US3853471A - Diagnostic composition for the detection of peroxidatively active substances in body fluids - Google Patents
Diagnostic composition for the detection of peroxidatively active substances in body fluids Download PDFInfo
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- US3853471A US3853471A US00376249A US37624973A US3853471A US 3853471 A US3853471 A US 3853471A US 00376249 A US00376249 A US 00376249A US 37624973 A US37624973 A US 37624973A US 3853471 A US3853471 A US 3853471A
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- US
- United States
- Prior art keywords
- test strip
- formula
- acid amide
- test
- dimethylamino
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- Expired - Lifetime
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- 239000013543 active substance Substances 0.000 title claims abstract description 13
- 210000001124 body fluid Anatomy 0.000 title claims abstract description 13
- 239000010839 body fluid Substances 0.000 title claims abstract description 13
- 238000001514 detection method Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 title description 7
- 238000012360 testing method Methods 0.000 claims abstract description 78
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 14
- 210000004369 blood Anatomy 0.000 claims abstract description 11
- 239000008280 blood Substances 0.000 claims abstract description 11
- 239000003381 stabilizer Substances 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
- BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical compound NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 claims abstract description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001408 amides Chemical class 0.000 claims description 13
- -1 phosphoric acid dimethylamide dimorpholide Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000872 buffer Substances 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 239000012190 activator Substances 0.000 claims description 6
- 239000000080 wetting agent Substances 0.000 claims description 6
- WXMQHPKQCPCDQO-UHFFFAOYSA-N 4-dimorpholin-4-ylphosphorylmorpholine Chemical group C1COCCN1P(N1CCOCC1)(=O)N1CCOCC1 WXMQHPKQCPCDQO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000002562 thickening agent Substances 0.000 claims description 5
- 239000002250 absorbent Substances 0.000 claims description 4
- 230000002745 absorbent Effects 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- HVBMYHDTXIDFKE-UHFFFAOYSA-N diethyl hydrogen phosphate;ethyl dihydrogen phosphate Chemical group CCOP(O)(O)=O.CCOP(O)(=O)OCC HVBMYHDTXIDFKE-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000123 paper Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 150000002432 hydroperoxides Chemical class 0.000 description 9
- 238000005470 impregnation Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 102000001554 Hemoglobins Human genes 0.000 description 2
- 108010054147 Hemoglobins Proteins 0.000 description 2
- 208000032843 Hemorrhage Diseases 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 210000001635 urinary tract Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SBUBPFHJZHQNNT-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.OO.CC(C)C1=CC=CC=C1C(C)C SBUBPFHJZHQNNT-UHFFFAOYSA-N 0.000 description 1
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- MFTPYWSYEMICNR-UHFFFAOYSA-N CN(P(=O)N(C)C)C.C1=CC=CC=C1 Chemical compound CN(P(=O)N(C)C)C.C1=CC=CC=C1 MFTPYWSYEMICNR-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-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
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- WZKXBGJNNCGHIC-UHFFFAOYSA-N Leucomalachite green Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=CC=C1 WZKXBGJNNCGHIC-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 102000036675 Myoglobin Human genes 0.000 description 1
- 108010062374 Myoglobin Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 238000001792 White test Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000004374 forensic analysis Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000008362 succinate buffer Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/904—Oxidation - reduction indicators
Definitions
- ABSTRACT Test strips are provided for detecting even small amounts of blood or other peroxidatively active substances in body fluids; the strips comprising a carrier containing a hydroperoxide, at least one chromogen and, as a stabilizer, at least one phosphoric or phosphonic acid amide of the formula wherein R is a dimethylamino, alkoxy, aryloxy, alkyl, aryl or N-morpholine radical; and R and R which may be the same or different, are
- hemorrhages in the stomach, intestines and urinary tract.
- Such hemorrhages are caused, for example, by tumors, ulcers or inflammations of the organs in question.
- free hemoglobin can also occur in the urine and plasma due to the influence of certain hemolytic toxins.
- Blood and hemoglobin are peroxidate-active, i.e., they liberate oxygen from hydroperoxides and transfer it to certain acceptors. Other peroxidate-active substances also occur in leukocytes and bacteria. The detection of these substances is important for the diagnosis of diseases and infections of the kidneys and urinary tract.
- Myoglobin which is also peroxidateactive, is found, for example, in the urine after a cardiac infarct. Blood occurs especially frequently in the urine when calculi are present in the bladder or kidneys.
- the peroxidate-activity is especially suitable for a sensitive detection of all of these substances.
- the oxygen liberated from a hydroperoxide can be transferred to a chromogen which is oxidized to a colored material and thus indicates the presence of the peroxidateactive substance.
- This reaction has already been used for quite a long time in medicinal and forensic analysis, especially for the detection of blood. It is usually carried out in test tubes or by spot tests, hydrogen peroxide usually being used as the hydroperoxide (oxidation agent).
- chromogen there is preferably used benzidine, o-tolidine or leuco malachite green.
- tests of this type have also been developed in various ways for the detection of blood in body fluids.
- Rapid tests are usually absorbent carriers, preferably papers, which have been impregnated with all of the reagents necessary for the detection reaction and, after simply dipping into the body fluid to be tested, show a color reaction.
- Test papers of this type are described, for example, in U.S. Pat. Nos. 3,012,976 and 3,092,464.
- organic hydroperoxides for example cumol hydroperoxide or p-menthane hydroperoxide.
- the invention comprises test strips having hydroperoxides applied thereto together with at least one phosphoric or phosphonic acid amide of the general formula wherein R, is a dimethylamino, alkoxy, aryloxy, alkyl, aryl or N-morpholine radical and R and R which may be the same or different, are dimethylamino or N- morpholine radicals.
- the alkoxy or alkyl radicals R preferably contain up to 10 carbon atoms.
- the aryl or aryloxy radicals can be, for example, phenyl or naphthyl radicals which are optionally substituted by halogen atoms or lower alkyl or alkoxy radicals.
- test papers according to the present invention can be produced by dissolving a hydroperoxide in a solvent, preferably in a water-alcohol mixture, together with an-amide of general formula (I) and optionally together with a buffer and a wetting agent and impregnating filter paper with this solution followed by drying.
- a solvent preferably in a water-alcohol mixture
- an-amide of general formula (I) optionally together with a buffer and a wetting agent
- filter paper can be continuously impregnated and dried without difficulty.
- the present invention provides a test strip for the detection of peroxidate-active substances in body fluids, comprising a carrier containing a hydroperoxide, at least one chromogen and a compound of general formula (I), as stabilizer.
- test strips according to the present invention are most surprising since substances, the action of which, as stabilizers for hydrogen peroxide, is known, for example, urea, mannitol, acetanilide and the like, here show no stabilizing action whatsoever.
- the compounds of general formula (I) are preferably used in a ratio of at least one mole per mole hydroperoxide group, a two to fourfold excess having proved to be especially useful.
- hydroperoxides there can be used the common representatives when they are not too volatile, for example, tert.-butyl hydroperoxide.
- the solid compounds 2,5-dimethylhexane-2,S-dihydroperoxide, tetraline hydroperoxide and diisopropyl-benzene dihydroperoxide have proved to be especially useful but liquid compounds, such as diisopropyl-benzene-hydroperoxide, cumol hydroperoxide, p-menthane hydroperoxide and pinane hydroperoxide can also be used.
- the hydroperoxides can be used in amounts of 0.5- g., preferably of l-3 g., per 100 ml. of impregnation solution
- Further components of the test papers according to the present invention include chromogens, buffers, wetting agents, thickening agents and possibly activators.
- chromogens there can be used all those which can easily be oxidized to give deep-colored compounds. These include, in particular, benzidine and its homologues, especially o-tolidine. Furthermore, the heterocyclic azines according to German Pat. No. l,648,840 have also proved to be useful.
- the chromogens can be used in amounts of from 0.05-5 g., preferably of 0.2-1 .0 g., per 100 ml. impregnation solution.
- buffers there can be used, for example, citrate, phosphate, phthalate or succinate buffers, the pH value and capacity thereof being selected in such a manner that, after dipping the test strip into the body fluid, there is obtained a pH value of 4-7 and preferably of 5-6.
- a complex former for example sodium metaphosphate or ethylene-diamine tetraacetic acid, falsely positive reaction which can be caused by traces of metals thereby being avoided.
- test papers can tend to bleed due to the relatively large amounts of water-soluble substances present therein, it can be desirable to add to the formulation thickening agents, for example methyl cellulose and especially of gelatine, in amounts of about 0.5-5 g. per 100 ml.
- thickening agents for example methyl cellulose and especially of gelatine
- activators can also be added. These include, for example, quinoline and derivatives thereof according to German Pat. No. 1,242,905.
- wetting agents there are preferably used longchain organic sulfates or sulfonates, for example sodium dodecylbenzene sulfonate, dioctyl sodium sulfosuccinate or sodium lauryl sulfate, which, as is known, stabilize radical cations, such as oxidized o-tolidine.
- longchain organic sulfates or sulfonates for example sodium dodecylbenzene sulfonate, dioctyl sodium sulfosuccinate or sodium lauryl sulfate, which, as is known, stabilize radical cations, such as oxidized o-tolidine.
- absorbent carriers for example filter paper, cellulose or synthetic fiber fleeces, which are impregnated with solutions of the reagents in readily volatile solvents.
- the impregnation is preferably carried out in two steps. First, impregnation is carried out with a solution which contains an amide of general formula (I), as well as a hydroperoxide, a wetting agent, a buffer and possibly a thickening agent. Thereafter, impregnation is carried out with a solution of the indicator and possibly of the activator..When using hydrophobic monohydroperoxides, it is advisable to apply the buffer and the hydroperoxide to the carrier in separate impregnation steps.
- reagents for the production of water-stable films, all the reagents, together with a stabilizer of general formula (I), are introduced into a solution or dispersion of a filmforming substance, for example, a polyvinyl ester or polyamide and mixed homogeneously. The mixture is then applied in a thin layer to a substrate, for example a synthetic resin carrier, and dried.
- a filmforming substance for example, a polyvinyl ester or polyamide
- test strips according to the present invention are, after drying, cut up into strips and preferably sealed between a synthetic resin film and a fine-mesh material in the manner described in German Pat. No. 2,1 18,455.
- dioctyl sodium sulphosuccinate 200 g. ethylenediaminc-tetraacetic acid, l0 g. disodium salt 2,5-dimethyl-hexane-2,5dihydro- 160 g. peroxide phosphoric acid trimorpholide 1270 g. citrate buffer (1.2 molar, pH 5.25) 3.5 liters ethanol 3.0 liters distilled water ad 10.0 liters
- the solution is placed into a trough which is provided with deflection rollers. Thereafter, a filter paper strip is drawn continuously at a speed of about 2 meters/minute through the solution and dried in a drying canal with a length of 15 meters in a current of air with a temperature of 40C.
- the paper pre-treated in this manner is further impregnated in the same manner with a 0.3% solution of o-tolidine in toluene which contains 0.2% quinine as activator.
- test papers which, instead of phosphoric acid trimorpholide, contain equimolar amounts of the following amides: phosphoric acid dimethylamide dimorpholide, phosphoric acid ethyl ester dimorpholide and ethane phosphonic acid dimorpholide.
- test papers thus obtained were characterized by an outstanding stability and do not become discolored.
- test papers which, instead of benzene phosphonic acid dimorpholide, contain equimolar amounts of the following amides: benzene phosphonic acid bis-(dimethylamide) or phosphoric acid phenyl ester dimorpholide.
- Test strip for the detection of peroxidatively active substances in body fluids, comprising a carrier containing a hydroperoxide, at least one chromogen and, as a stabilizer, at least one phosphoric or phosphonic acid amide of the formula wherein I R, is dimethylamino, alkoxy, aryloxy, alkyl, aryl or N-morpholino and contains not more than carbon atoms; R and R are individually selected from dimethylamino and N-morpholino. 2. Test strip as claimed in claim 1, wherein R, in the formula is dimethylamino.
- Test strip as claimed in claim 1 wherein the carrier is a water-stable film containing the reagents.
- Test strip as claimed in claim 1 wherein there is at least one mole of said acid amide per mole of hydroperoxide.
- Test strip as claimed in claim 1 also containing at least one of a complex former, a thickening agent, an activator and a wetting agent.
- Method of detecting a peroxidatively active substance in a body fluid comprises contacting a test sample with a test strip as claimed in claim 1.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2235127A DE2235127C2 (de) | 1972-07-18 | 1972-07-18 | Diagnostisches Mittel zum Nachweis von Blut und anderen peroxidatisch wirksamen Substanzen in Körperflüssigkeiten |
Publications (1)
Publication Number | Publication Date |
---|---|
US3853471A true US3853471A (en) | 1974-12-10 |
Family
ID=5850903
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00376249A Expired - Lifetime US3853471A (en) | 1972-07-18 | 1973-07-03 | Diagnostic composition for the detection of peroxidatively active substances in body fluids |
Country Status (5)
Country | Link |
---|---|
US (1) | US3853471A (en:Method) |
JP (1) | JPS583679B2 (en:Method) |
DE (1) | DE2235127C2 (en:Method) |
FR (1) | FR2198644A5 (en:Method) |
GB (1) | GB1390899A (en:Method) |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3917452A (en) * | 1973-12-20 | 1975-11-04 | Boehringer Mannheim Gmbh | Diagnostic agent for the detection of peroxidatively active substances |
DE2460903A1 (de) | 1974-12-21 | 1976-06-24 | Boehringer Mannheim Gmbh | Verwendung von 3,3',5,5'-tetraalkylbenzidinen als oxidationsindikatoren in schnelltesten |
US3966414A (en) * | 1974-01-16 | 1976-06-29 | Bio-Medical Sciences, Inc. | Time temperature indicators |
US4063894A (en) * | 1975-11-21 | 1977-12-20 | Shionogi & Co., Ltd. | Test strip for the detection of occult blood in excreta |
US4071317A (en) * | 1977-03-14 | 1978-01-31 | Miles Laboratories, Inc. | Test composition and device for determining peroxidatively active substances and process for preparing same |
US4071321A (en) * | 1977-03-14 | 1978-01-31 | Miles Laboratories, Inc. | Test composition and device for determining peroxidatively active substances |
US4071318A (en) * | 1977-03-14 | 1978-01-31 | Miles Laboratories, Inc. | Test composition and device for determining peroxidatively active substances |
DE2803955A1 (de) * | 1977-03-14 | 1978-09-21 | Miles Lab | Pruefmittel und verfahren zur bestimmung peroxidativ wirksamer substanzen |
US4161507A (en) * | 1977-06-23 | 1979-07-17 | Behringwerke Aktiengesellschaft | Stabilized diagnostic test strip for the detection of urobilinogen |
US4175923A (en) * | 1978-06-26 | 1979-11-27 | Friend William G | Method and apparatus for occult blood testing in the home |
EP0029917A1 (en) * | 1979-11-13 | 1981-06-10 | Miles Laboratories, Inc. | Indicator composition and test device containing amine oxide |
US4329317A (en) * | 1981-01-29 | 1982-05-11 | Smithkline Instruments, Inc. | Method of stabilizing a specimen slide for occult blood testing |
US4372746A (en) * | 1980-07-04 | 1983-02-08 | Behringwerke Aktiengesellschaft | Agent for detecting peroxidatively active substances and the use of a polyvinylmethylacylamide in such an agent |
US4382064A (en) * | 1981-01-29 | 1983-05-03 | Smithkline Instruments, Inc. | Specimen slide for occult blood testing |
EP0130520A1 (en) * | 1983-06-29 | 1985-01-09 | Miles Laboratories, Inc. | Stabilized test composition, device and method for the determination of peroxidatively active substances |
WO1985002018A1 (en) * | 1983-11-04 | 1985-05-09 | Immuno Concepts, Inc. | Stabilization of indicators for detecting enzyme activity |
DE2462952C2 (en:Method) * | 1974-12-21 | 1987-10-01 | Boehringer Mannheim Gmbh, 6800 Mannheim, De | |
US4755472A (en) * | 1986-01-16 | 1988-07-05 | Miles Inc. | Stable composition for the determination of peroxidatively active substances |
US4956300A (en) * | 1982-01-05 | 1990-09-11 | Helena Laboratories Corporation | Aid for determining the presence of occult blood, method of making the aid, and method of using the aid |
US5081040A (en) * | 1987-06-29 | 1992-01-14 | Helena Laboratories Corporation | Composition and kit for testing for occult blood in human and animal excretions, fluids, or tissue matrixes |
US5089420A (en) * | 1990-01-30 | 1992-02-18 | Miles Inc. | Composition, device and method of assaying for a peroxidatively active substance utilizing amine borate compounds |
US5196167A (en) * | 1989-04-04 | 1993-03-23 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
US5217874A (en) * | 1989-04-04 | 1993-06-08 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
US5273888A (en) * | 1984-01-16 | 1993-12-28 | Helena Laboratories Corporation | Chemical test kit and method for determining the presence of blood in a specimen and for verifying the effectiveness of the chemicals |
US5369013A (en) * | 1987-06-22 | 1994-11-29 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Method, reagent mixture and kit for determining the presence of bacterial or somatic cells in urine |
EP0697481A2 (en) | 1994-07-23 | 1996-02-21 | Ciba-Geigy Ag | Aqueous textile treatment compositions containing an ultra-violet absorbing agent |
US5702913A (en) * | 1983-12-21 | 1997-12-30 | Helena Laboratories Corporation | Chromgen-reagent test system |
US5827677A (en) * | 1996-02-01 | 1998-10-27 | Universal Lavel | Method and device for specifically detecting myoglobin using a non-discriminating peroxidase sensitive assay |
WO1999004755A1 (en) * | 1997-07-23 | 1999-02-04 | Lemmerman, Pranee | Tongue wash |
US20060131241A1 (en) * | 2002-08-30 | 2006-06-22 | Johnsondiversey, Inc. | Phosphonamide and phosphonamide blend compositions and method to treat water |
US7846383B2 (en) | 2006-12-15 | 2010-12-07 | Kimberly-Clark Worldwide, Inc. | Lateral flow assay device and absorbent article containing same |
US8012761B2 (en) | 2006-12-14 | 2011-09-06 | Kimberly-Clark Worldwide, Inc. | Detection of formaldehyde in urine samples |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2436598C2 (de) * | 1974-07-30 | 1983-04-07 | Boehringer Mannheim Gmbh, 6800 Mannheim | Stabiler Teststreifen zum Nachweis von Inhaltsstoffen in Flüssigkeiten |
CS175782B1 (en:Method) * | 1974-10-16 | 1977-05-31 | ||
CS176664B1 (en:Method) * | 1975-02-14 | 1977-06-30 | ||
JPS6139779A (ja) * | 1984-07-31 | 1986-02-25 | Sony Corp | 同期信号発生装置 |
JPS61290872A (ja) * | 1985-06-19 | 1986-12-20 | Canon Inc | 映像信号再生装置 |
JPS6271975U (en:Method) * | 1985-10-23 | 1987-05-08 | ||
US5318894A (en) * | 1990-01-30 | 1994-06-07 | Miles Inc. | Composition, device and method of assaying for peroxidatively active substances |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3252762A (en) * | 1961-05-04 | 1966-05-24 | Miles Lab | Stabilized occult blood diagnostic |
US3290117A (en) * | 1963-06-24 | 1966-12-06 | Miles Lab | Occult blood diagnostic composition with color enhancing agent |
-
1972
- 1972-07-18 DE DE2235127A patent/DE2235127C2/de not_active Expired
-
1973
- 1973-07-03 US US00376249A patent/US3853471A/en not_active Expired - Lifetime
- 1973-07-16 GB GB3373073A patent/GB1390899A/en not_active Expired
- 1973-07-18 JP JP48082404A patent/JPS583679B2/ja not_active Expired
- 1973-07-18 FR FR7326254A patent/FR2198644A5/fr not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3252762A (en) * | 1961-05-04 | 1966-05-24 | Miles Lab | Stabilized occult blood diagnostic |
US3290117A (en) * | 1963-06-24 | 1966-12-06 | Miles Lab | Occult blood diagnostic composition with color enhancing agent |
Cited By (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3917452A (en) * | 1973-12-20 | 1975-11-04 | Boehringer Mannheim Gmbh | Diagnostic agent for the detection of peroxidatively active substances |
US3966414A (en) * | 1974-01-16 | 1976-06-29 | Bio-Medical Sciences, Inc. | Time temperature indicators |
DE2460903A1 (de) | 1974-12-21 | 1976-06-24 | Boehringer Mannheim Gmbh | Verwendung von 3,3',5,5'-tetraalkylbenzidinen als oxidationsindikatoren in schnelltesten |
DE2462952C2 (en:Method) * | 1974-12-21 | 1987-10-01 | Boehringer Mannheim Gmbh, 6800 Mannheim, De | |
US4063894A (en) * | 1975-11-21 | 1977-12-20 | Shionogi & Co., Ltd. | Test strip for the detection of occult blood in excreta |
US4071317A (en) * | 1977-03-14 | 1978-01-31 | Miles Laboratories, Inc. | Test composition and device for determining peroxidatively active substances and process for preparing same |
US4071321A (en) * | 1977-03-14 | 1978-01-31 | Miles Laboratories, Inc. | Test composition and device for determining peroxidatively active substances |
US4071318A (en) * | 1977-03-14 | 1978-01-31 | Miles Laboratories, Inc. | Test composition and device for determining peroxidatively active substances |
DE2803955A1 (de) * | 1977-03-14 | 1978-09-21 | Miles Lab | Pruefmittel und verfahren zur bestimmung peroxidativ wirksamer substanzen |
US4161507A (en) * | 1977-06-23 | 1979-07-17 | Behringwerke Aktiengesellschaft | Stabilized diagnostic test strip for the detection of urobilinogen |
US4175923A (en) * | 1978-06-26 | 1979-11-27 | Friend William G | Method and apparatus for occult blood testing in the home |
EP0029917A1 (en) * | 1979-11-13 | 1981-06-10 | Miles Laboratories, Inc. | Indicator composition and test device containing amine oxide |
US4372746A (en) * | 1980-07-04 | 1983-02-08 | Behringwerke Aktiengesellschaft | Agent for detecting peroxidatively active substances and the use of a polyvinylmethylacylamide in such an agent |
US4329317A (en) * | 1981-01-29 | 1982-05-11 | Smithkline Instruments, Inc. | Method of stabilizing a specimen slide for occult blood testing |
US4382064A (en) * | 1981-01-29 | 1983-05-03 | Smithkline Instruments, Inc. | Specimen slide for occult blood testing |
US4956300A (en) * | 1982-01-05 | 1990-09-11 | Helena Laboratories Corporation | Aid for determining the presence of occult blood, method of making the aid, and method of using the aid |
EP0130520A1 (en) * | 1983-06-29 | 1985-01-09 | Miles Laboratories, Inc. | Stabilized test composition, device and method for the determination of peroxidatively active substances |
US4615972A (en) * | 1983-11-04 | 1986-10-07 | Immuno Concepts, Inc. | Stabilization of indicators for detecting enzyme activity |
WO1985002018A1 (en) * | 1983-11-04 | 1985-05-09 | Immuno Concepts, Inc. | Stabilization of indicators for detecting enzyme activity |
AU570522B2 (en) * | 1983-11-04 | 1988-03-17 | Immuno Concepts Inc. | Stabilization of indicators for detecting enzyme activity |
US5702913A (en) * | 1983-12-21 | 1997-12-30 | Helena Laboratories Corporation | Chromgen-reagent test system |
US5273888A (en) * | 1984-01-16 | 1993-12-28 | Helena Laboratories Corporation | Chemical test kit and method for determining the presence of blood in a specimen and for verifying the effectiveness of the chemicals |
US4755472A (en) * | 1986-01-16 | 1988-07-05 | Miles Inc. | Stable composition for the determination of peroxidatively active substances |
US5369013A (en) * | 1987-06-22 | 1994-11-29 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Method, reagent mixture and kit for determining the presence of bacterial or somatic cells in urine |
US5081040A (en) * | 1987-06-29 | 1992-01-14 | Helena Laboratories Corporation | Composition and kit for testing for occult blood in human and animal excretions, fluids, or tissue matrixes |
US5196167A (en) * | 1989-04-04 | 1993-03-23 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
US5217874A (en) * | 1989-04-04 | 1993-06-08 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
US5089420A (en) * | 1990-01-30 | 1992-02-18 | Miles Inc. | Composition, device and method of assaying for a peroxidatively active substance utilizing amine borate compounds |
EP0697481A2 (en) | 1994-07-23 | 1996-02-21 | Ciba-Geigy Ag | Aqueous textile treatment compositions containing an ultra-violet absorbing agent |
US5827677A (en) * | 1996-02-01 | 1998-10-27 | Universal Lavel | Method and device for specifically detecting myoglobin using a non-discriminating peroxidase sensitive assay |
WO1999004755A1 (en) * | 1997-07-23 | 1999-02-04 | Lemmerman, Pranee | Tongue wash |
US20060131241A1 (en) * | 2002-08-30 | 2006-06-22 | Johnsondiversey, Inc. | Phosphonamide and phosphonamide blend compositions and method to treat water |
US7077976B2 (en) * | 2002-08-30 | 2006-07-18 | Johnsondiversey, Inc. | Phosphonamide and phosphonamide blend compositions to treat water |
US8012761B2 (en) | 2006-12-14 | 2011-09-06 | Kimberly-Clark Worldwide, Inc. | Detection of formaldehyde in urine samples |
US7846383B2 (en) | 2006-12-15 | 2010-12-07 | Kimberly-Clark Worldwide, Inc. | Lateral flow assay device and absorbent article containing same |
Also Published As
Publication number | Publication date |
---|---|
GB1390899A (en) | 1975-04-16 |
FR2198644A5 (en:Method) | 1974-03-29 |
DE2235127C2 (de) | 1974-08-08 |
JPS583679B2 (ja) | 1983-01-22 |
DE2235127A1 (en:Method) | 1974-01-10 |
DE2235127B1 (de) | 1974-01-10 |
JPS4954093A (en:Method) | 1974-05-25 |
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