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
- 239000000126 substance Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 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
- 230000005284 excitation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 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
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000588917 Citrobacter koseri Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 1
- 102000003983 Flavoproteins Human genes 0.000 description 1
- 108010057573 Flavoproteins Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000588729 Hafnia alvei Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- 241000588912 Pantoea agglomerans Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241001148134 Veillonella Species 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000011482 antibacterial activity assay Methods 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- WIVXEZIMDUGYRW-UHFFFAOYSA-L copper(i) sulfate Chemical compound [Cu+].[Cu+].[O-]S([O-])(=O)=O WIVXEZIMDUGYRW-UHFFFAOYSA-L 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- YMCDYRGMTRCAPZ-UHFFFAOYSA-N ethyl 2-acetyl-3-oxobutanoate Chemical class CCOC(=O)C(C(C)=O)C(C)=O YMCDYRGMTRCAPZ-UHFFFAOYSA-N 0.000 description 1
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 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
- 238000012544 monitoring process Methods 0.000 description 1
- 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)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Analytical Chemistry (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (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 (enExample) |
| EP (1) | EP1124986B1 (enExample) |
| JP (1) | JP5116918B2 (enExample) |
| AT (1) | ATE266101T1 (enExample) |
| AU (1) | AU762575B2 (enExample) |
| CA (1) | CA2348710C (enExample) |
| DE (1) | DE69917061T2 (enExample) |
| ES (1) | ES2221485T3 (enExample) |
| FR (1) | FR2785620B1 (enExample) |
| WO (1) | WO2000028073A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687239B2 (en) * | 2003-07-12 | 2010-03-30 | Accelrs Technology Corporation | Sensitive and rapid determination of antimicrobial susceptibility |
| US20120077206A1 (en) * | 2003-07-12 | 2012-03-29 | Accelr8 Technology Corporation | Rapid Microbial Detection and Antimicrobial Susceptibility Testing |
| DE602005011584D1 (de) * | 2004-03-22 | 2009-01-22 | Evonik Goldschmidt Gmbh | Verfahren und testkit zum nachweis und zur quantifizierung von organismen |
| GB0505777D0 (en) * | 2005-03-22 | 2005-04-27 | Amersham Biosciences Uk Ltd | Enzyme detection method and reagent |
| WO2008030120A1 (en) * | 2006-09-07 | 2008-03-13 | Auckland Uniservices Limited | A 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 |
| FR2948681A1 (fr) | 2009-07-30 | 2011-02-04 | Biomerieux Sa | Nouveaux substrats enzymatiques de nitroreductases |
| FR2948682A1 (fr) | 2009-07-30 | 2011-02-04 | Biomerieux Sa | Nouveaux substrats enzymatiques de nitroreductase |
| FR2948683B1 (fr) * | 2009-07-30 | 2011-08-19 | Biomerieux Sa | Nouveaux substrats enzymatiques de nitroreductase |
| 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 |
| US9434937B2 (en) | 2011-03-07 | 2016-09-06 | Accelerate Diagnostics, Inc. | 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 |
|---|---|---|---|---|
| EP0091837B1 (en) * | 1982-04-14 | 1989-07-26 | Radiometer Corporate Development Limited | Microbiological test processes and apparatus |
| US4728608A (en) * | 1985-04-08 | 1988-03-01 | Cambridge Bioscience Corporation | Bacterial screening system with enhanced shelf life |
| ES2076313T3 (es) * | 1989-05-08 | 1995-11-01 | Metal Box Plc | Deteccion electroquimica del crecimiento de microorganismos. |
| 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 DE DE69917061T patent/DE69917061T2/de not_active Expired - Lifetime
- 1999-11-05 AT AT99971865T patent/ATE266101T1/de not_active IP Right Cessation
- 1999-11-05 EP EP99971865A patent/EP1124986B1/fr not_active Expired - Lifetime
- 1999-11-05 JP JP2000581239A patent/JP5116918B2/ja not_active Expired - Lifetime
- 1999-11-05 CA CA2348710A patent/CA2348710C/fr not_active Expired - Lifetime
- 1999-11-05 AU AU11639/00A patent/AU762575B2/en not_active Expired
- 1999-11-05 WO PCT/FR1999/002704 patent/WO2000028073A1/fr not_active Ceased
- 1999-11-05 ES ES99971865T patent/ES2221485T3/es 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 |
|---|---|
| DE69917061D1 (de) | 2004-06-09 |
| EP1124986A1 (fr) | 2001-08-22 |
| FR2785620A1 (fr) | 2000-05-12 |
| FR2785620B1 (fr) | 2003-02-07 |
| JP2002529478A (ja) | 2002-09-10 |
| DE69917061T2 (de) | 2005-04-21 |
| WO2000028073A1 (fr) | 2000-05-18 |
| US6555332B2 (en) | 2003-04-29 |
| AU762575B2 (en) | 2003-06-26 |
| CA2348710C (fr) | 2011-09-13 |
| CA2348710A1 (fr) | 2000-05-18 |
| JP5116918B2 (ja) | 2013-01-09 |
| EP1124986B1 (fr) | 2004-05-06 |
| AU1163900A (en) | 2000-05-29 |
| ATE266101T1 (de) | 2004-05-15 |
| US20020031795A1 (en) | 2002-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2221485T3 (es) | Nitrocumarinas para la deteccion de todo tipo de microorganismos. | |
| Zimmerman et al. | A new fluorogenic substrate for chymotrypsin | |
| Olleik et al. | Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens | |
| Wei et al. | Off-on fluorogenic substrate harnessing ESIPT and AIE features for in situ and long-term tracking of β-glucuronidase in Escherichia coli | |
| US20160298167A1 (en) | Naphthalene derived chromogenic enzyme substrates | |
| Khan et al. | Synthesis and Biological Screening of 2‐Substituted 5, 6‐Dihydro‐5‐oxo‐4H‐1, 3, 4‐oxadiazine‐4‐propanenitriles and of Their Intermediates | |
| Brynes et al. | 6-Aminoquinoline as a fluorogenic leaving group in peptide cleavage reactions: a new fluorogenic substrate for chymotrypsin | |
| JP2010528095A (ja) | 新規ペプチダーゼ基質 | |
| CA2423328C (en) | Cephem compound and esbl-detecting reagent containing the same | |
| James et al. | Fluorogenic substrates for the detection of microbial nitroreductases | |
| Wolfson et al. | Inhibition of isocitrate lyase: the basis for inhibition of growth of two Arthrobacter species by pyruvate | |
| US8211662B2 (en) | Nitroreductase enzymatic substrates | |
| CN100372841C (zh) | 作为酶底物的吩嗪酮衍生物及其在检测具有肽酶活性的微生物中作为指示剂的用途 | |
| US6733986B1 (en) | Method and agent for determining a deaminase enzymatic activity | |
| JP2007501018A6 (ja) | 酵素基質としての新規フェノキサジノン（ｐｈｅｎｏｘａｚｉｎｏｎｅ）誘導体、及び、ペプチダーゼ活性を有する微生物の検出における指標としてのその使用 | |
| Davis et al. | Synthesis and Microbiological Properties of 3-Amino-3, 4-dihydro-1-hydroxycarbostyril1 | |
| Lakshmi et al. | Synthesis and their possible biological activities of few formazans of 3-amino-2-sulphanyl-2, 3, 4, 5, 6, 7, 8-hexahydro (1) benzothieno (2, 3-d) pyrimidin-4 (1H)-one | |
| ES2527624T3 (es) | Nuevos sustratos de peptidasa | |
| US8592175B2 (en) | Nitroreductase enzymatic substrates | |
| US20120129205A1 (en) | Novel Nitroreductase Enzymatic Substrates | |
| CN102482709B (zh) | 新的肽酶底物 | |
| IJEOMAH et al. | SYNTHESIS, CHARACTERISATION AND ANTIBACTERIAL ACTIVITY OF 2-(PHENYL SULFONYL) AMINO PYRIDINE. | |
| GB2334100A (en) | Chromogenic substrates, media and methods for the detection of salmonella spp. | |
| ES2527615T3 (es) | Nuevos sustratos de peptidasa | |
| Bhuvaa et al. | international Journal of Health and Pharmaceutical sciences |