JPH0463073B2 - - Google Patents

Info

Publication number: JPH0463073B2
Authority: JP; Japan
Prior art keywords: usually; group; formula; compounds; poly
Prior art date: 1989-03-20
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

Application number

JP1066476A

Other languages

English (en)

Japanese (ja)

Other versions

JPH01308273A (ja

Inventor

Raru Kanna Piaaru

Fuitsushaa Uruman Edoin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Syva Co

Original Assignee

Syva Co

Priority date (The priority date 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 date listed.)

1989-03-20

Filing date

1989-03-20

Publication date

1992-10-08

1989-03-20 Application filed by Syva Co filed Critical Syva Co

1989-03-20 Priority to JP1066476A priority Critical patent/JPH01308273A/ja

1989-12-12 Publication of JPH01308273A publication Critical patent/JPH01308273A/ja

1991-10-30 Priority to JP91311969A priority patent/JPH05310800A/ja

1992-10-08 Publication of JPH0463073B2 publication Critical patent/JPH0463073B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 85
-1 poly(amino acid) Polymers 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000004429 atom Chemical group 0.000 claims description 16
229920001308 poly(aminoacid) Polymers 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 13
239000000427 antigen Substances 0.000 claims description 10
102000036639 antigens Human genes 0.000 claims description 10
108091007433 antigens Proteins 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
239000012491 analyte Substances 0.000 claims description 8
125000002843 carboxylic acid group Chemical group 0.000 claims description 5
239000000370 acceptor Substances 0.000 claims 1
230000002860 competitive effect Effects 0.000 claims 1
238000000159 protein binding assay Methods 0.000 claims 1
239000003446 ligand Substances 0.000 description 57
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
239000000047 product Substances 0.000 description 31
239000000203 mixture Substances 0.000 description 29
108090000623 proteins and genes Proteins 0.000 description 29
102000004169 proteins and genes Human genes 0.000 description 28
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 25
229910052757 nitrogen Inorganic materials 0.000 description 25
239000007787 solid Substances 0.000 description 24
229910052799 carbon Inorganic materials 0.000 description 23
229910052760 oxygen Inorganic materials 0.000 description 21
239000001301 oxygen Substances 0.000 description 21
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
229940079593 drug Drugs 0.000 description 17
239000003814 drug Substances 0.000 description 17
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 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
150000001408 amides Chemical class 0.000 description 16
238000011156 evaluation Methods 0.000 description 16
125000005647 linker group Chemical group 0.000 description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
239000000126 substance Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000010521 absorption reaction Methods 0.000 description 15
125000004435 hydrogen atom Chemical class [H]* 0.000 description 15
239000002207 metabolite Substances 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
230000027455 binding Effects 0.000 description 13
239000000872 buffer Substances 0.000 description 13
150000001787 chalcogens Chemical class 0.000 description 13
238000010791 quenching Methods 0.000 description 13
230000000171 quenching effect Effects 0.000 description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
229910052798 chalcogen Inorganic materials 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
238000003018 immunoassay Methods 0.000 description 12
229910052717 sulfur Inorganic materials 0.000 description 12
239000011593 sulfur Substances 0.000 description 12
229940027941 immunoglobulin g Drugs 0.000 description 11
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class 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 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000003556 assay Methods 0.000 description 10
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 10
238000004809 thin layer chromatography Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
125000005842 heteroatom Chemical group 0.000 description 9
239000002609 medium Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
125000006850 spacer group Chemical group 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
230000000890 antigenic effect Effects 0.000 description 8
230000008033 biological extinction Effects 0.000 description 8
DCPHSBOTFHCNQC-UHFFFAOYSA-N 3',6'-dihydroxy-4',5'-dimethoxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylic acid Chemical compound O1C(=O)C2=CC=C(C(O)=O)C=C2C21C1=CC=C(O)C(OC)=C1OC1=C2C=CC(O)=C1OC DCPHSBOTFHCNQC-UHFFFAOYSA-N 0.000 description 7
125000001931 aliphatic group Chemical group 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
125000001309 chloro group Chemical group Cl* 0.000 description 7
230000021615 conjugation Effects 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
229960005181 morphine Drugs 0.000 description 7
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
230000009870 specific binding Effects 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
229940088597 hormone Drugs 0.000 description 6
239000005556 hormone Substances 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
238000002372 labelling Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
108090000765 processed proteins & peptides Proteins 0.000 description 6
150000003568 thioethers Chemical group 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 5
229930182566 Gentamicin Natural products 0.000 description 5
229960004821 amikacin Drugs 0.000 description 5
LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
239000000975 dye Substances 0.000 description 5
229960002518 gentamicin Drugs 0.000 description 5
150000004676 glycans Chemical class 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229920001282 polysaccharide Polymers 0.000 description 5
239000005017 polysaccharide Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
102000004196 processed proteins & peptides Human genes 0.000 description 5
210000002966 serum Anatomy 0.000 description 5
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
108060003951 Immunoglobulin Proteins 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
DEXMFYZAHXMZNM-UHFFFAOYSA-N Narceine Chemical compound OC(=O)C1=C(OC)C(OC)=CC=C1C(=O)CC1=C(CCN(C)C)C=C(OCO2)C2=C1OC DEXMFYZAHXMZNM-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
125000000129 anionic group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
235000017168 chlorine Nutrition 0.000 description 4
239000012530 fluid Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
102000018358 immunoglobulin Human genes 0.000 description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
150000002540 isothiocyanates Chemical class 0.000 description 4
229930027917 kanamycin Natural products 0.000 description 4
229960000318 kanamycin Drugs 0.000 description 4
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 4
229930182823 kanamycin A Natural products 0.000 description 4
229920001184 polypeptide Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
239000004380 Cholic acid Substances 0.000 description 3
102400000739 Corticotropin Human genes 0.000 description 3
101800000414 Corticotropin Proteins 0.000 description 3
108010051696 Growth Hormone Proteins 0.000 description 3
102100038803 Somatotropin Human genes 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002411 adverse Effects 0.000 description 3
229930013930 alkaloid Natural products 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
150000001409 amidines Chemical class 0.000 description 3
239000012736 aqueous medium Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 3
235000019416 cholic acid Nutrition 0.000 description 3
229960002471 cholic acid Drugs 0.000 description 3
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical class O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 3
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 3
229960000258 corticotropin Drugs 0.000 description 3
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000010828 elution Methods 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
125000001033 ether group Chemical group 0.000 description 3
230000005284 excitation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
125000000743 hydrocarbylene group Chemical group 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
244000005700 microbiome Species 0.000 description 3
150000007523 nucleic acids Chemical class 0.000 description 3
102000039446 nucleic acids Human genes 0.000 description 3
108020004707 nucleic acids Proteins 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
150000003463 sulfur Chemical class 0.000 description 3
238000012360 testing method Methods 0.000 description 3
229960000707 tobramycin Drugs 0.000 description 3
NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 3
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
229930182837 (R)-adrenaline Natural products 0.000 description 2
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
QFYYAIBEHOEZKC-UHFFFAOYSA-N 2-Methoxyresorcinol Chemical compound COC1=C(O)C=CC=C1O QFYYAIBEHOEZKC-UHFFFAOYSA-N 0.000 description 2
FLLKEIPUAOSBCF-UHFFFAOYSA-N 2-chloro-4-methoxybenzene-1,3-diol Chemical compound COC1=CC=C(O)C(Cl)=C1O FLLKEIPUAOSBCF-UHFFFAOYSA-N 0.000 description 2
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SFVVQRJOGUKCEG-OPQSFPLASA-N β-MSH Chemical compound C1C[C@@H](O)[C@H]2C(COC(=O)[C@@](O)([C@@H](C)O)C(C)C)=CCN21 SFVVQRJOGUKCEG-OPQSFPLASA-N 0.000 description 1

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Pyrane Compounds (AREA)
Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Peptides Or Proteins (AREA)

JP1066476A 1989-03-20 1989-03-20 新規エーテル置換フルオレセイン化合物の複合体 Granted JPH01308273A (ja)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
JP1066476A JPH01308273A (ja)	1989-03-20	1989-03-20	新規エーテル置換フルオレセイン化合物の複合体
JP91311969A JPH05310800A (ja)	1989-03-20	1991-10-30	新規エーテル置換フルオレセイン化合物の複合体

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP1066476A JPH01308273A (ja)	1989-03-20	1989-03-20	新規エーテル置換フルオレセイン化合物の複合体
JP91311969A JPH05310800A (ja)	1989-03-20	1991-10-30	新規エーテル置換フルオレセイン化合物の複合体

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15178980A Division JPS5782387A (en)	1980-10-29	1980-10-29	Novel ether substituted fluorescein compound

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP91311969A Division JPH05310800A (ja)	1989-03-20	1991-10-30	新規エーテル置換フルオレセイン化合物の複合体

Publications (2)

Publication Number	Publication Date
JPH01308273A JPH01308273A (ja)	1989-12-12
JPH0463073B2 true JPH0463073B2 (fr)	1992-10-08

Family

ID=26407668

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP1066476A Granted JPH01308273A (ja)	1989-03-20	1989-03-20	新規エーテル置換フルオレセイン化合物の複合体
JP91311969A Pending JPH05310800A (ja)	1989-03-20	1991-10-30	新規エーテル置換フルオレセイン化合物の複合体

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP91311969A Pending JPH05310800A (ja)	1989-03-20	1991-10-30	新規エーテル置換フルオレセイン化合物の複合体

Country Status (1)

Country	Link
JP (2)	JPH01308273A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01308273A (ja) *	1989-03-20	1989-12-12	Syva Co	新規エーテル置換フルオレセイン化合物の複合体
US7691953B2 (en)	2007-06-27	2010-04-06	H R D Corporation	System and process for production of polyvinyl chloride

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01308273A (ja) *	1989-03-20	1989-12-12	Syva Co	新規エーテル置換フルオレセイン化合物の複合体

1989
- 1989-03-20 JP JP1066476A patent/JPH01308273A/ja active Granted
1991
- 1991-10-30 JP JP91311969A patent/JPH05310800A/ja active Pending

Also Published As

Publication number	Publication date
JPH01308273A (ja)	1989-12-12
JPH05310800A (ja)	1993-11-22

Publication	Publication Date	Title
US4318846A (en)	1982-03-09	Novel ether substituted fluorescein polyamino acid compounds as fluorescers and quenchers
JPH034596B2 (fr)	1991-01-23
US4481136A (en)	1984-11-06	Alkyl substituted fluorescent compounds and conjugates
EP0214847B1 (fr)	1992-04-08	Conjugué d'un colorant quadratique, procédé pour sa préparation et son application dans des méthodes d'analyse ainsi que des trousses
US4160016A (en)	1979-07-03	Receptor fluorescent immunoassay
US4510251A (en)	1985-04-09	Fluorescent polarization assay for ligands using aminomethylfluorescein derivatives as tracers
US4668640A (en)	1987-05-26	Fluorescence polarization immunoassay utilizing substituted carboxyfluoresceins
US9720004B2 (en)	2017-08-01	Immunoassays employing non-particulate chemiluminescent reagent
US4272506A (en)	1981-06-09	Purification of reagents by disulfide immobilization
US4161515A (en)	1979-07-17	Double receptor fluorescent immunoassay
US4588697A (en)	1986-05-13	Method for performing fluorescent protein binding assay employing novel alkyl substituted fluorescent compounds and conjugates
US4255329A (en)	1981-03-10	Double receptor fluorescent immunoassay
EP0050684B1 (fr)	1986-01-22	Dérivés de fluorescéine substitués par des groupements éthers utilisés comme agents fluorescents et extincteurs
JP3172522B2 (ja)	2001-06-04	改良された化学ルミネセントエステル，チオエステルおよびアミドを用いるアッセイ法
GB2111476A (en)	1983-07-06	Substituted carboxy- fluoresceins and their use in fluorescence polarization immunoassay
EP0218010A2 (fr)	1987-04-15	Méthode de détection de ligands et carboxyfluorescéines substituées comme traceurs pour sa mise en oeuvre
US4614823A (en)	1986-09-30	Aminomethylfluorescein derivatives
EP0170415B1 (fr)	1988-04-20	Ester de phénanthridinium servant de composé de marquage pour immuno-analyse luminométrique
JPH1045764A (ja)	1998-02-17	４’−メチル置換フルオレセイン誘導体
US4774191A (en)	1988-09-27	Fluorescent conjugates bound to a support
CA1178269A (fr)	1984-11-20	Test d'immunofluorescence-polarisation utilisant des carboxyfluoresceines substituees
JPH0115827B2 (fr)	1989-03-20
WO1989000291A1 (fr)	1989-01-12	Proteines conjuguees de fluoresceine a fluorescence augmentee
US4952691A (en)	1990-08-28	Fluorescence polarization immunoassay
CA1248086A (fr)	1989-01-03	Dosage immunologique par polarisation de la fluorescence