| 906093-12-7

• CAS: 906093-12-7
• 化学式: Br*C₃H₆O₆Tc
• 分子量: 316.981
• InChiKey: SDXAVHIRMDDCQI-MXGYIUITSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (4-((2-aminoethyl)(2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)amino)butyl)triphenylphosphonium trifluoroacetate 、 以 水 为溶剂， 反应 0.5h， 以95%的产率得到
  参考文献：
  名称：

  Mono- and dicationic Re(I)/99mTc(I) tricarbonyl complexes for the targeting of energized mitochondria

  摘要：

  The enhanced negative mitochondrial membrane potential of tumor cells can increase the cell accumulation of triphenylphosphonium (TPP) derivatives, which prompted us to investigate TPP-containing Re(I)/Tc-99m organometallic compounds as probes for in vivo targeting of energized mitochondria. Novel compounds (Re1-Re4/Tc1-Tc4) were obtained with bifunctional chelators of the pyrazole-diamine (N,N,N-donors) and pyrazole-aminocarboxylic (N,N,O-donors) type, functionalized with TPP pharmacophores that have been introduced at the central amine of the chelators using different spacers. In this way, dicationic (Re1-Re2, Tc1-Tc2) and monocationic (Re3-Re4, Tc3-Tc4) complexes with variable lipophilicity were synthesized. The Tc-99m complexes (Tc1-Tc4) are highly stable under physiological conditions and their chemical identification was done by HPLC comparison with the Re congeners (Re1-Re4), which were fully characterized by common analytical techniques (electrospray ionization mass spectrometry (ESI-MS), IR, multinuclear NMR). The in vitro biological evaluation of Tc1-Tc4 was performed in a panel of human tumor cell lines (PC-3, MCF-7 and H69), including cell lines overexpressing P-glycoprotein (MCF-7/MDR1 and H69/Lx4), and in isolated mitochondria. All the tested complexes showed a low to moderate cellular and mitochondrial uptake and did not undergo significant P-glycoprotein (Pgp)-mediated efflux processes. In particular, the dication Tc2 and the monocation Tc4 presented the highest cellular and mitochondrial uptake. Their cellular uptake was shown to depend on the mitochondrial (Delta psi(m)) and plasma membrane (Delta psi(p)) potentials. Altogether, the biological properties of these compounds suggest that they might be relevant for the design of radioactive metalloprobes for in vivo targeting of mitochondria. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2013.02.008

文献信息

• Isostructural Re(<scp>i</scp>)/^99mTc(<scp>i</scp>) tricarbonyl complexes for cancer theranostics
  作者：Patrique Nunes、Goreti Ribeiro Morais、Elisa Palma、Francisco Silva、Maria Cristina Oliveira、Vera F. C. Ferreira、Filipa Mendes、Lurdes Gano、Hugo Vicente Miranda、Tiago F. Outeiro、Isabel Santos、António Paulo

  DOI：10.1039/c5ob00124b

  日期：——

  Novel cysteamine-based (N,S,O)-chelators were successfully applied in the synthesis of isostructural M(i) (M = Re, ^99mTc) tricarbonyl complexes for cancer theranostics.

  新型基于半胱氨酸的（N，S，O）配体成功应用于合成同构的M（i）（M = Re，99mTc）三羰基配合物，用于癌症治疗和诊断。
• Long-chain rhenium and technetium glucosamine conjugates
  作者：Meryn L. Bowen、Zhen-Feng Chen、Adrienne M. Roos、Ripen Misri、Urs Häfeli、Michael J. Adam、Chris Orvig

  DOI：10.1039/b914309b

  日期：——

  A series of five glucosamine-conjugated organometallic complexes of the tricarbonyl cores of technetium-99m and rhenium were made. Glucosamine was derivatized at the C-2 nitrogen with long chain alkyl spacers linked to either pyridyl-tert-nitrogen-phenol tridentate chelates or cyclopentadienyl ligating groups. The metal complexes of the tridentate ligands were formed by refluxing with [Re(CO)3(H2O)3]Br, or with a base and [99mTc(CO)3(H2O)3]+. These ligands were found to be competent chelates in binding the [99mTc(CO)3]+ core as radiolabeling yields ranged from 87 to 93% and the resulting complexes are stable to cysteine and histidine challenges for 24 h. The cyclopentadienyl analogues were formed using a double ligand transfer reaction for the rhenium complexes and a single ligand transfer for the technetium-99m complexes. All five rhenium complexes were tested as substrates of hexokinase; two of these complexes were tested as hexokinase inhibitors and they were found to be competent inhibitors, suggesting that they may be able to interact with hexokinase. MTT cytotoxicity studies were performed and the complexes tested were found to be non-toxic to the concentrations tested (100 μM or 1 mM). GLUT-1 mediated cell uptake studies were performed on all five technetium-99m complexes, and their cell entry was found to parallel their lipophilicities, suggesting that cellular uptake is by passive diffusion and is not mediated by GLUT-1.

  制备了一系列五种氨基葡萄糖与锝-99m 和铼的三羰基核心的有机金属络合物。葡萄糖胺的 C-2 氮被长链烷基间隔物衍生化，与吡啶基-叔氮-苯酚三叉螯合物或环戊二烯配位基相连。通过与[Re(CO)3(H2O)3]Br或与碱和[99mTc(CO)3( )3]+回流形成三叉配体的金属配合物。研究发现，这些配体是结合[99m锝（CO）3]+ 核的有效螯合物，其放射性标记产率为 87% 至 93%，所生成的配合物对半胱氨酸和组氨酸的挑战稳定 24 小时。所有五种铼络合物都作为己糖激酶的底物进行了测试；其中两种络合物作为己糖激酶抑制剂进行了测试，结果发现它们是合格的抑制剂，这表明它们可能能够与己糖激酶相互作用。进行了 MTT 细胞毒性研究，发现所测试的复合物在测试浓度（100 μM 或 1 mM）下无毒性。对所有五种锝-99m 复合物都进行了 GLUT-1 介导的细胞摄取研究，发现它们进入细胞的速度与它们的亲脂性平行，这表明细胞摄取是通过被动扩散，而不是由 GLUT-1 介导。
• Targeting of G‐quadruplex DNA with 99mTc(I)/Re(I) Tricarbonyl Complexes Carrying Pyridostatin Derivatives
  作者：Elisa Palma、Cigdem Içhedef、Célia Fernandes、Ana Belchior、Paula Raposinho、Lurdes Gano、André Miranda、David Moreira、Pedro Lourenço、Carla Cruz、Ana Salomé Pires、Maria Filomena Botelho、António Paulo

  DOI：10.1002/chem.202400285

  日期：2024.4.16

  New (Radio)metalated G4 binders: Re(I) and 99mTc(I) complexes carrying pyridostatin derivatives for the targeting of G-quadruplex structures. The Re complex can bind to G4 DNA and RNA with selectivity over double-stranded DNA, exhibiting cytotoxic activity in MCF-7 human breast cancer and PC3 human prostate cancer cell lines. The 99mTc congener is stable in vivo with a fast blood clearance in normal

  新型（放射性）金属化 G4 结合剂：带有吡啶他汀衍生物的 Re(I) 和99m Tc(I) 配合物，用于靶向 G-四链体结构。 Re 复合物可以比双链 DNA 选择性地结合 G4 DNA 和 RNA，在 MCF-7 人乳腺癌和 PC3 人前列腺癌细胞系中表现出细胞毒活性。 99m Tc 同源物在体内稳定，在正常小鼠中具有快速的血液清除率。