公开(公告)号：US06617445B2

公开(公告)日：2003-09-09

申请号：US09976842

申请日：2001-10-11

申请人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

发明人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

IPC分类号： C07H1904

CPC分类号： C07H21/00 ,  C07C39/38 ,  C09B11/00 ,  C09B11/08 ,  C12Q1/6869

摘要： A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure wherein Y1 and Y2 are individually hydroxyl, amino, imminium, or oxygen, R1-R8 are hydrogen, fluorine, chlorine, alkyl, alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof and R9 is acetylene, alkane, alkene, cyano, substituted phenyl, and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure where substituents R3-R7 correspond to like-referenced substituents in the structure of described above, and Y2 is hydroxyl or amine. In another aspect the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labeled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, 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不对称单苯并氧杂蒽类化合物，其中Y1和Y2分别是羟基，氨基，氨基或氧，R1-R8是氢，氟，氯，烷基，烯烃，炔烃，磺酸酯，氨基，酰氨基 腈，烷氧基，连接基团及其组合，R 9为乙炔，烷烃，烯烃，氰基，取代的苯基及其组合。 本发明还包括可用于合成具有一般结构的不对称苯并氧杂蒽化合物的新型中间体化合物，其中取代基R3-R7对应于上述结构中相似的取代基，而Y2是羟基或胺。 另一方面，本发明包括合成上述染料化合物和中间体的方法。 在另一方面，本发明包括用不对称苯并氧杂蒽染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸，亚磷酰胺和多核苷酸。 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。

公开(公告)号：US06303775B1

公开(公告)日：2001-10-16

申请号：US09495111

申请日：2000-02-01

申请人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

发明人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

IPC分类号： C07H2104

CPC分类号： C07H21/00 ,  C07C39/38 ,  C09B11/00 ,  C09B11/08 ,  C12Q1/6869

摘要： A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure wherein Y1 and Y2 are individually hydroxyl, amino, imminium, or oxygen, R1-R8 are hydrogen, fluorine, chlorine, alkyl, alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof, and R9 is acetylene, alkane, alkene, cyano, substituted phenyl, and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure where substituents R3-R7 correspond to like-referenced substituents in the structure of described above, and Y2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labeled with the asymmetric benoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, 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不对称单苯并氧杂蒽类化合物，其中Y1和Y2分别是羟基，氨基，氨基或氧，R1-R8是氢，氟，氯，烷基，烯烃，炔烃，磺酸酯，氨基，酰氨基 腈，烷氧基，连接基团及其组合，R 9为乙炔，烷烃，烯烃，氰基，取代的苯基及其组合。 本发明还包括可用于合成具有一般结构的不对称苯并氧杂蒽化合物的新型中间体化合物，其中取代基R3-R7对应于上述结构中相似的取代基，而Y2是羟基或胺。 另一方面，本发明包括合成上述染料化合物和中间体的方法。 在另一方面，本发明包括用不对称的苯氧蒽染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸，亚磷酰胺和多核苷酸。 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。

公开(公告)号：US07179906B2

公开(公告)日：2007-02-20

申请号：US10656826

申请日：2003-09-05

申请人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan D. Hauser

发明人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan D. Hauser

IPC分类号： C07H19/04 ,  C07D311/78 ,  C07D311/82

CPC分类号： C07H21/00 ,  C07C39/38 ,  C09B11/00 ,  C09B11/08 ,  C12Q1/6869

摘要： A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure wherein Y1 and Y2 are individually hydroxyl, amino, imminium, or oxygen, R1–R8 are hydrogen, fluorine, chlorine, alkyl, alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof, and R9 is acetylene, alkane, alkene, cyano, substituted phenyl, and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure where substituents R3–R7 correspond to like-referenced substituents in the structure of described above, and Y2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labeled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, 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不对称单苯并氧蒽化合物，其具有其中Y 1和Y 2 2各自为羟基，氨基，亚氨基或氧的结构， 烷基，烯烃，炔烃，磺酸盐，氨基，酰氨基，腈，烷氧基，连接基团及其组合，R 1，R 2，R 2， 9是乙炔，烷烃，烯烃，氰基，取代的苯基及其组合。 本发明还包括可用于合成具有通式结构的不对称苯并氧杂蒽化合物的新型中间体化合物，其中取代基R 3〜R 7在其结构中对应于相似的取代基 并且Y 2是羟基或胺。 另一方面，本发明包括合成上述染料化合物和中间体的方法。 在另一方面，本发明包括用不对称苯并氧杂蒽染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸，亚磷酰胺和多核苷酸。 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。

公开(公告)号：US6020481A

公开(公告)日：2000-02-01

申请号：US626085

申请日：1996-04-01

申请人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

发明人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

IPC分类号： C12N15/00 ,  C07C39/14 ,  C07C39/38 ,  C07D311/78 ,  C07F9/24 ,  C07H19/06 ,  C07H19/16 ,  C07H21/00 ,  C09B11/00 ,  C09B11/08 ,  C09B11/28 ,  C09K11/06 ,  C12N15/09 ,  C12Q1/68 ,  G01N33/533 ,  C07H21/04

CPC分类号： C07H21/00 ,  C07C39/38 ,  C09B11/00 ,  C09B11/08 ,  C12Q1/6869

摘要： A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure ##STR1## wherein Y.sub.1 and Y.sub.2 are individually hydroxyl amino, imminium, or oxygen, R.sub.1 -R.sub.8 are hydrogen, fluorine, chlorine, alkyl, alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof, and R.sub.9 is acetylene, alkane, alkene, cyano, substituted phenyl, and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure ##STR2## where substituents R.sub.3 -R.sub.7 correspond to like-referenced substituents in the structure of described above, and Y.sub.2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labeled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, 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不对称单苯并氧蒽化合物，其结构是其中Y 1和Y 2分别是羟基氨基，亚氨基或氧，R 1 -R 8是氢，氟，氯，烷基，烯烃，炔烃，磺酸酯，氨基，酰胺基 腈，烷氧基，连接基团及其组合，R 9为乙炔，烷烃，烯烃，氰基，取代的苯基及其组合。 本发明还包括可用于合成具有通式结构的不对称苯并氧杂蒽化合物的新型中间体化合物，其中取代基R 3〜R 7对应于上述结构中的相同取代基，Y 2为羟基或胺。 另一方面，本发明包括合成上述染料化合物和中间体的方法。 在另一方面，本发明包括用不对称苯并氧杂蒽染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸，亚磷酰胺和多核苷酸。 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。

公开(公告)号：US5840999A

公开(公告)日：1998-11-24

申请号：US824102

申请日：1997-03-26

申请人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

发明人： Scott C. Benson ,  Steven M. Menchen ,  Peter D. Theisen ,  Kevin M. Hennessey ,  Vergine C. Furniss ,  Joan Hauser

IPC分类号： C12N15/00 ,  C07C39/14 ,  C07C39/38 ,  C07D311/78 ,  C07F9/24 ,  C07H19/06 ,  C07H19/16 ,  C07H21/00 ,  C09B11/00 ,  C09B11/08 ,  C09B11/28 ,  C09K11/06 ,  C12N15/09 ,  C12Q1/68 ,  G01N33/533 ,  C07C37/68

CPC分类号： C07H21/00 ,  C07C39/38 ,  C09B11/00 ,  C09B11/08 ,  C12Q1/6869

摘要： A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure ##STR1## wherein Y.sub.1, and Y.sub.2 are individually hydroxyl, amino, imminium, or oxygen, R.sub.1 -R.sub.8 are hydrogen, fluorine, chlorine, alkyl alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof, and R.sub.9 is acetylene, alkane, alkene, cyano, substituted phenyl and combinations thereof The invention ftrther includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure ##STR2## where substituents R.sub.3 -R.sub.7 correspond to like-referenced substituents in the structure of described above, and Y.sub.2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labeled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, 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不对称单苯并氧蒽化合物，其结构为：其中Y 1和Y 2分别是羟基，氨基，亚氨基或氧，R 1 -R 8是氢，氟，氯，烷基烯烃，炔烃磺酸盐 氨基，酰氨基，腈，烷氧基，连接基团及其组合，并且R 9是乙炔，烷烃，烯烃，氰基，取代的苯基及其组合。本发明包括可用于合成具有一般性的不对称苯并氧杂蒽化合物的新型中间体化合物 结构其中取代基R3-R7对应于上述结构中的相同取代基，而Y2是羟基或胺。 另一方面，本发明包括合成上述染料化合物和中间体的方法。 在另一方面，本发明包括用不对称苯并氧杂蒽染料化合物标记的试剂，包括脱氧核苷酸，双脱氧核苷酸，亚磷酰胺和多核苷酸。 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。