CA2655875C - Detection d'antibiotiques - Google Patents

Detection d'antibiotiques Download PDF

Info

Publication number: CA2655875C
Authority: CA; Canada
Prior art keywords: antibiotic; test; serum albumin; bovine serum; protein
Prior art date: 1992-10-06
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 - Lifetime

Application number

CA2655875A

Other languages

English (en)

Other versions

CA2655875A1 (fr

Inventor

Cornelis Jacobus Ven Der Laken

Roger Piasio

Jagdish Chander Kapur

Nicolaas Cornelis Maria Emanuel Barendse

Henry Gerard Julius Hirs

Jan Verweij

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.)

Neogen Corp

Original Assignee

Neogen Corp

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.)

1992-10-06

Filing date

1993-10-06

Publication date

2010-07-20

1993-10-06 Application filed by Neogen Corp filed Critical Neogen Corp

1994-04-07 Publication of CA2655875A1 publication Critical patent/CA2655875A1/fr

2010-07-20 Application granted granted Critical

2010-07-20 Publication of CA2655875C publication Critical patent/CA2655875C/fr

2013-10-06 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003242 anti bacterial agent Substances 0.000 title description 22
229940088710 antibiotic agent Drugs 0.000 title description 15
238000001514 detection method Methods 0.000 title description 7
229940098773 bovine serum albumin Drugs 0.000 claims abstract description 23
108091003079 Bovine Serum Albumin Proteins 0.000 claims abstract description 15
230000003115 biocidal effect Effects 0.000 description 61
238000012360 testing method Methods 0.000 description 30
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
229940088598 enzyme Drugs 0.000 description 22
102000014914 Carrier Proteins Human genes 0.000 description 21
108091008324 binding proteins Proteins 0.000 description 21
238000000034 method Methods 0.000 description 21
102000004190 Enzymes Human genes 0.000 description 20
108090000790 Enzymes Proteins 0.000 description 20
239000000243 solution Substances 0.000 description 20
102000004169 proteins and genes Human genes 0.000 description 13
108090000623 proteins and genes Proteins 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 11
238000011534 incubation Methods 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000008267 milk Substances 0.000 description 10
210000004080 milk Anatomy 0.000 description 10
235000013336 milk Nutrition 0.000 description 10
239000000758 substrate Substances 0.000 description 10
229910019142 PO4 Inorganic materials 0.000 description 9
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
239000010452 phosphate Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
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 8
108010001336 Horseradish Peroxidase Proteins 0.000 description 8
238000003556 assay Methods 0.000 description 8
239000000872 buffer Substances 0.000 description 8
229930182566 Gentamicin Natural products 0.000 description 7
HRNLUBSXIHFDHP-UHFFFAOYSA-N N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC1=NC=CC(C=2C=NC=CC=2)=N1 HRNLUBSXIHFDHP-UHFFFAOYSA-N 0.000 description 7
238000002523 gelfiltration Methods 0.000 description 7
239000007790 solid phase Substances 0.000 description 7
125000006850 spacer group Chemical group 0.000 description 7
239000002253 acid Substances 0.000 description 5
230000021615 conjugation Effects 0.000 description 5
239000011159 matrix material Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000012064 sodium phosphate buffer Substances 0.000 description 5
239000012089 stop solution Substances 0.000 description 5
229920005654 Sephadex Polymers 0.000 description 4
239000012507 Sephadex™ Substances 0.000 description 4
230000008859 change Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
238000011161 development Methods 0.000 description 4
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244000005700 microbiome Species 0.000 description 4
239000000203 mixture Substances 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000193385 Geobacillus stearothermophilus Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
-1 benzylpenicillin Chemical class 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
239000012888 bovine serum Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000003431 cross linking reagent Substances 0.000 description 3
238000000502 dialysis Methods 0.000 description 3
238000010828 elution Methods 0.000 description 3
235000019371 penicillin G benzathine Nutrition 0.000 description 3
229940056360 penicillin g Drugs 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
125000003396 thiol group Chemical group [H]S* 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
JWDFQMWEFLOOED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(pyridin-2-yldisulfanyl)propanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCSSC1=CC=CC=N1 JWDFQMWEFLOOED-UHFFFAOYSA-N 0.000 description 2
QMXCRMQIVATQMR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-pyridin-2-ylsulfanylpropanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCSC1=CC=CC=N1 QMXCRMQIVATQMR-UHFFFAOYSA-N 0.000 description 2
OBYNJKLOYWCXEP-UHFFFAOYSA-N 2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-4-isothiocyanatobenzoate Chemical compound C=12C=CC(=[N+](C)C)C=C2OC2=CC(N(C)C)=CC=C2C=1C1=CC(N=C=S)=CC=C1C([O-])=O OBYNJKLOYWCXEP-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical group C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 2
239000011324 bead Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
238000010382 chemical cross-linking Methods 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 2
239000006166 lysate Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000010998 test method Methods 0.000 description 2
XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
WXKRKQBCEWPFLB-UHFFFAOYSA-N 3-pyridin-2-ylsulfanylpropanoic acid Chemical compound OC(=O)CCSC1=CC=CC=N1 WXKRKQBCEWPFLB-UHFFFAOYSA-N 0.000 description 1
YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 1
102000002260 Alkaline Phosphatase Human genes 0.000 description 1
108020004774 Alkaline Phosphatase Proteins 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000283707 Capra Species 0.000 description 1
UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
102000016943 Muramidase Human genes 0.000 description 1
108010014251 Muramidase Proteins 0.000 description 1
108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
108010071390 Serum Albumin Proteins 0.000 description 1
102000007562 Serum Albumin Human genes 0.000 description 1
101000582398 Staphylococcus aureus Replication initiation protein Proteins 0.000 description 1
241000194020 Streptococcus thermophilus Species 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
238000005411 Van der Waals force Methods 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000001042 affinity chromatography Methods 0.000 description 1
230000004075 alteration Effects 0.000 description 1
229960003022 amoxicillin Drugs 0.000 description 1
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
229960000723 ampicillin Drugs 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
239000003708 ampul Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229960000686 benzalkonium chloride Drugs 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
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
229960002685 biotin Drugs 0.000 description 1
239000011616 biotin Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229960004350 cefapirin Drugs 0.000 description 1
ZBHXIWJRIFEVQY-IHMPYVIRSA-N ceftiofur Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC(=O)C1=CC=CO1 ZBHXIWJRIFEVQY-IHMPYVIRSA-N 0.000 description 1
229960005229 ceftiofur Drugs 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000003115 checkerboard titration Methods 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000012875 competitive assay Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
235000013365 dairy product Nutrition 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
229940061607 dibasic sodium phosphate Drugs 0.000 description 1
FRTGEIHSCHXMTI-UHFFFAOYSA-N dimethyl octanediimidate Chemical compound COC(=N)CCCCCCC(=N)OC FRTGEIHSCHXMTI-UHFFFAOYSA-N 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000012149 elution buffer Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000013100 final test Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
102000037865 fusion proteins Human genes 0.000 description 1
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230000002068 genetic effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
238000002649 immunization Methods 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000011005 laboratory method Methods 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
229960000274 lysozyme Drugs 0.000 description 1
239000004325 lysozyme Substances 0.000 description 1
235000010335 lysozyme Nutrition 0.000 description 1
238000013507 mapping Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
102000013415 peroxidase activity proteins Human genes 0.000 description 1
108040007629 peroxidase activity proteins Proteins 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000002731 protein assay Methods 0.000 description 1
230000006916 protein interaction Effects 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010079 rubber tapping Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
238000006177 thiolation reaction Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229960004906 thiomersal Drugs 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Investigating Or Analysing Biological Materials (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA2655875A 1992-10-06 1993-10-06 Detection d'antibiotiques Expired - Lifetime CA2655875C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP92203084		1992-10-06
EP92203084.6		1992-10-06
CA 2107856 CA2107856C (fr)	1992-10-06	1993-10-06	Detection d'antibiotiques

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2107856 Division CA2107856C (fr)	1992-10-06	1993-10-06	Detection d'antibiotiques

Publications (2)

Publication Number	Publication Date
CA2655875A1 CA2655875A1 (fr)	1994-04-07
CA2655875C true CA2655875C (fr)	2010-07-20

Family

ID=8210952

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA 2107856 Expired - Lifetime CA2107856C (fr)	1992-10-06	1993-10-06	Detection d'antibiotiques
CA2655875A Expired - Lifetime CA2655875C (fr)	1992-10-06	1993-10-06	Detection d'antibiotiques

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA 2107856 Expired - Lifetime CA2107856C (fr)	1992-10-06	1993-10-06	Detection d'antibiotiques

Country Status (6)

Country	Link
JP (1)	JPH06207936A (fr)
AT (1)	ATE170292T1 (fr)
AU (1)	AU662656B2 (fr)
CA (2)	CA2107856C (fr)
DE (1)	DE69320583T2 (fr)
NZ (1)	NZ248864A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LT3368681T (lt) *	2015-11-20	2019-08-26	Centrient Pharmaceuticals Netherlands B.V.	Tyrimo būdas, skirtas antibiotikams nuotekose nustatyti
JP7601324B2 (ja) *	2020-06-02	2024-12-17	公立大学法人福島県立医科大学	化合物を基板上に固定する方法および固定化した化合物の検出方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4239852A (en) *	1978-06-12	1980-12-16	Penicillin Assays, Inc.	Antibiotic detection method
US4347312A (en) *	1980-03-20	1982-08-31	Research Triangle Institute	Detection of antibiotics in milk

1993
- 1993-09-24 DE DE1993620583 patent/DE69320583T2/de not_active Expired - Lifetime
- 1993-09-24 AT AT93202754T patent/ATE170292T1/de not_active IP Right Cessation
- 1993-10-05 NZ NZ24886493A patent/NZ248864A/en not_active IP Right Cessation
- 1993-10-05 AU AU48792/93A patent/AU662656B2/en not_active Expired
- 1993-10-06 JP JP25027493A patent/JPH06207936A/ja active Pending
- 1993-10-06 CA CA 2107856 patent/CA2107856C/fr not_active Expired - Lifetime
- 1993-10-06 CA CA2655875A patent/CA2655875C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2107856C (fr)	2009-04-28
CA2655875A1 (fr)	1994-04-07
AU4879293A (en)	1994-04-21
AU662656B2 (en)	1995-09-07
NZ248864A (en)	1994-10-26
DE69320583D1 (de)	1998-10-01
ATE170292T1 (de)	1998-09-15
DE69320583T2 (de)	1999-01-14
CA2107856A1 (fr)	1994-04-07
JPH06207936A (ja)	1994-07-26

Legal Events

Date	Code	Title	Description
2009-03-09	EEER	Examination request
2013-12-09	MKEX	Expiry	Effective date: 20131007

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