16-bromo-1-hexadecanethiol | 1362855-77-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: 16-bromo-1-hexadecanethiol
• 英文别名: 16-Bromo-1-hexadecanethiol；16-bromohexadecane-1-thiol
• CAS: 1362855-77-3
• 化学式: C₁₆H₃₃BrS
• 分子量: 337.408
• InChiKey: DYYIACMPWUIXJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  octa acid 、 16-bromo-1-hexadecanethiol 在 sodium hydroxide 作用下， 以 重水 为溶剂， 生成
  参考文献：
  名称：

  Electrostatic Control of Macrocyclization Reactions within Nanospaces

  摘要：

  The intrinsic structural complexity of proteins makes it hard to identify the contributions of each noncovalent interaction behind the remarkable rate accelerations of enzymes. Coulombic forces are evidently primary, but despite developments in artificial nanoreactor design, a picture of the extent to which these can contribute has not been forthcoming. Here we report on two supramolecular capsules that possess structurally identical inner-spaces that differ in the electrostatic potential (EP) field that envelops them: one positive and one negative. This architecture means that only changes in the EP field influence the chemical properties of encapsulated species. We quantify these influences via acidity and rates of cyclization measurements for encapsulated guests, and we confirm the primary role of Coulombic forces with a simple mathematical model approximating the capsules as Born spheres within a continuum dielectric. These results reveal the reaction rate accelerations possible under Coulombic control and highlight important design criteria for nanoreactors.

  DOI：

  10.1021/jacs.9b02287
• 作为产物：
  描述：

  1,16-二溴十六烷 在 sodium methylate 、 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 16-bromo-1-hexadecanethiol
  参考文献：
  名称：

  Cationic surface modification of gold nanoparticles for enhanced cellular uptake and X-ray radiation therapy

  摘要：

  具有阳离子表面修饰的金纳米颗粒可以通过增强细胞摄取来增强X射线放疗的效果。

  DOI：

  10.1039/c5tb00766f

文献信息

• Solution NMR Analysis of Ligand Environment in Quaternary Ammonium-Terminated Self-Assembled Monolayers on Gold Nanoparticles: The Effect of Surface Curvature and Ligand Structure
  作者：Meng Wu、Ariane M. Vartanian、Gene Chong、Arun Kumar Pandiakumar、Robert J. Hamers、Rigoberto Hernandez、Catherine J. Murphy

  DOI：10.1021/jacs.8b11445

  日期：2019.3.13

  diameter of the particles increases from 1.2 nm to ∼13 nm. Molecular dynamics simulations of 4, 6, and 8 nm (11-mercaptoundecyl)trimethylammonium bromide-capped AuNSs confirm greater hydrophobic chain packing order and saturation of charged headgroups within the same spherical ligand shell at larger nanoparticle sizes and higher ligand densities. Combining the NMR studies and MD simulations, we suggest

  我们报告了基于溶液 NMR 的（16-巯基十六烷基）三甲基溴化铵（MTAB）自组装单分子层在胶体金纳米球（AuNSs）上的分析，其直径为 1.2 到 25 nm，金纳米棒（AuNRs）的纵横比为 1.4 到 3.9 . 来自溶剂暴露的结合配体头部基团的质子信号的化学位移分析表明，随着纳米粒子的尺寸增加超过~10 nm，头部基团在配体壳上饱和。定量 NMR 表明 MTAB-AuNSs 的配体密度与尺寸有关。配体密度范围从 25 nm 颗粒的每 nm2 〜3 个分子到〜10 nm 的每 nm2 高达 5-6 个分子，以及用于原位测量结合配体的更小颗粒；在 I2/I- 处理蚀刻掉金核后，配体密度范围从 25 nm 颗粒的每纳米 2 分子到 10 纳米和更小颗粒的每纳米 4-5 个分子。T2 弛豫分析表明，随着颗粒直径从 1.2 nm 增加到 13 nm，烃链的有序性更高，头部运动更少。4、6 和
• Quantitative Replacement of Cetyl Trimethylammonium Bromide by Cationic Thiol Ligands on the Surface of Gold Nanorods and Their Extremely Large Uptake by Cancer Cells
  作者：Leonid Vigderman、Pramit Manna、Eugene R. Zubarev

  DOI：10.1002/anie.201107304

  日期：2012.1.16

  Stable and biocompatible: The chemical composition of synthesized cationic thiolate‐monolayer‐protected gold nanorods was precisely determined. In vitro cell culture experiments showed no cytotoxicity of these nanorods, and the number of nanorods that were taken up by each cancer cell exceeded two million particles (see picture).

  稳定且具有生物相容性：精确确定了合成的阳离子硫醇盐单层保护的金纳米棒的化学组成。体外细胞培养实验显示这些纳米棒没有细胞毒性，每个癌细胞吸收的纳米棒数量超过200万个颗粒（见图）。
• DRUG DELIVERY FROM IMPLANTS USING SELF-ASSEMBLED MONOLAYERS-THERAPEUTIC SAMS
  申请人：Agrawal C. Mauli

  公开号：US20090123516A1

  公开（公告）日：2009-05-14

  Disclosed are medical devices comprising one or more surfaces, one or more SAM molecules attached to the one or more surfaces of the medical device, and one or more therapeutic agents attached to the one or more self-assembled monolayer molecules. Also disclosed are medical devices comprising one or more surfaces, one or more self-assembled monolayer molecules attached to the one or more surfaces of the medical device, one or more linkers comprising a first functional group and a second functional group, the first functional group attached to the self-assembled monolayer molecule and a therapeutic agent attached to the second functional group. The therapeutic agent may be attached to the SAM molecule via a linker. The present invention also concerns methods of administering a therapeutic agent to a subject, comprising contacting the subject with one of the medical devices set forth herein.
• [EN] DRUG DELIVERY FROM IMPLANTS USING SELF-ASSEMBLED MONOLAYERS - THERAPEUTIC SAMS<br/>[FR] LIBERATION DE MEDICAMENTS PAR DES IMPLANTS COMPRENANT DES MONOCOUCHES AUTO-ASSEMBLEES (SAM) SAM THERAPEUTIQUES
  申请人：UNIV TEXAS

  公开号：WO2007019478A2

  公开（公告）日：2007-02-15

  [EN] Disclosed are medical devices comprising one or more surfaces, one or more SAM molecules attached to the one or more surfaces of the medical device, and one or more therapeutic agents attached to the one or more self-assembled monolayer molecules. Also disclosed are medical devices comprising one or more surfaces, one or more self-assembled monolayer molecules attached to the one or more surfaces of the medical device, one or more linkers comprising a first functional group and a second functional group, the first functional group attached to the self-assembled monolayer molecule and a therapeutic agent attached to the second functional group. The therapeutic agent may be attached to the SAM molecule via a linker. The present invention also concerns methods of administering a therapeutic agent to a subject, comprising contacting the subject with one of the medical devices set forth herein.
  [FR] L'invention concerne des dispositifs médicaux comprenant une ou plusieurs surfaces, une ou plusieurs molécules SAM attachées à une ou plusieurs surfaces du dispositif médical, et un ou plusieurs agents thérapeutiques fixés sur les molécules de la ou des monocouches auto-assemblées. L'invention concerne en outre des dispositifs médicaux comprenant une ou plusieurs surfaces, une ou plusieurs molécules de monocouche auto-assemblée fixées à la surface ou aux surfaces du dispositif médical, un ou plusieurs lieurs comprenant un premier groupe fonctionnel et un second groupe fonctionnel, le premier groupe fonctionnel étant attaché à la molécule de la monocouche auto-assemblée, et un agent thérapeutique attaché au second groupe fonctionnel. L'agent thérapeutique peut être fixé sur la molécule SAMS par l'intermédiaire d'un lieur. L'invention porte également sur des procédés d'administration d'un agent thérapeutique à un sujet consistant appliquer un dispositif médical du type décrit à un sujet.