N,N'-二(3-氨基丁基)丁烷-1,4-二胺 | 137946-03-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N'-二(3-氨基丁基)丁烷-1,4-二胺
• 中文别名: 丁二酸,氯-,4-乙基1-甲基酯(9CI)
• 英文名称: α,α'-dimethylspermine
• 英文别名: 2,13-diamino-5,10-diazatetradecane；α,α'-Me2Spm；Rac-Me2Spm；α-dimethylspermine；1-N-[4-(3-aminobutylamino)butyl]butane-1,3-diamine
• CAS: 137946-03-3
• 化学式: C₁₂H₃₀N₄
• 分子量: 230.397
• InChiKey: LXKFTCVCBKNJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  76.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N¹,N⁴-bis<3-<(carbobenzyloxy)amino>butyryl>-1,4-diaminobutane 在 platinum(IV) oxide 硼烷四氢呋喃络合物 、 氢气 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 N,N'-二(3-氨基丁基)丁烷-1,4-二胺
  参考文献：
  名称：

  .alpha.-Methyl polyamines: metabolically stable spermidine and spermine mimics capable of supporting growth in cells depleted of polyamines

  摘要：

  In order to assess the tolerance of the target enzyme spermine synthase for alpha-substituents on the aminopropyl moiety of the substrate spermidine, 1-methylspermidine (MeSpd, 2) was synthesized. It was determined that MeSpd is a poor substrate for spermine synthase and is not a substrate for spermidine N1-acetyltransferase, suggesting that alpha-methylated polyamines might be metabolically stable and therefore useful tools for studying polyamine effects in intact cells. On the basis of initial cellular results with 2, 1-methylspermine (MeSpm, 3) and 1,12-dimethylspermine (Me2Spm, 4) were also synthesized. When added to cells (L1210, SV-3T3, or HT29) depleted of both putrescine and spermidine by prior treatment with alpha-(difluoromethyl)ornithine (DFMO), these alpha-methylated polyamines were able to restore cell growth to that observed in the absence of DFMO. In accord with the enzyme data noted above, metabolic studies indicated a slow conversion of 2 to 3, but no metabolism of 4 in these cells. It was concluded from these results that the alpha-methylated polyamines are able to substitute for the natural polyamines spermidine and spermine in critical biochemical processes which involve polyamines for continued cell growth. In accord with the hypothesis, preliminary data indicate that MeSpd and Me2Spm are as effective as spermidine and spermine, respectively, in promoting the conversion of B-DNA to Z-DNA.

  DOI：

  10.1021/jm00082a013

文献信息

• New syntheses of α-methyl- and α,α′-dimethylspermine
  作者：N. A. Grigorenko、J. Vepsalainen、A. Jarvinen、T. A. Keinanen、L. Alhonen、J. Janne、A. R. Khomutov

  DOI：10.1007/s11171-005-0025-5

  日期：2005.3

  α-Methylspermine and α,α′-dimethylspermine were synthesized in high overall yields starting from N-(benzyloxycarbonyl)-3-aminobutanol in order to study polyamine biochemistry in vitro and in vivo.

  为了研究体外和体内多胺生物化学，我们从 N-（苄氧羰基）-3-氨基丁醇开始，高产合成了 α-甲基精胺和 α,α′-二甲基精胺。
• α-Methyl Polyamines:  Efficient Synthesis and Tolerance Studies in Vivo and in Vitro. First Evidence for Dormant Stereospecificity of Polyamine Oxidase
  作者：Aki J. Järvinen、Marc Cerrada-Gimenez、Nikolay A. Grigorenko、Alex R. Khomutov、Jouko J. Vepsäläinen、Riitta M. Sinervirta、Tuomo A. Keinänen、Leena I. Alhonen、Juhani E. Jänne

  DOI：10.1021/jm050872h

  日期：2006.1.1

  Efficient syntheses of metabolically stable a-methylspermidine 1, alpha-methylspermine 2, and bis-alpha,alpha'methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N-1-acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.
• METHODS AND PREPARATIONS FOR PROTECTING CRITICALLY ILL PATIENTS
  申请人：Winderickx Joris

  公开号：US20120015901A1

  公开（公告）日：2012-01-19

  The present invention relates to a method of treating a life threatening condition in a critically ill human patient with a non-infectuous disorder, wherein the critically ill patient is a patient receiving enteral or parenteral nutrition, the method comprising the step of administering to said patient an autophagy inducing agent.
• .alpha.-Methyl polyamines: metabolically stable spermidine and spermine mimics capable of supporting growth in cells depleted of polyamines
  作者：John R. Lakanen、James K. Coward、Anthony E. Pegg

  DOI：10.1021/jm00082a013

  日期：1992.2

  In order to assess the tolerance of the target enzyme spermine synthase for alpha-substituents on the aminopropyl moiety of the substrate spermidine, 1-methylspermidine (MeSpd, 2) was synthesized. It was determined that MeSpd is a poor substrate for spermine synthase and is not a substrate for spermidine N1-acetyltransferase, suggesting that alpha-methylated polyamines might be metabolically stable and therefore useful tools for studying polyamine effects in intact cells. On the basis of initial cellular results with 2, 1-methylspermine (MeSpm, 3) and 1,12-dimethylspermine (Me2Spm, 4) were also synthesized. When added to cells (L1210, SV-3T3, or HT29) depleted of both putrescine and spermidine by prior treatment with alpha-(difluoromethyl)ornithine (DFMO), these alpha-methylated polyamines were able to restore cell growth to that observed in the absence of DFMO. In accord with the enzyme data noted above, metabolic studies indicated a slow conversion of 2 to 3, but no metabolism of 4 in these cells. It was concluded from these results that the alpha-methylated polyamines are able to substitute for the natural polyamines spermidine and spermine in critical biochemical processes which involve polyamines for continued cell growth. In accord with the hypothesis, preliminary data indicate that MeSpd and Me2Spm are as effective as spermidine and spermine, respectively, in promoting the conversion of B-DNA to Z-DNA.