1,3-propanediamine-N,N,N′-triacetic acid | 60972-23-8

• 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: 1,3-propanediamine-N,N,N′-triacetic acid
• 英文别名: 1,3-propanediamine-N,N,N’-triacetatic acid；Trimethylendiamin-N,N,N'-triessigsaeure；N-{3-[Bis(carboxymethyl)amino]propyl}glycine；2-[3-[bis(carboxymethyl)amino]propylamino]acetic acid
• CAS: 60972-23-8
• 化学式: C₉H₁₆N₂O₆
• 分子量: 248.236
• InChiKey: RMUGHYFYHCCULM-UHFFFAOYSA-N

物化性质

• 沸点：
  529.0±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  rhodium(III) chloride trihydrate 、 1,3-propanediamine-N,N,N′-triacetic acid 以12.43%的产率得到cis-Polar-[Rh(1,3-pd3a)(H₂O)].2H₂O
  参考文献：
  名称：

  Rhodium(III) in a cage of the 1,3-propanediamine-N,N,N′-triacetate chelate: X-ray structure, solution equilibria, computational study and biological behavior

  摘要：

  Two new octahedral Rh(Ill) complexes that are potential chemotherapeutic agents have been synthesized from the 1,3-propanediamine-N,N,N'-triacetate ligand (1,3-pd3a): [Rh(1,3-pd3a)(H2O)1.2H(2)O (1) and Na [Rh(1,3-pd3a)Cl]center dot 2H(2)O (2). Both complexes were characterized by IR, UV-Vis and NMR spectroscopy, as well as elemental analysis. Only the structure of 2 was determined by a single crystal X-ray diffraction study. The asymmetric unit contains the negatively charged rhodium complex, a sodium ion and two water molecules. The positions of the carboxylate groups define the cis-polar geometry. DFT calculations on 1 and 2 have also been done to confirm experimental results. In order to determine the protonation constants of 1,3-H3pd3a, stability constants and the stoichiometry of the complexes in aqueous solution, pH-potentiometry and UV-Vis spectrophotometry were used. Docking of 1 to human serum albumin (HSA) gives the reasonable assumption that this complex can be easily transported to the target cells. The complexes, as well as the 1,3-pd3a and ed3a ligands, were tested against various cancer and one normal human cell lines. Complex 2 and both ligands display significant cytotoxicity against the HeLa cancer cell line, while 1 shows good antitumor activity against MCF-7. Flow cytometry analysis showed the apoptotic death of the cells with cell cycle arrest in the G2/M phase (Na[Rh(1,3-pd3a)CI]center dot 2H(2)O) and GO/G1 phase (1,3-pd3a). (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.08.075
• 作为产物：
  描述：

  1,3-丙二胺 、 氯乙酸 在 calcium oxide 作用下， 以 水 为溶剂， 反应 6.5h， 生成 1,3-丙二胺四乙酸 、 1,3-二氨基丙烷-N,N'-二乙酸 、 1,3-propanediamine-N,N,N′-triacetic acid
  参考文献：
  名称：

  具有五齿1,3-pd3a型配体的镍（II）配合物的晶体结构，构型和密度泛函理论分析

  摘要：

  OONNO型五齿配体H（3）1,3-pd3a和H（3）1,3-pd2ap（H（3）1,3-pd3a代表1,3-丙二胺-N，N，N'-三乙酸； H（3）1,3-pd2ap代表1,3-丙二胺-N，N'-二烯丙基-N-3-丙酸），并已制备并表征了相应的新型八面体镍（II）配合物。H（3）1,3-pd3a和H（3）1,3-pd2ap配体通过五个供体原子（三个去质子化的羧酸根原子和两个胺氮）与镍（II）离子配位，在所有研究的Ni情况下均提供八面体几何形状（二）配合物。八面体中的第六位已被水分子占据。晶体学上已为K [Ni（1,3-pd3a）（H2O）]中心点3H（2）O络合物建立了六坐标八面体几何形状。与相似的螯合镍（II）配合物相关的结构数据已用于广泛的应变分析。关于针对类似复合物获得的信息进行讨论。解释了配合物的红外和电子吸收光谱，并将其与已知几何形状的相关配合物进行了比较。密度泛函理论（DFT

  DOI：

  10.1016/j.ica.2013.01.014

文献信息

• Crystal structure, configurational and density functional theory analysis of nickel(II) complexes with pentadentate 1,3-pd3a-type ligands
  作者：Svetlana Belošević、Marina Ćendić、Maja Djukić、Miorad Vasojević、Auke Meetsma、Zoran D. Matović

  DOI：10.1016/j.ica.2013.01.014

  日期：2013.4

  obtained for similar complexes. The infra-red and electronic absorption spectra of the complexes are interpreted and compared with related complexes of known geometries. Density functional theory (DFT) has been used to model the most stable geometry isomer and Natural Energy Decomposition Analysis (NEDA) to reveal the energetic relationship of these compounds. The results from density functional studies

  OONNO型五齿配体H（3）1,3-pd3a和H（3）1,3-pd2ap（H（3）1,3-pd3a代表1,3-丙二胺-N，N，N'-三乙酸； H（3）1,3-pd2ap代表1,3-丙二胺-N，N'-二烯丙基-N-3-丙酸），并已制备并表征了相应的新型八面体镍（II）配合物。H（3）1,3-pd3a和H（3）1,3-pd2ap配体通过五个供体原子（三个去质子化的羧酸根原子和两个胺氮）与镍（II）离子配位，在所有研究的Ni情况下均提供八面体几何形状（二）配合物。八面体中的第六位已被水分子占据。晶体学上已为K [Ni（1,3-pd3a）（H2O）]中心点3H（2）O络合物建立了六坐标八面体几何形状。与相似的螯合镍（II）配合物相关的结构数据已用于广泛的应变分析。关于针对类似复合物获得的信息进行讨论。解释了配合物的红外和电子吸收光谱，并将其与已知几何形状的相关配合物进行了比较。密度泛函理论（DFT
• Rhodium(III) in a cage of the 1,3-propanediamine-N,N,N′-triacetate chelate: X-ray structure, solution equilibria, computational study and biological behavior
  作者：Marija S. Jeremić、Marko D. Radovanović、Franco Bisceglie、Vesna V. Kojić、Ratomir Jelić、Zoran D. Matović

  DOI：10.1016/j.poly.2018.08.075

  日期：2018.12

  Two new octahedral Rh(Ill) complexes that are potential chemotherapeutic agents have been synthesized from the 1,3-propanediamine-N,N,N'-triacetate ligand (1,3-pd3a): [Rh(1,3-pd3a)(H2O)1.2H(2)O (1) and Na [Rh(1,3-pd3a)Cl]center dot 2H(2)O (2). Both complexes were characterized by IR, UV-Vis and NMR spectroscopy, as well as elemental analysis. Only the structure of 2 was determined by a single crystal X-ray diffraction study. The asymmetric unit contains the negatively charged rhodium complex, a sodium ion and two water molecules. The positions of the carboxylate groups define the cis-polar geometry. DFT calculations on 1 and 2 have also been done to confirm experimental results. In order to determine the protonation constants of 1,3-H3pd3a, stability constants and the stoichiometry of the complexes in aqueous solution, pH-potentiometry and UV-Vis spectrophotometry were used. Docking of 1 to human serum albumin (HSA) gives the reasonable assumption that this complex can be easily transported to the target cells. The complexes, as well as the 1,3-pd3a and ed3a ligands, were tested against various cancer and one normal human cell lines. Complex 2 and both ligands display significant cytotoxicity against the HeLa cancer cell line, while 1 shows good antitumor activity against MCF-7. Flow cytometry analysis showed the apoptotic death of the cells with cell cycle arrest in the G2/M phase (Na[Rh(1,3-pd3a)CI]center dot 2H(2)O) and GO/G1 phase (1,3-pd3a). (C) 2018 Elsevier Ltd. All rights reserved.