puromycin | 5682-30-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: puromycin
• 英文别名: bacteriomycin；N⁶,N⁶-dimethyl-3'-[(O-methyl-tyrosyl)-amino]-3'-deoxy-adenosine；2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9-purinyl]-4-hydroxy-2-(hydroxymethyl)-3-oxolanyl]-3-(4-methoxyphenyl)propanamide；2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
• CAS: 5682-30-4
• 化学式: C₂₂H₂₉N₇O₅
• 分子量: 471.516
• InChiKey: RXWNCPJZOCPEPQ-ZRKVXJNMSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  puromycin 在 吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 Thymidylyl(3'->5')puromycin triethylammonium salt
  参考文献：
  名称：

  Synthesis of an Oligonucleotide with a Terminal Puromycin

  摘要：

  DOI：

  10.1055/s-1983-30368
• 作为产物：
  描述：

  Puromycin dihydrochloride 在 吡啶 作用下， 生成 puromycin
  参考文献：
  名称：

  Synthesis of an Oligonucleotide with a Terminal Puromycin

  摘要：

  DOI：

  10.1055/s-1983-30368

文献信息

• Composition
  申请人：Cheng Woei Ping

  公开号：US20100029544A1

  公开（公告）日：2010-02-04

  Novel polyallylamine (PAA) based graft polymers are provided, including groups such as cholesteryl, cetyl, palmitoyl, which are adapted to deliver an entity that is normally of poor solubility in an aqueous medium, said entity being such as a drug, peptide, protein, or polynucleotide that is releasably contained within the said polymer, the resulting complex being of nanoparticle range sizes with a T g of less than 37° C. and deliverable in aqueous media as micelles of typically 100 to 500 nm in hydrodynamic diameter, thereby offering a delivery vehicle capable of oral or parenteral administration that protects the entity from enzymes and critical pH changes.

  提供了基于新型聚烯丙胺（PAA）的接枝聚合物，其中包括胆固醇基团、十六烷基基团和棕榈酰基团等基团，适用于输送通常在水性介质中溶解性较差的实体，所述实体可以是药物、肽、蛋白质或聚核苷酸，该实体可释放地包含在所述聚合物中，所得的复合物为纳米颗粒范围大小，其Tg低于37°C，并且在水性介质中可作为典型的100至500纳米的动力直径的胶束交付，从而提供一种输送载体，能够口服或经静脉给药，保护实体免受酶和关键pH变化的影响。
• Puromycin Prodrug Activation by Thioredoxin Reductase Overcomes Its Promiscuous Cytotoxicity
  作者：Bingbing Chang、Qianhe Xu、Hairui Guo、Miao Zhong、Ruipeng Shen、Lanning Zhao、Jintao Zhao、Tao Ma、Yajun Chu、Junmin Zhang、Jianguo Fang

  DOI：10.1021/acs.jmedchem.2c01509

  日期：2023.3.9

  of tumors. The antibiotic puromycin (Puro) is a protein synthesis inhibitor causing premature polypeptide chain termination during translation. The well-defined action mechanism of Puro makes it a useful tool in biomedical studies. However, the nonselective cytotoxicity of Puro limits its therapeutic applications. We report herein the construction and evaluation of two Puro prodrugs, that is, S1-Puro

  硒蛋白硫氧还蛋白还原酶 (TrxR) 的过度表达已在恶性组织中得到证实，并且对许多类型的肿瘤具有病理学意义。抗生素嘌呤霉素 (Puro) 是一种蛋白质合成抑制剂，会在翻译过程中导致多肽链过早终止。Puro 明确的作用机制使其成为生物医学研究中的有用工具。然而，Puro 的非选择性细胞毒性限制了其治疗应用。我们在此报告了两种 Puro 前药的构建和评估，即具有五元环状二硫键触发的 S1-Puro 和具有线性二硫键触发的 S2-Puro。S1-Puro 被 TrxR 选择性激活并对癌细胞显示出 TrxR 依赖性细胞毒性，而 S2-Puro 很容易被硫醇激活。此外，S1-Puro 在血浆中表现出比 S2-Puro 更高的稳定性。我们期望这种前药策略可以促进 Puro 作为治疗剂的进一步发展。
• Methods of treatment with drug loaded polymeric materials
  申请人：Saltzman Mark William

  公开号：US20060002971A1

  公开（公告）日：2006-01-05

  Polymeric microparticles have been developed which encapsulate therapeutic compounds such as drugs, cellular materials or components, and antigens, and can have targeting ligands directly bound to the microparticle surface. Preferred applications include use in tissue engineering matrices, wound dressings, bone repair or regeneration materials, and other applications where the microparticles are retained at the site of application or implantation. Another preferred application is in the use of microparticles to deliver anti-proliferative agents to the lining of blood vessels following angioplasty, transplantation or bypass surgery to prevent or decrease restenosis, and in cancer therapy. In still another application, the microparticles are used to treat or prevent macular degeneration when administered to the eye, where agents such as complement inhibitors are administered.

  已开发出的聚合微粒可封装药物、细胞材料或成分和抗原等治疗化合物，并可将靶向配体直接结合到微粒表面。首选应用包括用于组织工程基质、伤口敷料、骨修复或再生材料，以及微颗粒可保留在应用或植入部位的其他应用。另一种优选应用是在血管成形术、移植或搭桥手术后，使用微颗粒向血管内壁输送抗增殖剂，以防止或减少血管再狭窄，以及用于癌症治疗。在另一种应用中，微粒可用于治疗或预防眼部黄斑变性，在眼部施用补体抑制剂等药剂。
• Targeted and high density drug loaded polymeric materials
  申请人：Saltzman Mark William

  公开号：US20060002852A1

  公开（公告）日：2006-01-05

  Polymeric delivery devices have been developed which combine high loading/high density of molecules to be delivered with the option of targeting. As used herein, “high density” refers to microparticles having a high density of ligands or coupling agents, which is in the range of 1000-10,000,000, more preferably between 10,000 and 1,000,000 ligands per square micron of microparticle surface area. A general method for incorporating molecules into the surface of biocompatible polymers using materials with an HLB of less than 10, more preferably less than 5, such as fatty acids, has been developed. Because of its ease, generality and flexibility, this method has widespread utility in modifying the surface of polymeric materials for applications in drug delivery and tissue engineering, as well other other fields. Targeted polymeric microparticles have also been developed which encapsulate therapeutic compounds such as drugs, cellular materials or components, and antigens, and have targeting ligands directly bound to the microparticle surface. Preferred applications include use in tissue engineering matrices, wound dressings, bone repair or regeneration materials, and other applications where the microparticles are retained at the site of application or implantation. Another preferred application is in the use of microparticles to deliver anti-proliferative agents to the lining of blood vessels following angioplasty, transplantation or bypass surgery to prevent or decrease restenosis, and in cancer therapy. In still another application, the microparticles are used to treat or prevent macular degeneration when administered to the eye, where agents such as complement inhibitors are administered.

  现已开发出将高负载/高密度输送分子与靶向选择相结合的聚合物输送装置。本文所用的 "高密度 "是指配体或偶联剂密度较高的微粒，其范围在 1000-10,000,000 之间，每平方毫米微粒表面积的配体密度最好在 10,000-1,000,000 之间。利用 HLB 小于 10，更优选小于 5 的材料（如脂肪酸）将分子加入生物相容性聚合物表面的一般方法已经开发出来。由于其简便性、通用性和灵活性，这种方法在改性聚合物材料表面以应用于药物输送和组织工程以及其他领域具有广泛的实用性。此外，还开发出了靶向聚合物微粒，这种微粒可封装药物、细胞材料或成分和抗原等治疗化合物，并将靶向配体直接结合到微粒表面。首选应用包括用于组织工程基质、伤口敷料、骨修复或再生材料，以及微颗粒可保留在应用或植入部位的其他应用。另一种优选应用是在血管成形术、移植或搭桥手术后，使用微颗粒向血管内壁输送抗增殖剂，以防止或减少血管再狭窄，以及用于癌症治疗。在另一种应用中，微粒可用于治疗或预防眼部黄斑变性，在眼部施用补体抑制剂等药剂。
• TARGETED AND HIGH DENSITY DRUG LOADED POLYMERIC MATERIALS
  申请人：Yale University

  公开号：EP1768692A2

  公开（公告）日：2007-04-04