N-[2-[bis(carboxymethyl)amino]ethyl]-N-[2-(dodecylamino)-2-oxoethyl]glycine

• 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-[2-[bis(carboxymethyl)amino]ethyl]-N-[2-(dodecylamino)-2-oxoethyl]glycine
• 英文别名: 2-[2-[Bis(carboxymethyl)amino]ethyl-[2-(dodecylamino)-2-oxoethyl]amino]acetic acid；2-[2-[bis(carboxymethyl)amino]ethyl-[2-(dodecylamino)-2-oxoethyl]amino]acetic acid
• 化学式: C₂₂H₄₁N₃O₇
• 分子量: 459.583
• InChiKey: IBFJSFVYOJZWJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  32
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  十二烷基伯胺 、 乙二胺-N,N,N’,N’-四乙酸单酸酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以55%的产率得到N-[2-[bis(carboxymethyl)amino]ethyl]-N-[2-(dodecylamino)-2-oxoethyl]glycine
  参考文献：
  名称：

  Self-emulsifying drug delivery systems comprising chlorhexidine and alkyl-EDTA: A novel approach for augmented antimicrobial activity

  摘要：

  The aim of the study was to develop a self-emulsifying drug delivery systems (SEDDS) comprising chlorhexidine (CX) and monododecylamide-EDTA (alkyl-EDTA) exhibiting enhanced microbicidal properties. SEDDS containing 20% Captex 300, 45% Cremophor EL, 17% Tween 80 and 18% DMSO were loaded with 3% (m/v) alkyl-EDTA (F-A) and formulations of 1% CX and 1.5% (m/v) alkyl-EDTA (F-A-CX1% and F-A-ED1.5%) were prepared separately as well as in combination (F-A-CX1%ED1.5%). Resazurin assay was performed to assess the biocompatibility of SEDDS in concentrations of 0.5% and 1%. Alkyl-EDTA SEDDS were also evaluated for their binding affinity towards Ca2+ and Mg2+ as well as for augmented antimicrobial properties using E. coli as model germ. Biocompatibility assay of SEDDS revealed that >85% of cells remained viable after 4 h. SEDDS F-A efficiently bound 770 +/- 19 mu mol/g of calcium and 784 +/- 16 mu mol/g of magnesium, respectively. SEDDS F-A-CX1%ED1.5% showed a 343- and 12.9-fold enhanced antimicrobial effect compared to F-A-ED1.5% and FA-CX1%, respectively. The combination of CX with alkyl-EDTA in SEDDS seems therefore to be a promising strategy to enhance the antimicrobial activity of this antiseptic drug. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2019.111649

文献信息

• Self-emulsifying drug delivery systems comprising chlorhexidine and alkyl-EDTA: A novel approach for augmented antimicrobial activity
  作者：Aamir Jalil、Mulazim Hussain Asim、Zeynep Burcu Akkus、Martin Schoenthaler、Barbara Matuszczak、Andreas Bernkop-Schnürch

  DOI：10.1016/j.molliq.2019.111649

  日期：2019.12

  The aim of the study was to develop a self-emulsifying drug delivery systems (SEDDS) comprising chlorhexidine (CX) and monododecylamide-EDTA (alkyl-EDTA) exhibiting enhanced microbicidal properties. SEDDS containing 20% Captex 300, 45% Cremophor EL, 17% Tween 80 and 18% DMSO were loaded with 3% (m/v) alkyl-EDTA (F-A) and formulations of 1% CX and 1.5% (m/v) alkyl-EDTA (F-A-CX1% and F-A-ED1.5%) were prepared separately as well as in combination (F-A-CX1%ED1.5%). Resazurin assay was performed to assess the biocompatibility of SEDDS in concentrations of 0.5% and 1%. Alkyl-EDTA SEDDS were also evaluated for their binding affinity towards Ca2+ and Mg2+ as well as for augmented antimicrobial properties using E. coli as model germ. Biocompatibility assay of SEDDS revealed that >85% of cells remained viable after 4 h. SEDDS F-A efficiently bound 770 +/- 19 mu mol/g of calcium and 784 +/- 16 mu mol/g of magnesium, respectively. SEDDS F-A-CX1%ED1.5% showed a 343- and 12.9-fold enhanced antimicrobial effect compared to F-A-ED1.5% and FA-CX1%, respectively. The combination of CX with alkyl-EDTA in SEDDS seems therefore to be a promising strategy to enhance the antimicrobial activity of this antiseptic drug. (C) 2019 Elsevier B.V. All rights reserved.