6-O-tosyl-β-cyclodextrine | 23734-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-tosyl-β-cyclodextrine
• 英文别名: heptakis-(6-O-tosyl)-β-cyclodextrin；heptakis(6-O-(p-tosyl))-β-cyclodextrin；6^A,6^B,6^C,6^D,6^E,6^F,6^G-Hepta-O-(p-toluenesulfonyl)-β-cyclodextrin；per-6-O-tosyl-β-cyclodextrin；6-O-(p-toluenesulfonyl)-β-cyclodextrin；mono-6-deoxy-6-(p-tolylsulfonyl)cyclodextrin；Cyclohepta(amylose 6-toluolsulfonat)；per-6-o-tosyl-b-cyclodextrin；β-cyclodextrin；[1,2,3,4,5,6,7]O⁶-heptakis-(toluene-4-sulfonyl)-cyclo-lin-hepta[1α=>4]-D-glucopyranosyl；[1,2,3,4,5,6,7]O⁶-Heptakis-(toluol-4-sulfonyl)-cyclo-lin-hepta[1α=>4]-D-glucopyranosyl；mono-6-deoxy-6-(p-tolylsulfonyl)-β-cyclodextrin；6-deoxy-(p-toluenesulfonyl)-β-cyclodextrin；6-OTs-β-CD；toluenesulfonyl β-cyclodextrin；[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis[(4-methylphenyl)sulfonyloxymethyl]-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]methyl 4-methylbenzenesulfonate
• CAS: 23734-54-5
• 化学式: C₉₁H₁₁₂O₄₉S₇
• 分子量: 2214.32
• InChiKey: LPAMSVVGVRAUAW-ACXPUUNTSA-N

物化性质

• 熔点：
  216-217 °C (decomp)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  147
• 可旋转键数：
  28
• 环数：
  28.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  775
• 氢给体数：
  14
• 氢受体数：
  49

反应信息

• 作为反应物：
  描述：

  6-O-tosyl-β-cyclodextrine 在 吡啶 、 二溴三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以58%的产率得到七(6-溴-6-脱氧)-beta-环糊精
  参考文献：
  名称：

  Synthesis of 6-bromo-6-dezoxy-β-cyclodextrin from its silyl and tosyl derivatives

  摘要：

  DOI：

  10.1134/s1070363206120231
• 作为产物：
  描述：

  对甲苯磺酰氯 、 β-环糊精 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以20%的产率得到6-O-tosyl-β-cyclodextrine
  参考文献：
  名称：

  Construction of micelles based on biocompatible pseudo-graft polymers via β-cyclodextrin/cholesterol interaction for protein delivery

  摘要：

  在水中，通过宿主-客体包合作用，利用(6-(2-氨乙基)-氨基-6-脱氧)-环糊精(β-CDen)修饰的聚天冬氨酸(PASP-CD)与胆固醇修饰的聚(d,l-乳酸)(PLA-Chol)自组装构建了一种伪嫁接共聚物胶束。

  DOI：

  10.1039/c4ra07175a

文献信息

• Polycationic Glycosides
  作者：Robert Engel、Ishrat Ghani、Diego Montenegro、Marie Thomas、Barbara Klaritch-Vrana、Alejandra Castaño、Laura Friedman、Jay Leb、Leah Rothman、Heidi Lee、Craig Capodiferro、Daniel Ambinder、Eva Cere、Christopher Awad、Faiza Sheikh、JaimeLee Rizzo、Lisa-Marie Nisbett、Erika Testani、Karin Melkonian

  DOI：10.3390/molecules16021508

  日期：——

  Cationic lipids have long been known to serve as antibacterial and antifungal agents. Prior efforts with attachment of cationic lipids to carbohydrate-based surfaces have suggested the possibility that carbohydrate-attached cationic lipids might serve as antibacterial and antifungal pharmaceutical agents. Toward the understanding of this possibility, we have synthesized several series of cationic lipids attached to a variety of glycosides with the intent of generating antimicrobial agents that would meet the requirement for serving as a pharmaceutical agent, specifically that the agent be effective at a very low concentration as well as being biodegradable within the organism being treated. The initial results of our approach to this goal are presented.

  阳离子脂质早已被认为具有抗菌和抗真菌的作用。此前将阳离子脂质附着到碳水化合物基表面的研究表明，碳水化合物附着的阳离子脂质可能作为抗菌和抗真菌药物。为了理解这种可能性，我们合成了几系列与各种糖苷相连的阳离子脂质，旨在开发符合药物要求的抗微生物剂，特别是要求在非常低的浓度下有效，并且在被治疗的生物体内可降解。我们针对这一目标的初步结果已被呈现。
• Magnetic calcined oyster shell functionalized with taurine immobilized on β-cyclodextrin (Fe3O4/COS@β-CD-SO3H NPs) as green and magnetically reusable nanocatalyst for efficient and rapid synthesis of spirooxindoles
  作者：Narges Mohammadian、Batool Akhlaghinia

  DOI：10.1007/s11164-019-03860-x

  日期：2019.10

  16–25 nm. The new magnetic nanocatalyst (Fe3O4/COS@β-CD-SO3H NPs) was found to be very effective in one-pot multi-component reaction of isatin, active methylene component, and 1,3-dicarbonyl compounds for rapid preparation of spirooxindoles with fused chromenes in water in excellent yield. The most promising features of the presented approach are the short reaction time (15–22 min), magnetic separation of

  摘要 固定在β环糊精牛磺酸官能磁性煅牡蛎壳（FE 3 ö 4 / COS @β-CD-SO 3H NPs是作为一种新的稳定，长寿命，高效和优异的可重复使用的磁性纳米结构催化剂制备的。所制备的固体酸性催化剂通过各种光谱和显微技术进行表征，例如傅立叶变换红外（FT-IR）光谱，X射线衍射（XRD）分析，扫描电子显微镜（SEM），能量色散X射线（EDX）光谱，透射电子显微镜（TEM），振动样品磁力法（VSM），热重分析（TGA）/差热重分析（DTG）和元素（CHNS）分析。结果清楚地表明，合成的超顺磁性催化剂以均匀的球形存在，平均粒径为16-25 nm。新的磁性纳米催化剂（FE 3 ö 4 / COS @β-CD-SO 3已发现H NPs在伊斯兰法，活性亚甲基组分和1,3-二羰基化合物的一锅多组分反应中非常有效，可在水中以优异的产率快速制备带有稠合色烯的螺硫醇。提出的方法最有希望的特点是反应时间
• Mimicking an antimicrobial peptidepolymyxin B by use of cyclodextrin
  作者：Hatsuo Yamamura、Ken Suzuki、Kazuma Uchibori、Atsushi Miyagawa、Masao Kawai、Chie Ohmizo、Takashi Katsu

  DOI：10.1039/c1cc16369h

  日期：——

  Cyclodextrin derivatives prepared to mimic a membrane active antibacterial peptide polymyxin B strongly permeabilized bacterial membrane and inhibited bacterial proliferation.

  环糊精衍生物可模拟膜活性抗菌肽多粘菌素 B，具有很强的渗透细菌膜和抑制细菌增殖的作用。
• Synthesis of a novel β-cyclodextrin-functionalized Fe₃O₄/BaMoO₄:Dy³⁺ magnetic luminescent hybrid nanomaterial and its application as a drug carrier
  作者：Sangita K. Swain、Anupam Sahoo、Sukanta K. Swain、S. K. Tripathy、G. Phaomei

  DOI：10.1039/d0dt02314k

  日期：——

  A magnetic luminescent hybrid nanoparticle Fe₃O₄/BaMoO₄:Dy³⁺ (MLHNP) was successfully synthesized by the co-precipitation method using ethylene glycol.

  一种磁性发光杂化纳米颗粒Fe3O4/BaMoO4：Dy3+（MLHNP）成功地通过使用乙二醇的共沉淀法合成。
• The influence of cyclodextrin modification on cellular uptake and transfection efficiency of polyplexes
  作者：Wenyu Li、Lina Chen、Zhixiong Huang、Xiaofei Wu、Yuanfeng Zhang、Qiaoling Hu、Youxiang Wang

  DOI：10.1039/c1ob05886j

  日期：——

  Cyclodextrin-modified polycations have been studied widely due to their low cytotoxicity, low immunogenicity and the ability to form inclusion complexes. However, the influence of CD modification on cellular uptake and transfection efficiency of polyplexes is still unclear. In this research, cyclodextrin-modified polyethylenimines (PEI-CD) with different CD-grafting levels were synthesized, which were named PEI-CD15 and PEI-CD41, respectively, according to the CD number per PEI chain. CD modification showed great influence on the DNA condensation ability of the polycation. PEI-CD15 could protect DNA completely above N/P ratio of 2. The particle sizes of these polyplexes were about 120 nm. However, PEI-CD41 could not protect DNA below N/P of 6, and PEI-CD41/DNA polyplexes were larger than 1 μm, even at N/P ratio of 10. Therefore, this research was mainly focused on PEI-CD15. It was interesting that the PEI-CD15/DNA polyplexes at N/P ratio of 8 and 10 displayed excellent stability in physiological salt conditions, probably due to the hydration shell of CDs. The influence of CD modification on the cellular uptake and transfection efficiency of polyplexes depended on the type of the cells. Uptake inhibition experiments indicated that PEI/DNA polyplexes were internalized by HEK293T cells by both clathrin-mediated endocytosis and caveolae-mediated endocytosis. The route of caveolae-mediated endocytosis was significantly promoted after CD modification. So the cell uptake and transfection efficiency of PEI-CD15/DNA polyplexes were significantly improved for HEK293T cells. However, the uptake and transfection efficiency of PEI-CD15/DNA polyplexes in HepG2 cells was similar to that of PEI/DNA polyplexes, probably due to the lack of endogenous caveolins.

  环糊精修饰的多聚阳离子具有低细胞毒性、低免疫原性和形成包涵复合物的能力，因此被广泛研究。然而，CD修饰对多聚体的细胞摄取和转染效率的影响仍不清楚。本研究合成了不同CD接枝水平的环糊精修饰聚乙烯亚胺（PEI-CD），根据每条PEI链的CD数量，分别命名为PEI-CD15和PEI-CD41。CD修饰对聚合阳离子的DNA缩合能力有很大影响。PEI-CD15在N/P比为2以上可以完全保护DNA。然而，PEI-CD41 在 N/P 比为 6 以下时不能保护 DNA，即使在 N/P 比为 10 时，PEI-CD41/DNA 多聚体也大于 1 μm。因此，这项研究主要集中在 PEI-CD15 上。有趣的是，N/P 比为 8 和 10 的 PEI-CD15/DNA 多聚体在生理盐分条件下表现出极佳的稳定性，这可能是由于 CD 的水合外壳所致。CD 修饰对多聚体的细胞摄取和转染效率的影响取决于细胞类型。摄取抑制实验表明，HEK293T 细胞通过凝集素介导的内吞和洞穴介导的内吞两种途径内化 PEI/DNA 多聚物。经 CD 修饰后，洞穴介导的内吞途径明显增加。因此，PEI-CD15/DNA 多聚物对 HEK293T 细胞的摄取和转染效率明显提高。然而，PEI-CD15/DNA多聚物在HepG2细胞中的摄取和转染效率与PEI/DNA多聚物相似，这可能是由于缺乏内源性洞穴素。