Hexamethoxy hypericin | 120667-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: Hexamethoxy hypericin
• 英文别名: hexamethylhypericin；5,7,11,18,22,24-Hexamethoxy-13,16-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
• CAS: 120667-79-0
• 化学式: C₃₆H₂₈O₈
• 分子量: 588.614
• InChiKey: LDHRJKFNPLJNGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Hexamethoxy hypericin 在 磷酸 、 potassium iodide 作用下， 生成 hypericin
  参考文献：
  名称：

  Brockmann et al., Chemische Berichte, 1957, vol. 90, p. 2302,2314

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5,7,4',5',7'-hexamethoxy-2,2'-dimethyl-[1,1']bianthryl-9,10,9',10'-tetraone 在 盐酸 、 铜 、 溶剂黄146 、 丙酮 作用下， 生成 Hexamethoxy hypericin
  参考文献：
  名称：

  Brockmann et al., Chemische Berichte, 1957, vol. 90, p. 2302,2314

  摘要：

  DOI：

文献信息

• ANTHRAQUINONES FOR USE AS RADIOSENSITIZERS IN CANCER TREATMENT
  申请人：Schaffer Moshe

  公开号：US20130267757A1

  公开（公告）日：2013-10-10

  Provided is an a combination therapy including a radiosensitizing agent and radiation, and being effective to inhibit proliferation of cancer stem cells. Further provided is a combination which includes a radiosensitizing agent and radiation, and effectively reduces incidence of at least one of cancer relapse and metastatic cancer in a subject having a cancer, wherein the cancer includes cancer stem cells. Also provided are anthraquinone derivatives for use as radiosensitizing agents in combination with radiations, the combination therapy being cancer specific. Further, the radiosensitizing agents were found to be cancer specific, namely, some being more effective against a cancer type as compared to others.

  提供了一种联合治疗方案，包括放射增敏剂和放射治疗，能够有效抑制癌干细胞的增殖。此外，还提供了一种联合治疗方案，包括放射增敏剂和放射治疗，能够有效降低患有癌症的受试者中至少一种癌症复发和转移的发生率，其中该癌症包括癌干细胞。同时，提供了蒽醌衍生物作为放射增敏剂与放射线联合使用，该联合治疗方案具有癌症特异性。此外，发现放射增敏剂具有癌症特异性，即某些放射增敏剂对某种癌症类型比其他放射增敏剂更有效。
• 10.1562/0031-8655(2001)074<0164:ivsotp>2.0.co;2
  作者：Delaey、Obermueller、Zupko、De Vos、Falk、De Witte

  DOI：10.1562/0031-8655(2001)074<0164:ivsotp>2.0.co;2

  日期：——

  analogs with an increased hydrophilic character were synthesized. As chemical modifications alter the lipophilicity/hydrophilicity balance together with the photophysical/chemical background of the molecule the influence of these structural changes on the cellular uptake, retention and subcellular localization in HeLa cells was investigated. Besides, their photocytotoxic effects using three cell lines

  摘要 在本研究中，合成了亲水性增强的金丝桃素类似物。由于化学修饰改变了亲脂性/亲水性平衡以及分子的光物理/化学背景，因此研究了这些结构变化对 HeLa 细胞中细胞摄取、保留和亚细胞定位的影响。此外，还评估了它们使用三种细胞系（HeLa、MCF-7、A431）的光细胞毒性作用以及它们的血浆蛋白结合。为了评估金丝桃素及其类似物的相对亲水/亲油特性，在反相高效液相色谱 (C-18) 柱上测定它们的保留时间。除二苄基四甲基金丝桃素（118 分钟）外，所有金丝桃素类似物的保留时间均 < 46 分钟，而金丝桃素的保留时间 >200 分钟（溶剂系统：甲醇/柠檬酸盐缓冲液 30 mM pH 7；70/30）。金丝桃素、六、五和二苄基四甲基金丝桃素在光敏化后在纳摩尔范围内显示出有效的抗增殖作用 (3.6 J/cm2)。相反，光活化的四磺金丝桃素和条纹石 D 对三种细胞系没有抗增殖作用，而金丝桃素聚乙二醇对 A431
• Spectroscopic Investigation of the Molecular Structure of Hypericin and its Salts
  作者：Evgeny I. Kapinus、Heinz Falk、Huyen T. N. Tran

  DOI：10.1007/pl00010243

  日期：1999.5

  Based on the interpretation of UV/Vis, IR, and NMR spectra of hypericin as well as of its salts: and the products of total O-methylation, it was concluded that hypericin transfers from solid state to low or moderate polar organic media as its 1,6-dioxo-tautomer, thereby conserving the molecular structure characteristic for the crystalline state of the material. In concentrated hypericin solutions, the 1,6-dioxo isomer converts slowly into the 7,14-dioxo isomer. Dilution of the solution or addition of pyridine DMSO, or other polar compounds accelerates the reaction. The metastable hypericin 1,6-dioxo-tautomer is stabilized in the solid phase and concentrated solutions by intermolecular hydrogen bonds. Salts of hypericin with alkali metals retain the structure of the 7,14-dioxo-tautomer both in solutions and crystalline state.
• Observation of Excited-State Tautomerization in the Antiviral Agent Hypericin and Identification of Its Fluorescent Species
  作者：F. Gai、M. J. Fehr、J. W. Petrich

  DOI：10.1021/j100073a036

  日期：1994.6

  The absorption spectra, fluorescence spectra, and fluorescence lifetimes of hypericin, an analog lacking hydroxyl groups, mesonaphthobianthrone, and hexamethylhypericin are obtained in aprotic and protic solvents. In aprotic solvents, mesonaphtobianthrone is nonfluorescent. In strong acids such as sulfuric or triflic acids, it becomes fluorescent. Furthermore, its spectrum is very similar to that of hypericin. Similarly, only in sulfuric acid does hexamethylhypericin afford absorption and emission spectra resembling those of hypericin. We therefore conclude that the fluorescent species of hypericin has one or both of its carbonyl groups protonated. The protonation equilibrium in both the ground and the excited state is discussed. The first detailed measurements of the primary processes in the antiviral agent, hypericin, are performed with picosecond resolution and a white-light continuum. Transient absorption measurements of hypericin with similar to 1-ps resolution indicate that upon optical excitation a new species is created that absorbs in the range of roughly 580-640 nm. This species exhibits a 6-12-ps decay, depending on the solvent. It is also observed that the stimulated emission signal, which arises from the fluorescent state, grows in with a time constant of 6-12 ps. Based upon the identification of the fluorescent species as hypericin with one or both carbonyl groups protonated, the rise time for the appearance of the stimulated emission signal is attributed to excited-state tautomerization.