6-(N-dipicoylaminoethyl)hexylamine | 893418-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(N-dipicoylaminoethyl)hexylamine
• 英文别名: dipicolyl-1,6-hexadiamine；N(1),N(1)-bis((pyridin-2-yl)methyl)hexane-1,6-diamine；N',N'-bis(pyridin-2-ylmethyl)hexane-1,6-diamine
• CAS: 893418-31-0
• 化学式: C₁₈H₂₆N₄
• 分子量: 298.431
• InChiKey: DBMKSJGEJNYVIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  万古霉素 、 6-(N-dipicoylaminoethyl)hexylamine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到dipi-van
  参考文献：
  名称：

  具有焦磷酸盐结合基团的万古霉素衍生物：对抗万古霉素耐药细菌的策略

  摘要：

  万古霉素是革兰氏阳性细菌感染的最后手段，但由于这种细菌出现耐药性，万古霉素也已失效。为了对抗耐万古霉素的细菌（VRB）的威胁，我们报道了二烯丙基-万古霉素共轭物（Dipi-van）的开发，该共轭物可增强VRB对细胞壁生物合成的抑制作用，并且其体外活性超过比万古霉素高两个数量级。二锌基部分（锌结合配体）的缀合赋予母体药物与细胞壁脂质的焦磷酸基团结合的能力，同时保持了对细胞壁前体五肽末端的固有结合亲和力。此外，经过数次连续传球后，未发现可检测到的抗性，VRB肾脏感染的小鼠模型中的-1。本报告中提出的发现强调了我们应对VRB感染策略的潜力。

  DOI：

  10.1002/anie.201601621
• 作为产物：
  描述：

  苄基(6-氨基己基)氨基甲酸酯盐酸盐(1:1) 在 10% Pd/C 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-(N-dipicoylaminoethyl)hexylamine
  参考文献：
  名称：

  Synthesis and characterization of well-defined l-lactic acid-caprolactone co-oligomers and their rhenium (I) and technetium(I) conjugates

  摘要：

  Staring from L-lactide and epsilon-caprolactone, the corresponding lactic-caprolactone cooligomer with hydroxyl and carboxylic acid groups were synthesized. These oligomers were connected with chelating groups through a long chain tether, ready for transition metal binding. Coordination of organometallic rhenium(I) and technetium(I) complexes generated the conjugates in high yield and short time, satisfying the requirements for short-lived radiopharmaceuticals in clinical applications. A reasonable pharmacophore model has been established to guide the design of well-defined lactic acid oligomer for nuclear medicine. Crown Copyright (C) 2012 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.06.001

文献信息

• Synthesis, Cytotoxicity, and Insight into the Mode of Action of Re(CO)3 Thymidine Complexes
  作者：Mark D. Bartholomä、Anthony R. Vortherms、Shawn Hillier、Birgit Ploier、John Joyal、John Babich、Robert P. Doyle、Jon Zubieta

  DOI：10.1002/cmdc.201000196

  日期：2010.9.3

  and C5 with spacers of various lengths. The corresponding organometallic thymidine complexes were fully characterized by IR and NMR spectroscopy and mass spectrometry. Their cytotoxicity was assessed against the A549 lung carcinoma cell line. Toxicity is dependent on the site and mode of conjugation as well as on the nature and the length of the tether. Moderate toxicity was observed for conjugates carrying

  核苷类似物被广泛用于癌症和病毒性疾病的治疗。迄今为止，几乎没有研究过有机or（I）配合物的抗增殖特性。在这里，我们介绍胸苷和尿苷的Re I（CO）3核心配合物的合成，表征和体外评估。用于绑定Re I（CO）3作为核心，在位置C5'，C2'，N3和C5处引入具有不同长度间隔基的三齿二聚二烯丙基胺金属螯合物。相应的有机金属胸苷配合物通过IR和NMR光谱法和质谱法充分表征。评估了它们对A549肺癌细胞系的细胞毒性。毒性取决于结合的部位和方式，以及系链的性质和长度。观察到用于承载铼部分在位置C5'或N3缀合物中等毒性（IC 50 = 124-160μ中号）。对于在C2'或C5处修饰的复合物，未观察到毒性。在C5'处带有十二碳烯间隔基的配合物53具有显着的毒性，并且比顺铂更有效，IC 50为50的6.0μ值中号。据我们所知，这是[M（CO）3 ] + 1-核苷结合物的抗增殖特性的首次报道。在使用A5
• Zn2+ fluorescent chemosensors and the influence of their spacer length on tuning Zn2+ selectivityElectronic supplementary information (ESI) available: job plot, partial 1H NMR spectra of free 3 and the 3–Zn2+ complex, Ca2+ and Mg2+ interference for Zn2+ sensing of 3, Kd measurements, and buffer preparation. See http://www.rsc.org/suppdata/p2/b2/b200462c/
  作者：Tae Woo Kim、Jung-hyun Park、Jong-In Hong

  DOI：10.1039/b200462c

  日期：2002.4.29

  Zn2+ fluorescent chemosensors based on the chelation-enhanced fluorescence (CHEF) mechanism were prepared and fine-tuning of their Zn2+ selectivity was achieved by control of the spacer length. The fluorescence emission response to metal ions shows a fluorescence decrease for Co2+, Cu2+ and Ni2+ and an increase for Ca2+, Cd2+ and Zn2+. Maximum Zn2+ selectivity over Ca2+ and Cd2+ was achieved with 3. The basic binding properties (stoichiometry, apparent dissociation constant, and pH dependence) were measured by fluorescence spectroscopy. Analysis of the Job plot for the 3–Zn2+ complex indicates the formation of a 1 ∶1 complex. The apparent dissociation constant Kd was determined as 0.98 (±0.43) nM for 3–Zn2+ at pH 7.5 [50 mM HEPES buffer I = 0.1 (NaNO3)]. The plateaus in the fluorescence intensity of 2 and the 2–Zn2+ complex in regions with a pH exceeding 7 imply that the fluorescence measurements should be little affected by physiological pH changes.

  基于配位增强荧光（CHEF）机制的Zn2+荧光化学传感器被制备出来，并通过控制间隔基长度实现了对Zn2+选择性的精细调节。对金属离子的荧光发射响应显示，Co2+、Cu2+和Ni2+使荧光减弱，而Ca2+、Cd2+和Zn2+使荧光增强。在3号传感器中实现了对Zn2+的最大选择性，优于Ca2+和Cd2+。基本结合特性（化学计量比、表观解离常数和pH依赖性）通过荧光光谱法测量。3号传感器与Zn2+的Job图分析表明形成了1:1的复合物。表观解离常数Kd在pH 7.5时为0.98（±0.43）nM [50 mM HEPES缓冲液，I = 0.1 (NaNO3)]。在pH超过7的区域，2号传感器及其与Zn2+的复合物的荧光强度平稳，表明荧光测量受生理pH变化的影响不大。
• Time-lapse imaging of cell death in cell culture and whole living organisms using turn-on deep-red fluorescent probes
  作者：Tia S. Jarvis、Felicia M. Roland、Kyle M. Dubiak、Paul W. Huber、Bradley D. Smith

  DOI：10.1039/c8tb01495g

  日期：——

  regression and apoptosis during growth and maturation. These new fluorescent probes are likely to be useful for time-resolved, non-invasive in vivo imaging of cell death process in range of living organisms. From a broader perspective, it should be possible to utilize the negative solvatochromism exhibited by benzothiazolium squaraine dyes for development of various “turn-on” deep-red fluorescent probes

  细胞死亡是发育生物学的核心过程，也是疾病状态和治疗效果的重要指标。描述了两种相关的荧光探针，它们是一种或两种锌二吡啶胺 (ZnDPA) 配位络合物与附加的溶剂化显色苯并噻唑鎓方酸染料的分子缀合物。这些探针旨在针对暴露在死亡和垂死细胞表面的阴离子磷脂磷脂酰丝氨酸（PS）。以脂质体和红细胞血影为模型的一系列光谱和显微镜研究表明，具有两个 ZnDPA 靶向单元的探针比具有一个 ZnDPA 的探针产生更高的亲和力、更强的荧光“开启”效应和更好的图像对比度。两种荧光探针都可以对培养物中的哺乳动物细胞死亡进行“免清洗”延时显微成像。带有两个 ZnDPA 单元的探针用于对非洲爪蟾（青蛙）胚胎发育过程中的细胞死亡进行非侵入性延时成像。体内荧光显微照片显示，探针在胚胎尾部、头部和脊柱区域内积累，这些区域在生长和成熟过程中正在经历退化和凋亡。这些新的荧光探针可能可用于对各种活体生物体的细胞死亡过程进行时间分辨
• Synthesis and radiolabelling of Re(CO)₃-<i>β</i>-elemene derivatives as potential therapeutic radiopharmaceuticals
  作者：Yunfeng Ren、Yanhong Sun、Kangmin Cheng、Guifeng Liu、Yumei Shen

  DOI：10.1002/jlcr.1580

  日期：2009.5.15

  β-Elemene, (1S, 2S, 4R)-(−)-(1-methy-1-vinyl-2,4-diisopropenyl cyclohexane) is an anticancer agent from the Traditional Chinese Herb Medicinal. Three novel Re(CO)3-β-elemene derivatives including their radioactive conjugates containing N,N,N tridentate ligands and tricarbonyl rhenium (complex 12, 13, 14) were synthesized. Their structures were characterized by infrared (IR), 1H-NMR and HRMS. Good radioactive yield (above 90%) and radioactive chemical purity with Re-188 (above 95%) were obtained for all of the three derivatives (complex 15, 16, 17). The antiproliferative activity of non-radioactive β-elemene-Re(CO)3 derivatives on Lewis lung cancer cells and HeLa cell lines were evaluated by WST-1 methods. The result shows substantial decrease in IC50 values compared with the parent compound β-elemene. The synthesis and radiosynthesis of β-elemene tricarbonyl rhenium conjugates provide the possibility to find a new kind of potential radiopharmaceuticals on β-elemene. Copyright © 2009 John Wiley & Sons, Ltd.

  β-榄香烯，(1S, 2S, 4R)-(-)-(1-甲基-1-乙烯基-2,4-二异亚丙烯基环己烷)是一种中草药抗癌剂。研究人员合成了三种新型 Re(CO)3-β 烯衍生物，包括含有 N,N,N三叉配体和三羰基铼的放射性共轭物（络合物 12、13、14）。红外光谱（IR）、1H-NMR 和 HRMS 对它们的结构进行了表征。三种衍生物（复合物 15、16、17）都获得了良好的放射性收率（90%以上）和 Re-188 放射性化学纯度（95%以上）。用 WST-1 方法评估了非放射性 β-烯-Re(CO)3 衍生物对 Lewis 肺癌细胞和 HeLa 细胞系的抗增殖活性。结果表明，与母体化合物 β-榄香烯相比，其 IC50 值大大降低。β-榄香烯三羰基铼共轭物的合成和放射性合成为寻找一种新的β-榄香烯放射性药物提供了可能。Copyright © 2009 John Wiley & Sons, Ltd. All Rights Reserved.
• [EN] GLYCOPEPTIDES CONJUGATES AND USES THEREOF<br/>[FR] CONJUGÉS DE GLYCOPEPTIDES ET LEURS UTILISATIONS
  申请人：JAWAHARLAL NEHRU CT FOR ADVANCED SCIENT RES JNCASR

  公开号：WO2016125193A1

  公开（公告）日：2016-08-11

  Vancomycin conjugates of Formula I, its stereoisomers, prodrugs, pharmaceutically acceptable salts, and metal coordination complexes thereof is described in the present disclosure. Further, the present disclosure relates to pharmaceutical compositions comprising vancomycin conjugates, its stereoisomers, prodrugs, pharmaceutically 10 acceptable salts, metal coordination complex thereof with one or more other pharmaceutical compositions or an antibiotic. The present disclosure also describes a process of preparing said conjugates, its stereoisomers, prodrugs, pharmaceutically acceptable salts, and metal coordination complex thereof, and pharmaceutical compositions as described above. Furthermore, the present disclosure describes 15 compositions and methods of treating conditions and diseases that are mediated by bacteria

  本公开描述了Formula I的万古霉素共轭物、其立体异构体、前药、药用可接受盐以及其金属配位络合物。此外，本公开涉及包括万古霉素共轭物、其立体异构体、前药、药用可接受盐、金属配位络合物及一种或多种其他药物组成的药物组合物或抗生素的药物组成。本公开还描述了制备上述共轭物、其立体异构体、前药、药用可接受盐以及金属配位络合物的过程，以及上述药物组成。此外，本公开描述了治疗由细菌介导的疾病和病症的组合物和方法。