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    Method and reagent for measuring nitroreductase enzyme activity
    1.
    发明授权
    Method and reagent for measuring nitroreductase enzyme activity 失效
    测定硝基还原酶活性的方法和试剂

    公开(公告)号：US08378120B2

    公开(公告)日：2013-02-19

    申请号：US12500730

    申请日：2009-07-10

    申请人： Richard Martin West ,  Rahman Aziz Ismail

    发明人： Richard Martin West ,  Rahman Aziz Ismail

    IPC分类号： C07D209/02 ,  C07D277/62 ,  C07D263/62

    CPC分类号： C12Q1/26 ,  C09B57/007 ,  C12Q1/32 ,  G01N2500/00

    摘要： Disclosed are nitro-substituted squaraine reporter dyes and methods using such dyes for detecting nitroreductase enzyme activity and nitroreductase gene expression in cellular assays. The dyes are of the structure: in which Z1 and Z2 independently represent a phenyl or a naphthyl ring system; X and Y are selected from oxygen, sulphur, —CH═CH— and the group: R1 and R2 are selected from C1-C4 alkyl, —(CH2)n—P, —{(CH2)2—O}p—R6 and group W; where P is selected from COOR7, SO3− and OH, W is mono- or di-substituted nitrobenzyl, R6 is methyl or ethyl, R7 is selected from H, C1-C4 alkyl and CH2OC(O)R8, where R8 is methyl, or t-butyl, n is an integer from 1 to 10, and p is an integer from 1 to 3; R3 and R4 are selected from hydrogen, NO2, halogen, SO3−, C1-C4 alkoxy and —(CH2)m—COOR7; where R7 is hereinbefore defined and m is 0 or an integer from 1 to 5; R5 is C1-C6 alkyl optionally substituted with COOR7, SO3−, or OH; where R7 is hereinbefore defined; and at least one of groups R1, R2, R3 and R4 comprises at least one NO2 group. Also provided are methods for screening for a test agent whose effect upon nitroreductase enzyme activity and nitroreductase gene expression is to be determined.

    摘要翻译： 公开了硝基取代的方酸标记物染料和使用这种染料在细胞测定中检测硝基还原酶活性和硝基还原酶基因表达的方法。 染料具有以下结构：其中Z 1和Z 2独立地表示苯基或萘基环系; X和Y选自氧，硫，-CH = CH-，且R 1和R 2选自C 1 -C 4烷基， - （CH 2）n -P， - {（CH 2）2 -O} p -R 6 和W组; 其中P选自COOR 7，SO 3 - 和OH，W是单取代或二取代的硝基苄基，R 6是甲基或乙基，R 7选自H，C 1 -C 4烷基和CH 2 OC（O）R 8，其中R 8是甲基， 或叔丁基，n为1至10的整数，p为1至3的整数; R3和R4选自氢，NO2，卤素，SO3-，C1-C4烷氧基和 - （CH2）m -COOR7; 其中R7如上定义，m为0或1至5的整数; R5是任选被COOR7，SO3-或OH取代的C1-C6烷基; 其中R7如上定义; 并且R 1，R 2，R 3和R 4中的至少一个包含至少一个NO 2基团。 还提供了筛选对硝基还原酶活性和硝基还原酶基因表达的影响的测试剂的方法。

    ACRIDONE DERIVATIVES AS LABELS FOR FLUORESCENCE DETECTION OF TARGET MATERIALS
    4.
    发明申请
    ACRIDONE DERIVATIVES AS LABELS FOR FLUORESCENCE DETECTION OF TARGET MATERIALS 有权

    公开(公告)号：US20080139788A1

    公开(公告)日：2008-06-12

    申请号：US11943628

    申请日：2007-11-21

    申请人： JOHN ANTHONY SMITH ,  RICHARD MARTIN WEST

    发明人： JOHN ANTHONY SMITH ,  RICHARD MARTIN WEST

    IPC分类号： C07H21/00 ,  C07D401/12 ,  C07D219/00 ,  C07K14/765

    CPC分类号： G01N33/582 ,  C09B15/00

    摘要： Disclosed are new acridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the acridone dyes and use of the labelled materials in biological assays. The acridone derivatives have the following structure: in which Z1 and Z2 represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R2, R3, R4 and R5 are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the group -E-F and the group —(CH2—)nY; R1 is selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the group -E-F and the group —(CH2—)nY; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent acridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis.

    ACRIDONE DERIVATIVES AS LABELS FOR FLUORESCENCE DETECTION OF TARGET MATERIALS
    7.
    发明申请
    ACRIDONE DERIVATIVES AS LABELS FOR FLUORESCENCE DETECTION OF TARGET MATERIALS 审中-公开
    作为目标物质荧光检测标签的阿司匹林衍生物

    公开(公告)号：US20120015373A1

    公开(公告)日：2012-01-19

    申请号：US13233365

    申请日：2011-09-15

    申请人： JOHN ANTHONY SMITH ,  RICHARD MARTIN WEST

    发明人： JOHN ANTHONY SMITH ,  RICHARD MARTIN WEST

    IPC分类号： G01N33/566

    CPC分类号： G01N33/582 ,  C09B15/00

    摘要： Disclosed are methods for assay of an analyte employing acridone dyes having the structure: Z1 and Z2 represent atoms necessary to complete one ring, two fused ring, three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R2, R3, R4 and R5 are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the groups -E-F and —(CH2—)nY; R1 is selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the groups -E-F and —(CH2—)nY; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl.

    摘要翻译： 公开了使用具有以下结构的吖啶酮染料测定分析物的方法：Z1和Z2表示完成一个环，两个稠环，三个稠环芳族或杂芳族体系所必需的原子，每个环具有选自碳原子的五或六个原子， 任选不超过两个选自氧，氮和硫的原子; R2，R3，R4和R5选自氢，卤素，酰胺，羟基，氰基，硝基，单或二硝基取代的苄基，氨基，单或二C1-C4烷基取代的氨基，巯基，羰基 ，羧基，C 1 -C 6烷氧基，丙烯酸酯，乙烯基，苯乙烯基，芳基，杂芳基，C 1 -C 20烷基，芳烷基，磺酸酯，磺酸，季铵，基团-EF和 - （CH 2 - ）n Y; R 1选自氢，一或二硝基取代的苄基，C 1 -C 20烷基，芳烷基，基团-E-F和 - （CH 2 - ）n Y; 其中E是间隔基，F是靶键合基团; Y选自磺酸盐，硫酸盐，膦酸盐，磷酸盐，季铵和羧基。

    Acridone derivatives as labels for fluorescence detection of target materials
    8.
    发明授权
    Acridone derivatives as labels for fluorescence detection of target materials 有权
    吖啶酮衍生物作为目标物质的荧光检测标签

    公开(公告)号：US08034558B2

    公开(公告)日：2011-10-11

    申请号：US11943628

    申请日：2007-11-21

    申请人： John Anthony Smith ,  Richard Martin West

    发明人： John Anthony Smith ,  Richard Martin West

    IPC分类号： C12Q1/68 ,  G01N33/53 ,  C07H19/04

    CPC分类号： G01N33/582 ,  C09B15/00

    摘要： Disclosed are new acridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the acridone dyes and use of the labelled materials in biological assays. The acridone derivatives have the following structure: in which Z1 and Z2 represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R2, R3, R4 and R5 are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the group -E-F and the group —(CH2—)nY; R1 is selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the group -E-F and the group —(CH2—)nY; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent acridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis.

    摘要翻译： 公开了具有特征荧光寿命的新的吖啶酮染料衍生物。 还公开了使用吖啶酮染料标记靶生物材料并在生物测定中使用标记物质的方法。 吖啶酮衍生物具有以下结构：其中Z 1和Z 2表示完成一个环，两个稠环或三个稠环芳族或杂芳族体系所必需的原子，每个环具有五个或六个选自碳原子的原子，并且任选地不再有 比选自氧，氮和硫的两个原子; R2，R3，R4和R5选自氢，卤素，酰胺，羟基，氰基，硝基，单或二硝基取代的苄基，氨基，单或二C1-C4烷基取代的氨基，巯基，羰基 ，羧基，C 1 -C 6烷氧基，丙烯酸酯，乙烯基，苯乙烯基，芳基，杂芳基，C 1 -C 20烷基，芳烷基，磺酸酯，磺酸，季铵，基团-EF和基团 - （CH 2 - ）n Y; R 1选自氢，一或二硝基取代的苄基，C 1 -C 20烷基，芳烷基，-E-F基和 - （CH 2 - ）n Y基; 其中E是间隔基，F是靶键合基团; Y选自磺酸盐，硫酸盐，膦酸盐，磷酸盐，季铵和羧基; 并且n是1至6的整数。本发明还涉及一组不同的荧光吖啶酮染料衍生物，每种染料具有不同的荧光寿命，该组染料特别适用于多参数分析。

    METHOD AND REAGENT FOR MEASURING NITROREDUCTASE ENZYME ACTIVITY
    9.
    发明申请
    METHOD AND REAGENT FOR MEASURING NITROREDUCTASE ENZYME ACTIVITY 失效
    用于测量硝酸酯酶活性的方法和试剂

    公开(公告)号：US20090325209A1

    公开(公告)日：2009-12-31

    申请号：US12500730

    申请日：2009-07-10

    申请人： RICHARD MARTIN WEST ,  Rahman Aziz Ismail

    发明人： RICHARD MARTIN WEST ,  Rahman Aziz Ismail

    IPC分类号： C12Q1/26 ,  C07D401/10 ,  C07D403/10

    CPC分类号： C12Q1/26 ,  C09B57/007 ,  C12Q1/32 ,  G01N2500/00

    摘要： Disclosed are nitro-substituted squaraine reporter dyes and methods using such dyes for detecting nitroreductase enzyme activity and nitroreductase gene expression in cellular assays. The dyes are of the structure: in which Z1 and Z2 independently represent a phenyl or a naphthyl ring system; X and Y are selected from oxygen, sulphur, —CH═CH— and the group: R1 and R2 are selected from C1-C4 alkyl, —(CH2)n—P, —{(CH2)2—O}p—R6 and group W; where P is selected from COOR7, SO3− and OH, W is mono- or di-substituted nitrobenzyl, R6 is methyl or ethyl, R7 is selected from H, C1-C4 alkyl and CH2OC(O)R8, where R8 is methyl, or t-butyl, n is an integer from 1 to 10, and p is an integer from 1 to 3; R3 and R4 are selected from hydrogen, NO2, halogen, SO3−, C1-C4 alkoxy and —(CH2)m—COOR7; where R7 is hereinbefore defined and m is 0 or an integer from 1 to 5; R5 is C1-C6 alkyl optionally substituted with COOR7, SO3−, or OH; where R7 is hereinbefore defined; and at least one of groups R1, R2, R3 and R4 comprises at least one NO2 group.Also provided are methods for screening for a test agent whose effect upon nitroreductase enzyme activity and nitroreductase gene expression is to be determined.

    摘要翻译： 公开了硝基取代的方酸标记物染料和使用这种染料在细胞测定中检测硝基还原酶活性和硝基还原酶基因表达的方法。 染料具有以下结构：其中Z 1和Z 2独立地表示苯基或萘基环系; X和Y选自氧，硫，-CH-CH-，R 1和R 2选自C 1 -C 4烷基， - （CH 2）n P， - {（CH 2）2 -O} p -R 6和基团 W; 其中P选自COOR 7，SO 3 - 和OH，W是单取代或二取代的硝基苄基，R 6是甲基或乙基，R 7选自H，C 1 -C 4烷基和CH 2 OC（O）R 8，其中R 8是甲基， 或叔丁基，n为1至10的整数，p为1至3的整数; R3和R4选自氢，NO2，卤素，SO3-，C1-C4烷氧基和 - （CH2）m -COOR7; 其中R7如上定义，m为0或1至5的整数; R5是任选被COOR7，SO3-或OH取代的C1-C6烷基; 其中R7如上定义; 并且R 1，R 2，R 3和R 4中的至少一个包含至少一个NO 2基团。 还提供了筛选对硝基还原酶活性和硝基还原酶基因表达的影响的测试剂的方法。

    Method and reagent for measuring nitroreductase enzyme activity
    10.
    发明授权
    Method and reagent for measuring nitroreductase enzyme activity 失效
    测定硝基还原酶活性的方法和试剂

    公开(公告)号：US07579140B2

    公开(公告)日：2009-08-25

    申请号：US11569682

    申请日：2005-05-24

    申请人： Richard Martin West ,  Rahman Aziz Ismail

    发明人： Richard Martin West ,  Rahman Aziz Ismail

    IPC分类号： C12Q1/00

    CPC分类号： C12Q1/26 ,  C09B57/007 ,  C12Q1/32 ,  G01N2500/00

    摘要： Disclosed are nitro-substituted squaraine reporter dyes and methods using such dyes for detecting nitroreductase enzyme activity and nitroreductase gene expression in cellular assays. The dyes are of the structure: in which Z1 and Z2 independently represent a phenyl or a naphthyl ring system; X and Y are selected from oxygen, sulphur, —CH═CH— and the group: R1 and R2 are selected from C1-C4 alkyl, —(CH2)n—P, —{(CH2)2—O}p—R6 and group W; where P is selected from COOR7, SO3− and OH, W is mono- or di-substituted nitrobenzyl, R6 is methyl or ethyl, R7 is selected from H, C1-C4 alkyl and CH2OC(O)R8, where R8 is methyl, or t-butyl, n is an integer from 1 to 10, and p is an integer from 1 to 3; R3 and R4 are selected from hydrogen, NO2, halogen, SO3−, C1-C4 alkoxy and —(CH2)m—COOR7; where R7 is hereinbefore defined and m is 0 or an integer from 1 to 5; R5 is C1-C6 alkyl optionally substituted with COOR7, SO3−, or OH; where R7 is hereinbefore defined; and at least one of groups R1, R2, R3 and R4 comprises at least one NO2 group. Also provided are methods for screening for a test agent whose effect upon nitroreductase enzyme activity and nitroreductase gene expression is to be determined.

    摘要翻译： 公开了硝基取代的方酸标记物染料和使用这种染料在细胞测定中检测硝基还原酶活性和硝基还原酶基因表达的方法。 染料具有以下结构：其中Z 1和Z 2独立地表示苯基或萘基环系; X和Y选自氧，硫，-CH-CH-，R 1和R 2选自C 1 -C 4烷基， - （CH 2）n P， - {（CH 2）2 -O} p -R 6和基团 W; 其中P选自COOR 7，SO 3 - 和OH，W是单取代或二取代的硝基苄基，R 6是甲基或乙基，R 7选自H，C 1 -C 4烷基和CH 2 OC（O）R 8，其中R 8是甲基， 或叔丁基，n为1至10的整数，p为1至3的整数; R3和R4选自氢，NO2，卤素，SO3-，C1-C4烷氧基和 - （CH2）m -COOR7; 其中R7如上定义，m为0或1至5的整数; R5是任选被COOR7，SO3-或OH取代的C1-C6烷基; 其中R7如上定义; 并且R 1，R 2，R 3和R 4中的至少一个包含至少一个NO 2基团。 还提供了筛选对硝基还原酶活性和硝基还原酶基因表达的影响的测试剂的方法。