2-(2-hydroxyl-ethyl)-6-(4-methylpiperazin-1-yl)-benzo[de]isoquinoline-1,3-dione | 361161-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(2-hydroxyl-ethyl)-6-(4-methylpiperazin-1-yl)-benzo[de]isoquinoline-1,3-dione
• 英文别名: 2-(2-hydroxyethyl)-6-(4-methylpiperazin-1-yl)benzo[de]isoquinoline-1,3-dione；N-(2-hydroxyethyl)-4-(4-methylpiperazine-1-yl)-1,8-naphthalimide
• CAS: 361161-28-6
• 化学式: C₁₉H₂₁N₃O₃
• 分子量: 339.394
• InChiKey: QQQPYFSDFVRXLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(5-(4-carboxylphenyl)-2-methyl-3-thienyl)]-2-[2-methyl-5-(4-vinylphenyl)-3-thienyl]perfluorocyclopentene 、 2-(2-hydroxyl-ethyl)-6-(4-methylpiperazin-1-yl)-benzo[de]isoquinoline-1,3-dione 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  Water-Soluble Polymeric Photoswitching Dyads Impart Super-Resolution Lysosome Highlighters

  摘要：

  In this report, we integrated a photoswitchable quencher, a highly emissive yet pH sensitive fluorophore, and a water-soluble polymer with controlled hydrophilicity into a functional nanosystem. The photoswitching quencher is based on dithienylethene (DTE) unit, while the pH-sensitive emitter is naphthalimide (NI) unit and the water-soluble polymer is obtained from polymerization of N-isopropylacrylamide (NIPAM). Together, these three units create a novel super-resolution lysosome highlighter, although individually none can function as a lysotracker. Because the emitter is sensitive to pH, the resulting polymer becomes highly fluorescent in acidic lysosomes. In addition, photoswitching regulates the fluorescence on and off and thus enables super-resolution localization of fluorescent polymers with sub-40 nm spatial resolution in imaging subcellular organelles. Thus, the concept presented here, including the photoswitchable DTE-pH-sensitive NI dyad, is promising to guide the development of future-generation super-resolution imaging agents.

  DOI：

  10.1021/ma501505w
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 以 乙醇 、 乙二醇甲醚 为溶剂， 反应 3.0h， 生成 2-(2-hydroxyl-ethyl)-6-(4-methylpiperazin-1-yl)-benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  通过使用4-哌嗪萘二甲酰亚胺衍生物对光交联的水溶胀性丙烯酸膜进行功能化而获得的固体荧光传感器

  摘要：

  为了进一步官能化，已经制备了基于乙烯基-吡咯烷酮/丙烯酸丁酯的光交联膜（M-Cl），其包含乙二醇二甲基丙烯酸酯作为交联剂和甲基丙烯酰氯作为反应性单体。已经使用两种方法合成了一系列羟基取代的哌嗪萘二甲酰亚胺化合物，作为pH敏感的Off-On荧光探针：微波和回流。通过Schotten-Baumann反应，选择了三种衍生物通过酰氯基团锚定在M-Cl膜上。使用不同的技术对所有获得的水溶胀膜进行表征。研究了光诱导电子转移（PET）及其pH依赖的光学变化，并使用pH依赖的吸收光谱和荧光光谱确定了各种光化学参数。在9.0-4.0的pH范围内，这些固体传感器经历了从哌嗪到萘二甲酰亚胺部分的PET处理，从而导致了荧光猝灭。但是，在4.0-1.0的pH范围内，PET被抑制以增强荧光。功能化膜对pH变化的敏感性取决于萘二甲酰亚胺取代基的大小和位置。

  DOI：

  10.1016/j.polymer.2017.07.039

文献信息

• Synthesis and luminescence properties of novel ferrocene–naphthalimides dyads
  作者：Jiaan Gan、He Tian、Zhaohui Wang、Kongchang Chen、J Hill、P.A Lane、M.D Rahn、A.M Fox、D.D.C Bradley

  DOI：10.1016/s0022-328x(01)01416-4

  日期：2002.2

  We attribute these differences due to different spacers used to link the ferrocenyl unit and the naphthalimide moiety. Measurements of the fluorescence spectrum and the fluorescence lifetime confirmed that the fluorescence of the naphthalimide is strongly quenched by the effective PET from the ferrocenyl units to the naphthalimide moieties. The PET path in 6-[4-(2-oxo-2-ferrocenyl-ethyl)-piperazin-1

  已经合成了包含连接在萘二甲酰亚胺环的4-位上的4-氨基-1，8-萘二甲酰亚胺的二茂铁衍生物。电化学数据和电荷分离的自由能（ΔGcs）表明，从二茂铁单元到萘二甲酰亚胺部分的光诱导电子转移（PET）对于这些二茂铁衍生物在热力学上是可行的。它们的吸收光谱表明，对于这些二茂铁衍生物，二茂铁基单元与萘二甲酰亚胺部分之间的电子相互作用非常不同。我们将这些差异归因于用于连接二茂铁基单元和萘二甲酰亚胺部分的不同间隔基。荧光光谱和荧光寿命的测量证实，萘二甲酰亚胺的荧光被有效的PET从二茂铁基单元至萘二甲酰亚胺部分强烈淬灭。6- [4-（2-氧代-2-二茂铁基-乙基）-哌嗪-1-基]-苯并[DE ]异喹啉-1,3-二酮可通过二茂铁单元的两个氧化和烷基化的胺基团的质子化被关闭。这些类型的二元组可以用作双模式化学（质子）/电致变色分子开关。
• Fluorescence detection and removal of copper from water using a biobased and biodegradable 2D soft material
  作者：Meng Li、Zhijiang Liu、Shuwen Wang、David G. Calatayud、Wei-Hong Zhu、Tony D. James、Lidong Wang、Boyang Mao、Hui-Ning Xiao

  DOI：10.1039/c7cc08035b

  日期：——

  We have developed a green and robust fluorogenic (λ_ex = 410 nm, λ_em = 510 nm) cellulose membrane using graphene oxide (GO) as a construct for simultaneous copper ion recognition and filtration at environmentally relevant levels.

  我们已经开发出一种绿色且强韧的荧光素（λ_ex = 410 nm，λ_em = 510 nm）纤维素膜，使用氧化石墨烯（GO）作为构建材料，可同时识别和过滤环境相关水平的铜离子。
• Positive and negative fluorescent imaging induced by naphthalimide polymers
  作者：He Tian、Jiaan Gan、Kongchang Chen、Jun He、Qun Liang Song、Xiao Yuan Hou

  DOI：10.1039/b200509c

  日期：2002.4.17

  Two novel polymers with naphthalimide pendant groups have been prepared. In poly(2-methylacrylic acid 2-[6-(4-methylpiperazin-1-yl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl]ethyl ester-co-methyl methacrylate) (copolymer 1), an alkylated tertiary amine acts as an electron donor and quenches the fluorescence of the naphthalimide fluorophore via the photo-induced electron transfer (PET) process. Protonation of the alkylated tertiary amine by an acid generated by a photoacid generator (PAG) can switch off the PET path and the fluorescence of the naphthalimide fluorophore would be recovered and enhanced. For poly(2-methylacrylic acid 2-[6-(4-methylpiperazin-1-yl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl]ethyl ester) (polymer 3), protonation both of the aromatic amine and the alkylated amine by the acids generated from may result in significant fluorescence quenching and alter the fluorophore. When protonation processes occur, the fluorescence enhancement (×2) of copolymer 1 or the fluorescence quenching (×15) of polymer 3 would be applied to generate positive or negative fluorescent patterned images on their net films.

  已经制备了两种具有萘酰亚胺侧基的新型聚合物。在聚(2-甲基丙烯酸2-[6-(4-甲基哌嗪-1-基)-1,3-二氧代-2,3-二氢-1H-苯并[去]异喹啉-2-基]乙酯-共聚中-甲基丙烯酸甲酯） （共聚物 1），烷基化叔胺充当电子供体，并通过光诱导电子转移 (PET) 过程猝灭萘二甲酰亚胺荧光团的荧光。光致产酸剂 (PAG) 产生的酸对烷基化叔胺进行质子化，可以关闭 PET 路径，并且萘二甲酰亚胺荧光团的荧光将恢复并增强。对于聚(2-甲基丙烯酸2-[6-(4-甲基哌嗪-1-基)-1,3-二氧代-2,3-二氢-1H-苯并[去]异喹啉-2-基]乙酯) (聚合物3), 芳香胺和烷基化胺被产生的酸质子化可能导致显着的荧光猝灭并改变荧光团。当质子化过程发生时，共聚物1的荧光增强（×2）或聚合物3的荧光猝灭（×15）将被应用在它们的网膜上产生正性或负性荧光图案图像。
• Fluorescent polymer prodrug nanoparticles with aggregation-induced emission (AIE) properties from nitroxide-mediated polymerization
  作者：Yinyin Bao、Elise Guégain、Valérie Nicolas、Julien Nicolas

  DOI：10.1039/c6cc09052d

  日期：——

  Aggregation-induced emission (AIE)-active polymer prodrug nanoparticles were readily prepared by growing short, well-defined polymer chains from an AIE dye by nitroxide-mediated polymerization, followed by co-nanoprecipitation of the resulting conjugates with similarly constructed anticancer polymer prodrugs. The nanoparticles had sharp fluorescence signal offering excellent imaging ability in living

  聚集诱导发射（AIE）-活性聚合物前体药物纳米颗粒的制备很容易，方法是通过氮氧化物介导的聚合反应从AIE染料中生长出清晰明确的短聚合物链，然后将所得的偶联物与类似构建的抗癌聚合物前体药物共纳米沉淀。纳米粒子具有清晰的荧光信号，可在活细胞中提供出色的成像能力，并且可以精确监控其细胞内定位。
• Water-Soluble Polymeric Photoswitching Dyads Impart Super-Resolution Lysosome Highlighters
  作者：Chong Li、Zhe Hu、Matthew P. Aldred、Ling-Xi Zhao、Hui Yan、Guo-Feng Zhang、Zhen-Li Huang、Alexander D. Q. Li、Ming-Qiang Zhu

  DOI：10.1021/ma501505w

  日期：2014.12.23

  In this report, we integrated a photoswitchable quencher, a highly emissive yet pH sensitive fluorophore, and a water-soluble polymer with controlled hydrophilicity into a functional nanosystem. The photoswitching quencher is based on dithienylethene (DTE) unit, while the pH-sensitive emitter is naphthalimide (NI) unit and the water-soluble polymer is obtained from polymerization of N-isopropylacrylamide (NIPAM). Together, these three units create a novel super-resolution lysosome highlighter, although individually none can function as a lysotracker. Because the emitter is sensitive to pH, the resulting polymer becomes highly fluorescent in acidic lysosomes. In addition, photoswitching regulates the fluorescence on and off and thus enables super-resolution localization of fluorescent polymers with sub-40 nm spatial resolution in imaging subcellular organelles. Thus, the concept presented here, including the photoswitchable DTE-pH-sensitive NI dyad, is promising to guide the development of future-generation super-resolution imaging agents.