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C4555

Methyl-β-cyclodextrin

powder, BioReagent, suitable for cell culture

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About This Item

CAS Number:
128446-36-6
MDL number:
MFCD00066764
UNSPSC Code:
12352201
NACRES:
NA.77
Form:
powder
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biological source

synthetic (organic)

Quality Segment

300

sterility

non-sterile

product line

BioReagent

form

powder

mol wt

~1320 g/mol

extent of labeling

1.5-2.1 methyl per mol glucose

technique(s)

cell culture | mammalian: suitable

mp

180-182 °C (lit.)

solubility

H2O: 50 mg/mL

storage temp.

room temp

SMILES string

O1C2OC(C(OC3OC(C(OC4OC(C(OC5OC(C(OC6OC(C(OC7OC(C(OC8OC(C1C(C8OC)O)COC)C(C7OC)O)COC)C(C6OC)O)COC)C(C5OC)O)COC)C(C4OC)O)COC)C(C3OC)O)COC)C(C2OC)O)COC

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

General description

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

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

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. It can be used to increase the solubility of non-polar substances such as fatty acids, lipids, vitamins and cholesterol for use in cell culture applications. 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.

Preparation Note

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.

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This Item
332615779776M7439
Methyl-β-cyclodextrin powder, BioReagent, suitable for cell culture

Sigma-Aldrich

C4555

Methyl-β-cyclodextrin

Methyl-β-cyclodextrin average Mn 1310

Sigma-Aldrich

332615

Methyl-β-cyclodextrin

Methyl-β-cyclodextrin Wacker Chemie AG, ≥95.0% cyclodextrin basis (calculated)

Sigma-Aldrich

779776

Methyl-β-cyclodextrin

Methyl-β-cyclodextrin

Sigma-Aldrich

M7439

Methyl-β-cyclodextrin

description

powder, BioReagent, suitable for cell culture

description

average Mn 1310

description

Wacker Chemie AG, ≥95.0% cyclodextrin basis (calculated)

description

-

solubility

H2O: 50 mg/mL

solubility

-

solubility

-

solubility

-

Quality Level

300

Quality Level

100

Quality Level

100

Quality Level

200

storage temp.

room temp

storage temp.

-

storage temp.

-

storage temp.

-

mp

180-182 °C (lit.)

mp

180-182 °C (lit.)

mp

180-182 °C (lit.)

mp

180-182 °C (lit.)

form

powder

form

powder

form

powder

form

powder

sterility

non-sterile

sterility

-

sterility

-

sterility

-

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

368.6 °F

flash_point_c

187 °C

ppe

Eyeshields, Gloves, type N95 (US)

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Questions

1–9 of 9 Questions  

  1. How to make 50mM stock of MbCD using PBS?

    1 answer

    1. The solubility of the material is tested at 50 mg/mL in water. However, cyclodextrins are typically soluble in water at a range of 40 - 50% (w/v). A 50 mM solution corresponds to approximately 66 mg/mL or roughly 6.6%. To prepare a solution, add the desired amount of powdered product to the appropriate volume of water while stirring, until clear. Please see the following links to review additional information regarding Cyclodextrins:

      Water-souble complexes - see page 2
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/215/062/c4555inf.pdf

      Cyclodextrin solubiity table
      https://www.sigmaaldrich.com/technical-documents/technical-article/cell-culture-and-cell-culture-analysis/cell-culture-media-preparation/cyclodextrin

      Helpful?

  2. How to make a 200 mM stock of methy Beta cyclodexterin ? Solublilty is 50mg/liter

    1 answer

    1. A 200 mM stock of Methyl-β-cyclodextrin is not recommended due to its maximal solubility of 50 mg/mL. Since the molecular mass of MβCD is 1310, the highest recommended concentration is 38 mM.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

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

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

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