γ-(N^γ-hexadecanoylamino)butyric acid succinimidyl ester | 240133-34-0

• 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
• 英文名称: γ-(N^γ-hexadecanoylamino)butyric acid succinimidyl ester
• 英文别名: N-{4-[(2,5-Dioxopyrrolidin-1-yl)oxy]-4-oxobutyl}hexadecanamide；(2,5-dioxopyrrolidin-1-yl) 4-(hexadecanoylamino)butanoate
• CAS: 240133-34-0
• 化学式: C₂₄H₄₂N₂O₅
• 分子量: 438.608
• InChiKey: VYBSJVVAXLPOFS-UHFFFAOYSA-N

物化性质

• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  棕榈酸 N-羟基琥珀酰亚胺酯 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 γ-(N^γ-hexadecanoylamino)butyric acid succinimidyl ester
  参考文献：
  名称：

  Potent Derivatives of Glucagon-like Peptide-1 with Pharmacokinetic Properties Suitable for Once Daily Administration

  摘要：

  A series of very potent derivatives of the 30-amino acid peptide hormone glucagon-like peptide-1 (GLP-1) is described. The compounds were all derivatized with fatty acids in order to protract their action by facilitating binding to serum albumin. GLP-1 had a potency (EC50 of 55 pM for the cloned human GLP-1 receptor. Many of the compounds had similar or even higher potencies, despite quite large substituents. All compounds derivatized with fatty acids equal to or longer than 12 carbon atoms were very protracted compared to GLP-1 and thus seem suitable for once daily administration to type 2 diabetic patients. A structure-activity relationship was obtained. GLP-1 could be derivatized with linear fatty acids up to the length of 16 carbon atoms, sometimes longer, almost anywhere in the C-terminal part without considerable loss of potency. Derivatization with two fatty acid substituents led to a considerable loss of potency. A structure-activity relationship on derivatization of specific amino acids generally was obtained. It was found that the longer the fatty acid, the more potency was lost. Simultaneous modification of the N-terminus tin order to obtain better metabolic stability) interfered with fatty acid derivatization and led to loss of potency.

  DOI：

  10.1021/jm9909645

文献信息

• GLP-2 compounds, formulations, and uses thereof
  申请人：——

  公开号：US20040122210A1

  公开（公告）日：2004-06-24

  The present invention relates to novel human glucagon-like peptide-2 (GLP-2) peptides and human glucagon-like peptide-2 derivatives which have a protracted profile of action as well as polynucleotide constructs encoding such peptides, vectors and host cells comprising and expressing the polynucleotide, pharmaceutical compositions, uses and methods of treatment.

  本发明涉及新型人类胰高血糖素样肽-2（GLP-2）肽和具有持久作用特性的人类胰高血糖素样肽-2衍生物，以及编码这些肽的多核苷酸构建物、包含和表达该多核苷酸的载体和宿主细胞、制药组合物、用途和治疗方法。
• NOVEL GLP-1 ANALOGUES
  申请人：Sun Pharmaceutical Industries Limited

  公开号：EP3774862B1

  公开（公告）日：2022-06-08
• Derivatives of GLP-1 analogs
  申请人：Knudsen Bjerre Liselotte

  公开号：US20060199763A1

  公开（公告）日：2006-09-07

  The present invention relates to a pharmaceutical composition comprising a GLP-1 derivative having a lipophilic substituent; and a surfactant.
• US7411039B2
  申请人：——

  公开号：US7411039B2

  公开（公告）日：2008-08-12
• [EN] NOVEL GLP-1 ANALOGUES<br/>[FR] NOUVEAUX ANALOGUES DE GLP-1
  申请人：SUN PHARMACEUTICAL IND LTD

  公开号：WO2019193576A1

  公开（公告）日：2019-10-10

  The present disclosure pertains to novel Glucagon like Peptide-1 (GLP-1) (7-37) analogs having an amino acid sequence with Leu or Ile at the C-terminal. The new analogs are potent GLP-1 agonists with reduced adverse effect and improved duration of action. The present disclosure further relates to acylated derivatives of the new analogs which have further improved potency and duration of action and are suitable for oral administration. The analogs of present disclosure may be useful in treatment of diabetes and obesity.