2-nitrodopamine hydrogensulfate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-nitrodopamine hydrogensulfate
• 英文别名: 6-nitrodopamine hydrogen sulfate；6-nitrodopamine hydrogen sulphate；6-nitrodopamine sulfuric acid；4-(2-Aminoethyl)-5-nitrobenzene-1,2-diol;sulfuric acid；4-(2-aminoethyl)-5-nitrobenzene-1,2-diol;sulfuric acid
• 化学式: C₈H₁₀N₂O₄*H₂O₄S
• 分子量: 296.258
• InChiKey: CFYSXWNTNIMJSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  195
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-nitrodopamine hydrogensulfate 在 盐酸 、 tin(ll) chloride 作用下， 反应 0.5h， 以76%的产率得到7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one
  参考文献：
  名称：

  A new oxidation pathway of the neurotoxin 6-aminodopamine. Isolation and characterisation of a dimer with a tetrahydro[3,4a]iminoethanophenoxazine ring system.

  摘要：

  Oxidation of the neurotoxin 6-aminodopamine (1) is known to proceed through the o-quinone 3, which undergoes intramolecular cyclisation to give 5,6-dihydroxyindole (6). In a re-examination of the reaction, we have found that at concentrations of 1 higher than 5 x 10(-3) M a quite different course prevails, leading to the formation of the novel 7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro [3,4a] iminoethanophenoxazine (7). Product 7 was formed by aerobic, chemical (persulphate, periodate) or enzymatic (tyrosinase, peroxidase/H2O2) oxidation of 1. on acetylation, 7 afforded the tetraacetate 8. Oxidation of the model compound 5-amino-4-methylcatechol (9) proceeded similarly as that of 1, to give the tetrahydrophenoxazinedione 11.

  DOI：

  10.1016/s0040-4020(01)86599-6
• 作为产物：
  描述：

  盐酸多巴胺 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以50 %的产率得到2-nitrodopamine hydrogensulfate
  参考文献：
  名称：

  Insulin loaded iron magnetic nanoparticle–graphene oxide composites: synthesis, characterization and application for in vivo delivery of insulin

  摘要：

  胰岛素给药的重点课题之一是开发胰岛素制剂，以保护原生胰岛素在胃内酸性 pH 值条件下不被降解。在这项工作中，我们首次发现基于氧化石墨烯（GO）的基质可以确保胰岛素在低 pH 值下的稳定性。我们制备了负载胰岛素的 GO 和用 2-硝基多巴胺包覆的磁性颗粒修饰的 GO（GOâMPdop）基质，并研究了 pH 触发的胰岛素释放。事实证明，当 pH 值小于 5.4 时，胰岛素在 GO 纳米材料上的负载量极高，GO 的负载量为 100 ± 3%，GOâMPdop 的负载量为 88 ± 3%。含胰岛素的GO基质在酸性pH值下稳定，而在碱性溶液（pH = 9.2）中则会释放胰岛素。以爪蟾卵母细胞为模型，我们发现 GO 和 GOâMPdop 在酸性条件下预处理后，减数分裂恢复率保持不变，而预孵育的胰岛素（不含 GO 纳米材料）几乎完全失去了成熟作用。这些结果表明，基于 GO 的纳米材料是一种很有前途的胰岛素保护系统。

  DOI：

  10.1039/c3ra46307a

文献信息

• Ultrastable Suspensions of Polyoxazoline-Functionalized ZnO Single Nanocrystals
  作者：Giulia Morgese、Valerio Causin、Michele Maggini、Stefano Corrà、Silvia Gross、Edmondo M. Benetti

  DOI：10.1021/acs.chemmater.5b00252

  日期：2015.4.28

  The synthesis and characterization of poly-2-methyl-2-oxazoline-stabilized ZnO single nanocrystals (PMOXA:ZnO NCs) featuring ultrastable suspensions are presented in this report. The inorganic NCs are first synthesized by the inverse w/o miniemulsion (ME) process in the presence of polymeric surfactants which are subsequently exchanged by PMOXA ligands with nitrodopamine (ND) anchors as chain ends. Interplay between ligand relative concentration and chain length allowed the preparation of PMOXA-stabilized suspensions of single NCs presenting a platelet-like morphology and a uniform polymer coating. The strong binding of ND-derivatized anchors to the metal oxide surfaces together with the high stability of PMOXA against chemical oxidation enable the formation of suspensions presenting excellent colloidal stability over very long incubation times in aqueous media (up to 9 months). The combination of the ME approach with engineered PMOXA-ND functionalities thus proved to be a highly efficient technique to design novel polymer/inorganic colloidal systems with enhanced stability for potential bioimaging applications.

  本报告介绍了具有超稳定悬浮液的聚-2-甲基-2-恶唑啉稳定的 ZnO 单纳米晶 (PMOXA:ZnO NCs) 的合成和表征。无机NC首先在聚合物表面活性剂存在下通过反相w/o细乳液(ME)工艺合成，随后通过PMOXA配体与硝基多巴胺(ND)锚作为链端进行交换。配体相对浓度和链长之间的相互作用允许制备具有片状形态和均匀聚合物涂层的单一NC的PMOXA稳定悬浮液。 ND 衍生锚与金属氧化物表面的强结合力以及 PMOXA 对化学氧化的高稳定性使得能够形成悬浮液，在水介质中很长的孵育时间（长达 9 个月）内呈现出优异的胶体稳定性。因此，ME 方法与工程化 PMOXA-ND 功能的结合被证明是一种高效的技术，可以设计新型聚合物/无机胶体系统，并增强潜在生物成像应用的稳定性。
• PNIPAm-based microgels with a UCST response
  作者：Gema Marcelo、Laurinda R.P. Areias、María Teresa Viciosa、J.M.G. Martinho、José Paulo S. Farinha

  DOI：10.1016/j.polymer.2017.03.071

  日期：2017.5

  34 °C to 40 °C. This novel material is based in poly(N-isopropyl acrylamide), pNIPAm, a polymer well known for its opposite temperature response (featuring a lower critical solution temperature, LCST). The unusual properties of our material are due to a small fraction of copolymerized methacrylic acid and nitrocatechol monomers. The collapsed conformation in PBS buffer below 34 °C is stabilized by hydrogen

  具有高临界溶液温度（UCST）响应（即，在较高温度下显示出体积膨胀）的热响应性微凝胶对于各种应用是非常期望的，但是非常罕见，特别是如果它们要在生理条件下工作时。在这里，我们介绍了一种新型的UCST型微凝胶，在生理条件下表现出显着的转变，其直径从34°C到40°C的增加幅度大于150％。这种新颖的材料基于聚（N-异丙基丙烯酰胺），pNIPAm，以相反的温度响应（具有较低的临界溶液温度LCST）而闻名的聚合物。我们材料的非凡性能是由于一小部分共聚的甲基丙烯酸和硝基邻苯二酚单体。低于34°C的PBS缓冲液中塌陷的构象通过氢键作用得以稳定，部分离子化的硝基邻苯二酚具有排斥力，而甲基丙烯酸单元则通过离子强度筛选，而甲基丙烯酸中的甲基则形成疏水簇。温度升高导致pNIPAm片段崩溃，从而破坏了超分子相互作用的平衡，从而导致凝胶的大量膨胀。
• GELLAN GUM HYDROGELS, PREPARATION, METHODS AND USES THEREOF
  申请人：STEMMATTERS, BIOTECNOLOGIA E MEDICINA REGENERATIVE, S.A.

  公开号：US20190330384A1

  公开（公告）日：2019-10-31

  Gellan gum-based hydrogels are disclosed herein for in vitro cell culture and tissue engineering and regenerative medicine applications. Such gellan gum-based hydrogels may be used alone or combined with live cells and/or biomolecules for application in humans and/or animals. Chemical modification of gellan gum with selected ion-chelating substituents affords novel gellan gum hydrogels endowed with tunable physicochemical and biological properties. The modified gellan gum hydrogels described herein present advantages over existing hydrogel systems, including solubility, ionic crosslinking versatility, ease of formulation and injectability and greater adhesiveness within biological tissues and surfaces, whilst maintaining encapsulated cells viable during long culture periods and up-regulating the expression of healthy extracellular matrix markers.

  本文介绍了基于格兰胶的水凝胶，用于离体细胞培养、组织工程和再生医学应用。这样的基于格兰胶的水凝胶可以单独使用或与活细胞和/或生物分子结合，应用于人类和/或动物。通过选择离子螯合取代基对格兰胶进行化学修饰，可以获得具有可调节物理化学和生物学性质的新型格兰胶水凝胶。所述改性格兰胶水凝胶相对于现有的水凝胶系统具有溶解性、离子交联多样性、易于制备和注射以及更高的在生物组织和表面上的粘附性等优点，同时在长时间培养期间保持封装的细胞的生存能力，并上调健康的细胞外基质标记的表达。
• Bioinspired, releasable quorum sensing modulators
  作者：José Gomes、Alexander Grunau、Adrien K. Lawrence、Leo Eberl、Karl Gademann

  DOI：10.1039/c2cc37287h

  日期：——

  We demonstrate the synthesis and immobilization of natural product hybrids featuring an acyl-homoserine lactone and a nitrodopamine onto biocompatible TiO2 surfaces through an operationally simple dip-and-rinse procedure. The resulting immobilized hybrids were shown to be powerful quorum sensing (QS) activators in Pseudomonas strains acting by slow release from the surface.

  我们通过一种操作简单的浸泡-冲洗程序，展示了以酰基高丝氨酸内酯和硝基多巴胺为特征的天然产物混合物在生物相容性二氧化钛表面的合成和固定。结果表明，固定化的混合物可通过从表面缓慢释放的方式，成为假单胞菌菌株体内强大的法定量感应（QS）激活剂。
• New prodrugs derived from 6-aminodopamine and 4-aminophenol as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT)
  作者：Sarah Knaggs、Hugh Malkin、Helen M. I. Osborn、Nana Aba O. Williams、Parveen Yaqoob

  DOI：10.1039/b506404j

  日期：——

  Two novel tyrosinase mediated drug delivery pathways have been investigated for the selective delivery of cytotoxic units to melanocytes from urea and thiourea prodrugs. The synthesis of these prodrugs is reported, as well as oximetry data that illustrate that the targets are substrates for tyrosinase. The stability of each of the prodrugs in (i) phosphate buffer and (ii) bovine serum is discussed, and the urea prodrugs are identified as lead candidates for further studies. Finally, HPLC studies and preliminary cytotoxicity studies in a melanotic and an amelanotic cell line, that illustrate the feasibility of the approach, are presented.

  我们研究了两种由酪氨酸酶介导的新型给药途径，利用尿素和硫脲原药向黑色素细胞选择性地输送细胞毒性单位。报告中介绍了这些原药的合成过程，并提供了血氧饱和度数据，说明这些原药的目标是酪氨酸酶的底物。讨论了每种原药在（i）磷酸盐缓冲液和（ii）牛血清中的稳定性，并确定脲原药为进一步研究的主要候选药物。最后，还介绍了高效液相色谱法研究以及在黑色素细胞系和黑色素细胞系中进行的初步细胞毒性研究，以说明该方法的可行性。