|Related Categories||Cell Biology, Cell Culture, Cell Signaling and Neuroscience, Chelation/Complexation Compounds, Chemical Synthesis,|
|extent of labeling||1.5-2.1 methyl per mol glucose|
|solubility||H2O: soluble50 mg/mL|
|suitability||suitable for cell culture|
Live Chat and Frequently Asked Questions are available for this Product.
Use to increase the solubility of non-polar substances such as fatty acids, lipids, vitamins and cholesterol for use in cell culture applications.
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.
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.
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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...
BioFiles 2008, 3.3, 32.
Keywords: Cell culture, Hormones, Nuclear magnetic resonance spectroscopy, Substitutions, Vitamins
Studies of cyclodextrin inclusion complexes. Cabra Marques, et al. Int. J. Pharmacol. 77, 297, (1991)
Comparative study on inclusion complexation of maltosyl-β-cyclodextrin, heptakis (2,6-di-O-methyl)-β-cyclodextrin and β-cyclodextrin with fucosterol. Acarturk, et al. J. Pharm. Pharmacol. 45, 1028, (1993)
Desmosterol can replace cholesterol in sustaining cell proliferation and regulating the SREBP pathway in a sterol-Delta24-reductase-deficient cell line. Rodríguez-Acebes S Biochem. J. 420(2), 305-15, (2009)
Increasing antiproliferative properties of endocannabinoids in N1E-115 neuroblastoma cells through inhibition of their metabolism. Hamtiaux L, Hansoulle L, Dauguet N, et al. PLoS ONE 6(10), e26823, (2011)
FT-IR 2 (1), 288:C / FT-NMR 1 (1), 312:B / RegBook 1 (1), 199:E
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