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    Cationic Oligonucleotides, Automated Methods for Preparing Same and Their Uses
    3.
    发明申请
    Cationic Oligonucleotides, Automated Methods for Preparing Same and Their Uses 有权
    阳离子寡核苷酸，自动制备方法及其用途

    公开(公告)号：US20090069262A1

    公开(公告)日：2009-03-12

    申请号：US12086599

    申请日：2006-12-14

    申请人： Jean-Paul Behr ,  Mitsuharu Kotera ,  Benedicte Pons ,  Emilie Voirin ,  Jean-Serge Remy

    发明人： Jean-Paul Behr ,  Mitsuharu Kotera ,  Benedicte Pons ,  Emilie Voirin ,  Jean-Serge Remy

    IPC分类号： A61K31/7088 ,  C07H21/00 ,  C07H21/04 ,  C07H21/02 ,  C12Q1/68

    CPC分类号： C07F9/22 ,  A61K47/59 ,  A61K48/0041 ,  C07H21/00 ,  C12N15/88

    摘要： The invention relates to oligonucleotide-oligocation molecules AiBjH that can be synthetized via automated phosphoramidite chemistry having oligonucleotides moieties Ai and oligocations moieties Bj, wherein. Ai is an i-mer oligonucleotide residue, with i=5 to 50, where nucleotide A is an oligomer with naturally or non naturally occurring nucleobases and/or pentafuranosyl groups and/or native phosphodiester bonds, for example selected from the group comprising deoxyribo, ribo, locked (LNA) nucleotides as well as their chemical modifications or substitutions such as phosphorothioate, 2′-fluoro, 2′-O-alkyl, or a marker group such as a fluorescent agent, Bj is a j-mer organic oligocation moiety, with j=1 to 50, where B is selected from the group comprising .—HPO3—R1—(X—R2n)n1—X—R3—O—, where R1, R2n and R3, identical or different, are lower alkylene, X is NH or NC(NH2)2, n varies from 1 to 5 and n1=2 to 20, .—HPO3—R4—CH(R5X1)—R6—O—, where R4 is lower alkylene, R5 and R6, identical or different, are lower alkylene and X1 is putrescine, spermidine or spermine residue, .—HPO3—R7-(aa)n2-R8—O—, where R7 is lower alkylene and R8 is lower alkylene, serine, a natural aminoalcohol, (aa)n2 is a peptide containing natural aminoacids with cationic side chains, such as Arginine, Lysine, Ornithine, -Histidine, Diaminopropionic acid and n2=2 to 20.

    摘要翻译： 本发明涉及可通过自动亚磷酰胺化学合成寡核苷酸寡聚分子AiBjH，其具有寡核苷酸部分A 1和寡聚部分B 1，其中。 Ai是i = 5至50的i-mer寡核苷酸残基，其中核苷酸A是具有天然或非天然存在的核碱基和/或五呋喃糖基和/或天然磷酸二酯键的寡聚体，例如选自脱氧核糖， 核苷酸，锁定（LNA）核苷酸以及它们的化学修饰或取代，例如硫代磷酸酯，2'-氟，2'-O-烷基或诸如荧光剂的标记基团，Bj是j-mer有机寡核苷酸部分 ，其中B选自包含-HPO 3 -R 1（X-R 2n）n1-X-R 3 -O-的基团，其中R 1，R 2n和R 3相同或不同，为低级亚烷基 ，X为NH或NC（NH 2）2，n为1至5，n 1 = 2至20，...-HPO 3 -R 4 -CH（R5X1）-R6-O-，其中R4为低级亚烷基，R5和R6， 相同或不同的是低级亚烷基，X 1是腐胺，亚精胺或精胺残基。-HPO3-R7-（aa）n2-R8-O-，其中R7是低级亚烷基，R8是低级亚烷基，丝氨酸，天然氨基醇， （aa）n2是肽c 使用阳离子侧链，如精氨酸，赖氨酸，鸟氨酸，组氨酸，二氨基丙酸，n2 = 2〜20。

    Cationic oligonucleotides, automated methods for preparing same and their uses
    5.
    发明授权
    Cationic oligonucleotides, automated methods for preparing same and their uses 有权
    阳离子寡核苷酸，自动制备方法及其用途

    公开(公告)号：US09090648B2

    公开(公告)日：2015-07-28

    申请号：US12086599

    申请日：2006-12-14

    申请人： Jean-Paul Behr ,  Mitsuharu Kotera ,  Bénédicte Pons ,  Emilie Voirin ,  Jean-Serge Remy

    发明人： Jean-Paul Behr ,  Mitsuharu Kotera ,  Bénédicte Pons ,  Emilie Voirin ,  Jean-Serge Remy

    IPC分类号： C07H21/00 ,  A61K47/00 ,  A61K47/48 ,  A61K48/00

    CPC分类号： C07F9/22 ,  A61K47/59 ,  A61K48/0041 ,  C07H21/00 ,  C12N15/88

    摘要： The invention relates to oligonucleotide-oligocation molecules AiBjH that can be synthetized via automated phosphoramidite chemistry having oligonucleotides moieties Ai and oligocations moieties Bj, wherein •Ai is an i-mer oligonucleotide residue, with i=5 to 50, where nucleotide A is an oligomer with naturally or non naturally occurring nucleobases and/or pentafuranosyl groups and/or native phosphodiester bonds, for example selected from the group comprising deoxyribo, ribo, locked (LNA) nucleotides as well as their chemical modifications or substitutions such as phosphorothioate, 2′-fluoro, 2′-O-alkyl, or a marker group such as a fluorescent agent, •Bj is a j-mer organic oligocation moiety, with j=1 to 50, where B is selected from the group comprising •—HPO3—R1—(X—R2n)n1—X—R3—O—, where R1, R2n and R3, identical or different, are lower alkylene, X is NH or NC(NH2)2, n varies from 1 to 5 and n1=2 to 20, •—HPO3—R4—CH(R5X1)—R6—O—, where R4 is lower alkylene, R5 and R6, identical or different, are lower alkylene and X1 is putrescine, spermidine or spermine residue, •—HPO3—R7-(aa)n2-R8—O—, where R7 is lower alkylene and R8 is lower alkylene, serine, a natural aminoalcohol, (aa)n2 is a peptide containing natural aminoacids with cationic side chains, such as Arginine, Lysine, Ornithine, -Histidine, Diaminopropionic acid and n2=2 to 20.

    摘要翻译： 本发明涉及可通过具有寡核苷酸部分A 1和寡核苷酸部分B 1的自动亚磷酰胺化学合成的寡核苷酸寡聚分子AiBjH，其中·Ai是i = 5〜50的i-mer寡核苷酸残基，其中核苷酸A为低聚物 与天然或非天然存在的核碱基和/或五五烷酰基基团和/或天然磷酸二酯键，例如选自脱氧核糖核酸，核糖体，锁定（LNA）核苷酸以及它们的化学修饰或取代，例如硫代磷酸酯， 氟，2'-O-烷基或标记基团如荧光剂，Bj是j-mer有机寡核苷酸部分，j = 1-50，其中B选自-HPO 3 -R 1 - （X-R2n）n1-X-R3-O-，其中R1，R2n和R3相同或不同，为低级亚烷基，X为NH或NC（NH2）2，n为1至5，n1 = 2 至20，-HPO 3 -R 4 -CH（R5X1）-R6-O-，其中R4较低 亚烷基，R 5和R 6相同或不同，为低级亚烷基，X 1为腐胺，亚精胺或精胺残基，-HPO3-R7-（aa）n2-R8-O-，其中R7为低级亚烷基，R8为低级亚烷基， 丝氨酸，天然氨基醇，（aa）n2是含有阳离子侧链的天然氨基酸的肽，例如精氨酸，赖氨酸，鸟氨酸，组氨酸，二氨基丙酸，n2 = 2〜20。

    Marking reagents bearing diazo and nitro functions, methods for the synthesis of such reagents and methods for detecting biological molecules
    6.
    发明授权
    Marking reagents bearing diazo and nitro functions, methods for the synthesis of such reagents and methods for detecting biological molecules 失效
    带有重氮和硝基功能的标记试剂，合成这些试剂的方法和检测生物分子的方法

    公开(公告)号：US08309695B2

    公开(公告)日：2012-11-13

    申请号：US12451502

    申请日：2008-06-09

    申请人： Alain Laurent ,  Ali Laayoun ,  Mitsuharu Kotera

    发明人： Alain Laurent ,  Ali Laayoun ,  Mitsuharu Kotera

    IPC分类号： C07C245/14 ,  C12Q1/68

    CPC分类号： C07D495/04 ,  Y10T436/13

    摘要： The present invention relates to a labeling reagent of formula: in which: R1 represents at least one detectable label, L and A are each a linker arm, n is an integer equal to 1, and u is an integer between 0 and 2. The present invention also describes a method of synthesizing said markers and also applications for the labeling of biological molecules, more particularly nucleic acids, with a labeling reagent bearing diazo and nitro functions. The invention is particularly suitable for use in the diagnostics field.

    摘要翻译： 本发明涉及下式的标记试剂：其中：R1表示至少一个可检测标记，L和A各自为连接臂，n为等于1的整数，u为0至2之间的整数。 本发明还描述了一种合成所述标记的方法，以及用于用具有重氮和硝基功能的标记试剂标记生物分子，更特别是核酸的应用。 本发明特别适用于诊断领域。

    Labeling reagents, methods for synthesizing such reagents and methods for detecting biological molecules
    7.
    发明授权
    Labeling reagents, methods for synthesizing such reagents and methods for detecting biological molecules 有权
    标记试剂，合成这些试剂的方法和检测生物分子的方法

    公开(公告)号：US07338805B2

    公开(公告)日：2008-03-04

    申请号：US10137454

    申请日：2002-05-03

    申请人： Cecile Bourget ,  Jean Lhomme ,  Ali Laayoun ,  Mitsuharu Kotera ,  Emmanuelle Trevisiol ,  Lionel Menou ,  Eloy Bernal Mendez

    发明人： Cecile Bourget ,  Jean Lhomme ,  Ali Laayoun ,  Mitsuharu Kotera ,  Emmanuelle Trevisiol ,  Lionel Menou ,  Eloy Bernal Mendez

    IPC分类号： G01N37/00 ,  G01N33/48

    CPC分类号： C07D209/08 ,  C07C245/14 ,  C07C245/18 ,  C07D311/90 ,  C07D495/04 ,  Y10T436/13 ,  Y10T436/143333

    摘要： The present invention relates to a temperature-stable labeling reagent of formula: in which R1 represents H or an alkyl, aryl or substituted aryl group, R2 represents a detectable marker or at least two detectable markers linked together by at least one multimeric structure, L is a linking arm containing a linear succession of at least two covalent bonds and n an integer equal to 0 or 1, R3 and R4 represent independently of each other: H, NO2, Cl, Br, F, I, R2-(L)n-Y—X—, OR, SR, NR2, R, NHCOR, CONHR, COOR with R=alkyl or aryl, A is a linking arm containing at least one covalent double bond allowing conjugation of the diazo functional group with the aromatic ring and u is an integer between 0 and 2, preferably equal to 0 or 1, and —Y—X— represents —CONH—, —NHCO—, —CH2O—, —CH2S—. The present invention also describes a method for synthesizing said markers as well as applications for labeling biological molecules, in particular nucleic acids, with a labeling reagent carrying the diazomethyl functional group.The invention finds a preferred application in the field of diagnosis.

    摘要翻译： 本发明涉及下式的温度稳定的标记试剂：其中R 1表示H或烷基，芳基或取代的芳基，R 2表示可检测标记 或至少两个通过至少一个多聚体结构连接在一起的可检测标记，L是含有至少两个共价键的线性连续并且n为等于0或1的整数的连接臂，R 3和 R 4彼此独立地表示：H，NO 2，Cl，Br，F，I，R 2 - （L） O-，-CH 2 S-。 本发明还描述了一种用于合成所述标记的方法以及用携带重氮甲基官能团的标记试剂标记生物分子，特别是核酸的应用。 本发明在诊断领域找到优选的应用。

    MARKING REAGENTS BEARING DIAZO AND NITRO FUNCTIONS, METHODS FOR THE SYNTHESIS OF SUCH REAGENTS AND METHODS FOR DETECTING BIOLOGICAL MOLECULES
    8.
    发明申请
    MARKING REAGENTS BEARING DIAZO AND NITRO FUNCTIONS, METHODS FOR THE SYNTHESIS OF SUCH REAGENTS AND METHODS FOR DETECTING BIOLOGICAL MOLECULES 失效
    携带DIAZO和NITRO功能的标记试剂，合成这些试剂的方法和检测生物分子的方法

    公开(公告)号：US20100136538A1

    公开(公告)日：2010-06-03

    申请号：US12451502

    申请日：2008-06-09

    申请人： Alain Laurent ,  Ali Laayoun ,  Mitsuharu Kotera

    发明人： Alain Laurent ,  Ali Laayoun ,  Mitsuharu Kotera

    IPC分类号： C12Q1/68 ,  C07D495/04 ,  C07H21/00 ,  C12P19/34

    CPC分类号： C07D495/04 ,  Y10T436/13

    摘要： The present invention relates to a labeling reagent of formula: in which: R1 represents at least one detectable label, L and A are each a linker arm, n is an integer equal to 1, and u is an integer between 0 and 2. The present invention also describes a method of synthesizing said markers and also applications for the labeling of biological molecules, more particularly nucleic acids, with a labeling reagent bearing diazo and nitro functions. The invention is particularly suitable for use in the diagnostics field.

    摘要翻译： 本发明涉及下式的标记试剂：其中：R1表示至少一个可检测标记，L和A各自为连接臂，n为等于1的整数，u为0至2之间的整数。 本发明还描述了一种合成所述标记的方法，以及用于用具有重氮和硝基功能的标记试剂标记生物分子，更特别是核酸的应用。 本发明特别适合用于诊断领域。