N-(4-amino-2-methoxyphenyl)-N',N'-[bis(2-pyridylmethyl)]ethylenediamine | 1041403-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-amino-2-methoxyphenyl)-N',N'-[bis(2-pyridylmethyl)]ethylenediamine
• 英文别名: 4-amino-2-methoxy-N-{2-[N',N'-bis(2-picolyl)]amino}ethylaniline；1-N-[2-[bis(pyridin-2-ylmethyl)amino]ethyl]-2-methoxybenzene-1,4-diamine
• CAS: 1041403-05-7
• 化学式: C₂₁H₂₅N₅O
• 分子量: 363.462
• InChiKey: GIOWAKQEEUHDQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-amino-2-methoxyphenyl)-N',N'-[bis(2-pyridylmethyl)]ethylenediamine 、 N-(6-(5-hydroxybenzo[d]oxazol-2-yl)naphthalen-2-yl)-N-methylglycine 在 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.17h， 以37%的产率得到N-(4-((2-(bis(pyridin-2-ylmethyl)amino)ethyl)amino)-3-methoxyphenyl)-2-((6-(5-hydroxybenzo[d]oxazol-2-yl)naphthalen-2-yl)(methyl)amino)acetamide
  参考文献：
  名称：

  使用双光子荧光探针对活组织中的胞质和线粒体锌离子进行双色成像†

  摘要：

  我们报告了Zn 2+离子的双光子探针，该探针可通过双色TPM成像同时检测活细胞和活组织中115毫米深度的细胞质和线粒体Zn 2+离子，而对其他生物学相关物种的干扰最小。

  DOI：

  10.1039/c4ob00101j
• 作为产物：
  描述：

  N-(2-methoxy-4-nitrophenyl)-N',N'-[bis(2-pyridylmethyl)]ethylenediamine 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 以80%的产率得到N-(4-amino-2-methoxyphenyl)-N',N'-[bis(2-pyridylmethyl)]ethylenediamine
  参考文献：
  名称：

  双光子荧光探针可检测活组织中的细胞内游离锌离子。

  摘要：

  DOI：

  10.1002/anie.200800929

文献信息

• Method for imaging zinc activation within a mitochondrion using a two-photon fluorescent probe, and method for manufacturing the two-photon fluorescent probe
  申请人：Kim Hwan Myung

  公开号：US09006452B2

  公开（公告）日：2015-04-14

  Provided is a two-photon fluorescent probe, and more particularly, a two-photon fluorescent probe which is one or more selected from compounds represented by Formulae 1 and 2, a method for manufacturing the same, and an imaging method of zinc ions within the mitochondrion using the same. Since two probes are introduced into one molecule, the two-photon fluorescent probe of the present invention can selectively dye the mitochondria, simultaneously with reacting with zinc ions, thereby generating intense fluorescence. Thus, the two-photon fluorescent probe of the present invention can be used for the imaging of zinc ion distribution and activation within the mitochondrion in living cells or intact biological tissues.

  本发明提供了一种双光子荧光探针，更具体地说，提供了一种由式1和式2所表示的化合物中选择一个或多个的双光子荧光探针、其制造方法以及使用该探针进行线粒体内锌离子成像的方法。由于将两个探针引入到一个分子中，本发明的双光子荧光探针可以选择性地染色线粒体，并与锌离子反应，从而产生强烈的荧光。因此，本发明的双光子荧光探针可用于活细胞或完整生物组织中线粒体内锌离子分布和激活的成像。
• A diketopyrrolopyrrole-based fluorescent probe for investigating mitochondrial zinc ions
  作者：Chenchen Du、Shibo Fu、Xiaolei Ren、Xiaohua Wang、Zhong Wang、Juan Zhou、Hongyu Wang

  DOI：10.1039/c7nj04940d

  日期：——

  DPP fluorophore. Upon an addition of Zn2+, the fluorescence intensities of both probes increased approximately 77-fold. Both probes exhibited a high binding constant, pH insensitivity, and high metal ion selectivity. The HeLa cell fluorescence imaging studies demonstrated that both probes were low toxicity and could monitor the changes in the intracellular Zn2+ concentrations. The confocal microscopic

  我们证明了在二酮吡咯并吡咯（DPP）荧光团的两个内酰胺部分的N-位上不对称地引入Zn 2+螯合剂（MeO-DPEN）和线粒体靶向基团（TPP）的策略。并报道了两种探针DPP-Mito和DPP-C2用于比较研究。由于从MeO-DPEN到DPP荧光团的光诱导电子转移（PET）过程，两种探针都显示出几乎无荧光。添加Zn 2+后，两种探针的荧光强度增加了约77倍。两种探针均显示出高结合常数，pH不敏感性和高金属离子选择性。HeLa细胞荧光成像研究表明，这两种探针均具有低毒性，并且可以监测细胞内Zn 2+浓度的变化。共聚焦显微镜研究表明，DPP-Mito专门定位于线粒体，而DPP-C2不是细胞器特异性的。
• A highly sensitive two-photon fluorescent probe for mitochondrial zinc ions in living tissue
  作者：Na Young Baek、Cheol Ho Heo、Chang Su Lim、Goutam Masanta、Bong Rae Cho、Hwan Myung Kim

  DOI：10.1039/c2cc31077e

  日期：——

  We report a highly sensitive two-photon probe (SZn2-Mito) which shows a 70-fold two-photon excited fluorescence enhancement in response to Zn(2+) and can selectively detect mitochondrial Zn(2+) in a rat hippocampal slice at a depth of 100-200 mum by using two-photon microscopy.

  我们报告了一个高灵敏度的双光子探针（SZn2-Mito），该探针显示响应Zn（2+）的70倍双光子激发的荧光增强，并可以在大鼠海马切片中选择性检测线粒体Zn（2+），通过使用双光子显微镜，可以观察到100-200微米的深度。
• Two-photon probe for real-time monitoring of intracellular free zinc ions, method for preparing the probe and method for real-time monitoring of intracellular free zinc ions using the probe
  申请人：Cho Bong-Rae

  公开号：US20090286275A1

  公开（公告）日：2009-11-19

  A two-photon probe for real-time monitoring of intracellular free zinc ions is provided. The two-photon probe is represented by Formula 1: wherein R is H or OCH 3 . The two-photon probe has high selectivity for Zn 2+ and enables very effective and long-term monitoring of intracellular free Zn 2+ present in the deep tissue. Further provided are a method for preparing the two-photon probe and a method for real-time monitoring of intracellular free zinc ions using the two-photon probe.

  提供了一种用于实时监测细胞内游离锌离子的双光子探针。该双光子探针由公式1表示：其中R为H或OCH3。该双光子探针具有高选择性的Zn2+，并能够非常有效和长期地监测深层组织中存在的细胞内自由Zn2+。还提供了制备双光子探针的方法和使用双光子探针实时监测细胞内游离锌离子的方法。
• Method for Imaging Zinc Activation within a Mitochondrion Using a Two-Photon Fluorescent Probe, and Method for Manufacturing the Two-Photon Fluorescent Probe
  申请人：Kim Hwan Myung

  公开号：US20130295599A1

  公开（公告）日：2013-11-07

  Provided is a two-photon fluorescent probe, and more particularly, a two-photon fluorescent probe which is one or more selected from compounds represented by Formulae 1 and 2, a method for manufacturing the same, and an imaging method of zinc ions within the mitochondrion using the same. Since two probes are introduced into one molecule, the two-photon fluorescent probe of the present invention can selectively dye the mitochondria, simultaneously with reacting with zinc ions, thereby generating intense fluorescence. Thus, the two-photon fluorescent probe of the present invention can be used for the imaging of zinc ion distribution and activation within the mitochondrion in living cells or intact biological tissues.