CA2754169A1 - Acridone derivatives as labels for fluorescence detection of target materials - Google Patents
Acridone derivatives as labels for fluorescence detection of target materials Download PDFInfo
- Publication number
- CA2754169A1 CA2754169A1 CA2754169A CA2754169A CA2754169A1 CA 2754169 A1 CA2754169 A1 CA 2754169A1 CA 2754169 A CA2754169 A CA 2754169A CA 2754169 A CA2754169 A CA 2754169A CA 2754169 A1 CA2754169 A1 CA 2754169A1
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- CA
- Canada
- Prior art keywords
- group
- chr
- groups
- dye
- nitro
- 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
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- 239000013077 target material Substances 0.000 title claims description 17
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 title abstract description 31
- 238000001917 fluorescence detection Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims abstract description 104
- -1 di-nitro-substituted benzyl Chemical group 0.000 claims abstract description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 25
- 125000004429 atom Chemical group 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 22
- 125000003710 aryl alkyl group Chemical class 0.000 claims abstract description 21
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims abstract description 21
- 125000001453 quaternary ammonium group Chemical class 0.000 claims abstract description 19
- 238000002372 labelling Methods 0.000 claims abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 16
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 125000005647 linker group Chemical group 0.000 claims abstract description 15
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 15
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005864 Sulphur Substances 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical class N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 13
- 239000010452 phosphate Chemical group 0.000 claims abstract description 13
- 125000006850 spacer group Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 150000001408 amides Chemical class 0.000 claims abstract description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004191 (C1-C6) alkoxy group Chemical class 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical class [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 9
- 125000005504 styryl group Chemical class 0.000 claims abstract description 9
- 229910021653 sulphate ion Inorganic materials 0.000 claims abstract description 9
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims abstract description 9
- 229920002554 vinyl polymer Chemical class 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000003837 (C1-C20) alkyl group Chemical class 0.000 claims abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 55
- 108020001162 nitroreductase Proteins 0.000 claims description 30
- 102000004459 Nitroreductase Human genes 0.000 claims description 28
- 239000007850 fluorescent dye Substances 0.000 claims description 25
- 230000027455 binding Effects 0.000 claims description 21
- 238000001514 detection method Methods 0.000 claims description 20
- 238000003556 assay Methods 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 17
- 230000009870 specific binding Effects 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 14
- 230000014509 gene expression Effects 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 10
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- 102000036639 antigens Human genes 0.000 claims description 9
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 108020004707 nucleic acids Proteins 0.000 claims description 8
- 102000039446 nucleic acids Human genes 0.000 claims description 8
- 150000007523 nucleic acids Chemical class 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 125000004437 phosphorous atom Chemical group 0.000 claims description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 5
- 108010090804 Streptavidin Proteins 0.000 claims description 5
- 229940088597 hormone Drugs 0.000 claims description 5
- 239000005556 hormone Substances 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 claims description 4
- 229960002685 biotin Drugs 0.000 claims description 4
- 235000020958 biotin Nutrition 0.000 claims description 4
- 239000011616 biotin Substances 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 150000002540 isothiocyanates Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 150000008300 phosphoramidites Chemical class 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 102000014914 Carrier Proteins Human genes 0.000 claims description 3
- 102000003886 Glycoproteins Human genes 0.000 claims description 3
- 108090000288 Glycoproteins Proteins 0.000 claims description 3
- 108090001090 Lectins Proteins 0.000 claims description 3
- 102000004856 Lectins Human genes 0.000 claims description 3
- 108091008324 binding proteins Proteins 0.000 claims description 3
- 239000002523 lectin Substances 0.000 claims description 3
- 102000005962 receptors Human genes 0.000 claims description 3
- 108020003175 receptors Proteins 0.000 claims description 3
- 230000001819 effect on gene Effects 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 abstract description 21
- 239000000463 material Substances 0.000 abstract description 15
- 239000012620 biological material Substances 0.000 abstract description 12
- 238000004458 analytical method Methods 0.000 abstract description 6
- 238000004166 bioassay Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 64
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- 229940098773 bovine serum albumin Drugs 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 21
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
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- 108020004414 DNA Proteins 0.000 description 18
- 239000012491 analyte Substances 0.000 description 17
- 239000002953 phosphate buffered saline Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000000523 sample Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000000499 gel Substances 0.000 description 14
- 238000002390 rotary evaporation Methods 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 13
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- 239000002244 precipitate Substances 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- UGFSLVCFIXAHDY-UHFFFAOYSA-N 6-(9-oxoacridin-10-yl)hexanoic acid Chemical compound C1=CC=C2N(CCCCCC(=O)O)C3=CC=CC=C3C(=O)C2=C1 UGFSLVCFIXAHDY-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
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- GXFFSMVXBZVDEI-UHFFFAOYSA-N 6-(2-bromo-9-oxoacridin-10-yl)hexanoic acid Chemical compound BrC1=CC=C2N(CCCCCC(=O)O)C3=CC=CC=C3C(=O)C2=C1 GXFFSMVXBZVDEI-UHFFFAOYSA-N 0.000 description 6
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [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
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- 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
- C09B15/00—Acridine dyes
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Food Science & Technology (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0113435.2 | 2001-06-04 | ||
| GBGB0113435.2A GB0113435D0 (en) | 2001-06-04 | 2001-06-04 | Acridone derivatives as labels for fluorescence detection of target materials |
| CA2449201A CA2449201C (en) | 2001-06-04 | 2002-05-30 | Acridone derivatives as labels for fluorescence detection of target materials |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2449201A Division CA2449201C (en) | 2001-06-04 | 2002-05-30 | Acridone derivatives as labels for fluorescence detection of target materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2754169A1 true CA2754169A1 (en) | 2002-12-12 |
Family
ID=9915775
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2754169A Abandoned CA2754169A1 (en) | 2001-06-04 | 2002-05-30 | Acridone derivatives as labels for fluorescence detection of target materials |
| CA2449201A Expired - Fee Related CA2449201C (en) | 2001-06-04 | 2002-05-30 | Acridone derivatives as labels for fluorescence detection of target materials |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2449201A Expired - Fee Related CA2449201C (en) | 2001-06-04 | 2002-05-30 | Acridone derivatives as labels for fluorescence detection of target materials |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US20040191792A1 (enExample) |
| EP (1) | EP1392776A2 (enExample) |
| JP (1) | JP4583027B2 (enExample) |
| CA (2) | CA2754169A1 (enExample) |
| GB (2) | GB0113435D0 (enExample) |
| WO (1) | WO2002099424A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200301698A (en) | 2001-12-21 | 2003-07-16 | Bristol Myers Squibb Co | Acridone inhibitors of IMPDH enzyme |
| GB0208989D0 (en) | 2002-04-19 | 2002-05-29 | Amersham Biosciences Uk Ltd | Methods for measuring enzyme activity |
| GB0217562D0 (en) * | 2002-07-30 | 2002-09-11 | Amersham Biosciences Uk Ltd | Site-specific labelling of proteins using acridone and quinacridone lifetime dyes |
| GB0317743D0 (en) | 2003-07-30 | 2003-09-03 | Amersham Biosciences Uk Ltd | Method for measuring aromatase activity |
| US7671218B2 (en) * | 2004-08-13 | 2010-03-02 | Elitech Holdings B.V. | Phosphonate fluorescent dyes and conjugates |
| US7767834B2 (en) * | 2004-08-13 | 2010-08-03 | Elitech Holding B.V. | Phosphonylated fluorescent dyes and conjugates |
| GB0421693D0 (en) | 2004-09-30 | 2004-11-03 | Amersham Biosciences Uk Ltd | Method for measuring binding of a test compound to a G-protein coupled receptor |
| CN100386624C (zh) * | 2005-01-27 | 2008-05-07 | 中国科学院大连化学物理研究所 | 一种荧光试剂的制备方法 |
| GB0505777D0 (en) * | 2005-03-22 | 2005-04-27 | Amersham Biosciences Uk Ltd | Enzyme detection method and reagent |
| JP4392502B2 (ja) * | 2005-06-10 | 2010-01-06 | 国立大学法人 岡山大学 | 蛍光性アミノ酸誘導体 |
| WO2007049057A2 (en) * | 2005-10-28 | 2007-05-03 | Iti Scotland Limited | Novel fluorescent dyes and uses thereof |
| GB0601183D0 (en) * | 2006-01-20 | 2006-03-01 | Perkinelmer Ltd | Improvements in and relating to imaging |
| JP2008013456A (ja) | 2006-07-04 | 2008-01-24 | Okayama Univ | 新規蛍光性アミノ酸誘導体およびその製造方法 |
| US20100173332A1 (en) * | 2006-09-07 | 2010-07-08 | Auckland Uniservices Limited | Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds |
| US10872686B2 (en) | 2007-02-22 | 2020-12-22 | WellDoc, Inc. | Systems and methods for disease control and management |
| US10860943B2 (en) | 2007-02-22 | 2020-12-08 | WellDoc, Inc. | Systems and methods for disease control and management |
| GB0712109D0 (en) * | 2007-06-22 | 2007-08-01 | Edinburgh Instr | Fluorescence lifetime and fluorescence assays |
| WO2009112791A1 (en) * | 2008-03-14 | 2009-09-17 | Assaymetrics Limited | Fluorogenic peptides and their method of production |
| US8828678B2 (en) | 2010-11-16 | 2014-09-09 | Enzo Life Sciences, Inc. | Self-immolative probes for enzyme activity detection |
| WO2012129507A1 (en) | 2011-03-24 | 2012-09-27 | WellDoc, Inc. | Adaptive analytical behavioral and health assistant system and related method of use |
| GB201122099D0 (en) | 2011-12-22 | 2012-02-01 | Almac Sciences Scotland Ltd | Dyes |
| US11361857B2 (en) | 2013-06-26 | 2022-06-14 | WellDoc, Inc. | Systems and methods for creating and selecting models for predicting medical conditions |
| US20150006192A1 (en) | 2013-06-26 | 2015-01-01 | WellDoc, Inc. | Systems and methods for clinical decision-making |
| JP6226318B2 (ja) * | 2013-09-02 | 2017-11-08 | 株式会社 資生堂 | 光学分割用化合物、光学分割用試薬、光学分割する方法及び光学異性体 |
| EP3072975A4 (en) * | 2013-11-21 | 2017-05-03 | The University of Tokyo | Method for detecting fluorescence or absorbance, method for suppressing background, method for measuring adp, method for measuring activity of adp-synthesizing enzyme, and method for measuring activity of glucosyltransferase |
| US11414387B2 (en) | 2017-11-20 | 2022-08-16 | Stingthera, Inc. | Oxoacridinyl acetic acid derivatives and methods of use |
| WO2019100061A1 (en) | 2017-11-20 | 2019-05-23 | Silicon Swat, Inc. | Oxoacridinyl acetic acid derivatives and methods of use |
| AU2019425175A1 (en) | 2019-01-21 | 2021-08-19 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Advanced methods for automated high-performance identification of carbohydrates and carbohydrate mixture composition patterns and systems therefore as well as methods for calibration of multi wavelength fluorescence detection systems therefore, based on new fluorescent dyes |
| EP3914650A1 (en) | 2019-01-21 | 2021-12-01 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Sulfonated 2(7)-aminoacridone and 1-aminopyrene dyes and their use as fluorescent tags, in particular for carbohydrate analysis |
| US20230040324A1 (en) | 2019-12-06 | 2023-02-09 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. | Aminoacridine and aminopyrene dyes and their use as fluorescent tags, in particular for carbohydrate analysis |
| DE102021207928A1 (de) * | 2021-07-23 | 2023-02-09 | Continental Reifen Deutschland Gmbh | Verbindung, Verfahren zu deren Herstellung sowie Verwendung der Verbindung als Alterungsschutzmittel und/oder Ozonschutzmittel und/oder Farbstoff |
| EP4663627A1 (en) | 2023-02-06 | 2025-12-17 | NOF Corporation | Amine hydrochloride having maleimide group, and method for producing same |
| US11866412B1 (en) | 2023-03-03 | 2024-01-09 | King Faisal University | Acridin-9-one compounds as antibacterial agents |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3021334A (en) * | 1962-02-13 | Process for n-methylacridone | ||
| GB649147A (en) | 1948-03-22 | 1951-01-17 | Ward Blenkinsop & Co Ltd | Improvements in or relating to the production of substituted diphenylamine 2-monocarboxylic acids |
| FR1192397A (fr) * | 1957-07-19 | 1959-10-26 | Ciba Geigy | Nouveaux colorants solubles dans l'eau, leur préparation et leur utilisation |
| US3681360A (en) * | 1971-04-09 | 1972-08-01 | Hoffmann La Roche | Antiviral substituted acridanones |
| US5268486A (en) * | 1986-04-18 | 1993-12-07 | Carnegie-Mellon Unversity | Method for labeling and detecting materials employing arylsulfonate cyanine dyes |
| US5262545A (en) * | 1989-03-09 | 1993-11-16 | Molecular Probes, Inc. | Fluorescent chloramphenicol derivatives for determination of chloramphenicol acetyltransferase activity |
| WO1992011531A1 (en) | 1990-12-22 | 1992-07-09 | Glyko, Inc. | Analysis of carbohydrates using 2-aminoacridone |
| US5296599A (en) * | 1991-09-19 | 1994-03-22 | Millipore Corporation | Activated carbamates compounds |
| EP0552108B1 (en) * | 1992-01-17 | 1999-11-10 | Lakowicz, Joseph R. | Energy transfer phase-modulation fluoro-immunoassay |
| US5472582A (en) * | 1993-04-23 | 1995-12-05 | Astromed Limited | Analysis of carbohydrates using 2-aminoacridone |
| JP3690825B2 (ja) * | 1993-07-26 | 2005-08-31 | エーザイ株式会社 | 三環式ヘテロ環含有スルホンアミドおよびスルホン酸エステル誘導体 |
| WO1995003279A1 (en) * | 1993-07-26 | 1995-02-02 | Eisai Co., Ltd. | Sulfonamide and sulfonic ester derivatives each having tricyclic hetero ring |
| US6309883B1 (en) * | 1994-02-17 | 2001-10-30 | Maxygen, Inc. | Methods and compositions for cellular and metabolic engineering |
| US5837458A (en) * | 1994-02-17 | 1998-11-17 | Maxygen, Inc. | Methods and compositions for cellular and metabolic engineering |
| US5622821A (en) * | 1994-06-29 | 1997-04-22 | The Regents Of The University Of California | Luminescent lanthanide chelates and methods of use |
| JP4111562B2 (ja) * | 1995-10-04 | 2008-07-02 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | アクリドン系化合物 |
| AU7145396A (en) | 1995-10-04 | 1997-04-28 | Eisai Co. Ltd. | Acridone compounds |
-
2001
- 2001-06-04 GB GBGB0113435.2A patent/GB0113435D0/en not_active Ceased
-
2002
- 2002-05-30 EP EP02727766A patent/EP1392776A2/en not_active Withdrawn
- 2002-05-30 WO PCT/GB2002/002509 patent/WO2002099424A2/en not_active Ceased
- 2002-05-30 CA CA2754169A patent/CA2754169A1/en not_active Abandoned
- 2002-05-30 JP JP2003502493A patent/JP4583027B2/ja not_active Expired - Fee Related
- 2002-05-30 US US10/479,578 patent/US20040191792A1/en not_active Abandoned
- 2002-05-30 CA CA2449201A patent/CA2449201C/en not_active Expired - Fee Related
- 2002-05-30 GB GB0326889A patent/GB2391870B/en not_active Expired - Fee Related
-
2007
- 2007-11-21 US US11/943,628 patent/US8034558B2/en not_active Expired - Fee Related
-
2011
- 2011-09-15 US US13/233,365 patent/US20120015373A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP4583027B2 (ja) | 2010-11-17 |
| EP1392776A2 (en) | 2004-03-03 |
| JP2005500406A (ja) | 2005-01-06 |
| GB2391870A (en) | 2004-02-18 |
| GB0113435D0 (en) | 2001-07-25 |
| US8034558B2 (en) | 2011-10-11 |
| CA2449201C (en) | 2011-12-20 |
| CA2449201A1 (en) | 2002-12-12 |
| GB2391870B (en) | 2005-12-14 |
| GB0326889D0 (en) | 2003-12-24 |
| US20080139788A1 (en) | 2008-06-12 |
| WO2002099424A3 (en) | 2003-12-04 |
| WO2002099424A2 (en) | 2002-12-12 |
| US20040191792A1 (en) | 2004-09-30 |
| US20120015373A1 (en) | 2012-01-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140530 |