91464-90-3 , gamma-Cyclodextrin,
Cyclomaltooctaose,
Cyclooctaamylose
Cas:91464-90-3
C48H80O40 / 1297.12
MFCD00009595
Gamma-cyclodextrin is a cyclic molecule formed by six glucose units. It has been shown to inhibit the growth of human immunodeficiency virus (HIV) and leucoxylon, as well as other viruses. Gamma-cyclodextrin's ability to bind to amide groups on proteins may be due to its structural similarity with nevirapine, an HIV drug. Gamma-cyclodextrin has also been shown to have anti-inflammatory properties and can be used for the treatment of osteoarthritis.
Gamma-Cyclodextrin Hydrate (γ-CD) is a cyclic oligosaccharide that belongs to the family of cyclodextrins. It is made up of eight glucose monomers arranged in a toroidal shape. The central cavity of γ-CD is hydrophobic, while the outer surface is hydrophilic. Due to its unique structural properties, it has been extensively studied for its potential applications in various fields of research and industry, such as drug delivery, food industry, environmental remediation, and material sciences. This paper aims to provide a comprehensive overview of γ-CD, including its definition, properties, synthesis, characterization, analytical methods, biological properties, toxicity, safety, applications, current state of research, potential implications, limitations, and future directions.
Definition and Background
Cyclodextrins (CDs) were first discovered in the 19th century as a degradation product of starch by Bacillus macerans. CDs are cyclic oligosaccharides made up of glucose monomers linked together by α-(1,4) glycosidic bonds. They have a toroidal shape with a central cavity, which can accommodate hydrophobic or lipophilic molecules. There are three types of CDs: alpha, beta, and gamma, depending on the number of glucose units in their structure. Gamma-Cyclodextrin Hydrate (γ-CD) is the largest of the three CDs and consists of eight glucose units.
Synthesis and Characterization
γ-CD is synthesized from amylose, a linear polymer of glucose units, through enzymatic or chemical methods. The enzymatic method involves the use of cyclodextrin glucosyltransferase (CGTase), an enzyme produced by Bacillus species, which catalyzes the transfer of glucose units from amylose to form γ-CD. Chemical methods involve the use of acid or alkaline hydrolysis of starch to form α-CD, which is subsequently converted to γ-CD using CGTase.
The characterization of γ-CD is done using various methods, such as nuclear magnetic resonance (NMR) spectroscopy, X-ray diffraction, differential scanning calorimetry (DSC), and thermal gravimetric analysis (TGA). These methods provide information about the structure, purity, and thermal stability of γ-CD.
Analytical Methods
Various analytical methods are used to determine the properties and purity of γ-CD. These methods include high-performance liquid chromatography (HPLC), gas chromatography (GC), mass spectrometry (MS), and capillary electrophoresis (CE). These methods are highly sensitive and can detect trace amounts of impurities in γ-CD.
Biological Properties
γ-CD has been extensively studied for its biological properties, such as its ability to form inclusion complexes with various molecules, enhance the solubility and stability of drugs, and improve their bioavailability. It has also been studied for its potential applications in food and environmental industries.
Toxicity and Safety in Scientific Experiments
The safety profile of γ-CD has been extensively investigated, and it is generally regarded as safe for human consumption. In animal studies, oral administration of γ-CD at high doses (up to 20 g/kg body weight) did not cause any significant toxic effects. However, certain studies have reported adverse effects of γ-CD on the gastrointestinal tract at higher doses. Hence, further studies are required to determine the optimal dosage and safety of γ-CD in humans.
Applications in Scientific Experiments
γ-CD has several applications in scientific experiments, such as drug delivery, food industry, environmental remediation, and material sciences. In drug delivery, γ-CD is used to form inclusion complexes with poorly soluble drugs, improve their solubility and bioavailability, and target specific tissues. In the food industry, γ-CD is used as a food additive, stabilizer, and emulsifier. In environmental remediation, γ-CD is used to remove pollutants from water, soil, and air. In material sciences, γ-CD is used to form supramolecular structures, such as hydrogels, nanoparticles, and thin films.
Current State of Research
Research on γ-CD has been increasing in recent years, with several studies focusing on its potential applications in drug delivery, food industry, environmental remediation, and material sciences. These studies have shown promising results in improving the solubility, stability, and bioavailability of drugs, enhancing the shelf life and taste of food products, removing pollutants from the environment, and developing novel materials for various applications.
Potential Implications in Various Fields of Research and Industry
The potential implications of γ-CD in various fields of research and industry are significant. In the pharmaceutical industry, γ-CD can be potentially used to develop novel drug formulations and platforms for drug delivery. In the food industry, γ-CD can be used to develop novel food products and improve the quality and safety of existing products. In environmental remediation, γ-CD can be used to develop effective and eco-friendly methods for removing pollutants from the environment. In the material sciences, γ-CD can be used to develop new materials with unique properties and applications.
Limitations and Future Directions
γ-CD has limitations in terms of its solubility, stability, and toxicity at high doses. Future research can focus on improving these aspects, exploring new applications of γ-CD in various fields, and evaluating its safety and efficacy in humans. Some future directions for research include:
- Developing novel γ-CD-based drug platforms for targeted drug delivery and controlled release.
- Studying the effects of γ-CD on the gut microbiome and evaluating its safety in long-term use.
- Developing γ-CD-based materials with unique optical, electrical, and mechanical properties.
- Studying the applications of γ-CD in gene delivery and other biological applications.
- Investigating the potential of γ-CD in plant growth promotion and agricultural applications.
Conclusion
Gamma-Cyclodextrin Hydrate is a cyclodextrin that has been extensively studied for its potential applications in various fields of research and industry, such as drug delivery, food industry, environmental remediation, and material sciences. Its unique structural properties make it a promising platform for developing novel drug formulations, food products, and materials. While further studies are necessary to optimize its safety, efficacy, and potential applications, γ-CD holds immense potential for revolutionizing various industries and addressing important scientific challenges.
CAS Number | 91464-90-3 |
Product Name | gamma-Cyclodextrin hydrate |
IUPAC Name | (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,38R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-5,10,15,20,25,30,35,40-octakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentacontane-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecol;hydrate |
Molecular Formula | C48H80O40 |
Molecular Weight | 1297.12 g/mol |
InChI | InChI=1S/C48H80O40.H2O/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;1H2/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 |
InChI Key | SPKUKQHKKVTYOE-SMTXKKGASA-N |
SMILES | C(C1C2C(C(C(O1)OC3C(OC(C(C3O)O)OC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)OC6C(OC(C(C6O)O)OC7C(OC(C(C7O)O)OC8C(OC(C(C8O)O)OC9C(OC(O2)C(C9O)O)CO)CO)CO)CO)CO)CO)CO)O)O)O.O |
Canonical SMILES | C(C1C2C(C(C(O1)OC3C(OC(C(C3O)O)OC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)OC6C(OC(C(C6O)O)OC7C(OC(C(C7O)O)OC8C(OC(C(C8O)O)OC9C(OC(O2)C(C9O)O)CO)CO)CO)CO)CO)CO)CO)O)O)O.O |
Isomeric SMILES | C([C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@@H]([C@@H]([C@H]8O)O)O[C@@H]9[C@H](O[C@H](O2)[C@@H]([C@H]9O)O)CO)CO)CO)CO)CO)CO)CO)O)O)O.O |
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