methyl 4-((4-(bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)amino)phenyl)ethynyl)-6-(((methylsulfonyl)oxy)methyl)picolinate | 1393108-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 4-((4-(bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)amino)phenyl)ethynyl)-6-(((methylsulfonyl)oxy)methyl)picolinate
• 英文别名: methyl 4-[4-ethynyl-N,N-bis(3,6,9-trioxodecyl)aniline]-6-[(methylsulfonyloxy)methyl]-2-picolinate；Methyl 4-[2-[4-[bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]amino]phenyl]ethynyl]-6-(methylsulfonyloxymethyl)pyridine-2-carboxylate
• CAS: 1393108-60-5
• 化学式: C₃₁H₄₄N₂O₁₁S
• 分子量: 652.763
• InChiKey: XUHLEZOFGIHMQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  45
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 4-((4-(bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)amino)phenyl)ethynyl)-6-(((methylsulfonyl)oxy)methyl)picolinate 、 methyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-3-acetate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以22%的产率得到dimethyl 6,6‘-((9-(2-methoxy-2-oxoethyl)-3,6,9-triaza-1(2,6)-pyridinacyclodecaphane-3,6-diyl)bis(methylene))bis (4-((4-(bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)amino)phenyl)ethynyl)picolinate)
  参考文献：
  名称：

  [EN] PYCLEN-BASED MACROCYCLIC LIGANDS, CHELATES THEREOF AND USES THEREOF
  [FR] LIGANDS MACROCYCLIQUES À BASE DE PYCLEN, LEURS CHÉLATES ET LEURS UTILISATIONS

  摘要：

  本发明涉及化合物配体的公式（A）：或其羧酸盐；其中Y1、Y2和Y3分别独立地代表-COOH或公式（i）的吡啶酸盐，其中每个R1独立地代表一个色团基团；L1、L2和L3分别独立地代表一个单键或一个连接基团；X1、X2和X3分别独立地代表氢原子、偶联功能或生物矢量化基团。本发明还涉及一种制备该配体的方法，以及通过该配体与稀土阳离子，优选为镧系阳离子，形成络合物的方法。本发明还涉及该配体和/或络合物在生物成像和/或光致发光成像中的应用。

  公开号：

  WO2019185901A1
• 作为产物：
  描述：

  C₃₀H₄₂N₂O₉ 、 甲基磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到methyl 4-((4-(bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)amino)phenyl)ethynyl)-6-(((methylsulfonyl)oxy)methyl)picolinate
  参考文献：
  名称：

  Ytterbium-Based Bioprobes for Near-Infrared Two-Photon Scanning Laser Microscopy Imaging

  摘要：

  DOI：

  10.1002/anie.201202212

文献信息

• Picolinate-appended tacn complexes for bimodal imaging: Radiolabeling, relaxivity, photophysical and electrochemical studies
  作者：Amaury Guillou、Margaux Galland、Amandine Roux、Balázs Váradi、Réka Anna Gogolák、Patricia Le Saëc、Alain Faivre-Chauvet、Maryline Beyler、Christophe Bucher、Gyula Tircsó、Véronique Patinec、Olivier Maury、Raphaël Tripier

  DOI：10.1016/j.jinorgbio.2019.110978

  日期：2020.4

  spectrocopies. While the zinc complex formed with HL1 possesses a moderate quantum yield of 5%, complexation of Cu2+ led to an extinction of the luminescence putatively attributed to a photo-induced electron transfer, as supported by spectroscopic and electrochemical evidences. The [Mn(L2)]+ complex is characterized by a fluorescence quantum yield close to 8% in CH2Cl2. The potential interest of such systems

  基于我们之前的工作，涉及两个基于1,4,7-三氮杂壬烷（tacn）的配体Hno2py1pa（1-吡啶甲酸-4,7-双（吡啶-2-基甲基）-1,4,7-三氮杂壬烷）和Hno1pa （1-Picolinic acid-1,4,7-triazacyclononane），我们在这里报告使用区域特异性N-官能化合成带有基于吡啶甲酸的π共轭ILCT（配体内电荷转移）过渡天线（HL1，HL2）的类似物Tacn骨架及其相关的过渡金属配合物（例如Cu2 +，Zn2 +和Mn2 +）的结构。研究了配位性质以及它们的光物理和电化学性质，以便量化这种天线对配合物的发光或弛豫性质的影响。使用UV-Vis吸收和荧光光谱学研究了目标配体和金属络合物的光谱性质。虽然由HL1形成的锌络合物具有5％的适度量子产率，但光谱和电化学证据支持，Cu2 +的络合物导致归因于光诱导电子转移的发光消失。[Mn（L2）] +络合物的特征是
• Near infrared two photon imaging using a bright cationic Yb(<scp>iii</scp>) bioprobe spontaneously internalized into live cells
  作者：Anh Thy Bui、Maryline Beyler、Alexei Grichine、Alain Duperray、Jean-Christophe Mulatier、Yannick Guyot、Chantal Andraud、Raphaël Tripier、Sophie Brasselet、Olivier Maury

  DOI：10.1039/c7cc02835k

  日期：——

  An Yb(III) complex based on a dimethyl cyclen macrocyclic ligand functionalized by charge transfer antennae was prepared. This cationic [YbL3]+ complex is stable and soluble in water and presents interesting photophysical nonlinear properties. It is spontaneously internalized and accumulates in live cells. High quality images have been obtained both in a classical NIR-to-vis configuration and in the

  制备了一种Yb（III）配合物，该配合物基于通过电荷转移天线功能化的二甲基环化大环配体。该阳离子[Yb L 3 ] +络合物稳定且可溶于水，并表现出令人感兴趣的光物理非线性特性。它是自发内在化并在活细胞中积累。在经典的近红外到近视配置和更具挑战性的近红外到近红外配置中，均获得了高质量的图像。
• Pyclen-Based Ln(III) Complexes as Highly Luminescent Bioprobes for <i>In Vitro</i> and <i>In Vivo</i> One- and Two-Photon Bioimaging Applications
  作者：Nadège Hamon、Amandine Roux、Maryline Beyler、Jean-Christophe Mulatier、Chantal Andraud、Christophe Nguyen、Marie Maynadier、Nadir Bettache、Alain Duperray、Alexei Grichine、Sophie Brasselet、Magali Gary-Bobo、Olivier Maury、Raphaël Tripier

  DOI：10.1021/jacs.0c03496

  日期：2020.6.3

  In addition to the already described ligand L-4a, two pyclen-based lanthanide chelators, L-4b and L-4c, bearing two specific picolinate two-photon antennas (tailor-made for each targeted metal) and one acetate arm arranged in a dissymmetrical manner, have been synthesized, to form a complete family of lanthanide luminescent bioprobes: [EuL4a], [SmL4a], [YbL4b], [TbL4c], and [DyL4c]. Additionally, the symmetrically arranged regioisomer L-4a' was also synthesized as well as its [EuL4a'] complex to highlight the astonishing positive impact of the dissymmetrical N-distribution of the functional chelating arms. The investigation clearly shows the high performance of each bioprobe, which, depending on the complexed lanthanide, could be used in various applications. Each presents high brightness, quantum yields, and lifetimes. Staining of the complexes into living human breast cancer cells was observed. In addition, in vivo two-photon microscopy was performed for the first time on a living zebrafish model with [EuL4a]. No apparent toxicity was detected on the growth of the zebrafish, and images of high quality were obtained.
• PYCLEN-BASED MACROCYCLIC LIGANDS, CHELATES THEREOF AND USES THEREOF
  申请人：Centre national de la recherche scientifique

  公开号：EP3774803A1

  公开（公告）日：2021-02-17