173094-60-5

Basic information

• Product Name: octakis(6-chloro-6-deoxy)-γ-cyclodextrin
• Synonyms: octakis(6-chloro-6-deoxy)-γ-cyclodextrin;6-Chloro-6-deoxy-gamma-cyclodextrin
• CAS NO: 173094-60-5
• Molecular Formula: C48H72Cl8O32
• Molecular Weight: 1444.69
• Mol File: 173094-60-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Density: 1.588±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Dimethylformamide (Sparingly, Sonicated), DMSO (Slightly)
• PKA: 11.60±0.70(Predicted)
• CAS DataBase Reference: octakis(6-chloro-6-deoxy)-γ-cyclodextrin(CAS DataBase Reference)
• NIST Chemistry Reference: octakis(6-chloro-6-deoxy)-γ-cyclodextrin(173094-60-5)
• EPA Substance Registry System: octakis(6-chloro-6-deoxy)-γ-cyclodextrin(173094-60-5)

Safety Data

• Hazardous Substances Data: 173094-60-5(Hazardous Substances Data)

Usage

Description

Octakis(6-chloro-6-deoxy)-γ-cyclodextrin is a modified form of γ-cyclodextrin, a cyclic oligosaccharide consisting of eight glucose units. The modification involves the substitution of six hydroxyl groups with chlorine atoms, which enhances its ability to form complexes with various guest molecules. This property makes it a versatile compound with potential applications in different industries.

Uses

Used in Pharmaceutical Industry:
Octakis(6-chloro-6-deoxy)-γ-cyclodextrin is used as a complexation agent for improving the solubility, stability, and bioavailability of poorly water-soluble drugs. Its ability to form inclusion complexes with a wide range of guest molecules allows for the development of more effective drug formulations.
Used in Supramolecular Chemistry:
In the field of supramolecular chemistry, octakis(6-chloro-6-deoxy)-γ-cyclodextrin is used as a host molecule for the construction of various supramolecular architectures. Its unique structure and functionalization enable the formation of stable complexes with a variety of guest molecules, facilitating the design and synthesis of novel supramolecular systems.
Used in Material Science:
Octakis(6-chloro-6-deoxy)-γ-cyclodextrin is used as a building block for the development of novel materials with specific properties. Its ability to form complexes with various guest molecules can be exploited to create materials with tailored characteristics, such as enhanced mechanical strength, improved thermal stability, or specific recognition capabilities.
Used in Preparation of Bilayer Vesicles:
Octakis(6-chloro-6-deoxy)-γ-cyclodextrin is used as a reagent for the preparation of bilayer vesicles of amphiphilic cyclodextrins. These vesicles serve as host membranes that can recognize and bind guest molecules, such as adamantane, via S-alkylation. This application is particularly relevant in the field of drug delivery and molecular recognition.

Upstream product

• 17465-86-0 cyclomaltooctaose 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 156297-61-9 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaazido-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin 

Relevant articles and documents

An improved synthesis of 6-deoxyhalo cyclodextrins via halomethylenemorpholinium halides Vilsmeier-Haack Type reagents

Per(6-bromo-6-deoxy)cyclomalto-hexaose, -heptaose, and -octaose and the corresponding per(6-chloro-6-deoxy) derivatives were prepared in high yield by reaction of bromomethylenemorpholinium bromide or chloromethylenemorpholinium chloride, respectively, with cyclomaltohexaose, cyclomaltoheptaose and cyclomaltooctaose in dimethylformamide.

Bilayer vesicles of amphiphilic cyclodextrins: Host membranes that recognize guest molecules

A family of amphiphilic cyclodextrins (6, 7) has been prepared through 6-S-alkylation (alkyl=n-dodecyl and n-hexadecyl) of the primary side and 2-O-PEGylation of the secondary side of α-, β-, and γ-cyclodextrins (PEG = poly(ethylene glycol)). These cyclodextrins form nonionic bilayer vesicles in aqueous solution. The bilayer vesicles were characterized by transmission electron microscopy, dynamic light scattering, dye encapsulation, and capillary electrophoresis. The molecular packing of the amphiphilic cyclodextrins was investigated by using small-angle X-ray diffraction of bilayers deposited on glass and pressure-area isotherms obtained from Langmuir monolayers on the air-water interface. The bilayer thickness is dependent on the chain length, whereas the average molecular surface area scales with the cyclodextrin ring size. The alkyl chains of the cyclodextrins in the bilayer are deeply interdigitated. Molecular recognition of a hydrophobic anion (adamantane carboxylate) by the cyclodextrin vesicles was investigated by using capillary electrophoresis, thereby exploiting the increase in electrophoretic mobility that occurs when the hydrophobic anions bind to the nonionic cyclodextrin vesicles. It was found that in spite of the presence of oligo(ethylene glycol) substituents, the β-cyclodextrin vesicles retain their characteristic affinity for adamantane carboxylate (association constant Ka = 7.1 × 103M-1), whereas γ-cyclodextrin vesicles have less affinity (Ka = 3.2 × 103M-1), and α-cyclodextrin or non-cyclodextrin, nonionic vesicles have very little affinity (Ka ≈100M -1). Specific binding of the adamantane carboxylate to β-cyclodextrin vesicles was also evident in competition experiments with β-cyclodextrin in solution. Hence, the cyclodextrin vesicles can function as host bilayer membranes that recognize small guest molecules by specific non-covalent interaction.

PROCESSES FOR PREPARATION OF SUGAMMADEX AND INTERMEDIATES THEREOF

The present invention relates to a process for preparation of 6-perdeoxy-6-per-chloro gamma-cyclodextrin which is a key intermediate useful in the synthesis of Sugammadex sodium. The present invention further relates to a process for preparation and purification of Sugammadex sodium.

Design and evaluation of folate-appended α-, β-, and γ-Cyclodextrins having a caproic acid as a tumor selective antitumor drug carrier in vitro and in vivo

We reported that per-6-folic acid (FA)-appended β-cyclodextrin (β-CyD) possessing two caproic acids between FA and a β-CyD molecule as a spacer (Fol-c2-β-CyD) could be useful as a promising antitumor drug carrier. However, the effects of the cavity size and the spacer length on the carrier ability are not still known. In this study, we designed and evaluated the FA-appended three kinds of CyDs possessing a caproic acid as a spacer between FA and a CyD molecule (Fol-c1-CyDs) as a tumor targeting carrier for antitumor drugs. The stability constant of the Fol-c 1-β-CyD/doxorubicin (DOX) complex was much higher than those of Fol-c1-α-CyD and Fol-c1-γ-CyD at pH 7.3. Antitumor activity of DOX was increased by the complexation with Fol-c 1-β-CyD, but not with Fol-c1-α-CyD or Fol-c1-γ-CyD in KB cells, a folate receptor-α-positive cell line. Also, Fol-c1-β-CyD increased antitumor activities of paclitaxel and vinblastine, but not 5-fluorouracil. Furthermore, Fol-c 1-β-CyD accelerated cellular uptake of DOX and inhibited its efflux from KB cells. The Fol-c1-β-CyD/DOX complex showed much higher antitumor activity than DOX alone after intratumoral and intravenous administrations to tumor-bearing mice with a negligible change of the blood chemistry values. These findings suggest that Fol-c1-β-CyD could be useful as a tumor-selective carrier for antitumor drugs.