CA1073813A - Fluorescent immunoassay of aminoglycoside antibiotics - Google Patents
Fluorescent immunoassay of aminoglycoside antibioticsInfo
- Publication number
- CA1073813A CA1073813A CA276,094A CA276094A CA1073813A CA 1073813 A CA1073813 A CA 1073813A CA 276094 A CA276094 A CA 276094A CA 1073813 A CA1073813 A CA 1073813A
- Authority
- CA
- Canada
- Prior art keywords
- gentamicin
- mixture
- fluorescence
- sample
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 title claims description 15
- 238000003018 immunoassay Methods 0.000 title description 9
- 229960002518 gentamicin Drugs 0.000 claims abstract description 62
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims abstract description 60
- 229930182566 Gentamicin Natural products 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 230000003115 biocidal effect Effects 0.000 claims abstract description 23
- 239000013060 biological fluid Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 43
- 238000003556 assay Methods 0.000 claims description 34
- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 7
- 241000283973 Oryctolagus cuniculus Species 0.000 claims description 6
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 claims description 6
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 3
- 229930193140 Neomycin Natural products 0.000 claims description 2
- 229960004821 amikacin Drugs 0.000 claims description 2
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 2
- 229960000318 kanamycin Drugs 0.000 claims description 2
- 229930027917 kanamycin Natural products 0.000 claims description 2
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 2
- 229930182823 kanamycin A Natural products 0.000 claims description 2
- 229960004927 neomycin Drugs 0.000 claims description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
- -1 Schering 20569 Chemical compound 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229960005322 streptomycin Drugs 0.000 claims 1
- 229960000707 tobramycin Drugs 0.000 claims 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 6
- 239000000523 sample Substances 0.000 description 25
- 210000002966 serum Anatomy 0.000 description 17
- 239000000872 buffer Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 230000000171 quenching effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004166 bioassay Methods 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 238000003127 radioimmunoassay Methods 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 230000037029 cross reaction Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000012455 bioassay technique Methods 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005206 flow analysis Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000013610 patient sample Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- NZKFUBQRAWPZJP-BXKLGIMVSA-N (2s,3r,4s,5s,6r)-4-amino-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N.N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NZKFUBQRAWPZJP-BXKLGIMVSA-N 0.000 description 1
- BLWINLJDTOJSRU-UHFFFAOYSA-N 2-methoxy-2,4-diphenylfuran-3-one Chemical compound O=C1C(OC)(C=2C=CC=CC=2)OC=C1C1=CC=CC=C1 BLWINLJDTOJSRU-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010013710 Drug interaction Diseases 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- 206010033109 Ototoxicity Diseases 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 241000473945 Theria <moth genus> Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000011545 carbonate/bicarbonate buffer Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000009137 competitive binding Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- ZFKJVJIDPQDDFY-UHFFFAOYSA-N fluorescamine Chemical compound C12=CC=CC=C2C(=O)OC1(C1=O)OC=C1C1=CC=CC=C1 ZFKJVJIDPQDDFY-UHFFFAOYSA-N 0.000 description 1
- DNYGXMICFMACRA-UHFFFAOYSA-N gentamicin C1A Natural products O1C(CNC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N DNYGXMICFMACRA-UHFFFAOYSA-N 0.000 description 1
- VEGXETMJINRLTH-BOZYPMBZSA-N gentamycin C1a Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N VEGXETMJINRLTH-BOZYPMBZSA-N 0.000 description 1
- XUFIWSHGXVLULG-JYDJLPLMSA-N gentamycin C2 Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)[C@@H](C)N)N)[C@@H](N)C[C@H]1N XUFIWSHGXVLULG-JYDJLPLMSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-RNFDNDRNSA-M iodine-131(1-) Chemical compound [131I-] XMBWDFGMSWQBCA-RNFDNDRNSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000009740 moulding (composite fabrication) Methods 0.000 description 1
- 231100000262 ototoxicity Toxicity 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 239000012857 radioactive material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Classifications
-
- 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
- G01N33/536—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
- G01N33/542—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase with steric inhibition or signal modification, e.g. fluorescent quenching
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/807—Apparatus included in process claim, e.g. physical support structures
- Y10S436/808—Automated or kit
-
- 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
- Y10S436/815—Test for named compound or class of compounds
Landscapes
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15736/76A GB1573212A (en) | 1976-04-15 | 1976-04-15 | Immunoassay for gentamicin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1073813A true CA1073813A (en) | 1980-03-18 |
Family
ID=10064574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA276,094A Expired CA1073813A (en) | 1976-04-15 | 1977-04-13 | Fluorescent immunoassay of aminoglycoside antibiotics |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4150949A (enExample) |
| JP (1) | JPS5338619A (enExample) |
| CA (1) | CA1073813A (enExample) |
| DE (1) | DE2716276A1 (enExample) |
| FR (1) | FR2348492A1 (enExample) |
| GB (1) | GB1573212A (enExample) |
| NL (1) | NL7704126A (enExample) |
| SE (1) | SE442679B (enExample) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53134647A (en) * | 1978-04-01 | 1978-11-24 | Iseki Agricult Mach | Threshing device |
| US4238195A (en) | 1979-01-18 | 1980-12-09 | Miles Laboratories, Inc. | Fluorescer-labeled specific binding assays |
| FR2452704A1 (fr) * | 1979-03-27 | 1980-10-24 | Anvar | Nouveau procede de dosage des aminoglycosides et reactifs pour la mise en oeuvre de ce procede |
| US4271123A (en) * | 1979-10-22 | 1981-06-02 | Bio-Rad Laboratories, Inc. | Automated system for performing fluorescent immunoassays |
| US4401764A (en) * | 1980-02-07 | 1983-08-30 | Technicon Instruments Corporation | Immunoassays employing labeled reagent and a conjugate having two binding sites |
| US4293310A (en) * | 1980-03-14 | 1981-10-06 | University Of Pittsburgh | Photoelectrochemical immunoassay |
| EP0047459B1 (de) * | 1980-09-08 | 1984-11-21 | International Diagnostic Technology, Inc. | Fluoreszierendes Reagenz und Immunofluoreszenz-Bestimmungsmethode |
| US4652531A (en) * | 1981-03-03 | 1987-03-24 | Syntex (U.S.A.) Inc. | Fluorescent protein binding assays with unsymmetrical fluorescein derivatives |
| US4604365A (en) * | 1981-06-02 | 1986-08-05 | Electro-Nucleonics, Inc. | Immunoprecipitation assay |
| WO1982004323A1 (en) * | 1981-06-02 | 1982-12-09 | O Neill Sean | Immunoprecipitation assay |
| JPS5977356A (ja) | 1982-06-30 | 1984-05-02 | Fuji Photo Film Co Ltd | 螢光アツセイ用多層分析要素およびそれを用いる螢光アツセイ法 |
| US4707441A (en) * | 1984-08-06 | 1987-11-17 | Technicon Instruments Corp. | Binding assays in automated apparatus with liposome compatible surfactants |
| JPS6451515U (enExample) * | 1987-09-28 | 1989-03-30 | ||
| WO2002051439A2 (en) * | 2000-12-22 | 2002-07-04 | Medlyte, Inc. | Compositions and methods for the treatment and prevention of cardiovascular diseases and disorders, and for identifying agents therapeutic therefor |
| US20040171062A1 (en) * | 2002-02-28 | 2004-09-02 | Plexxikon, Inc. | Methods for the design of molecular scaffolds and ligands |
| EP1558751A4 (en) * | 2002-09-16 | 2007-08-22 | Plexxikon Inc | CRYSTALLINE STRUCTURE OF PROTEIN KINASE PIM-1 |
| JP2007524374A (ja) * | 2003-02-28 | 2007-08-30 | プレキシコン，インコーポレーテッド | Ｐｙｋ２結晶構造および使用 |
| US20050079548A1 (en) * | 2003-07-07 | 2005-04-14 | Plexxikon, Inc. | Ligand development using PDE4B crystal structures |
| US7348338B2 (en) * | 2003-07-17 | 2008-03-25 | Plexxikon, Inc. | PPAR active compounds |
| NZ545326A (en) * | 2003-07-17 | 2009-12-24 | Plexxikon Inc | PPAR active compounds |
| WO2005028624A2 (en) * | 2003-09-15 | 2005-03-31 | Plexxikon, Inc. | Molecular scaffolds for kinase ligand development |
| CA2539452C (en) * | 2003-09-17 | 2013-10-29 | Guava Technologies, Inc. | Compositions and methods for analysis of target analytes |
| US20070066641A1 (en) * | 2003-12-19 | 2007-03-22 | Prabha Ibrahim | Compounds and methods for development of RET modulators |
| PT1696920E (pt) * | 2003-12-19 | 2015-01-14 | Plexxikon Inc | Compostos e métodos para o desenvolvimento de moduladores de ret |
| US7794713B2 (en) * | 2004-04-07 | 2010-09-14 | Lpath, Inc. | Compositions and methods for the treatment and prevention of hyperproliferative diseases |
| JP2008503446A (ja) | 2004-05-06 | 2008-02-07 | プレキシコン，インコーポレーテッド | Ｐｄｅ４ｂ阻害剤及びその使用 |
| TW200616632A (en) * | 2004-06-17 | 2006-06-01 | Plexxikon Inc | Compounds modulating c-kit activity and uses therefor |
| US7498342B2 (en) | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| CN101048407A (zh) * | 2004-09-03 | 2007-10-03 | 普莱希科公司 | 双环杂芳基pde4b抑制剂 |
| CA2588953A1 (en) * | 2004-11-30 | 2006-06-08 | Plexxikon, Inc. | Ppar active compounds |
| MX2007014377A (es) * | 2005-05-17 | 2008-02-06 | Plexxikon Inc | Inhibidores de proteina cinasa de derivados de pirrol (2,3-b) piridina. |
| PL1893612T3 (pl) | 2005-06-22 | 2012-01-31 | Plexxikon Inc | Pochodne pirolo-[2,3-b]pirydyny jako inhibitory kinazy białkowej |
| AU2006287513A1 (en) * | 2005-09-07 | 2007-03-15 | Plexxikon, Inc. | 1, 3-disubstituted indole derivatives for use as PPAR modulators |
| US20080213274A1 (en) * | 2005-10-28 | 2008-09-04 | Sabbadini Roger A | Compositions and methods for the treatment and prevention of fibrotic, inflammatory, and neovascularization conditions of the eye |
| US20090074720A1 (en) * | 2005-10-28 | 2009-03-19 | Sabbadini Roger A | Methods for decreasing immune response and treating immune conditions |
| US9274130B2 (en) | 2006-05-31 | 2016-03-01 | Lpath, Inc. | Prevention and treatment of pain using antibodies to lysophosphatidic acid |
| US8796429B2 (en) * | 2006-05-31 | 2014-08-05 | Lpath, Inc. | Bioactive lipid derivatives, and methods of making and using same |
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|---|---|---|---|---|
| US2797149A (en) * | 1953-01-08 | 1957-06-25 | Technicon International Ltd | Methods of and apparatus for analyzing liquids containing crystalloid and non-crystalloid constituents |
| US3399972A (en) * | 1964-08-24 | 1968-09-03 | Technicon Corp | Chromatography analysis apparatus and method |
| US3789116A (en) * | 1970-12-09 | 1974-01-29 | Abbott Lab | Fluorescent labeled antibody reagent |
| US3901654A (en) * | 1971-06-21 | 1975-08-26 | Biological Developments | Receptor assays of biologically active compounds employing biologically specific receptors |
| US3812181A (en) * | 1971-12-27 | 1974-05-21 | Hoffmann La Roche | O-(alpha-hydroxycinnamoyl)benzoic acid and related compounds |
| IL44165A (en) * | 1973-03-05 | 1977-06-30 | Sparamedica Ag | Method for fluorescently labelling a material with a furanone derivative and products formed by reacting such a material with the furanone derivative |
| US3998943A (en) * | 1973-10-02 | 1976-12-21 | Syva Company | Double receptor fluorescent immunoassay |
| US3935074A (en) * | 1973-12-17 | 1976-01-27 | Syva Company | Antibody steric hindrance immunoassay with two antibodies |
| US3996345A (en) * | 1974-08-12 | 1976-12-07 | Syva Company | Fluorescence quenching with immunological pairs in immunoassays |
| US3992516A (en) * | 1974-10-30 | 1976-11-16 | Sook Kyung Lim | Direct fluorescent antibody composition and method for P. Pneumocystis carinii |
| US4018884A (en) * | 1975-06-26 | 1977-04-19 | Hoffmann-La Roche Inc. | Fluorogenic materials and labeling techniques |
| US4036946A (en) * | 1975-10-20 | 1977-07-19 | Marcos Kleinerman | Immunofluorometric method for measuring minute quantities of antigens, antibodies and other substances |
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1976
- 1976-04-15 GB GB15736/76A patent/GB1573212A/en not_active Expired
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1977
- 1977-04-13 CA CA276,094A patent/CA1073813A/en not_active Expired
- 1977-04-13 SE SE7704244A patent/SE442679B/xx not_active IP Right Cessation
- 1977-04-13 DE DE19772716276 patent/DE2716276A1/de active Granted
- 1977-04-14 US US05/787,654 patent/US4150949A/en not_active Expired - Lifetime
- 1977-04-14 FR FR7711200A patent/FR2348492A1/fr active Granted
- 1977-04-15 JP JP4272077A patent/JPS5338619A/ja active Granted
- 1977-04-15 NL NL7704126A patent/NL7704126A/xx not_active Application Discontinuation
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| US4150949A (en) | 1979-04-24 |
| JPS5338619A (en) | 1978-04-08 |
| DE2716276C2 (enExample) | 1987-11-19 |
| SE7704244L (sv) | 1977-10-16 |
| GB1573212A (en) | 1980-08-20 |
| JPS6139623B2 (enExample) | 1986-09-04 |
| DE2716276A1 (de) | 1977-10-27 |
| SE442679B (sv) | 1986-01-20 |
| NL7704126A (nl) | 1977-10-18 |
| FR2348492A1 (fr) | 1977-11-10 |
| FR2348492B1 (enExample) | 1983-10-21 |
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