JPH0259151B2 - - Google Patents
Info
- Publication number
- JPH0259151B2 JPH0259151B2 JP4443181A JP4443181A JPH0259151B2 JP H0259151 B2 JPH0259151 B2 JP H0259151B2 JP 4443181 A JP4443181 A JP 4443181A JP 4443181 A JP4443181 A JP 4443181A JP H0259151 B2 JPH0259151 B2 JP H0259151B2
- Authority
- JP
- Japan
- Prior art keywords
- biopterin
- enzyme
- labeled
- maleimidobenzoyl
- fluorescence intensity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 108090000790 Enzymes Proteins 0.000 claims description 16
- 102000004190 Enzymes Human genes 0.000 claims description 16
- HNXQXTQTPAJEJL-UHFFFAOYSA-N 2-aminopteridin-4-ol Chemical class C1=CN=C2NC(N)=NC(=O)C2=N1 HNXQXTQTPAJEJL-UHFFFAOYSA-N 0.000 claims description 13
- -1 m-maleimidobenzoyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 102000005936 beta-Galactosidase Human genes 0.000 claims description 4
- 108010005774 beta-Galactosidase Proteins 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229940088598 enzyme Drugs 0.000 description 14
- LHQIJBMDNUYRAM-AWFVSMACSA-N D-erythro-biopterin Chemical compound N1=C(N)NC(=O)C2=NC([C@H](O)[C@H](O)C)=CN=C21 LHQIJBMDNUYRAM-AWFVSMACSA-N 0.000 description 12
- 239000000427 antigen Substances 0.000 description 12
- 102000036639 antigens Human genes 0.000 description 12
- 108091007433 antigens Proteins 0.000 description 12
- LHQIJBMDNUYRAM-UHFFFAOYSA-N L-erythro-Biopterin Natural products N1=C(N)NC(=O)C2=NC(C(O)C(O)C)=CN=C21 LHQIJBMDNUYRAM-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 229940098773 bovine serum albumin Drugs 0.000 description 10
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000008363 phosphate buffer Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920001184 polypeptide Polymers 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 102000002464 Galactosidases Human genes 0.000 description 2
- 108010093031 Galactosidases Proteins 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920002684 Sepharose Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000003053 immunization Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 150000003195 pteridines Chemical class 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- VWXIHLCLIOQWRA-UHFFFAOYSA-N 1h-pteridin-2-one Chemical class N1=CC=NC2=NC(O)=NC=C21 VWXIHLCLIOQWRA-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- XGXBEYPTWXSMTE-UHFFFAOYSA-N 2-methylsulfanyl-1h-pteridin-4-one Chemical compound C1=CN=C2NC(SC)=NC(=O)C2=N1 XGXBEYPTWXSMTE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 208000027219 Deficiency disease Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FEMXZDUTFRTWPE-DZSWIPIPSA-N L-erythro-7,8-dihydrobiopterin Chemical compound N1C(N)=NC(=O)C2=C1NCC([C@@H](O)[C@@H](O)C)=N2 FEMXZDUTFRTWPE-DZSWIPIPSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 201000011252 Phenylketonuria Diseases 0.000 description 1
- BMQYVXCPAOLZOK-UHFFFAOYSA-N Trihydroxypropylpterisin Natural products OCC(O)C(O)C1=CN=C2NC(N)=NC(=O)C2=N1 BMQYVXCPAOLZOK-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 230000037354 amino acid metabolism Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 150000008195 galaktosides Chemical class 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BMQYVXCPAOLZOK-XINAWCOVSA-N neopterin Chemical compound OC[C@@H](O)[C@@H](O)C1=CN=C2NC(N)=NC(=O)C2=N1 BMQYVXCPAOLZOK-XINAWCOVSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- FNKQXYHWGSIFBK-RPDRRWSUSA-N sapropterin Chemical compound N1=C(N)NC(=O)C2=C1NC[C@H]([C@@H](O)[C@@H](O)C)N2 FNKQXYHWGSIFBK-RPDRRWSUSA-N 0.000 description 1
- 229960004617 sapropterin Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4443181A JPS57158783A (en) | 1981-03-26 | 1981-03-26 | Pterin derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4443181A JPS57158783A (en) | 1981-03-26 | 1981-03-26 | Pterin derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57158783A JPS57158783A (en) | 1982-09-30 |
JPH0259151B2 true JPH0259151B2 (de) | 1990-12-11 |
Family
ID=12691297
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4443181A Granted JPS57158783A (en) | 1981-03-26 | 1981-03-26 | Pterin derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57158783A (de) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4308739C1 (de) * | 1993-03-19 | 1994-06-23 | Henning Berlin Gmbh | Pterinderivate, ihre Herstellung und ihre Verwendung |
-
1981
- 1981-03-26 JP JP4443181A patent/JPS57158783A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS57158783A (en) | 1982-09-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5202234A (en) | Myocardial infarction immunoassay | |
US4485177A (en) | Creatinine specific antibody | |
US7189582B2 (en) | Compositions and methods for detection of sirolimus | |
US5382515A (en) | Creative kinase-MB immunoassay for myocardial infarction and reagents | |
JPH0415240B2 (de) | ||
US4478934A (en) | Determination of adenosine by immunoassay involving acylation of the adenosine | |
US4261974A (en) | Valproic acid immunogen conjugates and antibodies thereto | |
EP0304292B1 (de) | Antikörper zum Propeptid des Prokollagen-III und seine Benutzung in einem Analyseverfahren | |
US4292425A (en) | βGalactosyl-umbelliferone valproic acid conjugates | |
JPS58111754A (ja) | クレアチニンの免疫学的測定法及びそのための試薬 | |
US7781570B2 (en) | Site-specific aminoglycoside derivatives for use in immunodiagnostic assays | |
US10351830B2 (en) | Conjugates for assays for oxycodone and oxymorphone | |
JPH0259151B2 (de) | ||
JP2587239B2 (ja) | 酵素標識トロンボキサンb▲下2▼類およびそれを用いた11−デヒドロ−トロンボキサンb▲下2▼の測定法 | |
JPH085904B2 (ja) | 新規ホスホリルコリン誘導体の製造法 | |
JP3864261B2 (ja) | マイコフェノリック酸アッセイのための試薬 | |
JP2968910B2 (ja) | 1α,25(OH)2ビタミンD3に対する抗体及びその用途 | |
Burd | [4] The homogeneous substrate-labeled fluorescent immunoassay | |
EP0052921B1 (de) | Verfahren und Zusammensetzungen zum Testen bei der Gewinnung von 1,4-Dihydropyridyl | |
JPH0262820B2 (de) | ||
JPH0317300B2 (de) | ||
JPH0782015B2 (ja) | D型バニリルマンデル酸の測定法およびそれに使用する試薬およびキット | |
JPH0255434B2 (de) | ||
JPH06316599A (ja) | ジフェンヒドラミンおよびその代謝産物の免疫学的測定のための組成物および方法 | |
CN110954707A (zh) | 丙戊酸衍生物及其在免疫检测中的用途 |