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C4555

Sigma-Aldrich

Methyl-β-cyclodextrin

powder, BioReagent, suitable for cell culture

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CAS Number:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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

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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This Item
M7439779873332615
Methyl-β-cyclodextrin powder, BioReagent, suitable for cell culture

Sigma-Aldrich

C4555

Methyl-β-cyclodextrin

Methyl-β-cyclodextrin

Sigma-Aldrich

M7439

Methyl-β-cyclodextrin

mp

180-182 °C (lit.)

mp

180-182 °C (lit.)

mp

180-182 °C (lit.)

mp

180-182 °C (lit.)

solubility

H2O: 50 mg/mL

solubility

-

solubility

-

solubility

-

storage temp.

room temp

storage temp.

-

storage temp.

-

storage temp.

-

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

100

biological source

synthetic (organic)

biological source

-

biological source

-

biological source

-

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

368.6 °F

Flash Point(C)

187 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Microdroplet in vitro fertilization can reduce the number of spermatozoa necessary for fertilizing oocytes
Hasegawa A, et al.
Journal of Reproduction and Development, 60(3), 187-193 (2014)
Redox Cell Biology and Genetics, Part 2
Methods in Enzymology, 60(3), 187-193 (2002)
Neuron-targeted caveolin-1 enhances signaling and promotes arborization of primary neurons
Head BP, et al.
The Journal of biological chemistry, 118(2-4), jbc-M111 (2011)
Cholesterol addition protects membrane intactness during cryopreservation of stallion sperm
Oliveira CH de, et al.
Animal Reproduction Science, 118(2-4), 194-200 (2010)
Ecancermedicalscience, 60(3), 187-193 (2008)

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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 in tissue culture, cell culture, or other water-based applications.

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