sub.3 --, CO.sub.2 -- and COOR.sub.3, where R.sub.3 is C1-C4 alkyl or aryl; andeach Z is independently selected from SO.sub.3 --, CO.sub.2 --, COOR.sub.4, Cl and OH, where R.sub.4 is C1-C4 alkyl or aryl, and n is 0, 1, or 2; the colorant is synthesized by condensing two moles of an N,N-bis(poly(oxyalkylene))-p-methoxyaniline and o-formylbenzene sulfonic acid.Type: GrantFiled: August 13, 1991Date of Patent: July 19, 1994Assignee: Milliken Research CorporationInventors: Timothy B. Gunnell, John B. Hines, Jr., Carey N. Barry, Jr.
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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: 5302731Abstract: Fluorescent pH indicator compounds which exhibit an increase in fluorescence intensity with decreasing pH. The indicators are derivatives of rhodamine and sulforhodamine type dyes and are particularly useful for measuring pH in acidic environments such as carbon dioxide production by microorganisms and pH of certain acidic intracellular compartments.Type: GrantFiled: July 13, 1992Date of Patent: April 12, 1994Assignee: Becton, Dickinson and CompanyInventors: J. Bruce Pitner, Randal A. Hoke
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Patent number: 5290682Abstract: Compounds which are useful as substrates for enzymes are disclosed. An enzyme-controlled process is provided for generating a colored species from an initially substantially colorless material as a result of enzymatic attack. The process can be exploited to provide an enzyme-amplified diagnostic assay method to detect an analyte of interest present in a test sample.Type: GrantFiled: May 31, 1991Date of Patent: March 1, 1994Assignee: Polaroid CorporationInventors: Frank A. Meneghini, Paul S. Palumbo
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Patent number: 5279656Abstract: A compound of Formula (1): ##STR1## wherein: X.sup.1 is a sulpho or carboxy group;each X.sup.2 independently is a substituent;m has a value of from 0 to 2;Y.sup.1 and Y.sup.2 are each independently alkyl or halo; andZ is a carboxy group.The above compounds may be used as colorants for ink jet printing inks either alone or as a mixture with a second magenta compound.Type: GrantFiled: November 9, 1992Date of Patent: January 18, 1994Assignee: Imperial Chemical Industries PLCInventors: Ronald W. Kenyon, Peter Gregory
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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: 5245049Abstract: Disclosed are a crystal and crystalline solvate of a fluoran compound represented by the formula ##STR1## wherein R.sub.1 is ##STR2## and which are useful as chromogenic compounds in recording materials such as pressure-sensitive and heat-sensitive recording materials, a process for preparation of said crystal and said crystalline solvate, and recording materials comprising said crystal or said crystalline solvate.Type: GrantFiled: July 12, 1991Date of Patent: September 14, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
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Patent number: 5231191Abstract: The invention provides a novel cleavage reagent for hydrolysing base-labile linking groups between a solid phase support and oligonucleotides. The cleavage reagent comprises a lower alkyl alcohol, water, and a non-nuccleophilic hindered alkylamine containing from 3 to 6 carbon atoms in a ratio of about 1:1:1 to about 1:3:1, respectively. An important property of the cleavage reagent is that it preserves the fluorescent characteristics of rhodamine dyes during cleavage, thereby making it possible to completely synthesize rhodamine-labeled oligonucleotides by solid phase methods. Rhodamine phosphoramidites are provided to further enhance the efficiency of synthesizing rhodamine-labeled oligonucleotides by such methods.Type: GrantFiled: October 22, 1990Date of Patent: July 27, 1993Assignee: Applied Biosystems, Inc.Inventors: Sam L. Woo, Steven M. Menchen, Steven Fung