AU2006301818A1 - Reagents for highly specific detection of peroxynitrite - Google Patents
Reagents for highly specific detection of peroxynitrite Download PDFInfo
- Publication number
- AU2006301818A1 AU2006301818A1 AU2006301818A AU2006301818A AU2006301818A1 AU 2006301818 A1 AU2006301818 A1 AU 2006301818A1 AU 2006301818 A AU2006301818 A AU 2006301818A AU 2006301818 A AU2006301818 A AU 2006301818A AU 2006301818 A1 AU2006301818 A1 AU 2006301818A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- aryl
- alkyl
- cycloalkenyl
- cycloalkyl
- 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.)
- Abandoned
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- CMFNMSMUKZHDEY-UHFFFAOYSA-N peroxynitrous acid Chemical compound OON=O CMFNMSMUKZHDEY-UHFFFAOYSA-N 0.000 title claims description 81
- 238000011895 specific detection Methods 0.000 title description 5
- 239000003153 chemical reaction reagent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 198
- 125000001072 heteroaryl group Chemical group 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- -1 cycloalkynyl Chemical group 0.000 claims description 93
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 66
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 66
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 45
- 229920000570 polyether Polymers 0.000 claims description 45
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 239000000523 sample Substances 0.000 claims description 26
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 24
- 210000004027 cell Anatomy 0.000 claims description 20
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000003642 reactive oxygen metabolite Substances 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229930194542 Keto Natural products 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 150000007942 carboxylates Chemical class 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000468 ketone group Chemical group 0.000 claims description 12
- 238000005259 measurement Methods 0.000 claims description 12
- 150000002485 inorganic esters Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000012472 biological sample Substances 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000007845 reactive nitrogen species Substances 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- VGIRNWJSIRVFRT-UHFFFAOYSA-N 2',7'-difluorofluorescein Chemical compound OC(=O)C1=CC=CC=C1C1=C2C=C(F)C(=O)C=C2OC2=CC(O)=C(F)C=C21 VGIRNWJSIRVFRT-UHFFFAOYSA-N 0.000 claims description 4
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 4
- QCPFFGGFHNZBEP-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 QCPFFGGFHNZBEP-UHFFFAOYSA-N 0.000 claims description 4
- BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 claims description 4
- 108010053210 Phycocyanin Proteins 0.000 claims description 4
- 108010004729 Phycoerythrin Proteins 0.000 claims description 4
- DPKHZNPWBDQZCN-UHFFFAOYSA-N acridine orange free base Chemical group C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 DPKHZNPWBDQZCN-UHFFFAOYSA-N 0.000 claims description 4
- 108010004469 allophycocyanin Proteins 0.000 claims description 4
- 125000005577 anthracene group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 claims description 4
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 claims description 4
- ZFKJVJIDPQDDFY-UHFFFAOYSA-N fluorescamine Chemical compound C12=CC=CC=C2C(=O)OC1(C1=O)OC=C1C1=CC=CC=C1 ZFKJVJIDPQDDFY-UHFFFAOYSA-N 0.000 claims description 4
- 238000013537 high throughput screening Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 4
- 238000012216 screening Methods 0.000 claims description 4
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims description 4
- MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 claims description 4
- IDLISIVVYLGCKO-UHFFFAOYSA-N 6-carboxy-4',5'-dichloro-2',7'-dimethoxyfluorescein Chemical compound O1C(=O)C2=CC=C(C(O)=O)C=C2C21C1=CC(OC)=C(O)C(Cl)=C1OC1=C2C=C(OC)C(O)=C1Cl IDLISIVVYLGCKO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 6
- 150000003573 thiols Chemical class 0.000 claims 6
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims 2
- 210000004102 animal cell Anatomy 0.000 claims 2
- WGTODYJZXSJIAG-UHFFFAOYSA-N tetramethylrhodamine chloride Chemical compound [Cl-].C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C(O)=O WGTODYJZXSJIAG-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- 238000002189 fluorescence spectrum Methods 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000012064 sodium phosphate buffer Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 239000007850 fluorescent dye Substances 0.000 description 7
- AKQLYAFBUYHFCK-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(OC)C=C1 AKQLYAFBUYHFCK-UHFFFAOYSA-N 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000000695 excitation spectrum Methods 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- NCGICGYLBXGBGN-UHFFFAOYSA-N 3-morpholin-4-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCOCC1 NCGICGYLBXGBGN-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- VEZIKIAGFYZTCI-VMPITWQZSA-N methyl 4-methoxycinnamate Chemical compound COC(=O)\C=C\C1=CC=C(OC)C=C1 VEZIKIAGFYZTCI-VMPITWQZSA-N 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- VFNKZQNIXUFLBC-UHFFFAOYSA-N 2',7'-dichlorofluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(O)C=C1OC1=C2C=C(Cl)C(O)=C1 VFNKZQNIXUFLBC-UHFFFAOYSA-N 0.000 description 3
- 101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 3
- 102100036790 Tubulin beta-3 chain Human genes 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- VEZIKIAGFYZTCI-UHFFFAOYSA-N methyl ester of p-methoxycinnamic acid Natural products COC(=O)C=CC1=CC=C(OC)C=C1 VEZIKIAGFYZTCI-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XDFNWJDGWJVGGN-UHFFFAOYSA-N 2-(2,7-dichloro-3,6-dihydroxy-9h-xanthen-9-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1C2=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C21 XDFNWJDGWJVGGN-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- NPOSMYDPUKBGQL-UHFFFAOYSA-N HPF Chemical compound C1=CC(O)=CC=C1OC1=CC=C2C3(C4=CC=CC=C4C(=O)O3)C3=CC=C(O)C=C3OC2=C1 NPOSMYDPUKBGQL-UHFFFAOYSA-N 0.000 description 2
- 101000713585 Homo sapiens Tubulin beta-4A chain Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 2
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 102100036788 Tubulin beta-4A chain Human genes 0.000 description 2
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/17—Nitrogen containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/245,529 US7705040B2 (en) | 2005-10-07 | 2005-10-07 | Reagents for highly specific detection of peroxynitrite |
| US11/245,529 | 2005-10-07 | ||
| PCT/CN2006/002177 WO2007041923A1 (en) | 2005-10-07 | 2006-08-25 | Reagents for highly specific detection of peroxynitrite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2006301818A1 true AU2006301818A1 (en) | 2007-04-19 |
Family
ID=37911450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006301818A Abandoned AU2006301818A1 (en) | 2005-10-07 | 2006-08-25 | Reagents for highly specific detection of peroxynitrite |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7705040B2 (enExample) |
| EP (1) | EP1943254A4 (enExample) |
| JP (1) | JP2009510462A (enExample) |
| CN (1) | CN101321767B (enExample) |
| AU (1) | AU2006301818A1 (enExample) |
| CA (1) | CA2624598A1 (enExample) |
| WO (1) | WO2007041923A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5228190B2 (ja) * | 2005-11-14 | 2013-07-03 | 国立大学法人 東京大学 | パーオキシナイトライト蛍光プローブ |
| US7858598B2 (en) * | 2007-03-12 | 2010-12-28 | Morningside Ventures Limited & Versitech Limited | Reagents for detection of hypochlorous acid |
| JPWO2009107769A1 (ja) * | 2008-02-29 | 2011-07-07 | 国立大学法人 東京大学 | 活性酸素測定用試薬 |
| US20110004203A1 (en) * | 2009-07-01 | 2011-01-06 | Ralph Zipper | Laser Device and Method for Decreasing the Size and/or Changing the Shape of Pelvic Tissues |
| US10743929B2 (en) * | 2009-07-01 | 2020-08-18 | Ralph Zipper | Bulbous tipped surgical device and method for decreasing the size and/or changing the shape of pelvic tissues |
| US8795264B2 (en) * | 2008-07-01 | 2014-08-05 | Ralph Zipper | Method for decreasing the size and/or changing the shape of pelvic tissues |
| US20100081159A1 (en) * | 2008-09-26 | 2010-04-01 | Lebedeva Irina V | Profiling reactive oxygen, nitrogen and halogen species |
| WO2012047212A1 (en) * | 2010-10-06 | 2012-04-12 | Hewlett-Packard Development Company, L.P. | Modified bodipy dye matrix |
| KR101174585B1 (ko) | 2011-04-11 | 2012-08-16 | 부산대학교 산학협력단 | 퍼옥시니트리트 검출용 바이오센서 및 이를 이용한 퍼옥시니트리트 검출방법 |
| CN102702768B (zh) * | 2012-06-04 | 2013-12-04 | 天津理工大学 | 一种新型红光bodipy荧光染料及其制备方法和应用 |
| CN102898858B (zh) * | 2012-10-19 | 2014-10-01 | 中国乐凯集团有限公司 | 一种3',6'-二甲氧基荧烷黄热敏染料的制备方法 |
| EP2948462A2 (en) * | 2013-01-28 | 2015-12-02 | Council of Scientific & Industrial Research | A novel aza bodipy compound for the selective detection of nitrite ions in water and a process for preparation thereof |
| CN103145685B (zh) * | 2013-03-20 | 2014-10-29 | 大连理工大学 | 一类荧光化合物和其在检测钌中的应用 |
| CN103342720B (zh) * | 2013-07-01 | 2015-08-26 | 南京大学 | 近红外bodipy类的羟基自由基探针及其合成方法和用途 |
| HU231175B1 (hu) * | 2015-12-04 | 2021-06-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Tetszőleges, előre meghatározott minőségű Latanoprostene bunod előállítása gravitációs kromatográfiával |
| GB2551567A (en) * | 2016-06-23 | 2017-12-27 | Sumitomo Chemical Co | Method, composition and sensor |
| CN108732299B (zh) * | 2018-06-01 | 2020-10-16 | 遵义医科大学 | 水质中亚硝酸盐的比色检测方法 |
| JP2021155362A (ja) * | 2020-03-27 | 2021-10-07 | 株式会社ナリス化粧品 | ペルオキシナイトライト活性阻害方法および、ペルオキシナイトライト活性阻害剤のスクリーニング方法 |
| CN114853779B (zh) * | 2022-06-09 | 2023-11-10 | 南京工业大学 | 细胞及生物体内生物硫醇检测与特异性快速标记巯基蛋白质的荧光探针、制备方法及应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0654311B2 (ja) * | 1986-10-28 | 1994-07-20 | コニカ株式会社 | 亜硝酸イオンによる口臭測定用分析素子 |
| US5185129A (en) * | 1991-02-28 | 1993-02-09 | President And Fellows Of Harvard College | Ozone monitors |
| PL317192A1 (en) * | 1994-05-13 | 1997-03-17 | Monsanto Co | Methods of using pernitrite decomposition catalyst and their pharmaceutic compositions |
| US5729697A (en) * | 1995-04-24 | 1998-03-17 | International Business Machines Corporation | Intelligent shopping cart |
| US6861262B2 (en) * | 2000-03-03 | 2005-03-01 | Quest Diagnostics Investments Incorporated | Composition and method for detecting an adulterant in an aqueous sample |
| US7087766B2 (en) * | 2000-02-29 | 2006-08-08 | Daiichi Pure Chemicals Co., Ltd. | Reagents for the quantitation of active oxygen |
| US7599855B2 (en) * | 2001-02-13 | 2009-10-06 | Lester Sussman | System and method for a complete and convenient shopping experience |
| JP4206381B2 (ja) | 2002-10-16 | 2009-01-07 | 哲雄 長野 | パーオキシナイトライト測定用試薬 |
| CN100427928C (zh) * | 2005-01-17 | 2008-10-22 | 浙江大学 | 硝酸盐、亚硝酸盐快速测定试纸及其应用 |
| US7389934B2 (en) * | 2005-05-27 | 2008-06-24 | International Business Machines Corporation | On-demand point-of-sale scanner access |
-
2005
- 2005-10-07 US US11/245,529 patent/US7705040B2/en active Active
-
2006
- 2006-08-25 AU AU2006301818A patent/AU2006301818A1/en not_active Abandoned
- 2006-08-25 CA CA002624598A patent/CA2624598A1/en not_active Abandoned
- 2006-08-25 CN CN200680045462.9A patent/CN101321767B/zh active Active
- 2006-08-25 WO PCT/CN2006/002177 patent/WO2007041923A1/en not_active Ceased
- 2006-08-25 JP JP2008533849A patent/JP2009510462A/ja not_active Abandoned
- 2006-08-25 EP EP06775495A patent/EP1943254A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US7705040B2 (en) | 2010-04-27 |
| CA2624598A1 (en) | 2007-04-19 |
| JP2009510462A (ja) | 2009-03-12 |
| CN101321767A (zh) | 2008-12-10 |
| EP1943254A1 (en) | 2008-07-16 |
| WO2007041923A1 (en) | 2007-04-19 |
| CN101321767B (zh) | 2012-02-08 |
| EP1943254A4 (en) | 2010-05-05 |
| US20070082403A1 (en) | 2007-04-12 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |