triphenyl(10-((3,4,5-trihydroxybenzoyl)oxy)decyl)phosphonium bromide | 1581234-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: triphenyl(10-((3,4,5-trihydroxybenzoyl)oxy)decyl)phosphonium bromide
• 英文别名: Triphenyl-[10-(3,4,5-trihydroxybenzoyl)oxydecyl]phosphanium;bromide；triphenyl-[10-(3,4,5-trihydroxybenzoyl)oxydecyl]phosphanium;bromide
• CAS: 1581234-54-9
• 化学式: Br*C₃₅H₄₀O₅P
• 分子量: 651.577
• InChiKey: KDIRFNXSUJACSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  10-溴-1-癸醇 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 triphenyl(10-((3,4,5-trihydroxybenzoyl)oxy)decyl)phosphonium bromide
  参考文献：
  名称：

  从苯甲酸衍生的亲脂性阳离子的连续流动合成作为人头颈癌细胞系中的新细胞毒性化学实体

  摘要：

  连续流动化学用于合成一系列离域亲脂性三苯基鏻阳离子 (DLC)，这些阳离子通过酯官能团与几种羟基化苯甲酸衍生物相连，并在反应时间和选择性方面进行评估。合成的化合物在头颈部肿瘤细胞系中显示出细胞毒活性和选择性。分子的作用机制涉及线粒体解偶联效应和细胞内 ATP 产生和细胞凋亡诱导的减少。

  DOI：

  10.1039/d0md00153h

文献信息

• Novel benzoate-lipophilic cations selectively induce cell death in human colorectal cancer cell lines
  作者：José Antonio Jara、Diego Rojas、Vicente Castro-Castillo、Sebastián Fuentes-Retamal、Cristian Sandoval-Acuña、Eduardo Parra、Mario Pavani、Juan Diego Maya、Jorge Ferreira、Mabel Catalán

  DOI：10.1016/j.tiv.2020.104814

  日期：2020.6

  triphenylphosphonium group as a vehicle to target tumour mitochondria and improve their activity. We evaluated the cytotoxicity, selectivity, and mechanism of action of these derivatives, including the effects on energy stress-induced apoptosis and metabolic behaviour in the human CRC cell lines HCT-15 and COLO-205. RESULTS The benzoic acid derivatives selectively targeted the tumour cells with high potency and efficacy

  引言大肠癌（CRC）是世界范围内的重要健康问题。与CRC相关的肝和肺转移率很高，为有效治疗提供了重要的障碍。包括CRC细胞在内的肿瘤细胞具有代谢改变，例如高水平的糖酵解活性，增加的细胞增殖和侵袭性以及化学和放射抗性。但是，这些细胞的线粒体跨膜电位异常升高也为开发选择性靶向肿瘤细胞线粒体功能的药物提供了机会。方法在这项工作中，我们使用了一批具有细胞毒性并与三苯基ester基团连接的苯甲酸酯，作为靶向肿瘤线粒体并提高其活性的媒介。我们评估了细胞毒性，选择性，这些衍生物的作用机理，包括对人CRC细胞HCT-15和COLO-205中能量应激诱导的细胞凋亡和代谢行为的影响。结果苯甲酸衍生物可以高效，高效地选择性靶向肿瘤细胞。衍生物诱导了氧化磷酸化系统的解偶联，降低了跨膜电位，并降低了ATP水平，同时增加了AMPK活化，从而触发了两种测试的肿瘤细胞系中肿瘤细胞的凋亡。结论尽管这些肿瘤细胞具有多种代谢特
• Antiproliferative and Uncoupling Effects of Delocalized, Lipophilic, Cationic Gallic Acid Derivatives on Cancer Cell Lines. Validation in Vivo in Singenic Mice
  作者：José A. Jara、Vicente Castro-Castillo、Jorge Saavedra-Olavarría、Liliana Peredo、Mario Pavanni、Fabián Jaña、María Eugenia Letelier、Eduardo Parra、María Inés Becker、Antonio Morello、Ulrike Kemmerling、Juan Diego Maya、Jorge Ferreira

  DOI：10.1021/jm500174v

  日期：2014.3.27

  Tumor cells principally exhibit increased mitochondrial transmembrane potential (ΔΨ(m)) and altered metabolic pathways. The therapeutic targeting and delivery of anticancer drugs to the mitochondria might improve treatment efficacy. Gallic acid exhibits a variety of biological activities, and its ester derivatives can induce mitochondrial dysfunction. Four alkyl gallate triphenylphosphonium lipophilic cations were synthesized, each differing in the size of the linker chain at the cationic moiety. These derivatives were selectively cytotoxic toward tumor cells. The better compound (TPP(+)C10) contained 10 carbon atoms within the linker chain and exhibited an IC50 value of approximately 0.4-1.6 μM for tumor cells and a selectivity index of approximately 17-fold for tumor compared with normal cells. Consequently, its antiproliferative effect was also assessed in vivo. The oxygen consumption rate and NAD(P)H oxidation levels increased in the tumor cell lines (uncoupling effect), resulting in a ΔΨ(m) decrease and a consequent decrease in intracellular ATP levels. Moreover, TPP(+)C10 significantly inhibited the growth of TA3/Ha tumors in mice. According to these results, the antineoplastic activity and safety of TPP(+)C10 warrant further comprehensive evaluation.
• Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines
  作者：Mabel Catalán、Vicente Castro-Castillo、Javier Gajardo-de la Fuente、Jocelyn Aguilera、Jorge Ferreira、Ricardo Ramires-Fernandez、Ivonne Olmedo、Alfredo Molina-Berríos、Charlotte Palominos、Marcelo Valencia、Marta Domínguez、José A. Souto、José A. Jara

  DOI：10.1039/d0md00153h

  日期：——

  Continuous flow chemistry was used for the synthesis of a series of delocalized lipophilic triphenylphosphonium cations (DLCs) linked by means of an ester functional group to several hydroxylated benzoic acid derivatives and evaluated in terms of both reaction time and selectivity. The synthesized compounds showed cytotoxic activity and selectivity in head and neck tumor cell lines. The mechanism of

  连续流动化学用于合成一系列离域亲脂性三苯基鏻阳离子 (DLC)，这些阳离子通过酯官能团与几种羟基化苯甲酸衍生物相连，并在反应时间和选择性方面进行评估。合成的化合物在头颈部肿瘤细胞系中显示出细胞毒活性和选择性。分子的作用机制涉及线粒体解偶联效应和细胞内 ATP 产生和细胞凋亡诱导的减少。