CA1279562C - Emploi de mordants polymeres pour accroitre l'intensite des teintures - Google Patents

Emploi de mordants polymeres pour accroitre l'intensite des teintures

Info

Publication number: CA1279562C
Authority: CA; Canada
Prior art keywords: substituted; unsubstituted; car; composition; benzphenalenone
Prior art date: 1986-01-31
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 - Fee Related

Application number

CA000506661A

Other languages

English (en)

Inventor

Annie L. Wu

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.)

Eastman Kodak Co

Original Assignee

Eastman Kodak 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.)

1986-01-31

Filing date

1986-04-15

Publication date

1991-01-29

1986-04-15 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1986-04-15 Priority to CA000506661A priority Critical patent/CA1279562C/fr

1991-01-29 Application granted granted Critical

1991-01-29 Publication of CA1279562C publication Critical patent/CA1279562C/fr

2008-01-29 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000007850 fluorescent dye Substances 0.000 title claims abstract description 41
239000000975 dye Substances 0.000 claims abstract description 71
239000000203 mixture Substances 0.000 claims abstract description 59
239000002243 precursor Substances 0.000 claims abstract description 47
150000001875 compounds Chemical class 0.000 claims description 32
238000000034 method Methods 0.000 claims description 20
WWBGWPHHLRSTFI-UHFFFAOYSA-N phenalen-1-one Chemical compound C1=CC(C(=O)C=C2)=C3C2=CC=CC3=C1 WWBGWPHHLRSTFI-UHFFFAOYSA-N 0.000 claims description 20
239000012491 analyte Substances 0.000 claims description 19
SJCPQBRQOOJBFM-UHFFFAOYSA-N benzo[a]phenalen-1-one Chemical compound C1=CC=C2C(C(=O)C=C3)=C4C3=CC=CC4=CC2=C1 SJCPQBRQOOJBFM-UHFFFAOYSA-N 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 16
125000006575 electron-withdrawing group Chemical group 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000004429 atom Chemical group 0.000 claims description 12
239000000523 sample Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 11
239000004094 surface-active agent Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000002091 cationic group Chemical group 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 8
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
239000012876 carrier material Substances 0.000 claims description 6
239000002250 absorbent Substances 0.000 claims description 5
230000002745 absorbent Effects 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 5
239000012992 electron transfer agent Substances 0.000 claims description 5
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
150000004053 quinones Chemical class 0.000 claims description 4
230000002829 reductive effect Effects 0.000 claims description 4
239000012472 biological sample Substances 0.000 claims description 3
230000002452 interceptive effect Effects 0.000 claims description 3
238000004163 cytometry Methods 0.000 abstract description 2
238000010186 staining Methods 0.000 abstract description 2
210000004027 cell Anatomy 0.000 description 28
-1 such 89 wster Substances 0.000 description 26
239000000243 solution Substances 0.000 description 18
238000003556 assay Methods 0.000 description 16
239000000872 buffer Substances 0.000 description 15
241000283690 Bos taurus Species 0.000 description 13
238000012360 testing method Methods 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000001514 detection method Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
210000002700 urine Anatomy 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
210000000265 leukocyte Anatomy 0.000 description 6
210000004940 nucleus Anatomy 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
229940088598 enzyme Drugs 0.000 description 5
239000012530 fluid Substances 0.000 description 5
230000000269 nucleophilic effect Effects 0.000 description 5
235000015097 nutrients Nutrition 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
240000004808 Saccharomyces cerevisiae Species 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000005284 excitation Effects 0.000 description 4
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
230000007480 spreading Effects 0.000 description 4
238000003892 spreading Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000233866 Fungi Species 0.000 description 3
108090000854 Oxidoreductases Proteins 0.000 description 3
102000004316 Oxidoreductases Human genes 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
210000001015 abdomen Anatomy 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000008859 change Effects 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000758 substrate Substances 0.000 description 3
QIXDHVDGPXBRRD-UHFFFAOYSA-N 2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 description 2
VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
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 description 2
108010024636 Glutathione Proteins 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
108090000604 Hydrolases Proteins 0.000 description 2
102000004157 Hydrolases Human genes 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
RMMPZDDLWLALLJ-UHFFFAOYSA-N Thermophillin Chemical compound COC1=CC(=O)C(OC)=CC1=O RMMPZDDLWLALLJ-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
239000011668 ascorbic acid Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000013060 biological fluid Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
229960002433 cysteine Drugs 0.000 description 2
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
235000018417 cysteine Nutrition 0.000 description 2
239000000032 diagnostic agent Substances 0.000 description 2
229940116441 divinylbenzene Drugs 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
229960003180 glutathione Drugs 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
244000005700 microbiome Species 0.000 description 2
210000002381 plasma Anatomy 0.000 description 2
239000011148 porous material Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
230000005855 radiation Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012064 sodium phosphate buffer Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
229940105324 1,2-naphthoquinone Drugs 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
OLBNOBQOQZRLMP-UHFFFAOYSA-N 2,6-dimethoxy-p-benzoquinone Chemical compound COC1=CC(=O)C=C(OC)C1=O OLBNOBQOQZRLMP-UHFFFAOYSA-N 0.000 description 1
UILUHPCHRFOCEL-UHFFFAOYSA-N 2-(hydroxymethyl)naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CO)=CC(=O)C2=C1 UILUHPCHRFOCEL-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
IJRKANNOPXMZSG-SSPAHAAFSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC(=O)CC(O)(C(O)=O)CC(O)=O IJRKANNOPXMZSG-SSPAHAAFSA-N 0.000 description 1
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
KOVJUPBGKDTUPF-UHFFFAOYSA-N 5-(hydroxymethyl)-2,3-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C(CO)=CC1=O KOVJUPBGKDTUPF-UHFFFAOYSA-N 0.000 description 1
102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
ULGJWNIHLSLQPZ-UHFFFAOYSA-N 7-[(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-yl)amino]-n-[2-(1h-indol-3-yl)ethyl]heptanamide Chemical compound C1CCCC2=NC3=CC(Cl)=CC(Cl)=C3C(NCCCCCCC(=O)NCCC=3C4=CC=CC=C4NC=3)=C21 ULGJWNIHLSLQPZ-UHFFFAOYSA-N 0.000 description 1
229940076442 9,10-anthraquinone Drugs 0.000 description 1
102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
108010082126 Alanine transaminase Proteins 0.000 description 1
108090000531 Amidohydrolases Proteins 0.000 description 1
102000004092 Amidohydrolases Human genes 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
102000004420 Creatine Kinase Human genes 0.000 description 1
108010042126 Creatine kinase Proteins 0.000 description 1
101710088194 Dehydrogenase Proteins 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
108010015776 Glucose oxidase Proteins 0.000 description 1
239000004366 Glucose oxidase Substances 0.000 description 1
108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
108010073450 Lactate 2-monooxygenase Proteins 0.000 description 1
241001082241 Lythrum hyssopifolia Species 0.000 description 1
229930192627 Naphthoquinone Natural products 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
102000002933 Thioredoxin Human genes 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
108010003977 aminoacylase I Proteins 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
MWPLVEDNUUSJAV-LSMJWXKXSA-N anthracene Chemical compound [13CH]1=[13CH][13CH]=[13CH][13C]2=CC3=CC=CC=C3C=[13C]21 MWPLVEDNUUSJAV-LSMJWXKXSA-N 0.000 description 1
150000001454 anthracenes Chemical class 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
229940127219 anticoagulant drug Drugs 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000012062 aqueous buffer Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
210000001175 cerebrospinal fluid Anatomy 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
229940039227 diagnostic agent Drugs 0.000 description 1
238000001736 differential pulse polarography Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000005518 electrochemistry Effects 0.000 description 1
230000005670 electromagnetic radiation Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
239000010408 film Substances 0.000 description 1
238000001506 fluorescence spectroscopy Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
229940116332 glucose oxidase Drugs 0.000 description 1
235000019420 glucose oxidase Nutrition 0.000 description 1
239000003673 groundwater Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
238000005213 imbibition Methods 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010410 layer Substances 0.000 description 1
DJQJFMSHHYAZJD-UHFFFAOYSA-N lidofenin Chemical compound CC1=CC=CC(C)=C1NC(=O)CN(CC(O)=O)CC(O)=O DJQJFMSHHYAZJD-UHFFFAOYSA-N 0.000 description 1
230000002934 lysing effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002791 naphthoquinones Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000004745 nonwoven fabric Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000005496 phosphonium group Chemical group 0.000 description 1
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
229940093916 potassium phosphate Drugs 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000004151 quinonyl group Chemical group 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000002356 single layer Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003335 steric effect Effects 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
108060008226 thioredoxin Proteins 0.000 description 1
229940094937 thioredoxin Drugs 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1

Landscapes

Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Investigating Or Analysing Biological Materials (AREA)

CA000506661A 1986-01-31 1986-04-15 Emploi de mordants polymeres pour accroitre l'intensite des teintures Expired - Fee Related CA1279562C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000506661A CA1279562C (fr)	1986-01-31	1986-04-15	Emploi de mordants polymeres pour accroitre l'intensite des teintures

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US824,755		1986-01-31
CA000506661A CA1279562C (fr)	1986-01-31	1986-04-15	Emploi de mordants polymeres pour accroitre l'intensite des teintures

Publications (1)

Publication Number	Publication Date
CA1279562C true CA1279562C (fr)	1991-01-29

Family

ID=4132892

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000506661A Expired - Fee Related CA1279562C (fr)	1986-01-31	1986-04-15	Emploi de mordants polymeres pour accroitre l'intensite des teintures

Country Status (1)

Country	Link
CA (1)	CA1279562C (fr)

1986
- 1986-04-15 CA CA000506661A patent/CA1279562C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1994-07-30	MKLA	Lapsed

Publication	Publication Date	Title
CA1336306C (fr)	1995-07-11	Substrats fluorescents hydrolysables et dosages analytiques faits a l'aide de ceux-ci
US4746607A (en)	1988-05-24	Use of substituted quinone electron transfer agents in analytical determinations
CA1206400A (fr)	1986-06-24	Inhibition de l'activite reductrice des leucocytes
EP0211898B1 (fr)	1992-04-15	Composes reductibles et compositions, elements et procedes analytiques utilisant ces composes
US4803161A (en)	1989-02-07	Biological and analytical uses of phenalenone and benzphenalenone compounds
US5780239A (en)	1998-07-14	Method for the determination of cast in urine
US4812393A (en)	1989-03-14	Fluorescent dyes and biological and analytical uses thereof
US4853186A (en)	1989-08-01	Water-compatible reducible compounds and their use in analytical compositions and methods
US5055414A (en)	1991-10-08	Phenalenimine fluorescent dyes and their use in analytical methods
US5154887A (en)	1992-10-13	Phenalenimine fluorescent dyes and their use in analytical compositions, elements and methods
CA1279562C (fr)	1991-01-29	Emploi de mordants polymeres pour accroitre l'intensite des teintures
US4803160A (en)	1989-02-07	Use of polymeric mordants to increase the intensity of rigid fluorescent dyes
US4885240A (en)	1989-12-05	Use of organic buffers to reduce dehydroascorbic acid interference in analytical methods
EP0255679A2 (fr)	1988-02-10	Composition et méthode utilisant les ortho-quinones substituées comme agents de transfert d'électrons dans les déterminations analytiques
US5045477A (en)	1991-09-03	Analytical methods utilizing reducible components
EP0261934A2 (fr)	1988-03-30	Différenciation rapide de bactéries en utilisant les antibiotiques polypeptides cycliques
CA1290226C (fr)	1991-10-08	Methode de differenciation rapide des champignons par rapport aux bacteries utilisant des antibiotiques au polyene
US5037762A (en)	1991-08-06	Water-compatible reducible compounds and their use in analytical compositions and methods
CA1273023A (fr)	1990-08-21	Substrats fluorescents hydrolysables pour phosphatases, et leur emploi dans des processus analytiques
US4927927A (en)	1990-05-22	Fluorescent dyes and biological and analytical uses thereof
US5082771A (en)	1992-01-21	Detecting cells using tellurapyrylium dihydroxides
US4885239A (en)	1989-12-05	Rapid differentiation of bacteria using polyether antibiotics
US5108902A (en)	1992-04-28	Reducible compounds which provide aniline dyes for analytical compositions and methods of using same
US5196519A (en)	1993-03-23	Reducible compounds which provide aniline dyes, and analytical compositions, elements and methods using same
JPS62291567A (ja)	1987-12-18	過酸化水素又はそれを生成する被検体の分析に対するメチン染料の使用