cucurbituril | 259886-50-5

• 物质功能分类: 催化剂及助剂 - 聚合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: cucurbituril
• 英文别名: cucuribit[7]uril；curcurbit[7]uril；cucrubit[7]uril；cucurbit[7]uril；cucurbituril[7]；CB[7]
• CAS: 259886-50-5
• 化学式: C₄₂H₄₂N₂₈O₁₄
• 分子量: 1162.97
• InChiKey: ZDOBFUIMGBWEAB-XGFHMVPTSA-N

物化性质

• 密度：
  2.69

计算性质

• 辛醇/水分配系数(LogP)：
  -6.61
• 重原子数：
  84.0
• 可旋转键数：
  0.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  329.7
• 氢给体数：
  0.0
• 氢受体数：
  14.0

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 干燥 |

SDS

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Section 1: Product Identification
Chemical Name: Cucurbit[7]uril (CB[7]) hydrate, 99+%
CAS Registry Number: 259886-50-5
Formula: C42H42N28O14.xH2O
EINECS Number: none
Chemical Family: macrocyclic compounds
Synonym: CB[7]

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 259886-50-5 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation, eyes
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: none
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container. Keep in a cool, dry, well-ventilated area.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white powder
Molecular Weight: 1162.96
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, nitrogen oxides, and organic fumes

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Not reportable under SARA 313
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

葫芦[7]脲是一种生物化学试剂，可用于生物材料或有机化合物的研究，在生命科学领域具有重要应用价值。

反应信息

• 作为反应物：
  描述：

  cucurbituril 在 potassium sulfate 、 dipotassium peroxodisulfate 、 水 作用下， 反应 12.0h， 以27%的产率得到monohydroxy-cucurbit[7]uril
  参考文献：
  名称：

  超分子维可牢尼龙搭扣，可逆的水下附着力

  摘要：

  粘性工作：超分子维可牢尼龙搭扣使用主体-客体化学和多价相互作用证明了出色的水下附着力以及出色的机械和化学可逆性（参见方案）。用葫芦[7]尿素（CB [7]）主体和氨基甲基二茂铁（Fc）客体功能化的硅表面（蓝色）由于其极高的亲和力而在水中粘附。

  DOI：

  10.1002/anie.201209382
• 作为产物：
  描述：

  聚合甲醛 、 甘脲 在 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 以16.78%的产率得到cucurbituril
  参考文献：
  名称：

  用于捕获多种铀酰物种的配位适应性多齿假轮烷配体

  摘要：

  铀酰在水环境中水解的倾向阻碍了在按需分离和定制合成的情况下对铀酰物种的精确控制。在此，我们以葫芦[7]脲（CB[7]）为大环分子，4,4'-联吡啶-N,N'-二氧化物（DPO）为弦分子，提出了一种新型多齿假轮烷配体， DPO@CB[7] 用于捕获不同 pH 值的铀酰。由于 DPO 对金属配位的非质子性质，DPO@CB[7] 配体的配位能力受 pH 值的影响较小，可以在较宽的 pH 值范围内工作。此外，通过自适应铀酰配位，这种非质子假轮烷配体可有效识别不同的铀酰物种，范围从单体到四聚体，源于不同 pH 值的水解，并成功获得了四种新型铀基-轮烷化合物（URC1-4）。单晶 X 射线衍射分析表明，由于 DPO@CB[7] 假轮烷配体的结构灵活性，DPO@CB[7] 配体以四种不同的模式与铀中心配位，从单体到四聚体。对DPO@CB[7]配体的构象灵活性进行了详细讨论，讨论了被困在CB[7]中的DP

  DOI：

  10.1021/acs.inorgchem.1c03204
• 作为试剂：
  描述：

  1-(氯甲基)-4-硝基苯 、 苯硼酸 在 potassium carbonate 、 sodium chloride 、 palladium dichloride 、 cucurbituril 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以45%的产率得到硝基二苯基甲烷
  参考文献：
  名称：

  葫芦[7]尿素在水性介质中促进PdCl 2催化苄基卤化物与芳基硼酸的交叉偶联反应

  摘要：

  该研究提供了一种新方法，可在乙醇水溶液中使用CB [7] -NaCl-PdCl 2催化苄基氯衍生物与芳基硼酸的Suzuki交叉偶联反应生产二芳基甲烷衍生物。

  DOI：

  10.1016/j.tetlet.2014.07.060

文献信息

• Molecular Containers Bind Drugs of Abuse in Vitro and Reverse the Hyperlocomotive Effect of Methamphetamine in Rats
  作者：Shweta Ganapati、Stephanie D. Grabitz、Steven Murkli、Flora Scheffenbichler、Maíra I. Rudolph、Peter Y. Zavalij、Matthias Eikermann、Lyle Isaacs

  DOI：10.1002/cbic.201700289

  日期：2017.8.17

  of five molecular container compounds (calabadions 1 and 2, CB[7], sulfocalix[4]arene, and HP-β-CD) toward seven drugs of abuse in homogenous aqueous solution at physiological pH by various methods (1H NMR, UV/Vis, isothermal titration calorimetry [ITC]) and found binding constants (Ka values) spanning from <102 to >108 m−1. We also report X-ray crystal structures of CB[7]⋅methamphetamine and 1⋅methamphetamine

  我们通过多种方法测量了在生理pH值下均质水溶液中5种分子容器化合物（卡拉巴第1和2，CB [7]，磺胺嘧啶[4]芳烃和HP-β-CD）对7种滥用药物的亲和力（1 1 H NMR，UV /可见，等温滴定量热法[ITC]），并发现结合常数（ķ一个值）从<10跨越2至> 10 8 米-1。我们还报告了CB [7] ·甲基苯丙胺和1 ·甲基苯丙胺的X射线晶体结构。我们发现2而不是CB [7]能够改善用甲基苯丙胺治疗的大鼠的超机车活动。aba草的生物利用度及其收敛的构件合成表明，有潜力进一步优化结构，作为可逆滥用非阿片类药物的中毒药物，目前尚无治疗方法。
• Cucurbit[7]uril Complexation Drives Thermal<i>trans</i>-<i>cis</i>-Azobenzene Isomerization and Enables Colorimetric Amine Detection
  作者：Jing Wu、Lyle Isaacs

  DOI：10.1002/chem.200901522

  日期：2009.11.2

  Complexation of yellow diaminoazobenzenes 1 and 3 inside cucurbit[7]uril (CB[7]) results in the formation of purple‐colored CB[7]⋅cis‐1⋅2 H+ and CB[7]⋅cis‐3⋅2 H+ complexes, respectively. The high binding affinity and selectivity displayed by CB[7] toward 1 and 3 pays the >10 kcal mol−1 thermodynamic cost for this isomerization. We investigated the behavior of these complexes as a function of pH and

  黄色diaminoazobenzenes络合1和3内葫芦[7]脲（CB [7]）导致紫色CB [7]的形成⋅顺- 1⋅ 2小时+和CB [7] ⋅顺- 3⋅ 2 H +配合物。CB [7]对1和3表现出的高结合亲和力和选择性为该异构化支付了> 10 kcal mol -1的热力学成本。我们研究了这些复合物的行为作为pH的函数和观察到的大的P ķ一个位移和高pH响应性，其是葫芦的特性[n ] uril分子容器。显着的黄色到紫色的变化被用于构建生物活性胺4 – 10的指示剂位移测定。该指标置换测定是能够量化伪麻黄碱（的5在Sudafed片剂在5-350μ）内容中号范围。
• Reversing Chemoselectivity: Simultaneous Positive and Negative Catalysis by Chemically Equivalent Rims of a Cucurbit[7]uril Host
  作者：Nazar Rad、Oksana Danylyuk、Volodymyr Sashuk

  DOI：10.1002/anie.201905027

  日期：2019.8.12

  Enzyme catalysis has always been an inspiration and an unattainable goal for chemists due to features such as high specificity, selectivity, and efficiency. Here, we disclose a feature neither common in enzymes nor ever described for enzyme mimics, but one that could prove crucial for the catalytic performance of the latter, namely the ability to catalyze and inhibit two different reactions at the

  由于具有高特异性，选择性和高效率等特点，酶催化一直是化学家的灵感和无法实现的目标。在这里，我们公开了一种既不存在于酶中也未描述过的酶模拟物的特征，但是可以证明对后者的催化性能至关重要的一个特征，即同时催化和抑制两种不同反应的能力。值得注意的是，这可以通过两个相同的，空间分辨的催化位点来实现。将来，这种同步的催化剂作用不仅可以用于控制化学选择性，如目前的情况，还可以用于调节其他类型的化学反应性。
• Dual Visible Light-Triggered Photoswitch of a Diarylethene Supramolecular Assembly with Cucurbit[8]uril
  作者：Guoxing Liu、Ying-Ming Zhang、Conghui Wang、Yu Liu

  DOI：10.1002/chem.201703562

  日期：2017.10.17

  only prompts the DAEs to form charge‐transfer complexes, but also restricts its intramolecular rotation to enhance fluorescence emission. In this CB[8]‐containing supramolecular system, the π‐conjugation is extended and its absorption is bathochromically shifted for visible light‐driven cyclization of DAEs. Meanwhile, the fluorescence of the supramolecular assembly can also be reversibly modulated by visible

  由可见光转换的光致变色分子的研究对于其在生物成像和刺激响应材料中的应用特别感兴趣。在这里，已经构建了由单电荷双吡啶鎓修饰的二芳烃（DAE）和葫芦[8] uril（CB [8]）组成的光开关超分子组件，该组件在两个方向的可见光下均表现出可逆的光致变色行为。CB [8]的转化不仅促使DAE形成电荷转移复合物，而且限制了其分子内旋转以增强荧光发射。在此包含CB [8]的超分子系统中，π共轭作用得以扩展，并且其吸收发生了红移，从而形成了可见光驱动的DAEs环化反应。同时，超分子组装体的荧光也可以被可见光可逆地调节。这些发现可能为开发可见光驱动的荧光生物材料和分子机器提供了新的策略。
• [EN] DYNAMIC HOST-GUEST INTERACTIVE SYSTEM<br/>[FR] SYSTÈME INTERACTIF HÔTE-INVITÉ DYNAMIQUE
  申请人：JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENT RESEARCH

  公开号：WO2019034945A1

  公开（公告）日：2019-02-21

  The present invention relates to a dynamic host-guest interactive system that possesses unique characteristics and finds utility in multitude of areas, specifically, in imaging and site directed drug delivery. An aspect of the present disclosure provides a dynamic host-guest interactive system including a host molecule and a guest molecule interacting with each other through non-covalent forces, wherein the host molecule is associated with any or a combination of a targeting moiety and a therapeutic agent with proviso that when the host molecule is associated with the targeting moiety, the guest molecule is associated with an imager, and when the host molecule is associated with the therapeutic agent, the guest molecule is associated with the targeting moiety, and when the host molecule is associated with a combination of the therapeutic agent and the targeting moiety, the guest molecule is associated with the imager. Another aspect provides a dynamic host-guest interactive system for site specific drug delivery of relatively less cell membrane permeable drug(s).

  本发明涉及一种具有独特特性并在多个领域中找到应用的动态宿主-客体交互系统，具体地，在成像和定向药物传递方面。本公开的一个方面提供了一种动态宿主-客体交互系统，包括通过非共价力相互作用的宿主分子和客体分子，其中宿主分子与任何或结合的靶向基团和治疗剂相关联，但前提是当宿主分子与靶向基团相关联时，客体分子与成像剂相关联，当宿主分子与治疗剂相关联时，客体分子与靶向基团相关联，当宿主分子与治疗剂和靶向基团的组合相关联时，客体分子与成像剂相关联。另一个方面提供了一种用于相对较少细胞膜渗透性药物的定位药物传递的动态宿主-客体交互系统。