17465-86-0

Usage

Uses

Used in Cell Culture Applications:
Cyclooctapentylose is used as a solubilizing agent for non-polar molecules, such as cholesterol, in cell culture applications. Its hydrophobic internal surface enables it to form inclusion complexes with these non-polar molecules, increasing their solubility in aqueous environments and facilitating their use in cell culture studies.
Used in Capillary Electrophoresis:
Cyclooctapentylose can be used as a precursor for the synthesis of Octakis-(2,3-di-O-methyl-6-O-carboxymethyl)-γ-cyclodextrin sodium salt (ODMCM). ODMCM is utilized in capillary electrophoresis as a chiral resolving agent, helping to separate enantiomers of chiral compounds during the analysis.
Used in Drug Delivery Systems:
Cyclooctapentylose is used as a carrier for the transportation of hydrophobic drugs. Its hydrophobic internal surface allows it to form inclusion complexes with hydrophobic drug molecules, improving their solubility and bioavailability, and enhancing their delivery to target sites within the body.
Used in Synthesis of Metal-Organic Frameworks:
Cyclooctapentylose can be used in the synthesis of renewable and biocompatible metal-organic frameworks. These frameworks have potential applications in various fields, including gas storage, catalysis, and drug delivery.
Used in Formation of Inclusion Complexes:
Cyclooctapentylose can be used to form inclusion complexes with a variety of guest molecules, increasing their solubility in water and other polar solvents. This property is particularly useful in the pharmaceutical industry, where it can help improve the solubility and bioavailability of poorly water-soluble drugs.
Used in Synthesis of Nanogels and Dendrimers:
Cyclooctapentylose can be used in the synthesis of γ-CD based nanogels and dendrimers, which serve as carriers and stabilizers for drug delivery applications. These nanostructures can enhance the delivery and targeting of drugs, improving their therapeutic efficacy.

Flammability and Explosibility

Nonflammable

Pharmaceutical Applications

Cyclodextrins are ‘bucketlike’ or ‘conelike’ toroid molecules, with a rigid structure and a central cavity, the size of which varies according to the cyclodextrin type. The internal surface of the cavity is hydrophobic and the outside of the torus is hydrophilic; this is due to the arrangement of hydroxyl groups within the molecule. This arrangement permits the cyclodextrin to accommodate a guest molecule within the cavity, forming an inclusion complex.Cyclodextrins may be used to form inclusion complexes with a variety of drug molecules, resulting primarily in improvements to dissolution and bioavailability owing to enhanced solubility and improved chemical and physical stability.Cyclodextrin inclusion complexes have also been used to mask the unpleasant taste of active materials and to convert a liquid substance into a solid material. γ-cyclodextrin has the largest cavity and can be used to form inclusion complexes with large molecules;it has low toxicity and enhanced water solubility. In parenteral formulations, cyclodextrins have been used to produce stable and soluble preparations of drugs that would otherwise have been formulated using a nonaqueous solvent. In eye drop formulations, cyclodextrins form water-soluble complexes with lipophilic drugs such as corticosteroids. They have been shown to increase the water solubility of the drug; to enhance drug absorption into the eye; to improve aqueous stability; and to reduce local irritation.Cyclodextrins have also been used in the formulation of solutions,suppositories, and cosmetics.

Safety

Cyclodextrins are starch derivatives and are mainly used in oral and parenteral pharmaceutical formulations. They are also used in topical and ophthalmic formulations. Cyclodextrins are also used in cosmetics and food products, and are generally regarded as essentially nontoxic and nonirritant materials. However, when administered parenterally, β-cyclodextrin is not metabolized but accumulates in the kidneys as insoluble cholesterol complexes, resulting in severe nephrotoxicity. Cyclodextrin administered orally is metabolized by microflora in the colon, forming the metabolites maltodextrin, maltose, and glucose; these are themselves further metabolized before being finally excreted as carbon dioxide and water. Although a study published in 1957 suggested that orally administered cyclodextrins were highly toxic, more recent animal toxicity studies in rats and dogs have shown this not to be the case, and cyclodextrins are now approved for use in food products and orally administered pharmaceuticals in a number of countries. Cyclodextrins are not irritant to the skin and eyes, or upon inhalation. There is also no evidence to suggest that cyclodextrins are mutagenic or teratogenic. γ-Cyclodextrin LD50 (rat, IP): 4.6 g/kg LD50 (rat ,IV): 4.0 g/kg LD50 (rat, oral): 8.0 g/kg

InChI:InChI=1/C48H80O40/c49-1-9-33-17(57)25(65)41(73-9)82-34-10(2-50)75-43(27(67)19(34)59)84-36-12(4-52)77-45(29(69)21(36)61)86-38-14(6-54)79-47(31(71)23(38)63)88-40-16(8-56)80-48(32(72)24(40)64)87-39-15(7-55)78-46(30(70)22(39)62)85-37-13(5-53)76-44(28(68)20(37)60)83-35-11(3-51)74-42(81-33)26(66)18(35)58/h9-72H,1-8H2/t9-,10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-/m1/s1

Upstream product

• 87832-35-7 C₄₈H₈₀O₄₀*C₁₆H₁₀ 
• 10016-20-3 alpha cyclodextrin 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 7585-39-9 β‐cyclodextrin 
• 34620-77-4 malto-hexaose 
• 66567-45-1 malto-octaose 
• 80800-17-5 C₄₈H₈₀O₄₀*C₁₅H₁₇BrNO⁽¹⁺⁾*Br^(1-) 

Downstream Products

• 89239-13-4 C₆₁H₈₈N₂O₄₁ 
• 90510-11-5 C₄₈H₈₀O₄₀*C₁₉H₃₁NO 
• 98928-66-6 C₄₈H₈₀O₄₀*C₁₄H₁₄N₃O₃S^(1-)*Na⁽¹⁺⁾ 
• 129371-88-6 octakis(3-O-benzyl-2,6-di-O-methyl)cyclomaltooctaose 
• 155677-87-5 6¹,6⁵-di-O-trityl-cyclomalto-octaose 
• 155677-86-4 6¹,6⁴-di-O-trityl-cyclomalto-octaose 
• 155660-78-9 6¹,6³-di-O-trityl-cyclomalto-octaose 
• 123155-06-6 octakis(6-O-tert-butyldimethylsilyl)cyclomalto-octaose 
• 97227-33-3 6^I-O-p-toluenesulfonyl-γ-cyclodextrin 
• 97227-32-2 2^I-O-(p-toluenesulfonyl)-γ-cyclodextrin 

Relevant academic research and scientific papers

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of v-cyclodextrin

Monosubstituted derivatives of γ-cyclodextrin (γ-CD) are suitable building blocks for supramolecular polymers, and can also serve as precursors for the synthesis of other regioselectively monosubstituted γ-CD derivatives. We prepared a set of monosubstituted 2I-O-, 3I-O-, and 6I-O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of γ-CD using two different methods. A key step of the first synthetic procedure is a cross-metathesis between previously described regioisomers of mono-O-allyl derivatives of γ-CD and 2-vinylnaphthalene which gives yields of about 16-25% (2-5% starting from γ-CD). To increase the overall yields, we have developed another method, based on a direct alkylation of γ-CD with 3-(naphthalen-2-yl)allyl chloride as the alkylating reagent. Highly regioselective reaction conditions, which differ for each regioisomer in a used base, gave the monosubstituted isomers in yields between 12-19%. Supramolecular properties of these derivatives were studied by DLS, ITC, NMR, and Cryo-TEM.

A spectroscopic study of the inclusion of azulene by β- And γ-cyclodextrins

The inclusion of azulene (AZ) inside the cavities of β-cyclodextrin (β-CD) and γ-cyclodextrin (γ-CD) was studied using absorption, fluorescence and induced-circular dichroism spectroscopy. The inclusion of AZ into the cavity of β-CD has a stoichiometry of 1:1, whereas that of AZ/γ-CD complex is 1:2. The equilibrium constants for the formation of the two complexes were calculated to be 780 ± 150 M-1 for AZ:β-CD and (4.5 ± 0.86) × 105 M-2 for AZ:(γ-CD)2. The latter is due to a stepwise equilibrium mechanism in which a 1:1 complex is formed with a binding constant of 775 M -1, followed by the formation of a 1:2 complex with a binding constant of 580 M-1. The difference between the two binding constant values is slight, indicating an almost equal contribution from each of the γ-CD molecules to the overall binding in AZ:(γ-CD)2. From the induced-circular dichroism spectra, the inclusion of AZ was found to be axial in AZ:β-CD and nearly axial in AZ:(γ-CD)2.

A novel cyclodextrin glucanotransferase from alkaliphilic Bacillus pseudalcaliphilus 20RF: Purification and properties

A new cyclodextrin glucanotransferase (CGTase, EC 2.4.1.19) from the obligated alkaliphile Bacillus pseudalcaliphilus 20RF, isolated from Bulgarian soils, was purified up to 18-fold by ultrafiltration and starch adsorption with a recovery of 63% activity. The enzyme was a monomer with a molecular weight 70 kDa estimated by SDS-PAGE. The CGTase exhibited two pH optima at pH 6.0 and 9.0 and was optimally active at 60 °C. The enzyme could be effectively used for conversion of raw starch into cyclodextrins (CDs) in a wide pH range, from 5.0 to 10.0 and temperatures 60-70 °C. The enzyme was more heat resistant after its pretreatment in alkaline pH 9.0 at high temperatures 65-70 °C, than at pH 6.0 under the same reaction conditions. The CGTase showed a significant stability in the presence of 15 mM various metal ions and reagents after 30 min incubation at 25 °C. The purified CGTase could be used for an efficient cyclodextrin production without any additives which is of an industrial interest. The achieved high conversion of an insoluble raw commercial corn starch into cyclodextrins (47%) with production of only two types of cyclodextrins, β- and γ-CD (80%:20%) in alkaline pH 9.0, makes B. pseudalcaliphilus 20RF CGTase industrially desired for cyclodextrin manufacture.

Enzyme-mediated dynamic combinatorial chemistry allows out-of-equilibrium template-directed synthesis of macrocyclic oligosaccharides

We show that the outcome of enzymatic reactions can be manipulated and controlled by using artificial template molecules to direct the self-assembly of specific products in an enzyme-mediated dynamic system. Specifically, we utilize a glycosyltransferase to generate a complex dynamic mixture of interconverting linear and macrocyclic α-1,4-d-glucans (cyclodextrins). We find that the native cyclodextrins (α, β and γ) are formed out-of-equilibrium as part of a kinetically trapped subsystem, that surprisingly operates transiently like a Dynamic Combinatorial Library (DCL) under thermodynamic control. By addition of different templates, we can promote the synthesis of each of the native cyclodextrins with 89-99% selectivity, or alternatively, we can amplify the synthesis of unusual large-ring cyclodextrins (δ and ?) with 9 and 10 glucose units per macrocycle. In the absence of templates, the transient DCL lasts less than a day, and cyclodextrins convert rapidly to short maltooligosaccharides. Templates stabilize the kinetically trapped subsystem enabling robust selective synthesis of cyclodextrins, as demonstrated by the high-yielding sequential interconversion of cyclodextrins in a single reaction vessel. Our results show that given the right balance between thermodynamic and kinetic control, templates can direct out-of-equilibrium self-assembly, and be used to manipulate enzymatic transformations to favor specific and/or alternative products to those selected in Nature.

Altered product specificity of a cyclodextrin glycosyltransferase by molecular imprinting with cyclomaltododecaose

Cyclodextrin glycosyltransferases (CGTases), members of glycoside hydrolase family 13, catalyze the conversion of amylose to cyclodextrins (CDs), circular α-(1,4)-linked glucopyranose oligosaccharides of different ring sizes. The CD containing 12 α-D-gluc

Effects of ionic surfactants and cyclodextrins on hydride-transfer reaction of l-Benzyl-l,4-dihydronicotinamide with methylene blue

The kinetics of the hydride-transfer reaction between methylene blue (MB+) and 1 -benzyl-1,4-dihydronictinamide (BNAH) were studied in media containing cyclodextrins (β- and γ-CD) and surfactants (sodium dodecyl sulfate (SDS), dodecyltrimethylammonium bromide, tetradecyltrimethylammonium bromide, and hexadecyltrimethylammonium bromide). Cationic surfactants decreased the apparent first-order rate constant (k obsd) above the cmc, while SDS increased kobsd just above the cmc and then decreased kobsd with increasing surfactant concentration. This behavior for cationic surfactants was typical of micellar effects due to a separation of the reactants by the micelles. BNAH associated with micelles, whereas MB+ ions were repelled from the cationic interface of the micelles. Binding of BNAH and MB to the same SDS micelle enhanced the reaction, but dilution of reagents within the micellar interface with the increase in [SDS] caused a decrease in Kobsd. In β-CD-cationic surfactant mixtures, the results were interpreted in terms of the model which takes into account the formation of CD-BNAH, CD-MB+, and CD-surfactant complexes and the association of BNAH with micelles. The decrease in Kobsd with increasing surfactant concentration observed in γ-CD-cationic surfactant mixtures can be explained by the decrease in the concentration of free γ-CD by the formation of 1:1 and 2:1 complexes of surfactant monomer with β-CD.

Optimized synthesis of specific sizes of maltodextrin glycosides by the coupling reactions of Bacillus macerans cyclomaltodextrin glucanyltransferase

Bacillus macerans cyclomaltodextrin glucanyltransferase (CGTase, EC 2.4.1.19), in reaction with cyclomaltohexaose and methyl α-d- glucopyranoside, methyl β-d-glucopyranoside, phenyl α-d- glucopyranoside, and phenyl β-d-glucopyranoside gave four kinds of maltodextrin glycosides. The reactions were optimized by using different ratios of the individual d-glucopyranosides to cyclomaltohexaose, from 0.5 to 5.0, to obtain the maximum molar percent yields of products, which were from 68.3% to 78.6%, depending on the particular d-glucopyranoside, and also to obtain different maltodextrin chain lengths. The lower ratios of 0.5-1.0 gave a wide range of sizes from d.p. 2-17 and higher. As the molar ratio was increased from 1.0 to 3.0, the larger sizes, d.p. 9-17, decreased, and the small and intermediate sizes, d.p. 2-8, increased; as the molar ratios were increased further from 3.0 to 5.0, the large sizes completely disappeared, the intermediate sizes, d.p. 4-8, decreased, and the small sizes, d.p. 2 and 3 became predominant. A comparison is made with the synthesis of maltodextrins by the reaction of CGTase with different molar ratios of d-glucose to cyclomaltohexaose.

Dynamics for the assembly of pyrene-γ-cyclodextrin host-guest complexes

Pyrene and γ-cyclodextrin (γ-CD) form complexes with 1:1, 1:2, and 2:2 (pyrene/CD) stoichiometries. The complexation dynamics was studied using stopped flow. The dynamics for the higher-order complexes (1:2 and 2:2) occurs in the millisecond time domain, which contrasts with the much faster dynamics for the 1:1 complex. When pyrene is mixed with γ-CD, a transient enhancement of the concentration for the 2:2 complex was observed between 0.2 and 1 s, which at longer times leads to the formation of the 1:2 complex. This enhancement of the nonthermodynamic product is an example of the kinetic formation of a host-guest complex, and these types of processes may be explored to build self-assemblies under kinetic control.

Isolation of Paenibacillus illinoisensis that produces cyclodextrin glucanotransferase resistant to organic solvents.

A bacterium that secreted cyclodextrin glucanotransferase (CGTase) in a medium overlaid with n-hexane was isolated and identified as Paenibacillus illinoisensis strain ST-12 K. The CGTase of the strain was purified from the culture supernatant. The molecular mass was 70 kDa. The enzyme was stable at pH 6 to 10 and active at pH 5.0 to 8.0. The optimum temperature at pH 7.0 was 65 degrees C in the presence of 5 mM CaCl2. The enzyme produced mainly beta-cyclodextrin. The total yield of alpha-, beta-, and gamma- cyclodextrins was increased 1.4-fold by the addition of ethanol. In particular, the yield of beta-cyclodextrins in the presence of 10% (vol/vol) ethanol was 1.6-fold that without ethanol. The CGTase was stable and active in the presence of large amounts of various organic solvents.

Catalysis of ester aminolysis by cyclodextrins. The reaction of alkylamines with p-nitrophenyl alkanoates

The effects of four cyclodextrins (α-CD, β-CD, hydroxypropyl-β-CD, and γ-CD) on the aminolysis of p-nitrophenyl alkanoates (acetate to heptanoate) by primary amines (n-propyl to n-octyl, isobutyl, isopentyl, cyclopentyl, cyclohexyl, benzyl) in aqueous solution have been investigated. Rate constants for amine attack on the free and CD-bound esters (k(N) and k(cN)) have ratios (k(cN)/k(N)) varying from 0.08 (retardation) to 180 (catalysis). For the kinetically equivalent process of free ester reacting with CD-bound amine (k(Nc)), the ratios k(Nc)/k(N) vary from 0.2 to 28. Either way, there is evidence of catalysis in some cases and retardation in others. Changes in reactivity parameters with structure indicate more than one mode of transition state binding to the CDs. Short esters react with short alkylamines by attack of free amine on the ester bound by its aryl group, but for longer amines, free ester reacts with CD-bound amine. Reaction of long esters with long amines, which is catalyzed by β-CD and γ-CD, involves inclusion of the alkylamino group and possibly the ester acyl group. The larger cavity of γ-CD may allow the inclusion of the ester aryl group, as well as the alkylamino group, in the transition state. Reaction between an ester bound to the CD by its acyl group and free amine appears not to be important.