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公开(公告)号：US07550570B2
公开(公告)日：2009-06-23
申请号：US10788660
申请日：2004-02-26
CPC分类号： C07D401/06 , C07D401/14 , C07D405/14 , C07D491/147 , C12Q1/6869 , C12Q2563/107 , C12Q2535/101
摘要： A set of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structures wherein R1-R6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group, or, when taken together, R1 and R6 is benzo, or, when taken together, R4 and R5 is benzo; R7-R10, R12-R16 and R18 may be hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group; R11 and R17 may be hydrogen, lower alkyl, lower alkene, lower alkyne, phenyl, aryl, linking group; Y1-Y4 are hydrogen, lower alkyl, or cycloalkyl, or, when taken together, Y1 and R2, Y2 and R1 Y3 and R3, and/or Y4 and R4 is propano, ethano, or substituted forms thereof; and X1-X3 taken separately are hydrogen, chlorine, fluorine, lower alkyl, carboxylate, sulfonate, hydroxymethyl, and linking group, or any combinations thereof. In another aspect, the invention includes reagents labeled with the 4,7-dichlororhodamine dye compounds, including deoxynucleotides, dideoxynucleotides, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.
摘要翻译： 公开了一组用作荧光染料的4,7-二氯罗丹明化合物，其中R1-R6是氢，氟，氯，低级烷基，低级烯，低级炔，磺酸，砜，氨基，酰氨基，腈，低级烷氧基 或连接基团时，或者当R 1和R 6一起时为苯并，或者合并时，R 4和R 5为苯并; R7-R10，R12-R16和R18可以是氢，氟，氯，低级烷基，低级烯烃，低级炔烃，磺酸盐，砜，氨基，酰氨基，腈，低级烷氧基，连接基团; R11和R17可以是氢，低级烷基，低级烯，低级炔，苯基，芳基，连接基团; Y1-Y4是氢，低级烷基或环烷基，或者当一起为Y1和R2，Y2和R1Y3和R3，和/或Y4和R4为丙酰，乙酸或其取代形式时; 单独使用的X 1 -X 3是氢，氯，氟，低级烷基，羧酸酯，磺酸酯，羟甲基和连接基团，或其任何组合。 另一方面，本发明包括用4,7-二氯罗丹明染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸和多核苷酸。 在另一方面，本发明包括利用这种染料化合物的方法和包括双脱氧多核苷酸测序和片段分析方法的试剂。
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公开(公告)号：US20090093623A1
公开(公告)日：2009-04-09
申请号：US12199441
申请日：2008-08-27
CPC分类号： C07D401/06 , C07D401/14 , C07D405/14 , C07D491/147 , C12Q1/6869 , C12Q2563/107 , C12Q2535/101
摘要： A set of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structures wherein R1-R6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group, or, when taken together, R1 and R6 is benzo, or, when taken together, R4 and R5 is benzo; R7-R10, R12-R16 and R18 may be hydrogen, fluorine, chlorine, lower alkyl lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group; R11 and R17 may be hydrogen, lower alkyl lower alkene, lower alkyne, phenyl, aryl, linking group; Y1-Y4 are hydrogen, lower alkyl or cycloalkyl, or, when taken together, Y1 and R2, Y2 and R1 Y3 and R3, and/or Y4 and R4 is propano, ethano, or substituted forms thereof, and X1-X3 taken separately are hydrogen, chlorine, fluorine, lower alkyl, carboxylate, sulfonate, hydroxymethyl, and linking group, or any combinations thereof. In another aspect, the invention includes reagents labeled with the 4,7-dichlororhodamine dye compounds, including deoxynucleotides, dideoxynucleotides, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.
摘要翻译： 公开了一组用作荧光染料的4,7-二氯罗丹明化合物，其中R1-R6是氢，氟，氯，低级烷基，低级烯，低级炔，磺酸，砜，氨基，酰氨基，腈，低级烷氧基 或连接基团时，或者当R 1和R 6一起时为苯并，或者合并时，R 4和R 5为苯并; R7-R10，R12-R16和R18可以是氢，氟，氯，低级烷基低级烯，低级炔，磺酸，砜，氨基，酰胺基，腈，低级烷氧基，连接基团; R11和R17可以是氢，低级烷基低级烯，低级炔，苯基，芳基，连接基; Y1-Y4是氢，低级烷基或环烷基，或者当Y1和R2，Y2和R1Y3和R3和/或Y4和R4分别为丙酰，乙酸或其取代形式时，分别取X1-X3 是氢，氯，氟，低级烷基，羧酸酯，磺酸酯，羟甲基和连接基团，或其任何组合。 另一方面，本发明包括用4,7-二氯罗丹明染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸和多核苷酸。 在另一方面，本发明包括利用这种染料化合物的方法和包括双脱氧多核苷酸测序和片段分析方法的试剂。
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公开(公告)号：US6025505A
公开(公告)日：2000-02-15
申请号：US38191
申请日：1998-03-10
申请人： Linda G. Lee , Scott C. Benson , Barnett B. Rosenblum , Sandra L. Spurgeon , Jonathan M. Cassel , Ronald J. Graham
发明人： Linda G. Lee , Scott C. Benson , Barnett B. Rosenblum , Sandra L. Spurgeon , Jonathan M. Cassel , Ronald J. Graham
IPC分类号： C12N15/09 , C07D311/80 , C07D311/82 , C07D405/12 , C07D491/22 , C07F9/6561 , C07H19/06 , C07H19/14 , C07H19/16 , C07H21/00 , C07H21/04 , C09B11/24 , C09B11/28 , C09K11/06 , C09K11/07 , C12P19/34 , C12Q1/68 , G01N21/78 , G01N27/447 , G01N33/58 , C07D311/78 , C07D311/88
摘要： A class of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structure ##STR1## wherein R.sub.1 -R.sub.6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group, or combinations thereof, or, when taken together, R.sub.1 and R.sub.6 is benzo, or, when taken together, R.sub.4 and R.sub.5 is benzo; Y.sub.1 -Y.sub.4 are hydrogen or lower alkyl, or, when taken together, Y.sub.1 and R.sub.2, Y.sub.2 and R.sub.1 Y.sub.3 and R.sub.3, or Y.sub.4 and R.sub.4 is propano, ethano, or substituted forms thereof, and X.sub.1 -X.sub.3 taken separately are selected from the group consisting of hydrogen, chlorine, fluorine, lower alkyl, carboxylate, sulfonic acid, --CH.sub.2 OH, and linking group. In another aspect, the invention includes reagents labeled with the 4,7-dichlororhodamine dye compounds, including deoxynucleotides, dideoxynucleotides, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.
摘要翻译： 公开了一类用作荧光染料的4,7-二氯罗丹明化合物，其结构是其中R 1 -R 6是氢，氟，氯，低级烷基，低级烯烃，低级炔烃，磺酸酯，砜，氨基，酰氨基，腈，低级烷氧基 或连接基团，或其组合，或者当R 1和R 6一起时为苯并，或者一起使用时，R 4和R 5为苯并; Y1-Y4是氢或低级烷基，或者当Y1和R2，Y2和R1Y3和R3，或Y4和R4是它们的丙酰，乙酸或取代形式时，分别选择的X1-X3选自 由氢，氯，氟，低级烷基，羧酸酯，磺酸，-CH 2 OH和连接基组成的组。 另一方面，本发明包括用4,7-二氯罗丹明染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸和多核苷酸。 在另一方面，本发明包括利用这种染料化合物的方法和包括双脱氧多核苷酸测序和片段分析方法的试剂。
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公开(公告)号：US20120172583A1
公开(公告)日：2012-07-05
申请号：US12882034
申请日：2010-09-14
IPC分类号： C07H21/00 , C07D311/90 , C07D311/88 , C07D407/12 , C07D491/22 , C07D491/16
CPC分类号： C07H21/04 , C07D311/90
摘要： Novel linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye are provided. These linkers facilitate the efficient transfer of energy between a donor and acceptor dye in an energy transfer dye. One of these linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye has the general structure R21Z1C(O)R22R28 where R21 is a C1-5 alkyl attached to the donor dye, C(O) is a carbonyl group, Z1 is either NH, sulfur or oxygen, R22 is a substituent which includes an alkene, diene, alkyne, a five and six membered ring having at least one unsaturated bond or a fused ring structure which is attached to the carbonyl carbon, and R28 includes a functional group which attaches the linker to the acceptor dye.
摘要翻译： 提供了用于将供体染料与能量转移荧光染料中的受体染料连接的新型接头。 这些接头促进能量转移染料中供体和受体染料之间的能量的有效转移。 用于将供体染料与能量转移荧光染料中的受体染料连接的这些接头之一具有通式结构R21Z1C（O）R22R28，其中R21是与供体染料连接的C 1-5烷基，C（O）是羰基 Z1是NH，硫或氧，R22是包含烯烃，二烯烃，炔烃，具有至少一个不饱和键的五元和六元环或连接到羰基碳上的稠环结构的取代基，R28 包括将接头连接到受体染料的官能团。
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公开(公告)号：US20100029923A1
公开(公告)日：2010-02-04
申请号：US12554845
申请日：2009-09-04
IPC分类号： C07H21/04
CPC分类号： C07H21/04 , C07D311/90
摘要： Novel linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye are provided. These linkers facilitate the efficient transfer of energy between a donor and acceptor dye in an energy transfer dye. One of these linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye has the general structure R21Z1C(O)R22R28 where R21 is a C1-5 alkyl attached to the donor dye, C(O) is a carbonyl group, Z1 is either NH, sulfur or oxygen, R22 is a substituent which includes an alkene, diene, alkyne, a five and six membered ring having at least one unsaturated bond or a fused ring structure which is attached to the carbonyl carbon, and R28 includes a functional group which attaches the linker to the acceptor dye.
摘要翻译： 提供了用于将供体染料与能量转移荧光染料中的受体染料连接的新型接头。 这些接头促进能量转移染料中供体和受体染料之间的能量的有效转移。 用于将供体染料与能量转移荧光染料中的受体染料连接的这些接头之一具有通式结构R21Z1C（O）R22R28，其中R21是与供体染料连接的C 1-5烷基，C（O）是羰基 Z1是NH，硫或氧，R22是包含烯烃，二烯烃，炔烃，具有至少一个不饱和键的五元和六元环或连接到羰基碳上的稠环结构的取代基，R28 包括将接头连接到受体染料的官能团。
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公开(公告)号：US06835827B2
公开(公告)日：2004-12-28
申请号：US10371985
申请日：2003-02-20
IPC分类号： C07H2100
摘要： Methods and compositions to label oligonucleotides and analogs directly on a solid-support having the structure where S is a solid-support, A is a cleavable linker, X is a moiety with three or more attachment sites, L is a label, Y is a nucleophile, i.e. O, NH, NR or S, and P1 is an acid cleavable protecting group are provided. The labelled solid-support is reacted in a cyclical fashion to synthesize a labelled oligonucleotide on a solid-support in the 5′ to 3′ direction, having the structure: Labelled oligonucleotides are also synthesized by reacting: (i) a label reagent bearing functionality consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid, (ii) an oligonucleotide on solid support with nucleophilic functionality, and (iii) a coupling reagent, whereby an ester, amide, thioester, sulfonamide, sulfonate, phosphonate, phosphoramidate, phosphorothioate, or phosphate bond is formed. The labelling reaction may be conducted at label sites including the 5′ terminus, the 3′ terminus, a nucleobase, an internucleotide linkage, a sugar, amino, sulfide, hydroxyl, and carboxyl.
摘要翻译： 方法和组合物直接在具有其中S是固体支持物的结构的固体支持物上标记寡核苷酸和类似物，A是可切割的接头，X是具有三个或更多个连接位点的部分，L是标记，Y是亲核试剂 ，即O，NH，NR或S，并且P1是可酸切割的保护基。 标记的固体支持物以循环方式反应以在5'至3'方向的固体支持物上合成标记的寡核苷酸，具有以下结构：标记的寡核苷酸还通过以下方式合成：（i）标记试剂载体官能团 包括羧酸，磺酸，膦酸或磷酸，（ii）具有亲核官能团的固体支持物上的寡核苷酸，和（iii）偶联剂，其中酯，酰胺，硫酯，磺酰胺，磺酸酯，膦酸酯，氨基磷酸酯 ，硫代磷酸酯或磷酸酯键。 标记反应可以在包括5'末端，3'末端，核碱基，核苷酸间键，糖，氨基，硫化物，羟基和羧基的标记位点进行。
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公开(公告)号：US06525183B2
公开(公告)日：2003-02-25
申请号：US10010717
申请日：2001-11-07
IPC分类号： C07H1900
摘要： Methods and compositions to label oligonucleotides and analogs directly on a solid-support having the structure where S is a solid-support, A is a cleavable linker, X is a moiety with three or more attachment sites, L is a label, Y is a nucleophile, i.e. O, NH, NR or S, and P1 is an acid cleavable protecting group are provided. The labelled solid-support is reacted in a cyclical fashion to synthesize a labelled oligonucleotide on a solid-support in the 5′ to 3′ direction, having the structure: Labelled oligonucleotides are also synthesized by reacting: (i) a label reagent bearing functionality consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid, (ii) an oligonucleotide on solid support with nucleophilic functionality, and (iii) a coupling reagent, whereby an ester, amide, thioester, sulfonamide, sulfonate, phosphonate, phosphoramidate, phosphorothioate, or phosphate bond is formed. The labelling reaction may be conducted at label sites including the 5′ terminus, the 3′ terminus, a nucleobase, an internucleotide linkage, a sugar, amino, sulfide, hydroxyl, and carboxyl.
摘要翻译： 方法和组合物直接在具有其中S是固体支持物的结构的固体支持物上标记寡核苷酸和类似物，A是可切割的接头，X是具有三个或更多个连接位点的部分，L是标记，Y是亲核试剂 ，即O，NH，NR或S，并且P1是可酸切割的保护基。 标记的固体支持物以循环方式反应以在5'至3'方向的固体支持物上合成标记的寡核苷酸，具有以下结构：标记的寡核苷酸还通过以下方式合成：（i）标记试剂载体官能团 包括羧酸，磺酸，膦酸或磷酸，（ii）具有亲核官能团的固体支持物上的寡核苷酸，和（iii）偶联剂，其中酯，酰胺，硫酯，磺酰胺，磺酸酯，膦酸酯，氨基磷酸酯 ，硫代磷酸酯或磷酸酯键。 标记反应可以在包括5'末端，3'末端，核碱基，核苷酸间键，糖，氨基，硫化物，羟基和羧基的标记位点进行。
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公开(公告)号：US07038063B2
公开(公告)日：2006-05-02
申请号：US10716165
申请日：2003-11-18
IPC分类号： C07D311/82
摘要： Atropisomeric energy-transfer dye compounds are disclosed. A variety of molecular biology applications utilize atropisomeric xanthene fluorescent dyes as labels for substrates such as nucleotides, nucleosides, polynucleotides, polypeptides and carbohydrates. Methods include DNA sequencing, DNA fragment analysis, PCR, SNP analysis, oligonucleotide ligation, amplification, minisequencing, and primer extension.
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9.发明授权Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis 失效不对称呫吨荧光染料的倾向异构体和DNA测序和片段分析方法公开(公告)号：US06649769B2
公开(公告)日：2003-11-18
申请号：US10227058
申请日：2002-08-21
IPC分类号： C07D40304
摘要： Atropisomeric energy-transfer dye compounds are disclosed. A variety of molecular biology applications utilize atropisomeric xanthene fluorescent dyes as labels for substrates such as nucleotides, nucleosides, polynucleotides, polypeptides and carbohydrates. Methods include DNA sequencing, DNA fragment analysis, PCR, SNP analysis, oligonucleotide ligation, amplification, minisequencing, and primer extension.
摘要翻译： 公开了异转移能量转移染料化合物。 各种分子生物学应用利用无异构呫吨荧光染料作为底物的标记，例如核苷酸，核苷，多核苷酸，多肽和碳水化合物。 方法包括DNA测序，DNA片段分析，PCR，SNP分析，寡核苷酸连接，扩增，minisequencing和引物延伸。
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公开(公告)号：US06316610B1
公开(公告)日：2001-11-13
申请号：US09813378
申请日：2001-03-20
IPC分类号： C12Q168
摘要： Methods and compositions to label oligonucleotides and analogs directly on a solid-support having the structure where S is a solid-support, A is a cleavable linker, X is a moiety with three or more attachment sites, L is a label, Y is a nucleophile, i.e. O, NH, NR or S, and P1 is an acid cleavable protecting group are provided. The labelled solid-support is reacted in a cyclical fashion to synthesize a labelled oligonucleotide on a solid-support in the 5′ to 3′ direction, having the structure: Labelled oligonucleotides are also synthesized by reacting: (i) a label reagent bearing functionality consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid, (ii) an oligonucleotide on solid support with nucleophilic functionality, and (iii) a coupling reagent, whereby an ester, amide, thioester, sulfonamide, sulfonate, phosphonate, phosphoramidate, phosphorothioate, or phosphate bond is formed. The labelling reaction may be conducted at label sites including the 5′ terminus, the 3′ terminus, a nucleobase, an internucleotide linkage, a sugar, amino, sulfide, hydroxyl, and carboxyl.
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