2,2'-(ethane-1,2-diylbis(methylazanediyl))diacetic acid | 6636-72-2

• 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: 2,2'-(ethane-1,2-diylbis(methylazanediyl))diacetic acid
• 英文别名: N,N'-dimethyl ethylenediamine-N,N'-diacetic acid；NN'-dimethylenediamine-NN'-diacetic acid；2,5-diazahexane-N,N'-diacetic acid；N,N'-dimethyl-N,N'-ethanediyl-bis-glycine；N,N'-Bis-carboxymethyl-N,N'-dimethyl-aethylendiamin；N,N'-Dimethyl-N,N'-aethandiyl-bis-glycin；((2-((Carboxymethyl)(methyl)amino)ethyl)(methyl)amino)acetic acid；2-[2-[carboxymethyl(methyl)amino]ethyl-methylamino]acetic acid
• CAS: 6636-72-2
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: AVHSSMVTBDPMIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-(ethane-1,2-diylbis(methylazanediyl))diacetic acid 在 亚磷酸 、 三氯化磷 作用下， 以 氯仿 、 氯苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and cytotoxicity of N,N′-dibisphosphonate ethylenediamine derivatives and platinum(II) complexes with high binding property to hydroxyapatite

  摘要：

  A series of N,N '-dibisphosphonate ethylenediamine derivatives (L1-L6) and their corresponding dichloroplatinum(II) complexes (1-6) have been prepared and characterized by elemental analysis, H-1 NMR, C-13 NMR, P-31 NMR, and HRMS spectra. The in vitro antitumor of compounds L1-L6 and 1-6 was tested by WST-8 assay with Cell Counting Kit-8, indicating that platinum-based complexes 1-6 showed higher cytotoxic efficacy than platinum-free compounds L1-L6 against SKOV3 and MG-63, especially complex 2 (R = CH3, n = 2) with comparable cytotoxicity to cisplatin after 72 h incubation. And complexes 1-6 were highly selective in cytotoxicity against MG-63 tumor cells than hFOB 1.19 normal cells. The in vitro hydroxyapatite binding test revealed that complexes 1 and 2 showed higher affinity (K ' = 4.2 and 3.5, respectively) for bone hydroxyapatite than cisplatin (K ' < 0.1) and zoledronate (K ' = 2.8). On basis of flow cytometry results, complex 2 induced cell death by apoptosis effect similar to cisplatin, different from zoledronate. Representative complex 2 has been proved to be a promising bone-targeting antitumor agent for subsequent in vivo study. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.12.006
• 作为产物：
  描述：

  氯乙酸 、 N,N'-二甲基乙二胺 在 aluminum trihydroxide 作用下， 生成 2,2'-(ethane-1,2-diylbis(methylazanediyl))diacetic acid
  参考文献：
  名称：

  Synthesis and cytotoxicity of N,N′-dibisphosphonate ethylenediamine derivatives and platinum(II) complexes with high binding property to hydroxyapatite

  摘要：

  A series of N,N '-dibisphosphonate ethylenediamine derivatives (L1-L6) and their corresponding dichloroplatinum(II) complexes (1-6) have been prepared and characterized by elemental analysis, H-1 NMR, C-13 NMR, P-31 NMR, and HRMS spectra. The in vitro antitumor of compounds L1-L6 and 1-6 was tested by WST-8 assay with Cell Counting Kit-8, indicating that platinum-based complexes 1-6 showed higher cytotoxic efficacy than platinum-free compounds L1-L6 against SKOV3 and MG-63, especially complex 2 (R = CH3, n = 2) with comparable cytotoxicity to cisplatin after 72 h incubation. And complexes 1-6 were highly selective in cytotoxicity against MG-63 tumor cells than hFOB 1.19 normal cells. The in vitro hydroxyapatite binding test revealed that complexes 1 and 2 showed higher affinity (K ' = 4.2 and 3.5, respectively) for bone hydroxyapatite than cisplatin (K ' < 0.1) and zoledronate (K ' = 2.8). On basis of flow cytometry results, complex 2 induced cell death by apoptosis effect similar to cisplatin, different from zoledronate. Representative complex 2 has been proved to be a promising bone-targeting antitumor agent for subsequent in vivo study. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.12.006

文献信息

• Studies of iron(ii) and iron(iii) complexes with fac-N2O, cis-N2O2 and N2O3 donor ligands: models for the 2-His 1-carboxylate motif of non-heme iron monooxygenases
  作者：Patrick J. Cappillino、John R. Miecznikowski、Laurie A. Tyler、Paul C. Tarves、Joshua S. McNally、Wayne Lo、Bala Sundari T. Kasibhatla、Matthew D. Krzyaniak、John McCracken、Feng Wang、William H. Armstrong、John P. Caradonna

  DOI：10.1039/c2dt11096b

  日期：——

  in the oxygen-activating class of mononuclear non-heme iron oxygenases (MNOs) contain a highly conserved iron center facially ligated by two histidine nitrogen atoms and one carboxylate oxygen atom that leave one face of the metal center (three binding sites) open for coordination to cofactor, substrate, and/or dioxygen. A comparative family of [FeII/III(N2On)(L)4−n)]±x, n = 1–3, L = solvent or Cl−

  单核非血红素铁氧合酶（MNOs）的氧激活类别中的酶包含高度保守的铁中心，其表面被两个人连接 组氨酸离开金属中心一个表面（三个结合位点）的氮原子和一个羧基氧原子开放，以与辅因子，底物和/或双氧进行配位。的的[Fe比较家族II / III（N 2 ö Ñ）（L）4- Ñ）] ± X，Ñ = 1-3，L =溶剂或Cl - ，模型复合物，基于配位体系列，支持经表面连接的N，N，O核，然后经过修饰以包含一个或两个附加的羧酸盐螯合臂，已在结构和光谱上得到了表征。EPR研究表明，高转速d 5Fe III g = 4.3信号随着整个系列Fe（N 2 O 3），Fe（N 2 O 2）和Fe（N 2 O 1）上羧酸盐配体数量的减少而变得更加对称，反映了E的增加随着可交换/溶剂配位点数量的增加，这些络合物的/ D应变增加，这与有助于谱线形状的电子结构分布的增强平行。Fe II -Fe III中观察到的系统变化氧
• Resin composition comprising water-soluble polyamide and vinyl alcohol-based polymer
  申请人：UNITIKA LTD.

  公开号：EP0039226A2

  公开（公告）日：1981-11-04

  A resin composition is described consisting essentially of from 0.5 to 100 parts by weight of a water-soluble polyamide and from 0.5 to 100 parts by weight of a vinyl alcohol-based polymer. The resin composition has excellent transparency and can be used, for example, to form light-sensitive resin compositions and adhesives.

  所述树脂组合物主要由 0.5 至 100 重量份的水溶性聚酰胺和 0.5 至 100 重量份的乙烯醇基聚合物组成。 该树脂组合物具有极佳的透明度，可用于制造光敏树脂组合物和粘合剂等。
• Use of n,n' -dibenzyl ethylene diamine-n, n'- diacetic acid derivatives as anti-pollution agent
  申请人：——

  公开号：US20040039059A1

  公开（公告）日：2004-02-26

  The invention concerns the use for topical application of at least a N,N′-dibenzyl ethylene diamine N,N′-acetic acid derivative or salt, a metal complex or an ester of such a derivative as anti-pollution agent, preferably as cosmetic anti-pollution agent.

  本发明涉及至少一种 N,N′-二苄基乙二胺 N,N′-乙酸衍生物或盐、金属络合物或此类衍生物的酯作为抗污染剂，最好是作为化妆品抗污染剂局部使用。
• Metal-ion complexation in aqueous solutions of 1 - thia-4,7-diazacyclononane-, 1-thia-4,8-diazacyclodecane and 2,5-diazahexane-N,N′-diacetic acid
  作者：Dorine M. Wambeke、Werner Lippens、Gerrit G. Herman、André M. Goeminne

  DOI：10.1039/dt9930002017

  日期：——

  The stability constants of the macrocyclic 1 -thia-4,7-diazacyclononane- and 1-thia-4,8-diazacyclodecane-N,N'-diacetic acid (H-2L1 and H-2L2) and of the open-chain 2,5-diazahexane-N,N'-diacetic acid (H-2L3) with Mg(II), Ca(II), Sr(II), Ba(II), Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Pb(II) and La(III) have been determined in aqueous solution (25-degrees-C, 0.1 mol dm-3 KNO3) by pH potentiometry, and in some cases in combination with visible absorption spectrophotometry. The complexation enthalpies with Cu(II) have been determined by adiabatic calorimetry. The electronic absorption spectra of the complexes of Cu(II) and Ni(II) were also recorded. All metal-ion complexes with H-2L1 are stronger than with H-2L3, even for the harder metal ions. The presence of the thioether donor particularly enhances covalent bonding with Cu(II) as indicated by a higher heat of complexation, a more favourable entropy change and a stronger ligand-field strength. The change in stability of the complexes upon replacing H-2L1 with a five-membered chelate ring between the metal ion and the two tertiary nitrogens, by H-2L2 having a six-membered one, is dependent on the metal-ion size. The larger metal ions are destabilised relative to the small metal ions: the metal ion size-based selectivity for this pair of ligands is controlled by the chelate-ring size. Binding of Cu(II) by H-2L2 is sterically much more efficient than by H-2L1 and is evidenced by a higher heat of complexation and a stronger ligand field.
• AGENTS CHELATANTS D'IONS METALLIQUES, LEURS PROCEDES DE PREPARATION ET LEURS APPLICATIONS
  申请人：COMMISSARIAT À L'ÉNERGIE ATOMIQUE ET AUX ÉNERGIES ALTERNATIVES

  公开号：EP2982669B1

  公开（公告）日：2017-05-10