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C4555 Sigma-Aldrich

Methyl-β-cyclodextrin

powder, BioReagent, suitable for cell culture

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Properties

Related Categories Cell Biology, Cell Culture, Cell Signaling and Neuroscience, Chelation/Complexation Compounds, Chemical Synthesis,
Quality Level   200
biological source   synthetic (organic)
sterility   non-sterile
product line   BioReagent
form   powder
mol wt   ~1320 g/mol
extent of labeling   1.5-2.1 methyl per mol glucose
application(s)   cell culture | mammalian: suitable
mp   180-182 °C (lit.)
solubility   H2O: 50 mg/mL
storage temp.   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

Description

General description

Cyclodextrins are cyclic oligosaccharides consisting of 6, 7, or 8 glucopyranose units, usually referred to as α-, β-, or γ-cyclodextrins, respectively. These compounds have rigid doughnut-shaped structures making them natural complexing agents. The unique structures of these compounds owe their stability to intramolecular hydrogen bonding between the C2- and C3-hydroxyl groups of neighboring glucopyranose units. The molecule takes on the shape of a torus with the C2- and C3-hydroxyls located around the larger opening and the more reactive C6-hydroxyl aligned around the smaller opening. The arrangement of C6-hydroxyls opposite the hydrogen bonded C2- and C3-hydroxyls forces the oxygen bonds into close proximity within the cavity, leading to an electron rich, hydrophobic interior. The size of this hydrophobic cavity is a function of the number of glucopyranose units forming the cyclodextrin.

The solubility of natural cyclodextrins is very poor. In the late 1960’s, it was discovered that chemical substitutions at the 2, 3, and 6 hydroxyl sites would greatly increase solubility. Most chemically modified cyclodextrins are able to achieve a 50% (w/v) concentration in water.

Cavity size is the major determinant as to which cyclodextrin is used in complexation. The cavity diameter of β-cyclodextrins or β-glucopyranose unit 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.

Methyl-β-cyclodextrin is a heptasaccharide, soluble in water, and has more affinity to cholesterol due to the presence of hydrophobic core.

Application

Methyl-β-cyclodextrin has been used:
• to study the effect of cholesterol depletion, from sperm membrane on sperm’s ability to undergo acrosome reaction.
• to determine the effect of caveolin overexpression and its loss on pro-survival and pro-growth signaling
• in conventional in vitro fertilization

Packaging

1, 5, 10 g in poly bottle

Biochem/physiol Actions

Methyl-β-cyclodextrin (MβCD) is commonly applicable as an inhibitor and modifies cholesterol domains on the cellular surface. It causes depletion of cholesterol on the membrane. It is also known to prevent the action of cholera toxin, nitric oxide (NO) synthase and glucose transporter through internalization. This is observed in specific to lipid rafts and caveolae endocytosis. MβCD induces eflux as well as influx of cholesterol. It can affect cell viability as the genes regulating cholesterol levels are upregulated, due to decreased cholesterol level by the action of MβCD.

Reconstitution

Solutions may be obtained by stirring 30 min at room temperature. Alternatively, sonication with cooling may be employed. Solutions may be stored for several months at 4°C. Solid should be stored tightly sealed at room temperature.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
368.6 °F
Flash Point(C) 
187 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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Protocols & Articles

Articles

Cyclodextrins

Many metabolically important compounds, such as lipid-soluble vitamins and hormones, have very low solubilities in aqueous solutions. Various techniques have been used to solubilize these compounds i...
Vicki Caligur
BioFiles 2008, 3.3, 32.
Keywords: Cell culture, Hormones, Nuclear magnetic resonance spectroscopy, Substitutions, Vitamins

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Peer-Reviewed Papers
15

References

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