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Merck
CN

C4555

Sigma-Aldrich

甲基-β-环糊精

powder, BioReagent, suitable for cell culture

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UNSPSC代码:
12352201
NACRES:
NA.77

生物来源

synthetic (organic)

质量水平

无菌性

non-sterile

产品线

BioReagent

形式

powder

分子量

~1320 g/mol

标记范围

1.5-2.1 methyl per mol glucose

技术

cell culture | mammalian: suitable

mp

180-182 °C (lit.)

溶解性

H2O: 50 mg/mL

储存温度

room temp

InChI

1S/C56H98O35/c1-64-15-22-36-29(57)43(71-8)50(78-22)86-37-23(16-65-2)80-52(45(73-10)30(37)58)88-39-25(18-67-4)82-54(47(75-12)32(39)60)90-41-27(20-69-6)84-56(49(77-14)34(41)62)91-42-28(21-70-7)83-55(48(76-13)35(42)63)89-40-26(19-68-5)81-53(46(74-11)33(40)61)87-38-24(17-66-3)79-51(85-36)44(72-9)31(38)59/h22-63H,15-21H2,1-14H3

InChI key

QGKBSGBYSPTPKJ-UHFFFAOYSA-N

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一般描述

甲基-β-环糊精是一种七糖,可溶于水,且由于存在疏水核心,对胆固醇具有更高亲和力。环糊精是由6、7或8个吡喃葡萄糖单元组成的环状低聚糖,通常分别称为α-、β-或γ-环糊精。这些化合物具有刚性环形结构,使其成为天然的络合剂。这些化合物的相邻吡喃葡萄糖单元的C2-和C3-羟基之间易于形成分子内氢键,使其独特结构具有稳定性。该分子具有圆环形状,其C2-和C3-羟基位于较大开口端周围,反应性更强的C6-羟基排列在较小开口端周围。与氢键合C2-和C3-羟基相对的C6-羟基排列迫使氧键在空腔内紧密靠近,产生一个富电子的疏水内部。该疏水性空腔的大小是形成环糊精的吡喃葡萄糖单元数的函数。

天然环糊精的溶解度非常低。在20世纪60年代后期,人们发现2、3和6羟基位置的化学取代能大大增加溶解度。大多数化学改性环糊精能够在水中达到50% (w/v)的浓度。

应用

甲基-β-环糊精已用于:
  • 研究精子膜上的胆固醇消耗对精子顶体反应能力的影响
  • 确定小窝蛋白过表达的作用及其丧失对生存和促生长信号传导的影响
  • 传统体外受精

生化/生理作用

甲基-β-环糊精(MβCD)通常用作抑制剂,同时可修饰细胞表面的胆固醇结构域。这会消耗膜上胆固醇。目前还确知,通过内化这一成分可阻止霍乱毒素、一氧化氮(NO)合酶和葡萄糖转运蛋白发挥作用。在观测脂质筏和小窝内吞作用时,这一现象尤为明显。MβCD可引起胆固醇外流及流入。由于MβCD作用导致胆固醇水平下降,胆固醇水平调控基因上调影响了细胞活力。这一成分可用于提高非极性物质(如脂肪酸、脂质、维生素和胆固醇)的溶解度,以便用于细胞培养应用。空穴大小是复合反应选用环糊精的主要决定因素。β-环糊精或β-吡喃葡萄糖单元化合物的空腔直径非常适合用于与激素、维生素以及许多组织和细胞培养常用化合物大小相近的分子。因此,β-环糊精最常用作络合剂。

重悬

在室温下搅拌30分钟即可得到溶液。另外,也可以采用冷却超声波。溶液可在4℃下保存数月。固体应在室温下密封保存。

WGK

WGK 3

闪点(°F)

368.6 °F

闪点(°C)

187 °C

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

涉药品监管产品

分析证书(COA)

输入产品批号来搜索 分析证书(COA) 。批号可以在产品标签上"批“ (Lot或Batch)字后找到。

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  1. What is the molecular weight of Methyl-β-cyclodextrin, Product No. C4555?

    The approximate molecular weight is 1320 g/mol. The molecular weight can vary from lot to lot due to variation in the methyl content of the product. The molecular weight of this product is dependent on the average number of methyl groups per glucose residue (reported on the lot specific Certificate of Analysis). View the specification sheet above.

  2. How can I make a solution of Methyl-β-cyclodextrin, Product C4555?

    This product is tested and found soluble at 50 mg/ml in 1 M NaOH yielding a clear, colorless solution.  This product is also soluble in water (150 mg/ml), yielding a clear, colorless solution. Aqueous solutions may be obtained by stirring 30 minutes at room temperature. Alternatively, sonication with cooling may be employed.

  3. How should a solution of Methyl-β-cyclodextrin, Product C4555, be sterilized?

    Solutions can be sterile filtered using a 0.2 μm membrane. We do not recommend autoclaving the solution. The product as supplied is not sterile.

  4. How does Methyl-β-cyclodextrin, Product C4555, work to solubilize products that have minimal solubility in aqueous solutions for use in cell culture?

    The cavity diameter of β -cyclodextrins compounds is well-suited for use with molecules the size of hormones, vitamins and many compounds frequently used in tissue and cell culture applications. For this reason, β-cyclodextrin is most commonly used as a complexing agent.  Hydrophobic molecules are incorporated into the cavity of cyclodextrins by displacing water. This reaction is favored by the repulsion of the molecule by water. This effectively encapsulates the molecule of interest within the cyclodextrin, rendering the molecule water soluble. When the water soluble complex is diluted in a much larger volume of aqueous solvent, the process is reversed, thereby releasing the molecule of interest into the solution.

  5. What concentration of Methyl-β-cyclodextrin, Product C4555, do I use to remove cholesterol from cell membranes?

    This product has been used to reduce the cholesterol content of cell membranes at 10 - 50 mM.References:Eur J Cell Biol. 1999 Jul, 78(7): 473-84.Lipids. 1996 Aug, 31(8): 817-28.

  6. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  7. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  8. What is Product C4555, Methyl-β-cyclodextrin?

    Methyl-β-cyclodextrin is used as a "carrier" molecule to facilitate the dissolution of compounds with low solubility in water.

  9. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  10. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  11. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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How palmitic acid, other fatty acids and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies.

棕榈酸等脂肪酸和其他细胞培养成分如何影响无血清、无蛋白细胞培养系统(用于生物制造包括单克隆抗体在内的异源蛋白)的性能。

Cyclodextrin solubilizes fat-soluble vitamins and hormones, enhancing their solubility in water for cell culture applications.

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