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Return to Web Version Cyclodextrins By: Vicki Caligur, BioFiles 2008, 3.3, 32. BioFiles 2008, 3.3, 32. 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. A frequently used approach is to use cyclodextrin as a “carrier” molecule to facilitate the dissolution of these compounds. Structural representations of β-cyclodextrin, α-cyclodextrin, and γ-cyclodextrin. The cyclodextrins are cyclic oligosaccharides consisting of 7, 6, or 8 (respectively) glucopyranose units. The solubility of natural cyclodextrins is very poor and initially this prevented cyclodextrins from becoming effective complexing agents. In the late 1960’s, it was discovered that chemical substitutions at the 2-, 3-, and 6-hydroxyl sites would greatly increase solubility. The degree of chemical substitution and the nature of the groups used for substitution determine the final maximum concentration of cyclodextrin in an aqueous medium. 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. “Fit” is critical to achieving good incorporation of cyclodextrins. α-Cyclodextrins have small cavities that are not capable of accepting many molecules. γCyclodextrins have much larger cavities than many molecules to be incorporated, and cyclodextrin hydrophobic charges cannot effectively interact to facilitate complexation. The cavity diameter of β-cyclodextrins has been found to be the most appropriate size for hormones, vitamins, and other 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. Sigma’s product line of water-soluble complexes includes cyclodextrins and soluble cyclodextrin-complexes of biochemicals commonly used in tissue and cell culture applications. Cyclodextrins Product Name α-Cyclodextrin Formula C36H60O30 Mol Wt. 972.84 Assay (%) ≥98 Application - Solubility Cat. No. H2O 50 mg/mL C46421G C46425G C464225G C46801G cell culture α-Cyclodextrin C36H60O30 972.84 ≥98 H2O 50 α-Cyclodextrin C36H60O30 972.84 ≥98 tested H2O 50 mg/mL 1M β-Cyclodextrin C42H70O35 1134.98 ≥98 - NH4OH 50 mg/mL C46805G C476725G C4767100G C48055G β-Cyclodextrin C42H70O35 1134.98 ≥98 cell culture tested 1 M NaOH 50 mg/mL C480525G C4805100G 1M γ-Cyclodextrin C48H80O40 1297.12 ≥99 - NH4OH 50 mg/mL C48921G C48925G 1 M NaOH γ-Cyclodextrin C48H80O40 (2-Hydroxypropyl)-βcyclodextrin - 1297.12 - ≥98 - cell culture 25 mg/mL, may be C4930100MG tested clear to C4930- slightly hazy 1G - H2O 45 % H1075G (w/v) H107100G (2-Hydroxypropyl)-βcyclodextrin extent of labeling 4 - 10 - - - cell culture H2O 100 C09265G tested mg/mL C0926- (determined by NMR) 10G (2-Hydroxypropyl)-βcyclodextrin 45 % (w/v) in (C6H9O5)7 · H2O (C3H7O)4.5 1393.82 - - - - H2O 450 mg/mL H578410ML H125- (2-Hydroxypropyl)-γcyclodextrin Methyl-β-cyclodextrin extent of labeling 1.5 - 2.1 methyl per 1 mol - - - - - - cell culture tested H2O 50 mg/mL 5G-I H125100G-I C45551G C45555G C455510G Materials Product # C4642 Image Description α-Cyclodextrin ≥98% Molecular Formula C36H60O30 Add to Cart pricing C4680 α-Cyclodextrin powder, C36H60O30 pricing BioReagent, suitable for cell culture, ≥98% C4767 β-Cyclodextrin ≥97% C42H70O35 pricing C4805 β-Cyclodextrin powder, C42H70O35 pricing BioReagent, suitable for cell culture, ≥97% C4892 γ-Cyclodextrin ≥99% C48H80O40 pricing C4930 γ-Cyclodextrin powder, BioReagent, suitable for cell culture, ≥98% C48H80O40 pricing C0926 (2-Hydroxypropyl)-βcyclodextrin powder, BioReagent, suitable for cell culture pricing H107 (2-Hydroxypropyl)-βcyclodextrin powder pricing H5784 (2-Hydroxypropyl)-βcyclodextrin solution pricing H125 (2-Hydroxypropyl)-γcyclodextrin solid pricing C4555 Methyl-β-cyclodextrin powder, BioReagent, suitable for cell culture pricing
