heptakis-{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin | 1215455-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis-{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin
• 英文别名: heptakis{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin；heptakis-{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-CD；HTβCD
• CAS: 1215455-33-6
• 化学式: C₆₃H₉₁N₂₁O₃₅
• 分子量: 1702.54
• InChiKey: XXFYZNHFTJWCID-BXGMBMETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -16.69
• 重原子数：
  119.0
• 可旋转键数：
  21.0
• 环数：
  28.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  769.02
• 氢给体数：
  21.0
• 氢受体数：
  56.0

反应信息

• 作为反应物：
  描述：

  泼尼松龙 、 heptakis-{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin 以 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  6-Triazolyl-6-deoxy-β-cyclodextrin derivatives: synthesis, cellular toxicity, and phase-solubility study

  摘要：

  Heptakis{6-(4-hydroxymethyl-1H-[1,2,3] triazol-1-yl)-6-deoxy}-beta-cyclodextrin (HTbCD) and heptakis{6(4-sulfonylmethyl-1H-[1,2,3] triazol-1-yl)-6-deoxy}-beta-cyclodextrin (STbCD) were prepared using copper(I)-catalyzed azide-alkyne cycloaddition between 6-azido-6-deoxy-beta-CD and one of two alkynes, propargyl alcohol, and sodium propargyl sulfonate, respectively. The structures of HTbCD and STbCD were characterized by NMR techniques. NMR interpretations and computer modeling suggested that the limited freedom of rotation of the triazole moieties keeps HTbCD and STbCD rigid and compact. Water solubility tests of HTbCD and STbCD showed that the minimum water solubility of HTbCD and STbCD is at least 20 times higher than that of beta-CD. MTT assay showed that HTbCD and STbCD did not influence the cell viability under 1 mM. A phase-solubility study of prednisolone with the CD derivatives showed increased solubility of prednisolone in the presence of increasing concentrations of HTbCD and STbCD. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.03.020
• 作为产物：
  描述：

  2-丙炔-1-醇 、 heptakis-6-azido-6-deoxy-beta-cyclodextrin 在 tris((4-(hydroxypropyl)triazol-1-yl)methyl)amine 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 aq. phosphate buffer 为溶剂， 生成 heptakis-{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin
  参考文献：
  名称：

  环糊精点击簇的合成，细胞毒性和相溶性研究。

  摘要：

  为了探索环糊精点击簇（CCCs）作为一种新的基于环糊精的赋形剂的可能性，我们制备了三种不同的CCCs。七aki {6-（4-羟甲基-1H- [1,2,3]三唑-1-基）-6-脱氧}-β-环糊精（HT-β-CD），七aki {6-（4-羟甲基- 1H- [1,2,3]三唑-1-基）-6-脱氧} {2,3-二-O-甲基} -bet a-环糊精（HT-beta-CD（OMe）2）和庚基{6-（4-磺酰基甲基-1H- [1,2,3]三唑-1-基）-6-脱氧}-β-环糊精（ST-β-CD）。使用铜（I）催化的叠氮基-炔烃环加成反应从6-叠氮基-6-脱氧-β-CD制备了CCC，并研究了它们的水溶性，细胞毒性和药物增溶作用。CCC的水浊度测试表明，CCC的最小水溶性至少比β-CD高20倍。与2，6-二甲基-β-环糊精相比，在HeLa细胞上进行的MTT细胞活力测定表明CCC的细胞毒性低。HT-β-CD（O

  DOI：

  10.1002/jps.24107

文献信息

• 정량적 질량 분석을 위한 수소 동위원소 치환 가능한 질량표지 분자로서의 트리아졸 유도체 및 그 제조방법
  申请人：Hannam University Institute for Industry-Academia Cooperation 한남대학교 산학협력단(220040178166) BRN ▼305-82-13430

  公开号：KR101884455B1

  公开（公告）日：2018-08-01

  본 발명은 정량적 질량 분석을 위한 수소 동위원소 치환 가능한 질량표지(Mass tag) 분자로서의 트리아졸 유도체에 관한 것으로서, 수소 동위원소 치환 가능한 질량표지(Mass tag) 분자로서의 트리아졸 유도체, 이를 제조하는 방법 및 질량표지(Mass tag) 분자로 상기 유도체를 사용하는 방법에 관한 것이다.

  本发明涉及三唑衍生物作为氢同位素可替代的质量标记(Mass tag)分子，用于定量质量分析，涉及三唑衍生物作为氢同位素可替代的质量标记(Mass tag)分子，制备方法以及使用该分子作为质量标记(Mass tag)分子的方法。
• Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens
  作者：Hye-Yeong Kim、Johann Sohn、Gihani T. Wijewickrama、Praneeth Edirisinghe、Teshome Gherezghiher、Madhubani Hemachandra、Pei-Yi Lu、R. Esala Chandrasena、Mary Ellen Molloy、Debra A. Tonetti、Gregory R.J. Thatcher

  DOI：10.1016/j.bmc.2009.11.046

  日期：2010.1

  Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E-2) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E-2 conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer-E-2 conjugates, CD-E-2 was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm. (C) 2009 Elsevier Ltd. All rights reserved.
• 6-Hydroxymethyltriazolyl-6-deoxy-β-cyclodextrin: a highly water soluble and structurally well-defined β-cyclodextrin click cluster
  作者：Dong-Hwan Kim、Jae Gyu Jang、Hoa Thi Le、Jin Young Kim、Choon Woo Lim、Tae Woo Kim

  DOI：10.1016/j.tetlet.2012.08.073

  日期：2012.10

  The structural, physical, and biological properties of heptakis6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy)-beta-cyclodextrin (HT beta CD) were investigated by a variety of methods, including NMR, UV/vis, circular dichroism spectroscopy, computer modeling, turbidity testing, K-a measurements, and the MTT assay. The experimental results suggest that HT beta CD is structurally well-defined, highly water-soluble, and has low cytotoxicity. These advantages of mixt) versus beta-CD indicate that beta-cyclodextrin click clusters may function both as host molecules and as potential, alternative excipients to beta-CD. (C) 2012 Elsevier Ltd. All rights reserved.