TWI227323B - Detection of analytes by fluorescent lanthanide metal chelate complexes containing substituted ligands - Google Patents
Detection of analytes by fluorescent lanthanide metal chelate complexes containing substituted ligands Download PDFInfo
- Publication number
- TWI227323B TWI227323B TW088103762A TW88103762A TWI227323B TW I227323 B TWI227323 B TW I227323B TW 088103762 A TW088103762 A TW 088103762A TW 88103762 A TW88103762 A TW 88103762A TW I227323 B TWI227323 B TW I227323B
- Authority
- TW
- Taiwan
- Prior art keywords
- analyte
- acid
- lanthanide metal
- group
- scope
- Prior art date
Links
- 229910052747 lanthanoid Inorganic materials 0.000 title claims abstract description 41
- 150000002602 lanthanoids Chemical class 0.000 title claims abstract description 41
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 34
- 239000002184 metal Substances 0.000 title claims abstract description 34
- 239000003446 ligand Substances 0.000 title claims description 38
- 239000013522 chelant Substances 0.000 title claims description 31
- 238000001514 detection method Methods 0.000 title claims description 9
- 239000012491 analyte Substances 0.000 claims abstract description 38
- 150000004697 chelate complex Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 230000008859 change Effects 0.000 claims abstract description 10
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 59
- 239000008103 glucose Substances 0.000 claims description 57
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000002738 chelating agent Substances 0.000 claims description 28
- -1 tritium chelate complex Chemical class 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 229910021645 metal ion Inorganic materials 0.000 claims description 15
- 229930091371 Fructose Natural products 0.000 claims description 14
- 239000005715 Fructose Substances 0.000 claims description 14
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 14
- 150000002500 ions Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000013110 organic ligand Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 229910052693 Europium Inorganic materials 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 238000004448 titration Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- 229910052722 tritium Inorganic materials 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000005487 catechin Nutrition 0.000 claims description 4
- 229950001002 cianidanol Drugs 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 4
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- AQLMHYSWFMLWBS-UHFFFAOYSA-N arsenite(1-) Chemical compound O[As](O)[O-] AQLMHYSWFMLWBS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002085 enols Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229910052691 Erbium Inorganic materials 0.000 claims 2
- 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 150000002829 nitrogen Chemical class 0.000 claims 2
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical group C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical group O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims 1
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 claims 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical group O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
- 229940075930 picrate Drugs 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 claims 1
- 239000003269 fluorescent indicator Substances 0.000 abstract description 4
- 230000027455 binding Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 13
- 235000000346 sugar Nutrition 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 150000008163 sugars Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 229910052692 Dysprosium Inorganic materials 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 238000003018 immunoassay Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 229910021644 lanthanide ion Inorganic materials 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 150000002178 europium compounds Chemical class 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-M 1-naphthaleneacetate Chemical compound C1=CC=C2C(CC(=O)[O-])=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000003512 Claisen condensation reaction Methods 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241001479493 Sousa Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- TUCIXUDAQRPDCG-UHFFFAOYSA-N benzene-1,2-diol Chemical compound OC1=CC=CC=C1O.OC1=CC=CC=C1O TUCIXUDAQRPDCG-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012875 competitive assay Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- BYYQOWAAZOHHFN-UHFFFAOYSA-N dioctylphosphane Chemical compound CCCCCCCCPCCCCCCCC BYYQOWAAZOHHFN-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 235000019985 fermented beverage Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-M gallate Chemical compound OC1=CC(C([O-])=O)=CC(O)=C1O LNTHITQWFMADLM-UHFFFAOYSA-M 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000007793 ph indicator Substances 0.000 description 1
- WAJUCMNAGKFHLB-UHFFFAOYSA-N phenylarsinic acid Chemical compound O[AsH](=O)C1=CC=CC=C1 WAJUCMNAGKFHLB-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-O phenylphosphanium Chemical compound [PH3+]C1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-O 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 230000004572 zinc-binding Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid 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
- G01N33/58—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
-
- 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
- G01N33/66—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood sugars, e.g. galactose
-
- 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]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, 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
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, 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
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
- Y10T436/144444—Glucose
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Organic Chemistry (AREA)
- Biotechnology (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Materials Engineering (AREA)
- Diabetes (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3796098A | 1998-03-11 | 1998-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI227323B true TWI227323B (en) | 2005-02-01 |
Family
ID=21897295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088103762A TWI227323B (en) | 1998-03-11 | 1999-03-11 | Detection of analytes by fluorescent lanthanide metal chelate complexes containing substituted ligands |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6344360B1 (enExample) |
| EP (1) | EP1062516A1 (enExample) |
| JP (1) | JP4625180B2 (enExample) |
| KR (1) | KR100718953B1 (enExample) |
| CN (1) | CN1159583C (enExample) |
| AU (1) | AU757901B2 (enExample) |
| CA (1) | CA2322858C (enExample) |
| TW (1) | TWI227323B (enExample) |
| WO (1) | WO1999046600A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI381162B (zh) * | 2005-05-26 | 2013-01-01 | Plagenom Co Ltd | A authenticity determination method, an authenticity determination device, a authenticity determination system, and a detection device terminal |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69633573T2 (de) | 1995-11-22 | 2005-10-06 | Medtronic MiniMed, Inc., Northridge | Detektion von biologischen molekülen unter verwendung von chemischer amplifikation und optischem sensor |
| US6766183B2 (en) | 1995-11-22 | 2004-07-20 | Medtronic Minimed, Inc. | Long wave fluorophore sensor compounds and other fluorescent sensor compounds in polymers |
| AU5446098A (en) | 1996-11-21 | 1998-06-10 | Lawrence Livermore National Laboratory | Detection of biological molecules using boronate-based chemical amplification and optical sensors |
| US6330464B1 (en) | 1998-08-26 | 2001-12-11 | Sensors For Medicine & Science | Optical-based sensing devices |
| FR2792072A1 (fr) * | 1999-04-08 | 2000-10-13 | Cis Bio Int | Methode homogene de detection ou de determination d'une interaction chimique ou physicochimique |
| US6673625B2 (en) | 1999-09-15 | 2004-01-06 | The Regents Of The University Of California | Saccharide sensing molecules having enhanced fluorescent properties |
| US6682938B1 (en) | 1999-09-15 | 2004-01-27 | The Regents Of The University Of California | Glucose sensing molecules having selected fluorescent properties |
| US6774102B1 (en) * | 1999-09-29 | 2004-08-10 | Gambro Dialysatoren Gmbh & Co. Kg | Extracorporeal endotoxin removal method |
| WO2001075450A2 (en) * | 2000-04-04 | 2001-10-11 | The Regents Of The University Of California | Fluorescent lifetime assays for non-invasive quantification of analytes |
| CN1446222A (zh) | 2000-08-04 | 2003-10-01 | 医药及科学传感器公司 | 水环境中分析物的检测 |
| US6653141B2 (en) * | 2000-12-05 | 2003-11-25 | The Regents Of The University Of California | Polyhydroxyl-substituted organic molecule sensing method and device |
| US7470420B2 (en) * | 2000-12-05 | 2008-12-30 | The Regents Of The University Of California | Optical determination of glucose utilizing boronic acid adducts |
| US6800451B2 (en) * | 2001-01-05 | 2004-10-05 | Sensors For Medicine And Science, Inc. | Detection of glucose in solutions also containing an alpha-hydroxy acid or a beta-diketone |
| US20020119581A1 (en) * | 2001-01-05 | 2002-08-29 | Daniloff George Y. | Detection of analytes |
| AU2002251944A1 (en) | 2001-02-15 | 2002-09-04 | Medtronic Minimed, Inc. | Polymers functionalized with fluorescent boronate motifs |
| JP4729734B2 (ja) * | 2001-05-16 | 2011-07-20 | 財団法人北九州産業学術推進機構 | キドセンサによる重金属イオン測定装置 |
| US9493806B2 (en) | 2001-06-01 | 2016-11-15 | Colorado State University Research Foundation | Enzymatic biosensing systems |
| US9493805B2 (en) | 2001-06-01 | 2016-11-15 | Colorado State University Research Foundation | Enzymatic biosensors with enhanced activity retention for detection of organic compounds |
| US20050164316A1 (en) * | 2001-06-27 | 2005-07-28 | Bray Terry L. | Biophotonic sensors and methods of use thereof |
| US20030215391A1 (en) * | 2001-07-19 | 2003-11-20 | Carlos Rabito | Fluorescent agents for real-time measurement of organ function |
| US7045361B2 (en) | 2001-09-12 | 2006-05-16 | Medtronic Minimed, Inc. | Analyte sensing via acridine-based boronate biosensors |
| ES2345194T3 (es) * | 2002-03-14 | 2010-09-17 | Sensors For Medicine And Science, Inc. | Deteccion de glucosa que tambien contienen un alfa hidroxiacido o una beta dicetona. |
| GB0210535D0 (en) * | 2002-05-08 | 2002-06-19 | Novartis Ag | Organic compounds |
| US7108659B2 (en) * | 2002-08-01 | 2006-09-19 | Healthetech, Inc. | Respiratory analyzer for exercise use |
| AU2003287735A1 (en) * | 2002-11-12 | 2004-06-03 | Argose, Inc. | Non-invasive measurement of analytes |
| US20040106163A1 (en) * | 2002-11-12 | 2004-06-03 | Workman Jerome James | Non-invasive measurement of analytes |
| JP4748791B2 (ja) * | 2003-02-24 | 2011-08-17 | 独立行政法人科学技術振興機構 | 蛍光性ランタニド錯体 |
| WO2005065241A2 (en) | 2003-12-24 | 2005-07-21 | Argose, Inc. | Smmr (small molecule metabolite reporters) for use as in vivo glucose biosensors |
| US7713745B2 (en) * | 2004-04-13 | 2010-05-11 | Sensors For Medicine And Science, Inc. | Non-covalent immobilization of indicator molecules |
| DE102004051830B4 (de) | 2004-10-25 | 2007-12-13 | Roche Diagnostics Gmbh | Multifunktionales Referenzsystem bei Analytbestimmungen durch Fluoreszenz |
| JP5057682B2 (ja) * | 2006-03-30 | 2012-10-24 | 株式会社東芝 | 照明装置、撮像装置及び携帯端末 |
| GB0613823D0 (en) | 2006-07-12 | 2006-08-23 | Univ Durham | Assay |
| US9796998B2 (en) | 2007-04-09 | 2017-10-24 | Colorado State University Research Foundation | Oxygenase-based biosensing systems for measurement of halogenated alkene concentrations |
| FR2917226B1 (fr) * | 2007-06-06 | 2009-09-11 | Inst Nat Sciences Appliq | Procede de marquage de materiaux a base de matrices organiques polymeriques thermoplastiques ou thermodurcissables |
| US20090247984A1 (en) * | 2007-10-24 | 2009-10-01 | Masimo Laboratories, Inc. | Use of microneedles for small molecule metabolite reporter delivery |
| WO2010014505A1 (en) * | 2008-07-28 | 2010-02-04 | Sensors For Medicine & Science, Inc. | Systems and methods for optical measurement of analyte concentration |
| US20120190123A1 (en) * | 2008-09-10 | 2012-07-26 | National University Corporation NARA Institute of Science and Technology | Structural analysis device and structural analysis method |
| WO2012071471A2 (en) | 2010-11-22 | 2012-05-31 | Colorado State University Research Foundation | Biosensing systems for measurement of lactose |
| JP6084172B2 (ja) | 2011-03-15 | 2017-02-22 | センセオニクス,インコーポレーテッド | 酸化感受性材料の統合的な触媒による保護 |
| US9051598B2 (en) * | 2011-05-02 | 2015-06-09 | The Hong Kong University Of Science And Technology | Specific detection of D-glucose by a tetraphenylethene-base fluorescent sensor |
| US9499853B2 (en) | 2011-08-02 | 2016-11-22 | Colorado State University Research Foundation | Biosensing system with extended lifetime via cofactor recycling |
| WO2013160547A1 (en) | 2012-04-24 | 2013-10-31 | Haermae Harri | Method for characterizing and/or determining samples |
| US9194802B2 (en) | 2012-09-14 | 2015-11-24 | Regents Of The University Of Minnesota | Luminescent probes having a phenanthridinyl antenna, and methods of use |
| CA2896749A1 (en) | 2012-12-28 | 2014-07-03 | Senseonics, Incorporated | Analyte permeable membrane systems for oxidative and optical stability |
| KR101660399B1 (ko) * | 2013-08-23 | 2016-09-28 | 주식회사 메디센서 | 금 나노 입자를 포함하는 형광 입자 및 그 제조방법 |
| US9963556B2 (en) | 2013-09-18 | 2018-05-08 | Senseonics, Incorporated | Critical point drying of hydrogels in analyte sensors |
| FI125111B (en) * | 2013-11-19 | 2015-06-15 | Kemira Oyj | A method for analyzing a sample comprising first and second anticaking agents |
| FI125102B (en) * | 2013-11-19 | 2015-06-15 | Kemira Oyj | Method for the determination of an antifouling agent in a sample |
| CN103881128A (zh) * | 2014-03-10 | 2014-06-25 | 黄鹏 | 基于荧光检测方法的原位葡萄糖检测膜的制备方法 |
| ES2998082T3 (en) | 2017-08-14 | 2025-02-19 | Senseonics Inc | Methods and systems for calculating analyte levels |
| EP3722379B1 (en) * | 2017-09-15 | 2023-10-11 | Dai Nippon Printing Co., Ltd. | Ink composition and printed matter |
| CN112047965B (zh) * | 2020-09-09 | 2022-04-26 | 黑龙江大学 | 一种具有激发态配体间质子转移特性的配合物的制备方法及应用 |
| CN115124731B (zh) * | 2022-08-12 | 2023-12-01 | 复旦大学 | 一种高值化豆科植物界面超组装SAFs荧光材料的制备方法 |
| CN118955414B (zh) * | 2024-10-17 | 2025-03-18 | 南昌大学 | 两亲性Eu配合物及其制备方法与在检测四环素中的应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4637988A (en) * | 1981-07-01 | 1987-01-20 | Eastman Kodak Company | Fluorescent labels for immunoassay |
| SE454115B (sv) * | 1982-09-13 | 1988-03-28 | Wallac Oy | Homogenfasanalys med lantanidkelat som merksubstans |
| EP0272320B1 (en) * | 1986-06-17 | 1994-03-23 | Baxter Diagnostics Inc. | Homogeneous fluoroassay methods employing fluorescent background rejection |
| US5512246A (en) * | 1989-09-21 | 1996-04-30 | Anthony P. Russell | Method and means for detecting polyhydroxyl compounds |
| US5246867A (en) * | 1992-01-17 | 1993-09-21 | University Of Maryland At Baltimore | Determination and quantification of saccharides by luminescence lifetimes and energy transfer |
| GB2284809B (en) * | 1993-11-07 | 1998-04-29 | Japan Res Dev Corp | A fluorescent phenylboronic acid suitable for use in the detection of saccharides |
| US5631364A (en) * | 1994-03-31 | 1997-05-20 | Axis Biochemicals Asa | Labelled boronic acid derivatives |
| DE69633573T2 (de) * | 1995-11-22 | 2005-10-06 | Medtronic MiniMed, Inc., Northridge | Detektion von biologischen molekülen unter verwendung von chemischer amplifikation und optischem sensor |
| JP2866043B2 (ja) * | 1995-12-21 | 1999-03-08 | 科学技術振興事業団 | カリックスアレーン誘導体 |
| US6001573A (en) * | 1996-06-14 | 1999-12-14 | Packard Bioscience B.V. | Use of porphyrins as a universal label |
-
1999
- 1999-03-11 WO PCT/US1999/005290 patent/WO1999046600A1/en not_active Ceased
- 1999-03-11 JP JP2000535930A patent/JP4625180B2/ja not_active Expired - Fee Related
- 1999-03-11 CN CNB998059862A patent/CN1159583C/zh not_active Expired - Fee Related
- 1999-03-11 US US09/265,979 patent/US6344360B1/en not_active Expired - Lifetime
- 1999-03-11 AU AU30785/99A patent/AU757901B2/en not_active Ceased
- 1999-03-11 TW TW088103762A patent/TWI227323B/zh not_active IP Right Cessation
- 1999-03-11 EP EP99912403A patent/EP1062516A1/en not_active Ceased
- 1999-03-11 KR KR1020007010146A patent/KR100718953B1/ko not_active Expired - Fee Related
- 1999-03-11 CA CA002322858A patent/CA2322858C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI381162B (zh) * | 2005-05-26 | 2013-01-01 | Plagenom Co Ltd | A authenticity determination method, an authenticity determination device, a authenticity determination system, and a detection device terminal |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3078599A (en) | 1999-09-27 |
| WO1999046600A1 (en) | 1999-09-16 |
| KR20010041855A (ko) | 2001-05-25 |
| CA2322858C (en) | 2009-06-02 |
| KR100718953B1 (ko) | 2007-05-16 |
| US6344360B1 (en) | 2002-02-05 |
| WO1999046600A9 (en) | 1999-11-18 |
| CN1159583C (zh) | 2004-07-28 |
| JP4625180B2 (ja) | 2011-02-02 |
| CA2322858A1 (en) | 1999-09-16 |
| CN1300368A (zh) | 2001-06-20 |
| EP1062516A1 (en) | 2000-12-27 |
| JP2002506973A (ja) | 2002-03-05 |
| AU757901B2 (en) | 2003-03-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI227323B (en) | Detection of analytes by fluorescent lanthanide metal chelate complexes containing substituted ligands | |
| Sun et al. | Mitochondria targetable time-gated luminescence probe for singlet oxygen based on a β-diketonate–europium complex | |
| Chen et al. | 2-Hydroxy benzothiazole modified rhodol: aggregation-induced emission and dual-channel fluorescence sensing of Hg2+ and Ag+ ions | |
| US5503770A (en) | Fluorescent compound suitable for use in the detection of saccharides | |
| Das et al. | Fluorescent probes for selective determination of trace level Al 3+: recent developments and future prospects | |
| EP2099807B1 (en) | Oxidation resistant indicator molecules | |
| US9051598B2 (en) | Specific detection of D-glucose by a tetraphenylethene-base fluorescent sensor | |
| Tümay | Tripodal structured blue-green emissive fluorescent sensors for highly selective bifunctional detection: Their logic gate operations and real sample applications | |
| TWI354101B (en) | Fluorimetric indicator for biosensing and manufact | |
| CN108752377B (zh) | 一种检测过氧亚硝基阴离子的荧光探针、合成方法和应用 | |
| JP2883824B2 (ja) | ボロン酸基を有する発蛍光性化合物 | |
| CN110229165A (zh) | 上转换荧光探针罗丹明衍生物及其应用 | |
| Eçik et al. | Synthesis of BODIPY-cyclotetraphosphazene triad systems and their sensing behaviors toward Co (II) and Cu (II) | |
| Jin et al. | A highly selective chemiluminescent probe for the detection of chromium (VI) | |
| Wang et al. | Boronate-based fluorescent probes as a prominent tool for H2O2 sensing and recognition | |
| Singh et al. | Incorporation of siderophore binding sites in a dipodal fluorescent sensor for Fe (III) | |
| Rong et al. | A long-wavelength mitochondria-targeted CO fluorescent probe for living cells and zebrafish imaging | |
| Zhang et al. | Supramolecular fluorescent probe based on acyclic cucurbituril for detection of cancer Labels in human urine | |
| CN105777578B (zh) | 一种酰腙类氰根离子传感器分子及其合成及在含水体系中检测氰根离子的应用 | |
| CN110669350B (zh) | 一种哌啶基bodipy类红光荧光染料及其制备方法和应用 | |
| CN114751898A (zh) | 分子探针化合物及其制备方法和应用 | |
| Liu et al. | Superlong afterglow reporter for the detection of porphyria in whole blood | |
| Li et al. | Comprehensive investigations of four ratiometric fluorescent chemosensors based on 4-(1H-imidazol-2-yl) benzaldehyde skeleton for malononitrile detection | |
| CN119977989B (zh) | 一种基于罗丹明衍生物检测次氯酸的荧光探针制备与应用 | |
| CN117486892A (zh) | 一种对Fe3+和Cr3+具双重响应的含噻吩结构的罗丹明类荧光探针及其合成方法与应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |