(10-hydroxydecyl)triphenylphosphonium bromide | 64417-10-3

• 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: (10-hydroxydecyl)triphenylphosphonium bromide
• 英文别名: 10-Hydroxy-n-decyltriphenylphosphonium bromide；10-hydroxydecyl(triphenyl)phosphanium;bromide
• CAS: 64417-10-3
• 化学式: Br*C₂₈H₃₆OP
• 分子量: 499.471
• InChiKey: BJVDVGYADREGEB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (10-hydroxydecyl)triphenylphosphonium bromide 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 29.0h， 生成 14Z-3-Oxotetracosen-24-olide
  参考文献：
  名称：

  Lermer, Leonard; Neeland, Edward G.; Ounsworth, James P., Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1427 - 1445

  摘要：

  DOI：
• 作为产物：
  描述：

  1,10-癸二醇 在 氢溴酸 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 90.0h， 生成 (10-hydroxydecyl)triphenylphosphonium bromide
  参考文献：
  名称：

  奉克瑞奇酸启发的新型有效凋亡抑制剂的分子设计，合成和评价

  摘要：

  邦克里克酸（BKA）是腺嘌呤核苷酸转位酶（ANT）的抑制剂。由于ANT的抑制与细胞色素c的抑制有关从线粒体释放，然后导致细胞凋亡的抑制，它已被用作细胞凋亡机制研究的工具。BKA由具有两个不对称中心的长碳链，一个非共轭烯烃，两个共轭二烯，三个甲基，一个甲氧基和三个羧酸组成。这种复杂的化学结构在合成，供应和生化机理研究中造成了困难。在这项研究中，我们设计并合成了更多受BKA分子结构启发的简单三羧酸。然后评估了它们在HeLa细胞中的细胞毒性和防止凋亡活性以及对HL-60细胞中线粒体内膜电位（ΔΨm）的影响。所有测试的三羧酸衍生物（包括BKA）对HeLa细胞的毒性均很小。BKA和两个合成的衍生物显着抑制星形孢菌素（STS）诱导的细胞活力降低。此外，通过用BKA和三羧酸衍生物预处理，STS诱导的ΔΨm塌陷得以显着恢复。其中三种羧酸之一被酯化的其他衍生物表现出强毒性，尤其是带有与BKA相同长度的碳链的

  DOI：

  10.1021/tx300315h

文献信息

• Phosphonioalkylthiosulfate zwitterions—new masked thiol ligands for the formation of cationic functionalised gold nanoparticles
  作者：Yon Ju-Nam、Neil Bricklebank、David W. Allen、Philip H. E. Gardiner、Mark E. Light、Michael B. Hursthouse

  DOI：10.1039/b610480k

  日期：——

  We report the synthesis and structural characterisation of a new family of stable phosphonioalkylthiosulfate zwitterions, R3P+(CH2)nS2O3− (R = Ph or Bu, n = 3,4,6, 8 or 10) which behave as cationic masked thiolate ligands with applications in the functionalisation of gold nanoparticles, having potential as new diagnostic biorecognition systems. The ligands were prepared by treatment of ω-bromoalkylphosphonium salts with sodium thiosulfate. The crystal and molecular structures of the zwitterions (R = Ph, n = 3) and (R = Bu, n = 3) were determined. A series of phosphonioalkanethiolate-capped gold nanoparticles dispersed in water was prepared by borohydride reduction of potassium tetrachloroaurate in the presence of the zwitterions in a dichloromethane–water system. UV-visible spectroscopy and scanning transmission electron-microscopy indicated that capped nanoparticles of ca. 5 nm diameter were present.

  我们报道了一类新型稳定的膦氧烷基硫代硫酸酯两性离子R3P+(CH2)nS2O3â的合成与结构表征，其中R为苯基或丁基，n为3、4、6、8或10，这些化合物作为阳离子型掩蔽硫醇盐配体，用于功能化金纳米粒子，具有作为新型生物诊断识别系统的潜力。这些配体是通过用硫代硫酸钠处理Ï-溴代烷基磷盐来制备的。我们对(R=苯基，n=3)和(R=丁基，n=3)两性离子的晶体和分子结构进行了测定。通过在二氯甲烷-水体系中，在两性离子存在下用硼氢化钠还原四氯金酸钾，制备了一系列分散于水的膦氧烷基硫醇盐包覆的金纳米粒子。紫外-可见光谱和扫描透射电子显微镜表明存在直径约为5纳米的包覆纳米粒子。
• Biosynthesis of iso-fatty acids in myxobacteria
  作者：Jeroen S. Dickschat、Helge B. Bode、Reiner M. Kroppenstedt、Rolf Müller、Stefan Schulz

  DOI：10.1039/b504889c

  日期：——

  The fatty acid (FA) profiles of the myxobacteria Stigmatella aurantiaca and Myxococcus xanthus were investigated by acidic methanolysis of total cell extracts and GC or GC-MS analysis. The main components were 13-methyltetradecanoic acid (iso-15:0) and (Z)-hexadec-11-enoic acid (16:1, ω-5 cis). The biosynthesis of iso-FAs was investigated in several feeding experiments. Feeding of isovaleric acid (IVA) to a mutant impaired in the degradation of leucine to isovaleryl-CoA (IV–CoA) (bkd mutant) of M. xanthus only increased the amount of iso-odd FAs, whereas feeding of isobutyric acid (IBA) gave increased amounts only of iso-even FAs. In contrast, a bkd mutant of S. aurantiaca gave increased amounts of iso-odd and iso-even fatty acids in both experiments. We assumed that in S. aurantiaca α-oxidation takes place. [D7]-15-Methylhexadecanoic acid (8) was synthesised and fed to S. aurantiaca as well as [D10]leucine and [D8]valine to elucidate this pathway in more detail. The iso-fatty acid 8 was degraded by α- and β-oxidation steps. [D10]Leucine was strongly incorporated into iso-odd and iso-even fatty acids, whereas the incorporation rates for [D8]valine into both types of fatty acids were low. Thus α-oxidation plays an important role in the biosynthesis of iso-fatty acids in S. aurantiaca. The incorporation rates observed after feeding of [D10]leucine and [D8]valine are the highest for iso-17:0 compared to the other acids. This indicates the central role of iso-17:0 in the biosynthesis of iso-FAs. The shorter homologues seem to be formed mainly by α-oxidation and β-oxidation of this acid. After feeding of 8 traces of unsaturated counterparts of this labelled FA occurred in the extracts indicating that desaturases are active in the biosynthesis of unsaturated fatty acids in S. aurantiaca.

  通过总细胞提取物的酸性甲醇分解和气相色谱或气相色谱-质谱分析，研究了粘细菌斯图亚特氏菌（Stigmatella aurantiaca）和黄杆菌（Myxococcus xanthus）的脂肪酸（FA）谱。主要成分是13-甲基十四烷酸（iso-15:0）和（Z）-十六碳-11-烯酸（16:1，ω-5顺式）。在几个喂养实验中研究了iso-FA的生物合成。将异戊酸（IVA）喂养给M. xanthus的一个突变体，该突变体在将亮氨酸降解为异戊酰-CoA（IV-CoA）过程中受损（bkd突变体），仅增加了iso-奇数FA的含量，而喂养异丁酸（IBA）仅增加了iso-偶数FA的含量。相比之下，S. aurantiaca的bkd突变体在两个实验中都增加了iso-奇数和iso-偶数脂肪酸的含量。我们假设S. aurantiaca中发生了α氧化。合成了[D7]-15-甲基十六烷酸（8），并将其与[D10]亮氨酸和[D8]缬氨酸一起喂养给S. aurantiaca，以更详细地阐明此途径。iso-脂肪酸8通过α和β氧化步骤降解。[D10]亮氨酸强烈掺入iso-奇数和iso-偶数脂肪酸中，而[D8]缬氨酸掺入这两种类型的脂肪酸中的速率较低。因此，α氧化在S. aurantiaca中iso-脂肪酸的生物合成中起重要作用。在喂养[D10]亮氨酸和[D8]缬氨酸后观察到的掺入速率，与其它酸相比，iso-17:0是最高的。这表明iso-17:0在iso-FA的生物合成中起核心作用。较短的同系物似乎主要通过这种酸的α氧化和β氧化形成。在喂养8后，提取物中出现了这种标记FA的未饱和对应物的痕迹，表明在S. aurantiaca中未饱和脂肪酸的生物合成中存在脱氢酶活性。
• 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
• Synthesis of insect sex pheromones and their homologues. 2. A convenient method for synthesizing (Z)-alkenols and their acetates.
  作者：Michio HORIIKE、Masaru TANOUCHI、Chisato HIRANO

  DOI：10.1271/bbb1961.44.257

  日期：——

  (Z)-Alkenols and Their acetates have been synthesized by the Wittig reaction of (ω-hydroxyalkyl)triphenylphosphonium salts with alkanals by a convenient procedure. The geometrical purity of the products was evaluated to be no less than 95% of the (Z)-configu-ration by means of GLC with a glass capillary column coated with CHDMS.

  通过一种简便的方法，利用Wittig反应将（ω-羟基烷基）三苯基膦盐与烷基醛反应，合成了（Z）-烯醇及其乙酸酯。通过涂有CHDMS的玻璃毛细管柱进行GC分析，评估产物的几何纯度不小于95%的（Z）构型。
• 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。