2-[6-[2-(Benzoylcarbamothioylamino)ethylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl 2-methylprop-2-enoate | 1279101-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-[6-[2-(Benzoylcarbamothioylamino)ethylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl 2-methylprop-2-enoate
• 英文别名: 2-[6-[2-(benzoylcarbamothioylamino)ethylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl 2-methylprop-2-enoate
• CAS: 1279101-90-4
• 化学式: C₂₈H₂₆N₄O₅S
• 分子量: 530.604
• InChiKey: RJFLLEIZWXOURG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-hydroxyethyl-4-bromine-1,8-naphthalimide 在 吡啶 作用下， 以 甲乙醚 、 丙酮 为溶剂， 反应 8.0h， 生成 2-[6-[2-(Benzoylcarbamothioylamino)ethylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl 2-methylprop-2-enoate
  参考文献：
  名称：

  Thermoresponsive Core Cross-Linked Micelles for Selective Ratiometric Fluorescent Detection of Hg²⁺ Ions

  摘要：

  We report on the fabrication of core cross-linked (CCL) micelles possessing thermoresponsive cores and their application as sensitive and selective ratiometric Hg2+ probes with thermo-tunable detection efficiency. Well-defined double hydrophilic block copolymer (DHBC) bearing naphthalimide-based Hg2+ -reactive moieties (NUMA, 4), PEO-b-P(NIPAM-co-NAS-co-NUMA), was synthesized via reversible addition - fragmentation chain transfer (RAFT) polymerization, where PEO, NIPAM, and NAS represent poly(ethylene oxide), N-isopropylacrylamide, and N-acryloxysuccinimide. At 25 degrees C, PEO-b-P(NIPAM-co-NAS-co-NUMA) unimers in aqueous solution can act as ratiometric Hg2+ probes with a detection limit of similar to 10.1 nM. After core cross-linking of the micellar nanoparticles formed at elevated temperatures, structurally stable CCL micelles with well-solvated PEO coronas and thermoresponsive cores embedded with Hg2+-reactive NUMA moieties were obtained. Upon Hg2+ addition, the aqueous dispersion of CCL micelles exhibit a colorimetric transition from yellowish to colorless and a fluorometric emission transition from green to bright blue. Moreover, Hg2+ detection limits of CCL micelles were considerably enhanced to 3.0 and 1.8 nM at 25 and 40 degrees C, when the thermoresponsive cores are at their swollen and collapsed state, respectively. The high selectivity of CCL micelles to Hg2+ over other common cations was also demonstrated. Furthermore, in vitro studies revealed that CCL micelles can effectively enter into living cells and sensitively respond to the presence of Hg2+ ions via the change of fluorescence emission color. This work represents the first example of DHBC-based CCL micelle acting as highly selective and sensitive ratiometric metal ion probes. The structural stability, water dispersibility, biocompatibility, and most importantly the thermo-tunable detection sensitivity of this novel type of CCL micelle-based sensing systems augur well for their future applications as multifunctional nanocarriers for drug delivery, sensing, imaging, and diagnosis.

  DOI：

  10.1021/la104911r

文献信息

• Thermoresponsive Core Cross-Linked Micelles for Selective Ratiometric Fluorescent Detection of Hg²⁺ Ions
  作者：Xuejuan Wan、Tao Liu、Shiyong Liu

  DOI：10.1021/la104911r

  日期：2011.4.5

  We report on the fabrication of core cross-linked (CCL) micelles possessing thermoresponsive cores and their application as sensitive and selective ratiometric Hg2+ probes with thermo-tunable detection efficiency. Well-defined double hydrophilic block copolymer (DHBC) bearing naphthalimide-based Hg2+ -reactive moieties (NUMA, 4), PEO-b-P(NIPAM-co-NAS-co-NUMA), was synthesized via reversible addition - fragmentation chain transfer (RAFT) polymerization, where PEO, NIPAM, and NAS represent poly(ethylene oxide), N-isopropylacrylamide, and N-acryloxysuccinimide. At 25 degrees C, PEO-b-P(NIPAM-co-NAS-co-NUMA) unimers in aqueous solution can act as ratiometric Hg2+ probes with a detection limit of similar to 10.1 nM. After core cross-linking of the micellar nanoparticles formed at elevated temperatures, structurally stable CCL micelles with well-solvated PEO coronas and thermoresponsive cores embedded with Hg2+-reactive NUMA moieties were obtained. Upon Hg2+ addition, the aqueous dispersion of CCL micelles exhibit a colorimetric transition from yellowish to colorless and a fluorometric emission transition from green to bright blue. Moreover, Hg2+ detection limits of CCL micelles were considerably enhanced to 3.0 and 1.8 nM at 25 and 40 degrees C, when the thermoresponsive cores are at their swollen and collapsed state, respectively. The high selectivity of CCL micelles to Hg2+ over other common cations was also demonstrated. Furthermore, in vitro studies revealed that CCL micelles can effectively enter into living cells and sensitively respond to the presence of Hg2+ ions via the change of fluorescence emission color. This work represents the first example of DHBC-based CCL micelle acting as highly selective and sensitive ratiometric metal ion probes. The structural stability, water dispersibility, biocompatibility, and most importantly the thermo-tunable detection sensitivity of this novel type of CCL micelle-based sensing systems augur well for their future applications as multifunctional nanocarriers for drug delivery, sensing, imaging, and diagnosis.