ES2221485T3 - Nitrocumarinas para la deteccion de todo tipo de microorganismos. - Google Patents
Nitrocumarinas para la deteccion de todo tipo de microorganismos.Info
- Publication number
- ES2221485T3 ES2221485T3 ES99971865T ES99971865T ES2221485T3 ES 2221485 T3 ES2221485 T3 ES 2221485T3 ES 99971865 T ES99971865 T ES 99971865T ES 99971865 T ES99971865 T ES 99971865T ES 2221485 T3 ES2221485 T3 ES 2221485T3
- Authority
- ES
- Spain
- Prior art keywords
- nitrocoumarin
- compound
- microorganisms
- microorganism
- sample
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 244000005700 microbiome Species 0.000 title claims abstract description 53
- 238000001514 detection method Methods 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 24
- 230000000694 effects Effects 0.000 claims abstract description 14
- 239000001963 growth medium Substances 0.000 claims abstract description 8
- DJPKHKOFYXFQRV-UHFFFAOYSA-N 7-nitro-2-oxochromene-3-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2OC(=O)C(C(=O)O)=CC2=C1 DJPKHKOFYXFQRV-UHFFFAOYSA-N 0.000 claims description 30
- 230000015572 biosynthetic process Effects 0.000 claims description 21
- XSECDQPYFOEVPU-UHFFFAOYSA-N 7-nitrochromen-2-one Chemical compound C1=CC(=O)OC2=CC([N+](=O)[O-])=CC=C21 XSECDQPYFOEVPU-UHFFFAOYSA-N 0.000 claims description 17
- 230000000813 microbial effect Effects 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 230000035945 sensitivity Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000003745 diagnosis Methods 0.000 claims description 3
- 230000036512 infertility Effects 0.000 claims description 3
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 abstract description 9
- 102000004316 Oxidoreductases Human genes 0.000 abstract description 9
- 125000004999 nitroaryl group Chemical group 0.000 abstract description 9
- 241000894006 Bacteria Species 0.000 abstract description 7
- -1 nitrocoumarin compound Chemical class 0.000 abstract description 6
- YTCVPEZECJYZRK-UHFFFAOYSA-N 3-nitrochromen-2-one Chemical class C1=CC=C2OC(=O)C([N+](=O)[O-])=CC2=C1 YTCVPEZECJYZRK-UHFFFAOYSA-N 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 17
- 241000588724 Escherichia coli Species 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 235000010633 broth Nutrition 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000010790 dilution Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
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- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- 108091007187 Reductases Proteins 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- JODTWWLHPOSNSU-UHFFFAOYSA-N methyl 7-nitro-2-oxochromene-3-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2OC(=O)C(C(=O)OC)=CC2=C1 JODTWWLHPOSNSU-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HHDPXULKSZZACU-UHFFFAOYSA-N 2-hydroxy-4-nitrobenzaldehyde Chemical compound OC1=CC([N+]([O-])=O)=CC=C1C=O HHDPXULKSZZACU-UHFFFAOYSA-N 0.000 description 4
- NXAVBNHRVBMRBT-UHFFFAOYSA-N 3-butanoyl-7-nitrochromen-2-one Chemical compound C1=C([N+]([O-])=O)C=C2OC(=O)C(C(=O)CCC)=CC2=C1 NXAVBNHRVBMRBT-UHFFFAOYSA-N 0.000 description 4
- OGFCYRNIJNJKBK-UHFFFAOYSA-N 4-methyl-7-nitrochromen-2-one Chemical compound C1=C([N+]([O-])=O)C=CC2=C1OC(=O)C=C2C OGFCYRNIJNJKBK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000305071 Enterobacterales Species 0.000 description 4
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH 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](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 4
- 150000004775 coumarins Chemical class 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- NFULPBQNQUBWKD-UHFFFAOYSA-N ethyl 7-nitro-2-oxochromene-3-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2OC(=O)C(C(=O)OCC)=CC2=C1 NFULPBQNQUBWKD-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000005497 microtitration Methods 0.000 description 4
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 4
- 229960001907 nitrofurazone Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- RMUMJVKGCQPYAZ-UHFFFAOYSA-N 3-acetyl-4-methyl-7-nitrochromen-2-one Chemical compound C1=C([N+]([O-])=O)C=C2OC(=O)C(C(=O)C)=C(C)C2=C1 RMUMJVKGCQPYAZ-UHFFFAOYSA-N 0.000 description 3
- 241000615866 Antho Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 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 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 2
- BXMIYUYEFPSYTN-UHFFFAOYSA-N 5-hydroxy-7-nitro-2-oxochromene-3-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2OC(=O)C(C(=O)O)=CC2=C1O BXMIYUYEFPSYTN-UHFFFAOYSA-N 0.000 description 2
- RRHXPUCIXLAHIY-UHFFFAOYSA-N 7-aminochromen-2-one Chemical compound C1=CC(=O)OC2=CC(N)=CC=C21 RRHXPUCIXLAHIY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000588921 Enterobacteriaceae Species 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 102000004459 Nitroreductase Human genes 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
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- 108020001162 nitroreductase Proteins 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000041 toxicology testing Toxicity 0.000 description 2
- WPVXOOFOWPVFTK-UHFFFAOYSA-N (2-formylphenyl) nitrate Chemical compound [O-][N+](=O)OC1=CC=CC=C1C=O WPVXOOFOWPVFTK-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- UMFDLIXUUJMPSI-UHFFFAOYSA-N 2-methyl-5-nitrophenol Chemical compound CC1=CC=C([N+]([O-])=O)C=C1O UMFDLIXUUJMPSI-UHFFFAOYSA-N 0.000 description 1
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- ACMLKANOGIVEPB-UHFFFAOYSA-N 2-oxo-2H-chromene-3-carboxylic acid Chemical class C1=CC=C2OC(=O)C(C(=O)O)=CC2=C1 ACMLKANOGIVEPB-UHFFFAOYSA-N 0.000 description 1
- DZSPIJIFGQMTAF-UHFFFAOYSA-N 3-acetyl-5-amino-4-methylchromen-2-one Chemical compound C1=CC=C2OC(=O)C(C(=O)C)=C(C)C2=C1N DZSPIJIFGQMTAF-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
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- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- SXUWFAHIDCNUIG-UHFFFAOYSA-N methyl 4-(hydroxyamino)benzoate Chemical compound COC(=O)C1=CC=C(NO)C=C1 SXUWFAHIDCNUIG-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- YOJAHJGBFDPSDI-UHFFFAOYSA-N methyl 4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1 YOJAHJGBFDPSDI-UHFFFAOYSA-N 0.000 description 1
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- 229940076266 morganella morganii Drugs 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- UPSFMJHZUCSEHU-JYGUBCOQSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@H](OC=2C=C3OC(=O)C=C(C)C3=CC=2)O[C@@H]1CO UPSFMJHZUCSEHU-JYGUBCOQSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 244000045947 parasite Species 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
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- 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
- C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
- C12Q1/04—Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor
-
- 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
Landscapes
- 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)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Toxicology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9814101 | 1998-11-05 | ||
| FR9814101A FR2785620B1 (fr) | 1998-11-05 | 1998-11-05 | Detection de tous micro-organismes dans un echantillon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2221485T3 true ES2221485T3 (es) | 2004-12-16 |
Family
ID=9532554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99971865T Expired - Lifetime ES2221485T3 (es) | 1998-11-05 | 1999-11-05 | Nitrocumarinas para la deteccion de todo tipo de microorganismos. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6555332B2 (https=) |
| EP (1) | EP1124986B1 (https=) |
| JP (1) | JP5116918B2 (https=) |
| AT (1) | ATE266101T1 (https=) |
| AU (1) | AU762575B2 (https=) |
| CA (1) | CA2348710C (https=) |
| DE (1) | DE69917061T2 (https=) |
| ES (1) | ES2221485T3 (https=) |
| FR (1) | FR2785620B1 (https=) |
| WO (1) | WO2000028073A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120077206A1 (en) * | 2003-07-12 | 2012-03-29 | Accelr8 Technology Corporation | Rapid Microbial Detection and Antimicrobial Susceptibility Testing |
| ES2661168T3 (es) | 2003-07-12 | 2018-03-27 | Accelerate Diagnostics, Inc. | Biodetección sensible y rápida |
| US20070264680A1 (en) * | 2004-03-22 | 2007-11-15 | Proteus S.A. | Method and Test-Kit for the Detection and Quantification of Organisms |
| GB0505777D0 (en) * | 2005-03-22 | 2005-04-27 | Amersham Biosciences Uk Ltd | Enzyme detection method and reagent |
| US20100173332A1 (en) * | 2006-09-07 | 2010-07-08 | Auckland Uniservices Limited | Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds |
| FR2916762B1 (fr) * | 2007-05-31 | 2013-11-15 | Biomerieux Sa | Nouveaux substrats enzymatiques de nitroreductase |
| FR2937338B1 (fr) | 2008-10-17 | 2013-03-22 | Biomerieux Sa | Milieu reactionnel pour la detection et/ou l'identification de bacteries du genre legionella |
| FR2948683B1 (fr) * | 2009-07-30 | 2011-08-19 | Biomerieux Sa | Nouveaux substrats enzymatiques de nitroreductase |
| FR2948682A1 (fr) | 2009-07-30 | 2011-02-04 | Biomerieux Sa | Nouveaux substrats enzymatiques de nitroreductase |
| FR2948681A1 (fr) | 2009-07-30 | 2011-02-04 | Biomerieux Sa | Nouveaux substrats enzymatiques de nitroreductases |
| EP2453021A1 (en) | 2010-11-11 | 2012-05-16 | Biosynth AG | Novel indicator compounds |
| US8828678B2 (en) | 2010-11-16 | 2014-09-09 | Enzo Life Sciences, Inc. | Self-immolative probes for enzyme activity detection |
| US10254204B2 (en) | 2011-03-07 | 2019-04-09 | Accelerate Diagnostics, Inc. | Membrane-assisted purification |
| WO2012122314A2 (en) | 2011-03-07 | 2012-09-13 | Accelr8 Technology Corporation | Rapid cell purification systems |
| US9677109B2 (en) | 2013-03-15 | 2017-06-13 | Accelerate Diagnostics, Inc. | Rapid determination of microbial growth and antimicrobial susceptibility |
| AU2016243656A1 (en) | 2015-03-30 | 2017-11-09 | Accelerate Diagnostics, Inc. | Instrument and system for rapid microorganism identification and antimicrobial agent susceptibility testing |
| US10253355B2 (en) | 2015-03-30 | 2019-04-09 | Accelerate Diagnostics, Inc. | Instrument and system for rapid microorganism identification and antimicrobial agent susceptibility testing |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3380263D1 (en) * | 1982-04-14 | 1989-08-31 | Radiometer Corporate Dev Limit | Microbiological test processes and apparatus |
| US4728608A (en) * | 1985-04-08 | 1988-03-01 | Cambridge Bioscience Corporation | Bacterial screening system with enhanced shelf life |
| EP0397362B1 (en) * | 1989-05-08 | 1995-06-21 | CarnaudMetalbox plc | Electrochemical detection of growth of micro-organisms |
| US5055594A (en) * | 1990-07-19 | 1991-10-08 | Becton, Dickinson And Company | Fluorogenic trypotophanase substrates |
| US5081044A (en) * | 1990-09-28 | 1992-01-14 | Miles Inc. | Detection of hydrogen peroxide with optical indicator chalcogen compounds |
| US5851785A (en) * | 1992-02-04 | 1998-12-22 | Kyowa Medex Co., Ltd. | Method of quantitative determination of substances using coumarin derivatives |
| US5696157A (en) * | 1996-11-15 | 1997-12-09 | Molecular Probes, Inc. | Sulfonated derivatives of 7-aminocoumarin |
-
1998
- 1998-11-05 FR FR9814101A patent/FR2785620B1/fr not_active Expired - Lifetime
-
1999
- 1999-11-05 WO PCT/FR1999/002704 patent/WO2000028073A1/fr not_active Ceased
- 1999-11-05 DE DE69917061T patent/DE69917061T2/de not_active Expired - Lifetime
- 1999-11-05 JP JP2000581239A patent/JP5116918B2/ja not_active Expired - Lifetime
- 1999-11-05 AT AT99971865T patent/ATE266101T1/de not_active IP Right Cessation
- 1999-11-05 AU AU11639/00A patent/AU762575B2/en not_active Expired
- 1999-11-05 ES ES99971865T patent/ES2221485T3/es not_active Expired - Lifetime
- 1999-11-05 CA CA2348710A patent/CA2348710C/fr not_active Expired - Lifetime
- 1999-11-05 EP EP99971865A patent/EP1124986B1/fr not_active Expired - Lifetime
-
2001
- 2001-05-04 US US09/848,250 patent/US6555332B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69917061T2 (de) | 2005-04-21 |
| CA2348710A1 (fr) | 2000-05-18 |
| JP2002529478A (ja) | 2002-09-10 |
| JP5116918B2 (ja) | 2013-01-09 |
| EP1124986B1 (fr) | 2004-05-06 |
| WO2000028073A1 (fr) | 2000-05-18 |
| AU762575B2 (en) | 2003-06-26 |
| US6555332B2 (en) | 2003-04-29 |
| AU1163900A (en) | 2000-05-29 |
| FR2785620B1 (fr) | 2003-02-07 |
| ATE266101T1 (de) | 2004-05-15 |
| EP1124986A1 (fr) | 2001-08-22 |
| CA2348710C (fr) | 2011-09-13 |
| FR2785620A1 (fr) | 2000-05-12 |
| DE69917061D1 (de) | 2004-06-09 |
| US20020031795A1 (en) | 2002-03-14 |
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