N-(4-guanidino-butyl)acrylamide | 181147-64-8

• 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
• 英文名称: N-(4-guanidino-butyl)acrylamide
• 英文别名: 1-acryloylagmatine；acryloyl-agmatine；acrylamidoagmatine；N-[4-(diaminomethylideneamino)butyl]prop-2-enamide
• CAS: 181147-64-8
• 化学式: C₈H₁₆N₄O
• 分子量: 184.241
• InChiKey: JCXRKALRUVXURQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-guanidino-butyl)acrylamide 、 (2-bromoisobutyryl)₆-maltotriosyl-N-acetylamino-hexanoic acid 在 三(2-吡啶基甲基)胺 、 copper(I) bromide 、 维生素 C 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以542 mg的产率得到(agmatinyl)₆-maltotriosyl-N-acetyl-aminohexanoic acid
  参考文献：
  名称：

  Novel Oligo-Guanidyl-PEG Carrier Forming Rod-Shaped Polyplexes

  摘要：

  A novel unconventional supramolecular oligocationic structure (Agm(6)-M-PEG-OCH3) has been synthesized to yield high efficiency therapeutic oligonucleotide (ON) delivery. Agm(6)-M-PEG-OCH3 was obtained by a multistep protocol that included the conjugation of agmatine (Agm) moieties to maltotriose (M), which was further derivatized with one poly(ethylene glycol) (PEG) chain. Gel electrophoresis analysis showed that the 19 base pairs dsDNA model ON completely associates with Agm(6)-M-PEG-OCH3 at 3 N/P molar ratio, which is in agreement with the in silico molecular predictions. Isothermal titration calorimetry (ITC) analyses showed that the Agm(6)-M-PEG-OCH3/ON association occurs through a combination of mechanisms depending on the N/P ratios resulting in different nanostructures. Dynamic light scattering (DLS) and transmission electron microscopy (TEM) revealed that the Agm(6)-M-PEG-OCH3/ON polyplexes have rod-shape structure with a mean diameter of 50-75 nm and aspect ratio depending on the N/P ratio. The polyplexes were stable over time in buffer, while a slight size increase was observed in the presence of serum proteins. Cell culture studies showed that neither Agm(6)-M-PEG-OCH3 nor polyplexes displayed cytotoxic effects. Cellular uptake depended on the cell line and polyplex composition: cellular internalization was higher in the case of MCF-7 and KB cells compared to MC3T3-E1 cells and polyplexes with smaller aspect ratio were taken-up by cells more efficiently than polyplexes with higher aspect ratio. Finally, preliminary studies showed that our novel carrier efficiently delivered ONs into cells providing gene silencing.

  DOI：

  10.1021/acs.molpharmaceut.9b00014
• 作为产物：
  描述：

  硫酸胍基丁胺 、 丙烯酰氯 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.5h， 以1 g的产率得到N-(4-guanidino-butyl)acrylamide
  参考文献：
  名称：

  [EN] STAR-LIKE (GUANIDYL)X-OLIGOSACCHARIDIC COMPOUNDS AND CONJUGATES OR COMPLEXES THEREOF
  [FR] COMPOSÉS DE TYPE ÉTOILE DE (GUANIDYL)X-OLIGOSACCHARIDES ET CONJUGUÉS OU COMPLEXES DE CEUX-CI

  摘要：

  本发明涉及一种具有星状结构的（胍基）x-寡糖化合物，具有携带和传递药物或生物分子（如寡核苷酸、多肽和蛋白质）穿过生物膜的能力。 （胍基）x-寡糖化合物可以与具有生物活性的化合物、荧光染料、放射性核素、宏观表面、靶向剂等功能基团形成共轭物，或与阴离子大分子（如ONs、多肽、蛋白质、核酸、药物、细胞膜）形成复合物。

  公开号：

  WO2018130282A1

文献信息

• METHOD OF MAKING LIGAND FUNCTIONALIZED SUBSTRATES
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US20170217880A1

  公开（公告）日：2017-08-03

  Ligand functionalized substrates, methods of making ligand functionalized substrates, and methods of using functionalized substrates are disclosed.

  本发明揭示了配体功能化基底、制备配体功能化基底的方法以及使用功能化基底的方法。
• [EN] METHOD FOR SYNTHESIS OF ACRYLAMIDE DERIVATIVES<br/>[FR] PROCEDE DE SYNTHESE DE DERIVES D'ACRYLAMIDE
  申请人：AMERSHAM BIOSCIENCES AB

  公开号：WO2005040092A1

  公开（公告）日：2005-05-06

  The present invention relates to a method for synthesis of an acrylamide derivative, starting with dissolving a salt of a nucleophilic amine in water to form an aqueous solution and desalting said solution with a base, comprising the following steps: a) addition of dissolved activated acrylic acid derivative to said solution; b) acidification of aqueous phase; and c) extraction of said aqueous phase. In a preferred embodiment the acryl amide derivative is an immobiline, preferably acrylamido agmatine. The preferred use of the immobilines is for production of 2D gels.

  本发明涉及一种合成丙烯酰胺衍生物的方法，起始于将亲核胺的盐在水中溶解以形成水溶液，并用碱脱盐该溶液，包括以下步骤：a）向该溶液中加入溶解的活化丙烯酸衍生物；b）使水相酸化；和c）从该水相中提取。在一种优选实施例中，丙烯酰胺衍生物是固定化的亚胺基，优选为丙烯酰胺基瓜胺。固定化亚胺基的优选用途是用于2D凝胶的生产。
• Method for lowering serum glucose
  申请人：GelTex Pharmaceutical, Inc.

  公开号：US20020187121A1

  公开（公告）日：2002-12-12

  A method for treating hyperglycemia and/or reducing serum glucose levels in a patient that includes administering to the patient a therapeutically effective amount of an amine polymer is disclosed. In one embodiment, the amine polymer is aliphatic. Examples of polymers useful in an embodiment of the invention include sevelamer hydrogen chloride and colesevelam. The invention includes the use of amine polymers such as a cross-linked polymer characterized by a repeat unit having the formula: 1 and salts and copolymers thereof, where n is a positive integer and x is zero or an integer between 1 and about 4. Also described is a use, for the manufacture of a medicament, of a polymer that lowers serum glucose.

  本发明公开了一种治疗高血糖和/或降低患者血清葡萄糖水平的方法，包括向患者投予治疗有效量的胺基聚合物。在一种实施例中，胺基聚合物是脂肪族的。本发明的实施例中有用的聚合物的例子包括盐酸西韦拉酰胺和考来西韦。本发明包括使用胺基聚合物，例如交联聚合物，其特征在于重复单元具有公式1，以及其盐和共聚物，其中n是正整数，x为零或介于1和约4之间的整数。本发明还描述了一种用于制造药物的降低血清葡萄糖的聚合物的用途。
• Method for treating gout and binding uric acid
  申请人：GelTex Pharmaceutical, Inc.

  公开号：US20030039627A1

  公开（公告）日：2003-02-27

  A method for treating gout and/or reducing serum uric acid levels in a patient is disclosed that includes administering to the patient a therapeutically effective amount of an amine polymer, for example, an aliphatic amine polymer. In one embodiment, the polymer binds to uric acid or a precursor thereof. Examples of polymers useful in an embodiment of the invention include sevelamer hydrochloride and colesevelam. The invention includes the use of amine polymers such as a cross-linked polymer characterized by a repeat unit having the formula: 1 and salts and copolymers thereof, where n is a positive integer and x is zero or an integer between 1 and about 4. Also described is a use, for the manufacture of a medicament, of a polymer that binds serum uric acid in a patient.

  本发明揭示了一种治疗痛风和/或减少患者血清尿酸水平的方法，包括向患者投予治疗有效量的胺基高分子，例如脂肪族胺基高分子。在一种实施例中，该高分子与尿酸或其前体结合。在本发明实施例中有用的高分子的例子包括盐酸西维拉麦和考来西韦。本发明包括使用胺基高分子，例如交联聚合物，其重复单元具有公式1，以及其盐和共聚物，其中n是正整数，x为0或介于1到约4之间的整数。本发明还描述了一种用于制造药物的用途，该药物能够结合患者血清尿酸。
• Method for synthesis of acrylamide derivatives
  申请人：Algotsson Mattias

  公开号：US20070106090A1

  公开（公告）日：2007-05-10

  The present invention relates to a method for synthesis of an acrylamide derivative, starting with dissolving a salt of a nucleophilic amine in water to form an aqueous solution and desalting said solution with a base, comprising the following steps: a) addition of dissolved activated acrylic acid derivative to said solution; b) acidification of aqueous phase; and c) extraction of said aqueous phase. In a preferred embodiment the acryl amide derivative is an immobiline, preferably acrylamido agmatine. The preferred use of the immobilines is for production of 2D gels.

  本发明涉及一种合成丙烯酰胺衍生物的方法，其以将亲核胺的盐在水中溶解形成水溶液，并用碱脱盐该溶液为起点，包括以下步骤：a)将溶解的活性丙烯酸衍生物加入该溶液中；b)酸化水相；c)提取该水相。在优选实施例中，丙烯酰胺衍生物是一种固定化物，优选为丙烯酰胺基的胍。所述固定化物的优选用途是用于2D凝胶的生产。