bis(phenylmethyl) 8,16-dioxo-2,9,12,15,22-pentaazatricosanedioate | 163778-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(phenylmethyl) 8,16-dioxo-2,9,12,15,22-pentaazatricosanedioate
• 英文别名: benzyl N-[6-oxo-6-[2-[2-[6-(phenylmethoxycarbonylamino)hexanoylamino]ethylamino]ethylamino]hexyl]carbamate
• CAS: 163778-62-9
• 化学式: C₃₂H₄₇N₅O₆
• 分子量: 597.755
• InChiKey: OBSJMLVUYCLYPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  43
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  147
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  bis(phenylmethyl) 8,16-dioxo-2,9,12,15,22-pentaazatricosanedioate 在 palladium on activated charcoal 吡啶 、 环己烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-[2-[2-[bis[2-(6-aminohexanoylamino)ethyl]carbamoyloxy]ethoxy]ethoxy]ethyl N,N-bis[2-(6-aminohexanoylamino)ethyl]carbamate
  参考文献：
  名称：

  Immunospecific Reduction of Antioligonucleotide Antibody-Forming Cells with a Tetrakis-oligonucleotide Conjugate (LJP 394), a Therapeutic Candidate for the Treatment of Lupus Nephritis

  摘要：

  A discrete tetravalent conjugate, 7a (LJP 394), consisting of four oligonucleotides attached to a common carrier or platform was prepared. Single-stranded oligonucleotide 20-mers consisting of alternating deoxycytidine-deoxyadenosine nucleotides, (CA)(10), were attached to a tetrabro-moacetylated platform by displacement with sulfhydryl-terminated linkers. The tetrabro-moacetylated platform 3a was synthesized in three steps using triethylene glycol bis-(chloroformate). The single-stranded conjugate was characterized by polyacrylamide gel electrophoresis, DNA sequencing, phosphate analysis, carbon and nitrogen combustion analysis, and correlation of stoichiometry to conversion in the conjugation process. HPLC and capillary electrophoretic methods were developed to evaluate purity. The tetrakis, single-stranded conjugate was annealed with a stoichiometric amount of a complementary single-stranded oligonucleotide 20-mer consisting of alternating thymidine-deoxyguanosine nucleotides, (TG)(10). The double-stranded conjugate LJP 394 was characterized by melt temperature and hyperchromicity, phosphate analysis, and carbon and nitrogen combustion analysis. LJP 394 inhibits binding of DNA to anti-double-stranded oligonucleotide antibodies and reduces anti-oligonucleotide-specific plaque (antibody)-forming cells in an immunized mouse model by a proposed mechanism involving cross-linking B cell surface immunoglobins.

  DOI：

  10.1021/jm00012a013
• 作为产物：
  描述：

  N-苄氧羰基--6-氨基己酸 、 二乙烯三胺 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 生成 bis(phenylmethyl) 8,16-dioxo-2,9,12,15,22-pentaazatricosanedioate
  参考文献：
  名称：

  Immunospecific Reduction of Antioligonucleotide Antibody-Forming Cells with a Tetrakis-oligonucleotide Conjugate (LJP 394), a Therapeutic Candidate for the Treatment of Lupus Nephritis

  摘要：

  A discrete tetravalent conjugate, 7a (LJP 394), consisting of four oligonucleotides attached to a common carrier or platform was prepared. Single-stranded oligonucleotide 20-mers consisting of alternating deoxycytidine-deoxyadenosine nucleotides, (CA)(10), were attached to a tetrabro-moacetylated platform by displacement with sulfhydryl-terminated linkers. The tetrabro-moacetylated platform 3a was synthesized in three steps using triethylene glycol bis-(chloroformate). The single-stranded conjugate was characterized by polyacrylamide gel electrophoresis, DNA sequencing, phosphate analysis, carbon and nitrogen combustion analysis, and correlation of stoichiometry to conversion in the conjugation process. HPLC and capillary electrophoretic methods were developed to evaluate purity. The tetrakis, single-stranded conjugate was annealed with a stoichiometric amount of a complementary single-stranded oligonucleotide 20-mer consisting of alternating thymidine-deoxyguanosine nucleotides, (TG)(10). The double-stranded conjugate LJP 394 was characterized by melt temperature and hyperchromicity, phosphate analysis, and carbon and nitrogen combustion analysis. LJP 394 inhibits binding of DNA to anti-double-stranded oligonucleotide antibodies and reduces anti-oligonucleotide-specific plaque (antibody)-forming cells in an immunized mouse model by a proposed mechanism involving cross-linking B cell surface immunoglobins.

  DOI：

  10.1021/jm00012a013

文献信息

• Valency platform molecules comprising aminooxy groups
  申请人：Jones S. David

  公开号：US20070191263A1

  公开（公告）日：2007-08-16

  Molecules comprising aminooxy groups are provided, wherein the aminooxy groups provide attachment sites for the covalent attachment of other molecules. In one embodiment, polyoxyethylene molecules comprising aminooxy groups are provided that can be conjugated to wide variety of biologically active molecules including poly(amino acids). In another embodiment, valency platform molecules comprising aminooxy groups are provided. The aminooxy groups can be used to form covalent bonds with biological molecules such as poly(amino acids). The aminooxy groups can, for example, react with poly(amino acids) modified to contain carbonyl groups, such as glyoxyl groups, to form a conjugate of the valency platform molecule and the biologically active molecule via an oxime bond. The valency platform molecules comprising aminooxy groups are advantageously reactive in the formation of conjugates, and they also can be readily synthesized to form a composition with very low polydispersity.

  提供了含有氨氧基团的分子，其中氨氧基团提供了其他分子的共价附着位点。在一个实施例中，提供了含有氨氧基团的聚氧乙烯分子，可以与各种生物活性分子共轭，包括聚（氨基酸）。在另一个实施例中，提供了含有氨氧基团的价数平台分子。氨氧基团可用于与生物分子（如聚（氨基酸））形成共价键。例如，氨氧基团可以与改性为含有羰基基团（如乙酰甘氨酸基团）的聚（氨基酸）反应，通过肟键形成价数平台分子和生物活性分子的共轭。含有氨氧基团的价数平台分子在共轭形成中具有优异的反应性，并且它们也可以被轻松地合成成具有非常低的聚分散度的组合物。
• Immunospecific Reduction of Antioligonucleotide Antibody-Forming Cells with a Tetrakis-oligonucleotide Conjugate (LJP 394), a Therapeutic Candidate for the Treatment of Lupus Nephritis
  作者：David S. Jones、Paul A. Barstad、Mark J. Feild、John P. Hachmann、Merle S. Hayag、Kenneth W. Hill、G. Michael Iverson、Douglas A. Livingston、Moorthy S. Palanki

  DOI：10.1021/jm00012a013

  日期：1995.6

  A discrete tetravalent conjugate, 7a (LJP 394), consisting of four oligonucleotides attached to a common carrier or platform was prepared. Single-stranded oligonucleotide 20-mers consisting of alternating deoxycytidine-deoxyadenosine nucleotides, (CA)(10), were attached to a tetrabro-moacetylated platform by displacement with sulfhydryl-terminated linkers. The tetrabro-moacetylated platform 3a was synthesized in three steps using triethylene glycol bis-(chloroformate). The single-stranded conjugate was characterized by polyacrylamide gel electrophoresis, DNA sequencing, phosphate analysis, carbon and nitrogen combustion analysis, and correlation of stoichiometry to conversion in the conjugation process. HPLC and capillary electrophoretic methods were developed to evaluate purity. The tetrakis, single-stranded conjugate was annealed with a stoichiometric amount of a complementary single-stranded oligonucleotide 20-mer consisting of alternating thymidine-deoxyguanosine nucleotides, (TG)(10). The double-stranded conjugate LJP 394 was characterized by melt temperature and hyperchromicity, phosphate analysis, and carbon and nitrogen combustion analysis. LJP 394 inhibits binding of DNA to anti-double-stranded oligonucleotide antibodies and reduces anti-oligonucleotide-specific plaque (antibody)-forming cells in an immunized mouse model by a proposed mechanism involving cross-linking B cell surface immunoglobins.