N-[3-[4-(3-氨基丙基氨基)丁基氨基]丙基]乙酰胺 | 25593-72-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-[3-[4-(3-氨基丙基氨基)丁基氨基]丙基]乙酰胺
• 英文名称: N1-acetylspermine
• 英文别名: N1-Acetyl-Spermine；N¹-acetylspermine；N-acetylspermine；N¹-acetyl-Spm；N-acetyl-spermine；N-[3-[4-(3-aminopropylamino)butylamino]propyl]acetamide
• CAS: 25593-72-0
• 化学式: C₁₂H₂₈N₄O
• 分子量: 244.381
• InChiKey: GUNURVWAJRRUAV-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±35.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  158 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  79.2
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2924199090

制备方法与用途

N-乙酰半胱氨酸是一种存在于尿液中的内源性代谢产物，可以用于白血病的研究。

反应信息

• 作为反应物：
  描述：

  N-[3-[4-(3-氨基丙基氨基)丁基氨基]丙基]乙酰胺 在 Saccharomyces cerevisiae recombinant polyamine oxidase Fms₁ 、 水 、 氧气 作用下， 生成 亚精胺 、 3-acetamidopropanal
  参考文献：
  名称：

  酵母多胺氧化酶 Fms1 中活性位点残基作用的机理和结构分析：N195A 和 D94N 酶的表征

  摘要：

  来自酿酒酵母的黄素蛋白 Fms1催化泛酸生物合成途径中精胺的氧化。同样的反应由哺乳动物多胺和精胺氧化酶催化。Fms1 的活性位点包含三个氨基酸残基，可与多胺底物 His67、Asn195 和 Asp94 相互作用。这三个残基形成一个氢键三联体，其中 Asn195 是中心残基。先前对 His67 突变影响的研究与该残基对于与底物相互作用和维持三联体中的氢键都很重要 [Adachi, MS, Taylor, AB, Hart, PJ, and Fitzpatrick, PF (2012)生物化学 51, 4888–4897]。N195A 和 D94N 酶现在已被表征以评估它们在催化中的作用。两种突变主要影响还原性半反应。以N 1 -乙酰精胺作为底物，两种突变的黄素还原速率常数都降低了约 450 倍；以精胺为底物的影响较小，为 20-40 倍。N 1 -乙酰精胺的k cat / K胺- 和k cat

  DOI：

  10.1021/bi3011434
• 作为产物：
  描述：

  精胺 、 α-D(+)-五乙酰葡萄糖 以 乙醇 为溶剂， 反应 24.0h， 以33%的产率得到N-[3-[4-(3-氨基丙基氨基)丁基氨基]丙基]乙酰胺
  参考文献：
  名称：

  The number and distances of positive charges of polyamine side chains in a series of perylene diimides significantly influence their ability to induce G-quadruplex structures and inhibit human telomerase

  摘要：

  We have synthesized eight polyamine perylene diimides to conjugate the efficiency of perylene derivatives in stabilizing G-quadruplex structures and the polyamines' biological activity, due to specific interactions with different DNA domains. Our study was carried out by investigating the ability of these derivatives to induce inter- and intramolecular G-quadruplex structures by polyacrylamide gel electrophoresis (PAGE) and to inhibit telomerase in a modified TRAP assay. The two properties appear to be satisfactorily correlated and they show that the number and distances of positive charges in the side chains dramatically influence both these features. Although our previous studies on perylene derivatives with mono-positively charged side chains indicated that self assembly in aqueous solution leads to a major efficiency, the result observed with the spermine derivative suggests that a too strong aggregation is unfavourable, because it determines a lower solubility of the compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.065

文献信息

• [EN] AMINO ACID DEPLETION AGENTS AS ANTIPROLIFERATIVE AGENTS<br/>[FR] AGENTS D'APPAUVRISSEMENT EN ACIDES AMINÉS EN GUISE D'AGENTS ANTIPROLIFÉRATIFS
  申请人：UNIV CENTRAL FLORIDA RES FOUND INC

  公开号：WO2020047361A1

  公开（公告）日：2020-03-05

  Novel compounds are described which decrease the intracellular levels of leucine and methionine. Treatment with these amino acid depletion agents affects many metabolic and life processes which rely upon methionine, leucine and their derivatives. Methionine depletion not only inhibits protein synthesis, but also polyamine biosynthesis and significantly reduces intracellular pools of the native polyamines, spermidine and spermine. Since methionine restriction has been shown to mimic caloric restriction in life extension studies across multiple species, these compounds are also expected to extend lifespan by limiting methionine supply.

  描述了几种新的化合物，这些化合物能够降低细胞内亮氨酸和蛋氨酸的水平。使用这些氨基酸剥夺剂影响许多依赖蛋氨酸、亮氨酸及其衍生物的代谢和生命过程。蛋氨酸剥夺不仅抑制蛋白质合成，还抑制聚胺生物合成，并显著减少细胞内天然聚胺，即亚精胺和精胺的池。由于蛋氨酸限制在多个物种的生命延长研究中已被证明可以模仿卡路里限制，因此预计这些化合物通过限制蛋氨酸供应也能延长寿命。
• Polyamine modification by acrolein exclusively produces 1,5-diazacyclooctanes: a previously unrecognized mechanism for acrolein-mediated oxidative stress
  作者：Ayumi Tsutsui、Rie Imamaki、Shinobu Kitazume、Shinya Hanashima、Yoshiki Yamaguchi、Masato Kaneda、Shinya Oishi、Nobutaka Fujii、Almira Kurbangalieva、Naoyuki Taniguchi、Katsunori Tanaka

  DOI：10.1039/c4ob00761a

  日期：——

  Acrolein, a toxic unsaturated aldehyde generated as a result of oxidative stress, readily reacts with a variety of nucleophilic biomolecules. Polyamines, which produced acrolein in the presence of amine oxidase, were then found to react with acrolein to produce 1,5-diazacyclooctane, a previously unrecognized but significant downstream product of oxidative stress. Although diazacyclooctane formation

  丙烯醛是氧化应激的结果，是一种有毒的不饱和醛，容易与多种亲核生物分子发生反应。然后发现在胺氧化酶的存在下生成丙烯醛的多胺与丙烯醛反应生成1，5-二氮杂环辛烷，这是以前无法识别的氧化应激下游产物。尽管二氮杂环辛烷的形成有效地中和了丙烯醛的毒性，但是通过顺序的二氮杂环辛烷聚合反应产生的二氮杂环辛烷水凝胶具有很高的细胞毒性。这项研究表明，二氮杂环辛烷的形成与丙烯醛介导的氧化应激的潜在机制有关。
• Towards Squalamine Mimics: Synthesis and Antibacterial Activities of Head-to-Tail Dimeric SterolPolyamine Conjugates
  作者：Wen-Hua Chen、Christine Wennersten、Robert C. Moellering、Steven L. Regen

  DOI：10.1002/cbdv.201100431

  日期：2013.3

  Four dimeric sterolpolyamine conjugates have been synthesized from the homo‐ and hetero‐connection of monomeric sterolpolyamine analogs in a head‐to‐tail manner. These dimeric conjugates show strong antibacterial activity against a broad spectrum of Gram‐positive bacteria, whereas their corresponding activities against Gram‐negative bacteria are relatively moderate. Though no significant difference

  已经从单体甾醇多胺类似物的同向和异质连接以头对尾的方式合成了四种二聚甾醇多胺偶联物。这些二聚体偶联物对广谱革兰氏阳性菌显示出很强的抗菌活性，而它们对革兰氏阴性菌的相应活性则相对适中。虽然在这些偶联物的活性中没有观察到显着差异，但含胆酸的二聚体偶联物通常比相应的脱氧胆酸衍生类似物表现出更高的活性。这与单体脱氧胆酸-精胺偶联物比相应的胆酸衍生类似物更具活性的发现相反。
• [EN] SMALL MOLECULE LIVER X RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS À PETITES MOLÉCULE DU RÉCEPTEUR NUCLÉAIRE DES OXYSTÉROLS ET LEURS UTILISATIONS
  申请人：UNIV HOUSTON SYSTEM

  公开号：WO2021046034A1

  公开（公告）日：2021-03-11

  Small molecule liver X receptor (LXR) modulators, and derivatives thereof, exhibit activity against tumor cells and less or no activity against dividing non-malignant cells, target the liver X receptor and disrupt key metabolic pathways preferred by cancer cells, and activate a newly discovered cell death mechanism which is distinct from the cell death induced by chemotherapeutic agents. These compounds can thus be a less toxic alternative to chemotherapy and can be used in combination with chemotherapy to increase efficacy and decrease the likelihood of cancer cells developing resistance. Moreover, they can be used as second-line treatments when chemotherapies are ineffective or if cancer cells develop resistance over time.

  小分子肝X受体（LXR）调节剂及其衍生物对肿瘤细胞具有活性，对分裂的非恶性细胞活性较低或无活性，靶向肝X受体并破坏癌细胞首选的关键代谢途径，并激活一种新发现的细胞死亡机制，该机制与化疗药物引起的细胞死亡不同。因此，这些化合物可以作为比化疗更少毒副作用的选择，并可与化疗结合使用，以提高疗效并降低癌细胞产生抗药性的可能性。此外，当化疗无效或癌细胞随时间产生抗药性时，它们可以作为二线治疗方法。
• Oxidation of acetylpolyamines by maize polyamine oxidase
  作者：Rodolfo Federico、Luca Ercolini、Maria Laurenzi、Riccardo Angelini

  DOI：10.1016/0031-9422(96)00316-0

  日期：1996.9

  Abstract The oxidation of acetylpolyamines by cell wall polyamine oxidase from maize shoots was investigated. The purified enzyme catalysed the oxidation of N 1 -acetylspermine, N 1 -acetylspermidine, and N 8 -acetylspermidine at the same optimal pH (6.5), but with lower relative velocities and higher K m than those found for spermine and spermidine oxidation. The enzyme cleaved N 1 -acetylspermine

  摘要 研究了玉米芽细胞壁多胺氧化酶对乙酰多胺的氧化反应。纯化的酶在相同的最佳 pH 值 (6.5) 下催化 N 1 - 乙酰精胺、N 1 - 乙酰亚精胺和 N 8 - 乙酰亚精胺的氧化，但相对速度低于精胺和亚精胺氧化时发现的相对速度和 K m 。该酶在与精胺和亚精胺氧化相同的位置裂解 N 1 -乙酰精胺和 N 8 -乙酰亚精胺，产生 H 2 O 2 、1,3-二氨基丙烷和相应的氨基醛。多胺氧化酶在催化作用下迅速失活，N 1 -乙酰精胺衍生的氨基醛作为该酶的竞争性抑制剂（K i = 20 μM）。