DE69720809T2 - Durch gruppen erweiterte fluorophore polymere, die eine hydrophobe und konformativ eingeschrankte mikroumgebung schaffen - Google Patents
Durch gruppen erweiterte fluorophore polymere, die eine hydrophobe und konformativ eingeschrankte mikroumgebung schaffen Download PDFInfo
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- DE69720809T2 DE69720809T2 DE69720809T DE69720809T DE69720809T2 DE 69720809 T2 DE69720809 T2 DE 69720809T2 DE 69720809 T DE69720809 T DE 69720809T DE 69720809 T DE69720809 T DE 69720809T DE 69720809 T2 DE69720809 T2 DE 69720809T2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/141111—Diverse hetero atoms in same or different rings [e.g., alkaloids, opiates, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/17—Nitrogen containing
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/18—Sulfur containing
Landscapes
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
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- Biotechnology (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/595,092 US5994143A (en) | 1996-02-01 | 1996-02-01 | Polymeric fluorophores enhanced by moieties providing a hydrophobic and conformationally restrictive microenvironment |
| US595092 | 1996-02-01 | ||
| PCT/US1997/001429 WO1997028447A1 (en) | 1996-02-01 | 1997-01-30 | Polymeric fluorophores enhanced by moieties providing a hydrophobic and conformationally restrictive microenvironment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69720809D1 DE69720809D1 (de) | 2003-05-15 |
| DE69720809T2 true DE69720809T2 (de) | 2004-04-01 |
Family
ID=24381697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69720809T Expired - Fee Related DE69720809T2 (de) | 1996-02-01 | 1997-01-30 | Durch gruppen erweiterte fluorophore polymere, die eine hydrophobe und konformativ eingeschrankte mikroumgebung schaffen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5994143A (OSRAM) |
| EP (1) | EP1019722B1 (OSRAM) |
| JP (1) | JP4255514B2 (OSRAM) |
| AT (1) | ATE237138T1 (OSRAM) |
| DE (1) | DE69720809T2 (OSRAM) |
| ES (1) | ES2197332T3 (OSRAM) |
| WO (1) | WO1997028447A1 (OSRAM) |
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Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4619990A (en) * | 1985-03-11 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Polymeric dyes with pendent chromophore groups capable of undergoing thermoplastic deformation |
| US4683202A (en) * | 1985-03-28 | 1987-07-28 | Cetus Corporation | Process for amplifying nucleic acid sequences |
| US4683195A (en) * | 1986-01-30 | 1987-07-28 | Cetus Corporation | Process for amplifying, detecting, and/or-cloning nucleic acid sequences |
| US5002883A (en) * | 1987-10-30 | 1991-03-26 | Abbott Laboratories | Covalent attachment of antibodies and antigens to solid phases using extended length heterobifunctional coupling agents |
| CA1323293C (en) * | 1987-12-11 | 1993-10-19 | Keith C. Backman | Assay using template-dependent nucleic acid probe reorganization |
| DE3921498A1 (de) * | 1988-09-28 | 1990-03-29 | Bayer Ag | Polymer-gebundene-farbstoffe, verfahren zu deren herstellung und verwendung |
| US5401469A (en) * | 1989-04-19 | 1995-03-28 | Ibiden Co., Ltd. | Plastic optical biomaterials assay device |
| EP0439182B1 (en) * | 1990-01-26 | 1996-04-24 | Abbott Laboratories | Improved method of amplifying target nucleic acids applicable to both polymerase and ligase chain reactions |
| US5401847A (en) * | 1990-03-14 | 1995-03-28 | Regents Of The University Of California | DNA complexes with dyes designed for energy transfer as fluorescent markers |
| DE4114482A1 (de) * | 1991-05-03 | 1992-11-05 | Bayer Ag | Polymere farbstoffe, verfahren zu deren herstellung und deren verwendung |
| WO1992020746A1 (en) * | 1991-05-14 | 1992-11-26 | Hybritech, Incorporated | Polymeric compositions having bound antibodies |
| JPH09500411A (ja) * | 1993-07-13 | 1997-01-14 | アボツト・ラボラトリーズ | 蛍光性ポリマー標識された接合体および中間体 |
-
1996
- 1996-02-01 US US08/595,092 patent/US5994143A/en not_active Expired - Lifetime
-
1997
- 1997-01-30 DE DE69720809T patent/DE69720809T2/de not_active Expired - Fee Related
- 1997-01-30 EP EP97904060A patent/EP1019722B1/en not_active Expired - Lifetime
- 1997-01-30 AT AT97904060T patent/ATE237138T1/de not_active IP Right Cessation
- 1997-01-30 JP JP52779397A patent/JP4255514B2/ja not_active Expired - Fee Related
- 1997-01-30 WO PCT/US1997/001429 patent/WO1997028447A1/en not_active Ceased
- 1997-01-30 ES ES97904060T patent/ES2197332T3/es not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10331093A1 (de) * | 2003-07-09 | 2005-02-10 | Schering Ag | Vorrichtung und Verfahren zur direkten quantitativen in vitro-Bestimmung einer in einer Probe enthaltenen Substanz |
| DE102004033050A1 (de) * | 2004-07-08 | 2006-01-26 | International University Bremen Gmbh | Photostabilisierung von Fluoreszenzfarbstoffen |
| US7511284B2 (en) | 2004-07-08 | 2009-03-31 | International University Bremen Gmbh | Photostabilisation of fluorescent dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE237138T1 (de) | 2003-04-15 |
| EP1019722B1 (en) | 2003-04-09 |
| EP1019722A1 (en) | 2000-07-19 |
| DE69720809D1 (de) | 2003-05-15 |
| WO1997028447A1 (en) | 1997-08-07 |
| US5994143A (en) | 1999-11-30 |
| JP4255514B2 (ja) | 2009-04-15 |
| JP2000509412A (ja) | 2000-07-25 |
| ES2197332T3 (es) | 2004-01-01 |
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