CA2336904A1 - Nouveaux chelates fluorescents aux lanthanides - Google Patents
Nouveaux chelates fluorescents aux lanthanides Download PDFInfo
- Publication number
- CA2336904A1 CA2336904A1 CA002336904A CA2336904A CA2336904A1 CA 2336904 A1 CA2336904 A1 CA 2336904A1 CA 002336904 A CA002336904 A CA 002336904A CA 2336904 A CA2336904 A CA 2336904A CA 2336904 A1 CA2336904 A1 CA 2336904A1
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- CA
- Canada
- Prior art keywords
- group
- dtpa
- iii
- compound
- formula
- 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.)
- Abandoned
Links
- 229910052747 lanthanoid Inorganic materials 0.000 title claims description 23
- 150000002602 lanthanoids Chemical class 0.000 title claims description 21
- 238000003556 assay Methods 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims description 32
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 238000004166 bioassay Methods 0.000 claims description 15
- 108010004469 allophycocyanin Proteins 0.000 claims description 10
- 108020004414 DNA Proteins 0.000 claims description 8
- 238000001917 fluorescence detection Methods 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000002738 chelating agent Substances 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 6
- 102000053602 DNA Human genes 0.000 claims description 5
- 229940058934 aminoquinoline antimalarials Drugs 0.000 claims description 5
- 150000003248 quinolines Chemical class 0.000 claims description 5
- 150000005010 aminoquinolines Chemical class 0.000 claims description 4
- 238000002372 labelling Methods 0.000 claims description 4
- 229920005646 polycarboxylate Polymers 0.000 claims description 4
- 229920002477 rna polymer Polymers 0.000 claims description 4
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 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 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims description 2
- WBMPYOXBHLVYMK-UHFFFAOYSA-N 1-amino-10h-acridin-9-one Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N WBMPYOXBHLVYMK-UHFFFAOYSA-N 0.000 claims description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- IEUANVROPGDRIN-UHFFFAOYSA-N 2-aminochromeno[3,2-b]pyridin-10-one Chemical class C1=CC=C2C(=O)C3=NC(N)=CC=C3OC2=C1 IEUANVROPGDRIN-UHFFFAOYSA-N 0.000 claims description 2
- BELZLSZHWJZDNM-UHFFFAOYSA-N 2-aminofluoren-1-one Chemical class C1=CC=C2C3=CC=C(N)C(=O)C3=CC2=C1 BELZLSZHWJZDNM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 10
- RAEOEMDZDMCHJA-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CCN(CC(O)=O)CC(O)=O)CC(O)=O RAEOEMDZDMCHJA-UHFFFAOYSA-N 0.000 claims 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000002868 homogeneous time resolved fluorescence Methods 0.000 abstract description 7
- 239000003504 photosensitizing agent Substances 0.000 abstract description 5
- 239000008139 complexing agent Substances 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229960003330 pentetic acid Drugs 0.000 description 13
- -1 lanthanide cations Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 150000005016 6-aminoquinolines Chemical class 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000013537 high throughput screening Methods 0.000 description 4
- 238000003018 immunoassay Methods 0.000 description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- LNPMZQXEPNWCMG-UHFFFAOYSA-N 4-(2-aminoethyl)aniline Chemical compound NCCC1=CC=C(N)C=C1 LNPMZQXEPNWCMG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000423 cell based assay Methods 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000001952 enzyme assay Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000009396 hybridization Methods 0.000 description 3
- 230000002055 immunohistochemical effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000001525 receptor binding assay Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000002820 assay format Methods 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 239000006071 cream Substances 0.000 description 2
- 238000002060 fluorescence correlation spectroscopy Methods 0.000 description 2
- 238000002875 fluorescence polarization Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 1
- RVGFNHMYNPTXRT-UHFFFAOYSA-N 2-(4-isothiocyanatophenyl)ethanamine Chemical compound NCCC1=CC=C(N=C=S)C=C1 RVGFNHMYNPTXRT-UHFFFAOYSA-N 0.000 description 1
- BHUDMBBYUOGKQI-UHFFFAOYSA-N 2-amino-8-bromo-10-oxochromeno[3,2-b]pyridine-3-carbonitrile;2-amino-8-ethyl-10-oxochromeno[3,2-b]pyridine-3-carbonitrile Chemical compound O1C2=CC=C(Br)C=C2C(=O)C2=C1C=C(C#N)C(N)=N2.N#CC1=C(N)N=C2C(=O)C3=CC(CC)=CC=C3OC2=C1 BHUDMBBYUOGKQI-UHFFFAOYSA-N 0.000 description 1
- JIDPRRVEJMGZKE-UHFFFAOYSA-N 2-aminoxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3OC2=C1 JIDPRRVEJMGZKE-UHFFFAOYSA-N 0.000 description 1
- OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 description 1
- 150000005014 3-aminoquinolines Chemical class 0.000 description 1
- CMUHFUGDYMFHEI-QMMMGPOBSA-N 4-amino-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N)C=C1 CMUHFUGDYMFHEI-QMMMGPOBSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- FBJXAUCDHRYFHZ-UHFFFAOYSA-N NC1=NC=2C(C3=CC=CC=C3OC2C=C1C#N)=O.NC=1C=CC=2C(C3=CC=CC=C3NC2C1)=O Chemical compound NC1=NC=2C(C3=CC=CC=C3OC2C=C1C#N)=O.NC=1C=CC=2C(C3=CC=CC=C3NC2C1)=O FBJXAUCDHRYFHZ-UHFFFAOYSA-N 0.000 description 1
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000012188 high-throughput screening assay Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 230000006916 protein interaction Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
- A61K49/0026—Acridine dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
- A61K49/0041—Xanthene dyes, used in vivo, e.g. administered to a mice, e.g. rhodamines, rose Bengal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
- A61K49/0052—Small organic molecules
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
Abstract
L'invention concerne des agents complexants de formule (I), qui contiennent des nouveaux photosensibilisants et produisent une fluorescence de longue durée, à utiliser dans les essais de bioaffinité, notamment les essais à fluorescence en temps différé homogène (HTRF).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9194498P | 1998-07-07 | 1998-07-07 | |
| US60/091,944 | 1998-07-07 | ||
| PCT/US1999/015366 WO2000001663A1 (fr) | 1998-07-07 | 1999-07-07 | Nouveaux chelates fluorescents aux lanthanides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2336904A1 true CA2336904A1 (fr) | 2000-01-13 |
Family
ID=22230424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002336904A Abandoned CA2336904A1 (fr) | 1998-07-07 | 1999-07-07 | Nouveaux chelates fluorescents aux lanthanides |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1095011A4 (fr) |
| JP (1) | JP2002519404A (fr) |
| CA (1) | CA2336904A1 (fr) |
| WO (1) | WO2000001663A1 (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6440389B1 (en) * | 2000-07-19 | 2002-08-27 | The General Hospital Corporation | Fluorescent agents for real-time measurement of organ function |
| KR20040010544A (ko) * | 2000-10-19 | 2004-01-31 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 양이온성 3족 촉매 시스템 |
| DE10163295B4 (de) * | 2001-12-21 | 2004-03-25 | Honeywell Specialty Chemicals Seelze Gmbh | Seltenerdmetall-Verbindungen und Gemische von diesen, Verfahren zu deren Herstellung sowie deren Verwendung |
| DE102004022628A1 (de) | 2004-05-07 | 2005-12-15 | Sensient Imaging Technologies Gmbh | FRET-Bioassay |
| DE102004024011A1 (de) * | 2004-05-14 | 2005-12-01 | Bayer Chemicals Ag | Difluorbenzo-1,3-dioxole |
| AU2005269819A1 (en) * | 2004-07-23 | 2006-02-09 | Amgen Inc. | Generic probes for the detection of phosphorylated sequences |
| AU2005280455A1 (en) * | 2004-08-26 | 2006-03-09 | Mallinckrodt Inc. | Luminescent metal complexes for monitoring renal function |
| US8193174B2 (en) | 2005-05-11 | 2012-06-05 | University Of Durham | Responsive luminescent lanthanide complexes |
| WO2006120444A1 (fr) * | 2005-05-11 | 2006-11-16 | University Of Durham | Complexes de lanthanide a reponse luminescente |
| EP1886685A1 (fr) | 2006-08-11 | 2008-02-13 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Méthodes, utilisations et compositions pour la modulation de la réplication du HCV par activation ou inhibition du récepteur farnesoid X |
| GB2451106A (en) * | 2007-07-18 | 2009-01-21 | Cis Bio Int | Lanthanide (III) ion complexing pyrazoyl-aza(thio)xanthone comprising compounds, their complexes and their use as fluorescent labels |
| CN102549438B (zh) | 2009-09-24 | 2014-10-29 | 国家健康与医学研究院 | Fkbp52-tau相互作用作为新颖治疗靶点用于治疗涉及tau机能失调的神经障碍 |
| WO2011083124A1 (fr) | 2010-01-05 | 2011-07-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Antagonistes du récepteur flt3 destinés au traitement ou à la prévention de troubles douloureux |
| DE102011001368B4 (de) | 2011-03-17 | 2013-01-31 | Bundesanstalt für Materialforschung und -Prüfung (BAM) | Lanthanoid-Chelate enthaltende Partikel, deren Herstellung sowie deren Verwendung in der Bioanalytik |
| DE102011101207B3 (de) | 2011-05-11 | 2012-05-10 | Sartorius Stedim Biotech Gmbh | Fluoreszenzfarbstoff für pH-Sensor |
| WO2012156476A2 (fr) | 2011-05-16 | 2012-11-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Procédés pour identifier par criblage des substances capables de moduler la réplication d'un virus de la grippe |
| WO2014053871A1 (fr) | 2012-10-04 | 2014-04-10 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Procédé de criblage d'un composé apte à inhiber l'activité transcriptionnelle de notch1 |
| JP6666848B2 (ja) | 2014-02-18 | 2020-03-18 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | Ｎｒｐ−１／ｏｂｒ複合体シグナル伝達経路により媒介される疾患の処置のための方法及び医薬組成物 |
| EP3131922B1 (fr) | 2014-04-17 | 2020-05-13 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Polypeptides et ses utilisations pour la réduction de la motilité cellulaire induite par cd95 |
| US20220098681A1 (en) | 2019-01-11 | 2022-03-31 | INSERM (Institute National de la Santé et de la Recherche Médicale) | Methods for screening inhibitors against chikungunya virus and for determining whether subjects are predisposed to infection by said virus |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162508A (en) * | 1987-12-18 | 1992-11-10 | Compagnie Oris Industrie | Rare earth cryptates, processes for their preparation, synthesis intermediates and application as fluorescent tracers |
| US5622821A (en) * | 1994-06-29 | 1997-04-22 | The Regents Of The University Of California | Luminescent lanthanide chelates and methods of use |
| DE19505960A1 (de) * | 1995-02-21 | 1996-08-22 | Deutsches Krebsforsch | Konjugat zur individuellen Dosierung von Arzneimitteln |
| GB9813776D0 (en) * | 1998-06-25 | 1998-08-26 | Smithkline Beecham Plc | Novel compounds |
-
1999
- 1999-07-07 WO PCT/US1999/015366 patent/WO2000001663A1/fr not_active Application Discontinuation
- 1999-07-07 JP JP2000558068A patent/JP2002519404A/ja active Pending
- 1999-07-07 CA CA002336904A patent/CA2336904A1/fr not_active Abandoned
- 1999-07-07 EP EP99932334A patent/EP1095011A4/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1095011A1 (fr) | 2001-05-02 |
| JP2002519404A (ja) | 2002-07-02 |
| EP1095011A4 (fr) | 2003-01-08 |
| WO2000001663A1 (fr) | 2000-01-13 |
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