mono(6-amino-6-deoxy)-per(2,3,6-O-methyl)-β-cyclodextrin | 129867-48-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono(6-amino-6-deoxy)-per(2,3,6-O-methyl)-β-cyclodextrin
• 英文别名: 6^I-amino-6^I-deoxy-2^I,3^I-di-O-methylhexakis(2^II-VII,3^II-VII,6^II-VII-tri-O-methyl)cyclomaltoheptaose；6A-Amino-6A-deoxy-2A,2B,2C,2D,2E,2F,2G,3A,3B,3C,3D,3E,3F,3G,6B,6C,6D,6E,6F,6G-eicosa-O-methyl-|A-cyclodextrin；[(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecamethoxy-10,15,20,25,30,35-hexakis(methoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methanamine
• CAS: 129867-48-7
• 化学式: C₆₂H₁₁₁NO₃₄
• 分子量: 1414.55
• InChiKey: HBOZSVVDCDBTLC-IQPKDVKNSA-N

物化性质

• 熔点：
  121-123 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• 沸点：
  1109.8±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  97
• 可旋转键数：
  27
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  340
• 氢给体数：
  1
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  mono(6-amino-6-deoxy)-per(2,3,6-O-methyl)-β-cyclodextrin 在 盐酸 作用下， 以99%的产率得到6-monoamino-6-monodeoxy-(2,3-di-O-methyl)hexakis(2,3,6-tri-O-methyl)-β-cyclodextrin hydrochloride
  参考文献：
  名称：

  A reliable synthesis of 2- and 6-amino-β-cyclodextrin and permethylated-β-cyclodextrin

  摘要：

  A new, reliable method for the introduction of an amine group at positions 2 or 6 of beta-cyclodextrin and permethyl-beta-cyclodextrin is described. It involves selective tosylation followed by azide substitution and almost quantitative reduction with triphenylphosphine followed by hydrolysis of the phosphinimine intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.099
• 作为产物：
  描述：

  mono-6-azido-6-deoxy-per-O-methyl-β-cyclodextrin 在 ammonium hydroxide 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60 %的产率得到mono(6-amino-6-deoxy)-per(2,3,6-O-methyl)-β-cyclodextrin
  参考文献：
  名称：

  Modification of Dispersin B with Cyclodextrin-Ciprofloxacin Derivatives for Treating Staphylococcal

  摘要：

  为了解决生物膜对抗生素的高耐受性问题，当务之急是开发出对抗这些细菌联盟的新策略。本文介绍了一种创新的抗生物膜纳米载体给药系统，该系统由Dispersin B-permethylated-β-cyclodextrin/ciprofloxacin adamantyl（DspB-β-CD/CIP-Ad）组成。为此，我们测试了 CIP-Ad 与(i) 未修饰的 β-CD 和 (ii) β-CD 的不同衍生物（2,3-O-二甲基-β-CD、2,6-O-二甲基-β-CD 和 2,3,6-O-三甲基-β-CD）之间的络合作用。通过核磁共振分析，β-CD/CIP-Ad 复合物的化学计量为 1/1。通过等温滴定量热法（ITC）实验，确定了 CIP-Ad 存在下 β-CD 及其不同衍生物复合物的 Ka、ΔH 和 ΔS 热力学参数。研究证实，β-CD/CIP-Ad 复合物的化学计量为 1/1，亲和力因甲基化类型而异。相溶解度研究表明，随着 CD 浓度的增加，CIP-Ad 的溶解度也在增加，这表明复合物已经形成。对表皮葡萄球菌（S. epidermidis）菌株进行了 CIP-Ad 和 2,3-O-二甲基-β-CD/CIP-Ad 或 2,3,6-O-三甲基-β-CD/CIP-Ad 复合物的抗菌活性评估。最低抑菌浓度（MIC）研究表明，CIP-Ad 和 2,3-O- 二甲基-β-CD 复合物的抗菌活性与单独的 CIP-Ad 相似，而与 2,3,6-O- 三甲基-β-CD 的相互作用则会提高 MIC 值。对表皮葡萄球菌生物膜的抗菌试验表明，2,3-O-二甲基-β-CDs/CIP-Ad 复合物在一定程度上保持了 DspB/CIP 联合作用的协同效应。为了获得这种能同时破坏生物膜基质和释放抗生素的 "多合一 "给药系统，我们将 DspB 共价接枝到三种具有不同长度间隔臂的羧基过甲基化 CD 衍生物上。实验证明，DspB-过甲基化-β-CD/环丙沙星-Ad 系统具有高效的抗生物膜活性，从而验证了这一策略。

  DOI：

  10.3390/molecules28145311

文献信息

• Amphiphilic cyclodextrin derivatives, method for preparation thereof and uses thereof
  申请人：Perly Bruno

  公开号：US20070142324A1

  公开（公告）日：2007-06-21

  The invention relates to cyclodextrin derivatives of formula (I): in which: R 1 ═—NH-E-AA-(L 1 ) p (L 2 ) q where E=a linear or branched Cl-Cl 5 hydrocarbon-based group with, optionally, one or more hetero atoms; AA=the residue of an amino acid; L 1 and L 2 =a C 6 -C 24 hydrocarbon-based group with, optionally, one or more hetero atoms; p and q=0 or 1, at least one being ≠0; R 2 ═H, —CH 3 , isopropyl, hydroxypropyl, sulphobutyl ether; R 3 ═H or R 2 , except when R 2 =hydroxypropyl; all the R 4 ═—OH or R 2 , except when R 2 =hydroxypropyl, or at least one of the R 4 ═R 1 ; n=5, 6 or 7. The invention also relates to a process for preparing them, and to inclusion complexes and organized surfactant systems comprising them.

  该发明涉及以下式（I）的环糊精衍生物： 其中： R 1 ═—NH-E-AA-(L 1 ) p (L 2 ) q 其中E=线性或支链的Cl-Cl 5 碳氢基团，可选地，含有一个或多个杂原子；AA=氨基酸的残基；L 1 和L 2 =含有一个或多个杂原子的C 6 -C 24 碳氢基团；p和q=0或1，至少一个不等于0； R 2 ═H，—CH 3 ，异丙基，羟丙基，磺丁基醚； R 3 ═H或R 2 ，除非R 2 =羟丙基； 所有的R 4 ═—OH或R 2 ，除非R 2 =羟丙基，或者至少一个R 4 ═R 1 ；n=5、6或7。该发明还涉及一种制备它们的方法，以及包含它们的包合物和有序表面活性剂系统。
• Synthesis of glycerolipidyl derivatives of permethylated β-cyclodextrin as potential nanovectors
  作者：Cédric Gervaise、Véronique Bonnet、Catherine Sarazin、Florence Djedaïni-Pilard

  DOI：10.1039/c2nj40689f

  日期：——

  This work reports the chemo-enzymatic synthesis of a new family of amphiphilic cyclodextrins for Nano Drug Delivery. Monoamino-permethylated β-CD 1 was used as the polar head of amphiphilic structures. Three derivatives of glycerol were grafted onto cyclodextrin with or without a spacer arm. The two free hydroxyl groups were submitted to lipase-catalyzed reaction in mild conditions, leading to mono- or diesterified compounds. The reactivity of the hydroxyl groups was discussed and the compounds were fully characterized by NMR and mass spectrometry. The surfactive properties of bicatenar compounds 8, 9, 12 and 14 were evaluated and low CAC were determined, suggesting very promising assembly properties of these compounds in aqueous media.

  这项研究报告了用于纳米药物递送的新型两亲性环糊精家族的化学-酶合成。单氨基全甲基化的β-环糊精1被用作两亲性结构的极性头部。三种甘油衍生物被接枝到环糊精上，带或不带间隔臂。两个自由羟基在温和条件下经过脂肪酶催化反应，生成单酯或双酯化合物。讨论了羟基的反应性，所合成的化合物通过核磁共振和质谱进行了完全表征。评估了化合物8、9、12和14的表面活性特性，并测定了低临界胶束浓度（CAC），这表明这些化合物在水相中具有非常有前景的组装特性。
• Nanoparticles based on lipidyl-β-cyclodextrins: synthesis, characterization, and experimental and computational biophysical studies for encapsulation of atazanavir
  作者：Aurélien L. Furlan、Sébastien Buchoux、Yong Miao、Vincent Banchet、Mathieu Létévé、Virginie Lambertyn、Jean Michel、Catherine Sarazin、Véronique Bonnet

  DOI：10.1039/c8nj03237h

  日期：——

  After showing tensioactive properties of the compounds, the formation, stability and morphology of nanoparticles were demonstrated.

  展示了化合物的表面活性特性后，展示了纳米颗粒的形成、稳定性和形态。
• Solvent-free chemo-enzymatic synthesis of fatty acyl-β-cyclodextrin
  作者：Véronique Bonnet、Audrey Favrelle、Frédéric Aubry、Catherine Sarazin、Florence Djedaïni-Pilard

  DOI：10.1007/s10847-012-0229-2

  日期：2013.12

  Lipase-catalyzed transesterifications were carried out without solvent and in mild conditions on permethylated β-cyclodextrins derivatives to obtain lipidyl-cyclodextrin, a new class of amphiphilic compounds with expected auto-assembly properties. Good conversion rate, of 6I-(N-hydroxyethylsuccinamido)-6I-deoxy-2I, 3I-di-O-methyl-hexakis (2II–VII,3II–VII,6II–VII-tri-O-methyl) cyclomaltoheptaose were obtained by using lipozyme as catalyst. Critical Aggregation Concentrations of these new derivatives of amphiphilic cyclodextrins (5.10−3 and 5.10−4 M) are in favor of an auto-association behavior. Finally, NMR experiments were carried out to evaluate the self-assembly of the compounds in water. The resulting supramolecular aggregates have potential to be used as nano-carriers for drug.

  脂肪酶催化的酯交换反应在无溶剂和温和条件下对全甲基化的β-环糊精衍生物进行，以获得脂质-环糊精，这是一类具有预期自组装特性的两亲化合物。使用脂肪酶作为催化剂，得到了良好的转化率，6I-(N-羟乙基琥珀酰胺基)-6I-脱氧-2I, 3I-二-O-甲基-六六糖（2II–VII,3II–VII,6II–VII-三-O-甲基）。这些新型的两亲性环糊精衍生物的临界聚集浓度（5.10−3和5.10−4 M）有利于自我关联行为。最后，进行了核磁共振实验，以评估化合物在水中的自组装情况。所得到的超分子聚集体有潜力用作药物的纳米载体。
• Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs
  作者：Christophe Len、Florian Hamon、Bruno Violeau、Frédéric Turpin、Mathilde Bellot、Laurent Bouteiller、Florence Djedaini-Pilard

  DOI：10.1055/s-0029-1217988

  日期：2009.10

  The synthesis of six new cyclodextrin derivatives having nucleobase moiety is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl groups. Example of association constants for complexation of adenine and thymine derivatives: K AT = 385 M-¹ using NMR methodology is reported. Study of interaction between four cyclodextrin derivatives and one adamantyl guest is described by ITC.

  描述了六种新型环糊精衍生物的合成，这些衍生物具有核苷碱基部分。这两部分通过不同的链间隔连接，例如氨乙基和1,2,3-三唑基团。报告了腺嘌呤和胸腺嘧啶衍生物的复合物结合常数示例：K AT = 385 M⁻¹，使用NMR方法进行测定。研究了四种环糊精衍生物与一种亚甲基客体之间的相互作用，使用微量热量法（ITC）进行了描述。