七(6-溴-6-脱氧)-beta-环糊精 | 53784-83-1

• 物质功能分类: 化学试剂 - 有机试剂 - 环糊精
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 七(6-溴-6-脱氧)-beta-环糊精
• 中文别名: 七-6-溴-6-脱氧-Β-环糊精
• 英文名称: heptakis(6-bromo-6-deoxy)-β-cyclodextrin
• 英文别名: Heptakis-6-bromo-6-deoxy-beta-cyclodextrin；(1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31S,33S,35S,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(bromomethyl)-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]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• CAS: 53784-83-1
• 化学式: C₄₂H₆₃Br₇O₂₈
• 分子量: 1575.27
• InChiKey: XNNRROJOWZLYCK-FOUAGVGXSA-N

物化性质

• 熔点：
  217-221°C
• 沸点：
  1495.8±60.0 °C(Predicted)
• 密度：
  1.948±0.06 g/cm3(Predicted)
• 溶解度：
  Soluble in DMF, DMSO. Insoluble in water, methanol, chloroform.
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  77
• 可旋转键数：
  7
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  412
• 氢给体数：
  14
• 氢受体数：
  28

安全信息

• 海关编码：
  29400000
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于阴凉干燥处

SDS

Name:	Heptakis-6-Bromo-6-Deoxy--Cyclodextrin Material Safety Data Sheet
Synonym:	None
CAS:	53784-83-1

Section 1 - Chemical Product MSDS Name:Heptakis-6-Bromo-6-Deoxy--Cyclodextrin Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
53784-83-1	Heptakis-6-Bromo-6-Deoxy--Cyclodextri	ca 100	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 53784-83-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: almost white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 220 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 1575.27

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 53784-83-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Heptakis-6-Bromo-6-Deoxy--Cyclodextrin - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 53784-83-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 53784-83-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 53784-83-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  七(6-溴-6-脱氧)-beta-环糊精 在 sodium azide 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以96%的产率得到heptakis-6-azido-6-deoxy-beta-cyclodextrin
  参考文献：
  名称：

  Per(6-guanidino-6-deoxy)cyclodextrins: synthesis, characterisation and binding behaviour toward selected small molecules and DNA

  摘要：

  过(6-胍基-6-脱氧)-环糊精 4a、4b 和 4c 是新型衍生物，是在α-、β-和γ-环糊精的原边均匀引入胍基后得到的。这些产物是从相应的氨基衍生物中获得的，因为直接对已知的溴环糊精进行胍基化会产生混合物。通过核磁共振光谱和其他分析方法对新化合物进行了全面鉴定，并研究了它们与客体分子的相互作用。观察到了与 4-硝基苯磷酸（NPP）二钠盐的强络合（Kbinding ∼5 × 104 M-1），而与非磷酸化底物硝基苯（NB）形成的络合非常弱。二维 ROESY 光谱显示这两种情况下都存在空腔包合，但 NPP 的方向与 NB 相反，即磷酸基团朝向面向胍基团的一侧。4 对磷酸化客体具有很强的亲和力，这表明它有可能与 DNA 发生相互作用。研究发现，在琼脂糖凝胶电泳过程中，新化合物能完全抑制超纯小牛胸腺 DNA 的迁移，而单独使用胍基或普通环糊精则没有任何效果。此外，原子力显微镜还证明了 DNA 在 4b 的存在下凝结成纳米颗粒，证实了生物聚合物与多聚产物 4 之间强烈的静电相互作用。因此，4 和 DNA 之间强烈的胍磷酸盐相互作用归因于环糊精初级区域的胍基团聚集。空穴效应无法评估。

  DOI：

  10.1039/b614899a
• 作为产物：
  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

文献信息

• Mannosylated Poly(ethylene imine) Copolymers Enhance saRNA Uptake and Expression in Human Skin Explants
  作者：Anna K. Blakney、Yamin Abdouni、Gokhan Yilmaz、Renjie Liu、Paul F. McKay、Clément R. Bouton、Robin J. Shattock、C. Remzi Becer

  DOI：10.1021/acs.biomac.0c00445

  日期：2020.6.8

  dose minimization. Here, we present a delivery platform for targeted delivery of saRNA using mannosylated poly(ethylene imine) (PEI) enabled by the host–guest interaction between cyclodextrin and adamantane. We show that the host–guest complexation does not interfere with the electrostatic interaction with saRNA and observed that increasing the degree of mannosylation inhibited transfection efficiency

  Messenger RNA（mRNA）是用于疫苗和治疗剂的有前途的平台，自扩增RNA（saRNA）特别有利，因为它可以实现更高的蛋白表达和最小剂量。在这里，我们介绍了一个通过甘露糖基化的聚亚乙基亚胺（PEI）定向递送saRNA的递送平台，该环化糊精和金刚烷之间的客体相互作用实现了该平台。我们发现宿主-客体的复合物不会干扰与saRNA的静电相互作用，并且观察到甘露糖基化程度的提高在体外抑制了转染效率，但在人皮肤外植体中表达GFP的细胞数量增加了8倍。此外，提高糖聚合物与saRNA的比例也提高了离体转染细胞的百分比。我们发现，这些甘露糖基化的PEIs以依赖于甘露糖的方式特异性地增加了人类皮肤中上皮细胞的蛋白质表达。该平台有望用于进一步研究PEI的糖基化和靶向saRNA的传递。
• Clustering of Escherichia coli Type-1 Fimbrial Adhesins by Using Multimeric Heptyl α-D-Mannoside Probes with a Carbohydrate Core
  作者：Mehdi Almant、Vincent Moreau、José Kovensky、Julie Bouckaert、Sébastien G. Gouin

  DOI：10.1002/chem.201100515

  日期：2011.8.29

  couple the multimers to a fluorescent label. A one‐pot synthetic approach was developed to tether the ligands and the fluorescein isothiocyanate (FITC) probe to the scaffold simultaneously. Isothermal calorimetry with the monomeric FimH lectin revealed nanomolar affinities and saturation of all structurally available binding sites on the multivalent HM ligands. Direct titrations domain showed almost strict

  庚基α- D-甘露糖苷（HM）是FimH凝集素的强抑制剂，可介导尿路致病性大肠杆菌（E. coli）的初始黏附）到膀胱细胞。我们基于碳水化合物核设计了一组多价HM配体，结构化合价范围为1到7。用于构建规则亲水结构的化学策略包括关键糖苷片段的重复。伯氨基在糖还原端接枝以将多聚体偶联至荧光标记。开发了一种单锅合成方法，可将配体和异硫氰酸荧光素（FITC）探针同时束缚到支架上。用单体FimH凝集素等温量热法显示纳摩尔亲和力和多价HM配体上所有结构上可用的结合位点饱和。直接滴定域显示出焓-熵补偿与配体价的增加几乎严格相关，而反向滴定量热法则表明二价庚基甘露糖苷的第一个和第二个结合位点之间存在负协同作用。但是，通过抑制1型毛细血管UTI89的血凝作用，观察到了多价效应。大肠杆菌，具有滴度低到60牛顿中号为七价HM配体。FITC标记的HM三聚体显示了溶液中活细菌的捕获和交联，这种现象以前没有用低价配体描述。
• Novel drug delivery compositions
  申请人：Wiebe Leonard

  公开号：US20070021380A1

  公开（公告）日：2007-01-25

  The present invention provides for a novel molecules useful for delivery of compounds to a mammal, more particularly for the intracellular delivery of nucleotides, nucleotide analogues or compounds with a heterocyclic base. Also provided for are novel therapeutic complexes comprising novel molecules complexed with nucleotide analogues or heterogeneous or homogenous oligomers comprised of nucleotide analogues.

  本发明提供了一种新型分子，用于将化合物传递给哺乳动物，更具体地用于核苷酸、核苷酸类似物或具有杂环碱基的化合物的细胞内传递。还提供了包括与核苷酸类似物或由核苷酸类似物组成的异质或同质寡聚体形成的新型治疗复合物。
• An improved synthesis of 6-deoxyhalo cyclodextrins via halomethylenemorpholinium halides Vilsmeier-Haack type reagents
  作者：Kazimierz Chmurski、Jacques Defaye

  DOI：10.1016/s0040-4039(97)10019-3

  日期：1997.10

  Per(6-bromo-6-deoxy)cyclomalto-hexaose, -heptaose, and -octaose and the corresponding per(6-chloro-6-deoxy) derivatives were prepared in high yield by reaction of bromomethylenemorpholinium bromide or chloromethylenemorpholinium chloride, respectively, with cyclomaltohexaose, cyclomaltoheptaose and cyclomaltooctaose in dimethylformamide.

  通过分别使溴化亚甲基吗啉溴化物或氯代亚​​甲基吗啉鎓反应高产率地制备每（6-溴-6-脱氧）环麦芽六糖，-庚糖和-八糖以及相应的每-（6-氯-6-脱氧）衍生物，在二甲基甲酰胺中含有环麦芽六糖，环麦芽七糖和环麦芽八糖。
• Pattern-Based Recognition of Heparin Contaminants by an Array of Self-Assembling Fluorescent Receptors
  作者：Richard B. C. Jagt、Rodolfo F. Gómez-Biagi、Mark Nitz

  DOI：10.1002/anie.200805238

  日期：2009.3.2

  potential killers: Strong host–guest interactions enable the facile combination of polycationic cyclodextrin binding motifs (blue) with fluorescent reporters (orange) tethered to a hydrophobic guest molecule (dark green). An array of supramolecular fluorescent receptors prepared by this modular approach was used for the pattern‐based recognition of negatively charged contaminants in the anticoagulant drug heparin

  追踪潜在的杀手：强力的宿主-客体相互作用使聚阳离子环糊精结合基序（蓝色）与荧光报告分子（橙色）轻松地结合到疏水的客体分子上（深绿色）。通过这种模块化方法制备的一系列超分子荧光受体用于基于模式的抗凝药物肝素中带负电荷的污染物识别。