5-oxo-5-((6-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-yl)amino)pentanoic acid | 1373261-91-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-oxo-5-((6-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-yl)amino)pentanoic acid
• 英文别名: 5-Oxo-5-(6-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-ylamino)pentanoic acid；5-oxo-5-[[6-(6-pyridin-2-yl-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-yl]amino]pentanoic acid
• CAS: 1373261-91-6
• 化学式: C₁₇H₁₇N₇O₃
• 分子量: 367.367
• InChiKey: SUFFREVWEYKIAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-oxo-5-((6-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-yl)amino)pentanoic acid 在 溶剂黄146 、 sodium nitrite 作用下， 反应 0.25h， 以92%的产率得到吡啶-四嗪-吡啶-丁酸
  参考文献：
  名称：

  Pretargeting kit, method and agents used therein

  摘要：

  描述了一种预靶向方法，以及相关的用于靶向医学成像和/或治疗的试剂盒，其中利用表现出彼此生物正交反应性的无机反应性化学基团。该发明涉及在预靶向探针和效应探针之间提供[4+2]逆电子需求（反）Diels-Alder化学反应的偶联。为此，其中一个探针包括富电子不足的四氮唑或其他适当的二烯，另一个包括一个具有一个或多个轴取代基的E-环辛烯。

  公开号：

  US09463256B2
• 作为产物：
  描述：

  3-氨基-6-氰基吡啶 在 肼 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 5-oxo-5-((6-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-yl)amino)pentanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of 18F-PTTCO-Cys40-Exendin-4 for PET imaging of ectopic insulinomas in rodents

  摘要：

  A major limitation in the development of radiolabeled Exendin-4 analogues (short half-life isotopes) is an inability to efficiently and rapidly separate final products from precursors. This is important as lack of purity in the final product decreases probe efficiency. The purpose of this study was to develop a method to prepare the highpurity imaging reagent [F-18] PITCO-Cys(40)-Exendin-4. To accomplish this, magnetic TCO-beads were incubated with the crude product to remove unlabeled Exendin-4. In rodents pre-treatment with purified [F-18] PITCO-Cys(40)-Exendin-4 (similar to 1.85 MBq) allowed precise microPET imaging of ectopic insulinomas. Moreover, analogue uptake was successfully blocked by administering non-labelled "cold" Exendin-4. Biodistribution data revealed that [F-18] PITCO-Cys(40)-Exendin-4 accumulated specifically in GLP-1R-enriched insulinomas in mice, confirming results obtained using miroPET. Investigation of [F-18] PITCO-Cys(40)-Exendin-4 as a tracer to image portal vein-transplanted pancreatic islets is proceeding in animals.

  DOI：

  10.1016/j.bioorg.2020.103718

文献信息

• Pretargeting kit, method and agents used therein
  申请人：Lub Johan

  公开号：US09463256B2

  公开（公告）日：2016-10-11

  Described is a pretargeting method, and related kits, for targeted medical imaging and/or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other an E-cyclooctene which has one or more axial substituents.

  描述了一种预靶向方法，以及相关的用于靶向医学成像和/或治疗的试剂盒，其中利用表现出彼此生物正交反应性的无机反应性化学基团。该发明涉及在预靶向探针和效应探针之间提供[4+2]逆电子需求（反）Diels-Alder化学反应的偶联。为此，其中一个探针包括富电子不足的四氮唑或其他适当的二烯，另一个包括一个具有一个或多个轴取代基的E-环辛烯。
• [EN] METHODS FOR INDUCING BIOORTHOGONAL REACTIVITY<br/>[FR] PROCÉDÉS POUR INDUIRE UNE RÉACTIVITÉ BIO-ORTHOGONALE
  申请人：FOX JOSEPH

  公开号：WO2017106427A1

  公开（公告）日：2017-06-22

  A method for catalytically converting a dihydrotetrazine 1 into a tetrazine 2, wherein one R group on the dihydrotetrazine 1 is a substituted or unsubstituted aryi, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, or heteroatom-containing group, and the other R group is selected from the group consisting of H and substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl,-or heteroatom-containing groups; 1, 2 wherein the method comprises oxidizing dihydrotetrazine 1 in a reaction medium in the presence of a catalyst and a stoichiometric oxidant.

  将二氢四氮唑1催化转化为四氮唑2的方法，其中二氢四氮唑1上的一个R基团是取代或未取代的芳基、杂环芳基、烷基、烯基、炔基、羰基或含杂原子的基团，另一个R基团选自H和取代或未取代的芳基、杂环芳基、烷基、烯基、炔基、羰基或含杂原子的基团；其中该方法包括在反应介质中在催化剂和化学计量氧化剂的存在下氧化二氢四氮唑1。
• PRETARGETING KIT, METHOD AND AGENTS USED THEREIN
  申请人：Lub Johan

  公开号：US20130189184A1

  公开（公告）日：2013-07-25

  Described is a pretargeting method, and related kits, for targeted medical imaging and/or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other an E-cyclooctene which has one or more axial substituents.

  描述了一种预靶向方法及相关试剂盒，用于靶向医学成像和/或治疗，其中利用表现出生物正交反应性的无机反应性化学基团。该发明涉及使用[4+2]逆电子需求（反）Diels-Alder化学在预靶向探针和效应探针之间提供偶联。为此，其中一种探针包括富电子缺陷的四唑或其他适当的双烯，另一种是具有一个或多个轴取代基的E-环辛烯。
• Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation
  作者：Han Zhang、William S. Trout、Shuang Liu、Gabriel A. Andrade、Devin A. Hudson、Samuel L. Scinto、Kevin T. Dicker、Yi Li、Nikifar Lazouski、Joel Rosenthal、Colin Thorpe、Xinqiao Jia、Joseph M. Fox

  DOI：10.1021/jacs.6b02168

  日期：2016.5.11

  thereby turning on reactivity toward trans-cyclooctene dienophiles. Alternately, the aerial oxidation of dihydrotetrazines can be efficiently catalyzed by nanomolar levels of horseradish peroxidase under peroxide-free conditions. Selection of dihydrotetrazine/tetrazine pairs of sufficient kinetic stability in aerobic aqueous solutions is key to the success of these approaches. In this work, polymer fibers

  使用空气作为氧化剂，可以通过可控的催化刺激来诱导快速生物正交反应性。用红光 (660 nm) 照射的亚甲基蓝 (4 μM) 催化二氢四嗪快速氧化为四嗪，从而开启对反式环辛烯亲二烯体的反应性。或者，在无过氧化物的条件下，纳摩尔水平的辣根过氧化物酶可以有效地催化二氢四嗪的空气氧化。选择在有氧水溶液中具有足够动力学稳定性的二氢四嗪/四嗪对是这些方法成功的关键。在这项工作中，携带潜在二氢四嗪的聚合物纤维被小分子、肽和蛋白质的反式环辛烯缀合物催化活化和共价修饰。除了用荧光团进行可视化之外，与细胞粘附肽缀合的纤维还表现出显着增强的介导细胞接触引导的能力。
• Methods for inducing bioorthogonal reactivity
  申请人：Fox Joseph

  公开号：US10875840B2

  公开（公告）日：2020-12-29

  A method for catalytically converting a dihydrotetrazine 1 into a tetrazine 2, wherein one R group on the dihydrotetrazine 1 is a substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, or heteroatom-containing group, and the other R group is selected from the group consisting of H and substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl,- or heteroatom-containing groups; 1, 2 wherein the method comprises oxidizing dihydrotetrazine 1 in a reaction medium in the presence of a catalyst and a stoichiometric oxidant.

  一种催化二氢四嗪1转化为四嗪2的方法，其中二氢四嗪1上的一个R基团是取代或未取代的芳基、杂芳基、烷基、烯基、炔基、羰基或含杂原子的基团，另一个R基团选自由H和取代或未取代的芳基、杂芳基、烷基、烯基、炔基、羰基或含杂原子的基团组成的组；1, 2 其中该方法包括在催化剂和定量氧化剂存在下，在反应介质中氧化二氢四嗪 1。