4-iodomethylene violet | 195193-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 4-iodomethylene violet
• 英文别名: 7-(Dimethylamino)-4-iodo-3H-phenothiazin-3-one；7-(dimethylamino)-4-iodophenothiazin-3-one
• CAS: 195193-88-5
• 化学式: C₁₄H₁₁IN₂OS
• 分子量: 382.225
• InChiKey: PWTHTNNPBKTNMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 4-iodomethylene violet 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 O-methyl 4-iodomethylene violet
  参考文献：
  名称：

  带正电荷的亚甲基紫类似物的光生物学特性

  摘要：

  摘要 制备了 O-甲基亚甲基紫 (OMeMV)、O-甲基溴亚甲基紫 (OMeBrMV) 和 O-甲基碘亚甲基紫 (OMeIMV) 以测试它们作为抗病毒和抗肿瘤光毒性染料的潜在用途。KB 细胞在 633 nm 照射下的光敏毒性率为 (×10−19 光子−1)：OMeIMV、OMeBrMV、亚甲基紫 (MV) 和 OMeMV 分别为 2.4、2.2、1.9 和 0.17。633 nm 辐照磷酸盐缓冲盐水中辛德毕斯病毒的光敏灭活率为 (×10−18 光子−1)：MV、OMeIMV、OMeBrMV 和 OMeMV 分别为 3.3、1.8、0.99、0.15。单线态氧形成的量子效率确定为 OMeIMV，0.64；OMeBrMV，0.40；OMeMV，0.054。用双链 (ds) DNA 滴定染料导致可见吸收光谱中的红移和减色效应。通过平衡透析和紫外吸收滴定数据的 Scatchard 分析确定甲基化染料与

  DOI：

  10.1562/0031-8655(2000)071<0020:ppopcm>2.0.co;2
• 作为产物：
  描述：

  亚甲紫 在 盐酸 、 potassium iodate 、 potassium iodide 、 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-iodomethylene violet
  参考文献：
  名称：

  Photobiological Properties of Methylene Violet

  摘要：

  AbstractThe interaction of methylene violet (MV) and 4‐bromo‐methylene violet (BrMV) with calf thymus and super‐coiled φX174 phage RF I DNA is reported. Measurements employing UV‐visible absorption spectroscopy and equilibrium dialysis give evidence for the formation of complexes by each dye with DNA in the dark. They covalently bind to DNA, and MV nicks DNA, when the nucleic acid/dye mixtures are irradiated with visible light in a deoxygenated environment. Quantum efficiencies for singlet oxygen formation are 0.27 and 0.25 for MV and BrMV, respectively. A higher value (0.49) is observed for 4‐iodomethyIene violet (IMV).SummaryThe MV and BrMV interact with DNA in the dark to form complexes that are observable by absorption and emission spectroscopy and by equilibrium dialysis. When mixtures of the dyes and DNA are irradiated with visible light, both incorporation of the dye into the nucleic acid and nicking of the DNA are observed. These dyes generate singlet oxygen with quantum yields ranging from 0.25 for MV to 0.49 for IMV.

  DOI：

  10.1111/j.1751-1097.1997.tb08650.x

文献信息

• Photobiological Properties of Positively Charged Methylene Violet Analogs
  作者：Melissa A. Houghtaling、Rushika Perera、Katherine E. Owen、Stephen Wagner、Richard J. Kuhn、Harry Morrison

  DOI：10.1562/0031-8655(2000)071<0020:ppopcm>2.0.co;2

  日期：——

  Abstract O-Methyl methylene violet (OMeMV), O-methyl bromomethylene violet (OMeBrMV) and O-methyl iodomethylene violet (OMeIMV) have been prepared in order to test their potential utility as anti-viral and anti-tumor phototoxic dyes. Rates of photosensitized toxicity of KB cells with 633 nm irradiation are (×10−19 photon−1): 2.4, 2.2, 1.9 and 0.17 for OMeIMV, OMeBrMV, methylene violet (MV) and OMeMV

  摘要 制备了 O-甲基亚甲基紫 (OMeMV)、O-甲基溴亚甲基紫 (OMeBrMV) 和 O-甲基碘亚甲基紫 (OMeIMV) 以测试它们作为抗病毒和抗肿瘤光毒性染料的潜在用途。KB 细胞在 633 nm 照射下的光敏毒性率为 (×10−19 光子−1)：OMeIMV、OMeBrMV、亚甲基紫 (MV) 和 OMeMV 分别为 2.4、2.2、1.9 和 0.17。633 nm 辐照磷酸盐缓冲盐水中辛德毕斯病毒的光敏灭活率为 (×10−18 光子−1)：MV、OMeIMV、OMeBrMV 和 OMeMV 分别为 3.3、1.8、0.99、0.15。单线态氧形成的量子效率确定为 OMeIMV，0.64；OMeBrMV，0.40；OMeMV，0.054。用双链 (ds) DNA 滴定染料导致可见吸收光谱中的红移和减色效应。通过平衡透析和紫外吸收滴定数据的 Scatchard 分析确定甲基化染料与
• Photobiological Properties of Methylene Violet
  作者：Harry Morrison、Taj Mohammad、Ravi Kurukulasuriya

  DOI：10.1111/j.1751-1097.1997.tb08650.x

  日期：1997.8

  AbstractThe interaction of methylene violet (MV) and 4‐bromo‐methylene violet (BrMV) with calf thymus and super‐coiled φX174 phage RF I DNA is reported. Measurements employing UV‐visible absorption spectroscopy and equilibrium dialysis give evidence for the formation of complexes by each dye with DNA in the dark. They covalently bind to DNA, and MV nicks DNA, when the nucleic acid/dye mixtures are irradiated with visible light in a deoxygenated environment. Quantum efficiencies for singlet oxygen formation are 0.27 and 0.25 for MV and BrMV, respectively. A higher value (0.49) is observed for 4‐iodomethyIene violet (IMV).SummaryThe MV and BrMV interact with DNA in the dark to form complexes that are observable by absorption and emission spectroscopy and by equilibrium dialysis. When mixtures of the dyes and DNA are irradiated with visible light, both incorporation of the dye into the nucleic acid and nicking of the DNA are observed. These dyes generate singlet oxygen with quantum yields ranging from 0.25 for MV to 0.49 for IMV.