160661-60-9

Basic information

• Product Name: Heptakis-(6-Mercapto-6-deoxy)-beta-Cyclodextrin
• Synonyms: Heptakis-(6-Mercapto-6-deoxy)-beta-Cyclodextrin;Heptakis-(6-Mercapto-6-deoxy)-β-Cyclodextrin;β-Cyclodextrin,6A,6B,6C,6D,6E,6F,6G-heptathio
• CAS NO: 160661-60-9
• Molecular Formula: C₄₂H₇₀O₂₈S₇
• Molecular Weight: 1247.44
• EINECS: 1312995-182-4
• Mol File: 160661-60-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 1502.1±60.0 °C(Predicted)
• Appearance: Off-white/Solid powder
• Density: 1.531±0.06 g/cm3(Predicted)
• Solubility: Soluble in DMF, DMSO. Insoluble in water, acetone, methanol, ch
• PKA: 8.58±0.10(Predicted)
• CAS DataBase Reference: Heptakis-(6-Mercapto-6-deoxy)-beta-Cyclodextrin(CAS DataBase Reference)
• NIST Chemistry Reference: Heptakis-(6-Mercapto-6-deoxy)-beta-Cyclodextrin(160661-60-9)
• EPA Substance Registry System: Heptakis-(6-Mercapto-6-deoxy)-beta-Cyclodextrin(160661-60-9)

Safety Data

• Hazardous Substances Data: 160661-60-9(Hazardous Substances Data)

Usage

Description

Heptakis-(6-azido-6-deoxy)-beta-cyclodextrin is an useful reactant for preparation for cyclodextrin amino acid derivatives.

Uses

Different sources of media describe the Uses of 160661-60-9 differently. You can refer to the following data:
1. Addition of Per-6-thio-β-cyclodextrin to a colloidal dispersion of Au nanoparticles results in the attachment of thiolated cyclodextrins to the Au particles.
2. Heptakis-(6-Mercapto-6-deoxy)-beta-Cyclodextrin（Cas#160661-60-9）is a modified beta-cyclodextrin as a reagent in lab& research institution. Sulphur is lively group by oxidation or replace to create higher levels of supramolecular structure.Mercaptoacetic extremely easy adherent to gold surface, thus realize novel applications.Mercaptoacetic cyclodextrins derivatives extremely suitable for drug induction of anesthesia neuromuscular reversal.

Synthesis

The thiuronium salt (12.2 g, 0.005 mol) was heated around 100 °C in deoxygenated (He/ultrasound) 0.25 M NaOH (120 mL) for 4 h. As the reaction was completed the reaction mixture was cooled to around 5-10 °C and the pH was adjusted to 1.0-1.5 with 3 M HCl solution, when the product started to crystallize. As the pH became stable, the suspension was allowed to crystallize for 15 min, the solids were removed by filtration, washed with deoxygenated deionized water to around pH 5-6, then dried in vacuo at rt in the presence of P2O5 and KOH, and yielded 6.5 g of dark orange, glassy crystals. The obtained product was recrystallized by dissolution in deoxygenated 1 M NaOH solution (12 mL) and precipitated with 1 M HCl (18 mL). Filtration and washing to neutral pH with deoxygenated water afforded 3.8 g (61% theor.) light orange crystals. RF = 0.00-0.05 10:7 dioxane/cc. NH3.3.5. Regeneration of thiol group from its oxidized statePartially oxidized heptakis(6-deoxy-6-thio)cyclomaltoheptaose (6.2 g, approx. 0.010 mol) was suspended in deoxygenated water and deoxygenated (He/ultrasound) 3 M NaOH solution (30 mL) was added at rt. Sodium borohydride (1.1 g, 0.030 mol) is added and stirred overnight. The occasionally found solids were filtered through a sintered glass funnel, the filtrate was cooled with an ice-water bath and the pH was adjusted to around 1.5-2 with 3 M HCl solution (approx. 45 mL). Upon acidification the product started to crystallize, and as the pH became stable and foaming stopped, the suspension was allowed to crystallize for an additional 15 min. The product was removed by filtration and washed to pH 5-7 with deoxygenated deionized water, then dried in vacuo at rt in the presence of P2O5 and KOH, yielded 3.2 g (50%) β-CDSH as a yellowish substance.

Upstream product

• 123155-24-8 2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G-tetradeca-O-acetyl-6^A,6^B,6^C,6^D,6^E,6^F,6^G-heptaiodo-6^A,6^B,6^C,6^D,6^E,6^F,6^G-heptadeoxy-β-cyclodextrin 
• 53784-83-1 heptakis(6-bromo-6-deoxy)-β-cyclodextrin 
• 30754-23-5 heptakis(6-deoxy-6-iodo)cyclomaltoheptaose 

Relevant articles and documents

Water soluble heptakis(6-deoxy-6-thio)cyclomaltoheptaose capped gold nanoparticles via metal vapour synthesis: NMR structural characterization and complexation properties

The complexation of heptakis(6-deoxy-6-thio)cyclomaltoheptaose to gold nanoparticles prepared by using the Metal Vapour Synthesis (MVS) led to water soluble gold nanoaggregates, thermally stable at 25 °C. The role of gold concentration in the MVS-derived starting solution as well as of the cyclodextrin to gold molar ratio on the size of cyclodextrin-capped gold nanoparticles were investigated. The ability of cyclodextrin bonded to gold nanoparticles to include deoxycytidine was also probed in comparison with that of 1-thio-β-d-glucose sodium salt.

Synthesis of a novel class of cyclodextrin-based nanotubes

The synthesis and characterization of a novel class of structurally well-defined nanotubes from β-cyclodextrin are described. These new hosts were formed using disulfide linkages that substitute all the primary hydroxyl groups of a β-cyclodextrin. A deep and rigid hydrophobic channel with a size of more than 1.5 nm is found in the molecules. Because of their unique geometry and the potential biodegradability of the disulfide bond, this class of molecules could find broad applications in biology and other areas of research.

Mannosylated Poly(ethylene imine) Copolymers Enhance saRNA Uptake and Expression in Human Skin Explants

Messenger RNA (mRNA) is a promising platform for both vaccines and therapeutics, and self-amplifying RNA (saRNA) is particularly advantageous, as it enables higher protein expression and dose minimization. Here, we present a delivery platform for targeted delivery of saRNA using mannosylated poly(ethylene imine) (PEI) enabled by the host-guest interaction between cyclodextrin and adamantane. We show that the host-guest complexation does not interfere with the electrostatic interaction with saRNA and observed that increasing the degree of mannosylation inhibited transfection efficiency in vitro, but enhanced the number of cells expressing GFP by 8-fold in human skin explants. Besides, increasing the ratio of glycopolymer to saRNA also enhanced the percentage of transfected cells ex vivo. We identified that these mannosylated PEIs specifically increased protein expression in the epithelial cells resident in human skin in a mannose-dependent manner. This platform is promising for further study of glycosylation of PEI and targeted saRNA delivery.

Micelles via self-assembly of amphiphilic beta-cyclodextrin block copolymers as drug carrier for cancer therapy

We developed intelligent, star-shaped amphiphilic β-cyclodextrin (β-CD) co-polymer nanocarriers to circumvent the poor drug loading and water-solubility of β-CD. The secondary hydroxyl groups of β-CD were methylated to improve solubility, and the primary hydroxyl groups were conjugated with mPEG-b-PCL-SH through disulfide linkage to amplify the hydrophobic cavity and enhance the stability of the nanocarrier. A series of amphiphilic β-CD block copolymers (CCPPs) differing in molecular weights were synthesized that could self-assemble into core-shell nanospheres measuring 50–70 nm in water. The different CCPP carriers were screened for their drug loading, encapsulation and release efficiencies, and CCPP-2 showed the highest drug loading capacity of 31.9% by weight. These nanocarriers accumulated at the tumor site through the EPR effect and released the drug in a controlled manner in the reductive tumor microenvironment, with negligible premature leakage and side effects. Therefore, CCPP-2 shows significant potential as a smart and efficient nanovehicle for anticancer drug delivery.

Electrochemical control of a non-covalent binding between ferrocene and beta-cyclodextrin

The forces required for the detachment of ferrocene (Fc) from β-cyclodextrin (βCD) in a single host (βCD)-guest (Fc) complex were investigated using force spectroscopy under electrochemical conditions. The redox state of the guest Fc moiety as well as the structure of the supporting matrix was found to decisively affect the nanomechanical properties of the complex. This journal is