4-azidophenylmethanol | 1617512-09-0

• 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: 4-azidophenylmethanol
• 英文别名: (4-azidophenyl)methyl N-(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)carbamate
• CAS: 1617512-09-0
• 化学式: C₂₄H₂₁N₅O₄
• 分子量: 443.462
• InChiKey: UHNQAQVLGQKNDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-azidophenylmethanol 在 sodiumsulfide nonahydrate 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 0.33h， 生成 N-butyl-4-amino-1,8-naphthalimide
  参考文献：
  名称：

  A colorimetric and ratiometric fluorescent probe for the imaging of endogenous hydrogen sulphide in living cells and sulphide determination in mouse hippocampus

  摘要：

  我们开发了一种基于萘啶酰亚胺-叠氮化物的比色法和比率法荧光探针 NAP-1，用于选择性和灵敏地检测硫化氢。探针 NAP-1 的优点包括检测限低（110 nM）、选择性好、灵敏度高和光稳定性好。在 PBS 缓冲液和牛血清中分别观察到了发射强度比和硫化物浓度之间的线性关系。我们的探针有助于活细胞中内源性 H2S 的比率测定和成像。此外，该探针还被成功应用于测量人血浆和小鼠海马中的内源性硫化物。在脂多糖诱导的神经炎症相关疾病小鼠模型的海马中观察到硫化物水平和 CBS mRNA 表达的明显降低，这表明内源性 H2S 水平的降低可能与神经炎症相关的神经退行性疾病的发病机制有关。

  DOI：

  10.1039/c4ob00285g
• 作为产物：
  描述：

  N-butyl-4-nitro-1,8-naphthalimide 在 盐酸 、 4-二甲氨基吡啶 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.25h， 生成 4-azidophenylmethanol
  参考文献：
  名称：

  Ratiometric Two-Photon Fluorescent Probes for Mitochondrial Hydrogen Sulfide in Living Cells

  摘要：

  Hydrogen sulfide (H2S) is an important signaling molecule with diverse biological roles. Various fluorescent probes for H2S with biological application have been developed. However, two-photon ratiometric imaging of mitochondrial H2S is scarce. In this paper, we report two ratiometric two-photon probes, AcHS-1 and AcHS-2, which employ 4-amino-1,8-naphthalimide as the fluorophore and 4azidobenzyl carbamate as the H2S response site. These probes exhibit high selectivity toward H2S over biothiols and other reactive species, low detection limits of 50-85 nM, low cytotoxicity, and high stability under physiological conditions. Furthermore, through cell imaging with one-photon and two-photon microscopy, MCF-7 cells incubated with two probes show a from marked change in emission color blue to green in response to I-Ie. Cell images es costraining with a mitochondria] dye reveal that AcHS-2 is a mitochondria-specific two-photon probe for H2S. These results show that AcHS-2 may find useful applications in biological research such as tracking mitochondria] H2S in living biological specimens.

  DOI：

  10.1021/jo5014838

文献信息

• A colorimetric and ratiometric fluorescent probe for the imaging of endogenous hydrogen sulphide in living cells and sulphide determination in mouse hippocampus
  作者：Ling Zhang、Sai Li、Mei Hong、Yuqing Xu、Shuaishuai Wang、Yi Liu、Yong Qian、Jing Zhao

  DOI：10.1039/c4ob00285g

  日期：——

  A naphthalimide-azide based colorimetric and ratiometric fluorescent probe, NAP-1, has been developed for the selective and sensitive detection of hydrogen sulphide. Advantages of the probe NAP-1 include a low detection limit (110 nM), good selectivity, high sensitivity and excellent photostability. A linear relationship between the emission intensity ratios and sulphide concentrations was observed in PBS buffer and bovine serum, respectively. Our probe facilitates ratiometric determination and imaging of endogenous H2S in living cells. Furthermore, this probe was successfully applied to the measurement of endogenous sulphide in human plasma and mouse hippocampus. A significant reduction in sulphide levels and CBS mRNA expression was observed in the hippocampus of mouse models of lipopolysaccharide-induced neuroinflammation-related diseases, suggesting that decreased levels of endogenous H2S might be involved in the pathogenesis of neuroinflammation-related neurodegenerative diseases.

  我们开发了一种基于萘啶酰亚胺-叠氮化物的比色法和比率法荧光探针 NAP-1，用于选择性和灵敏地检测硫化氢。探针 NAP-1 的优点包括检测限低（110 nM）、选择性好、灵敏度高和光稳定性好。在 PBS 缓冲液和牛血清中分别观察到了发射强度比和硫化物浓度之间的线性关系。我们的探针有助于活细胞中内源性 H2S 的比率测定和成像。此外，该探针还被成功应用于测量人血浆和小鼠海马中的内源性硫化物。在脂多糖诱导的神经炎症相关疾病小鼠模型的海马中观察到硫化物水平和 CBS mRNA 表达的明显降低，这表明内源性 H2S 水平的降低可能与神经炎症相关的神经退行性疾病的发病机制有关。
• Ratiometric Two-Photon Fluorescent Probes for Mitochondrial Hydrogen Sulfide in Living Cells
  作者：Xiu-Ling Liu、Xiao-Jiao Du、Chun-Guang Dai、Qin-Hua Song

  DOI：10.1021/jo5014838

  日期：2014.10.17

  Hydrogen sulfide (H2S) is an important signaling molecule with diverse biological roles. Various fluorescent probes for H2S with biological application have been developed. However, two-photon ratiometric imaging of mitochondrial H2S is scarce. In this paper, we report two ratiometric two-photon probes, AcHS-1 and AcHS-2, which employ 4-amino-1,8-naphthalimide as the fluorophore and 4azidobenzyl carbamate as the H2S response site. These probes exhibit high selectivity toward H2S over biothiols and other reactive species, low detection limits of 50-85 nM, low cytotoxicity, and high stability under physiological conditions. Furthermore, through cell imaging with one-photon and two-photon microscopy, MCF-7 cells incubated with two probes show a from marked change in emission color blue to green in response to I-Ie. Cell images es costraining with a mitochondria] dye reveal that AcHS-2 is a mitochondria-specific two-photon probe for H2S. These results show that AcHS-2 may find useful applications in biological research such as tracking mitochondria] H2S in living biological specimens.