81644-55-5

Usage

Uses

Used in Pharmaceutical Industry:
Mercapto-β-cyclodextrin is used as a solubility and stability enhancer for various pharmaceutical compounds. Its ability to form inclusion complexes with guest molecules improves the solubility and bioavailability of drugs, making them more effective and easier to administer.
Used in Chemical Industry:
In the chemical industry, Mercapto-β-cyclodextrin serves as a host molecule for sensing and drug delivery applications. Its unique properties allow it to selectively bind with specific molecules, making it an ideal candidate for targeted drug delivery systems and chemical sensing.
Used in Chromatography:
Mercapto-β-cyclodextrin is used as a chiral selector in chromatography. Its ability to form stable complexes with enantiomers allows for the separation and analysis of chiral compounds, which is crucial in the development and quality control of pharmaceuticals and other chiral molecules.
Used in Supramolecular Chemistry:
As a versatile compound in supramolecular chemistry, Mercapto-β-cyclodextrin is employed in the design and synthesis of various molecular systems. Its capacity to form stable complexes with a wide range of guest molecules contributes to the development of new materials and technologies in this field.

Upstream product

• 7585-39-9 β‐cyclodextrin 
• 67217-55-4 mono-6-deoxy-6-(p-tolylsulphonyl)-β-cyclodextrin 
• 17356-08-0 thiourea 

Downstream Products

• 81644-56-6 6-deoxy-6-<(3-thym-1-yl)propyl)thio>-β-cyclodextrin 

Relevant academic research and scientific papers

The effect of tether length on the affinity of ligands for bis (cyclodextrins)

Bis(cyclodextrin)s linked by alkyl chains of varying lengths were prepared and their ability to bind to fluorophoric ligands such as 6-toluidino-2-naphthalenesulfonate (TNS) was evaluated.

Efficient regioselective functionalizations of cyclodextrins carried out under microwaves or power ultrasound

Regioselective syntheses of differently functionalized cyclodextrins (CDs) were efficiently carried out under ultrasound or microwave irradiation. 6I-Deoxy-6I-thio-β-CD, 6I-deoxy-6I-formyl-β-CD, and 6A,6D-dideoxy-6A,6D-dithio-β-CD were prepared under microwave irradiation. A new rapid and efficient ultrasound-assisted protocol is described for the synthesis of 3I-azido-3I-deoxy-α, -β, and -γ-CD by selective tosylation followed by azide substitution.

Increasing the persistency of stable free-radicals: Synthesis and characterization of a nitroxide based [1]rotaxane

A persistent paramagnetic [1]rotaxane based on ss-cyclodextrin showing an increased persistency under reductive conditions has been prepared and characterized for the first time.

A novel water-soluble quantum dot-neutral red fluorescence resonance energy transfer probe for the selective detection of megestrol acetate

A novel water-soluble beta-cyclodextrin (β-CD)-functionalized ZnS quantum dot (QD)-neutral red (NR) fluorescence resonance energy transfer (FRET) probe for the selective determination of the concentration of megestrol acetate in river water has been developed. The water-soluble and low-toxicity β-CD-functionalized ZnS QDs were first synthesized, and their characterization was confirmed by transmission electron microscopy and infrared, UV-vis and fluorescence emission spectra. The NR molecule can enter the cavity of the β-CD anchored onto the surfaces of the ZnS QDs in its neutral form, forming the FRET probe. Compared with other steroid hormones, the probe can selectively recognize megestrol acetate at a lower concentration level. The possible underlying mechanism of the probe with nine steroid hormones was discussed in detail. The fluorescence quenching fractions of the probe presented a satisfactory linearity with the concentrations of megestrol acetate, and its limit of detection was calculated to be 0.0083 μM. Coupled with sample pretreatment procedures, the probe has been applied to the determination of megestrol acetate in river water. The average recoveries of megestrol acetate in the spiking levels of 0.001 μM-10 μM ranged from 97% to 110% with a relative standard deviation below 15%, which was similar to those for HPLC or MS techniques.

Insight into the Excitation-Dependent Fluorescence of Carbon Dots

High quantum yield, photoluminescence tunability, and sensitivity to the environment are a few distinct trademarks that make carbon nanodots (CDs) interesting for fundamental research, with potential to replace the prevalent inorganic semiconductor quantum dots. Currently, application and fundamental understanding of CDs are constrained because it is difficult to make a quantitative comparison among different types of CDs simply because their photoluminescence properties are directly linked to their size distribution, the surface functionalization, the carbon core structures (graphitic or amorphous) and the number of defects. Herein, we report a facile one-step synthesis of mono-dispersed and highly fluorescent nanometre size CDs from a ‘family’ of glucose-based sugars. These CDs are stable in aqueous solutions with photoluminescence in the visible range. Our results show several common features in the family of CDs synthesized in that the fluorescence, in the visible region, is due to a weak absorption in the 300–400 nm from a heterogeneous population of fluorophores. Fluorescence quenching experiments suggest the existence of not only surface-exposed fluorophores but more importantly solvent inaccessible fluorophores present within the core of CDs. Interestingly, time-resolved fluorescence anisotropy experiments directly suggest that a fast exchange of excitation energy occurs that results in a homo-FRET based depolarization within 150 ps of excitation.

Dual-responsive recurrent self-assembly of a supramolecular polymer based on the host-guest complexation interaction between β-cyclodextrin and azobenzene

In this work, we report a supramolecular polymer based on the host-guest interaction between β-cyclodextrin groups in β-CD-PEG and azobenzene groups in PAE-g-Azo. The supramolecular polymer PAE-g-Azo@β-CD-PEG could self-assemble into a regular nanostructu

Preparation and Stability Evaluation of Size-Controllable PDHCA-β-CD Nanoparticles as Drug Carrier

A novel biocompatible polymer was prepared by grafting the derivate of β-cyclodextrin (6-SH-β-CD) onto poly(3,4-dihydroxycinnamic acid) (PDHCA) via Michael addition. PDHCA-β-CD nanoparticles were prepared by the self-assembly of amphiphilic PDHCA-β-CD pol

Construction of giant branched nanotubes from cyclodextrin-based supramolecular amphiphiles

Giant branched nanotubes were successfully constructed using cyclodextrin-based amphiphiles. The 'backbone' of the nanotubes could branch out into two or multiple branches, from which thinner branches grow out.

Dendrimeric β-Cyclodextrin/GdIII chelate supramolecular host-guest adducts as high-relaxivity MRI probes

We have synthesized a new macromolecular architecture, (PAMAM)-CD 8, which consists of eight β-cyclodextrin units (β-CD) attached to a generation 1 poly(amidoamine) (PAMAM) dendrimer through a disulfide bond, which can be cleaved under reducing conditions. This system shows a pronounced hosting capability towards GdIII chelates functionalized with hydrophobic groups, thus leading to well-defined supramolecular adducts. 1H NMR relaxometric investigations were carried out to follow the formation of adducts with three GdIII chelates based on the ligand architectures of 6-amino-6-methylperhydro-1,4- diazepinetetraacetic acid (AAZTA) or 1,4,7,10-tetraazacyclododecane-1,4,7,10- tetraacetic acid (DOTA) suitably functionalized with benzyl or adamantyl (Ad) pendant groups. In particular, the ditopic complex composed of two AAZTA chelating units connected to a central aromatic ring that bears an adamantyl group showed a strong affinity (ca. 106 M-1) for the CD units of the dendrimer, which is two orders of magnitude higher than toward human serum albumin (HSA). Remarkable relaxivity enhancements (i.e., up to 71 % at 1 T and 25 C) were observed upon the formation of the macromolecular host-guest adducts due to a decrease in the molecular tumbling rate and fast water-exchange. Reduction experiments and competition studies between the paramagnetic dendrimer and HSA were carried out by relaxometric techniques. The results show that the metal complexes are not displaced by the protein, thus suggesting that this novel macromolecular probe is potentially suitable for applications in vivo.

Light-responsive aggregation of β-cyclodextrin covered silica nanoparticles

In this article, we report a light-responsive supramolecular system based on the host-guest interaction of β-cyclodextrin covered silica nanoparticles and a bifunctional, noncovalent azobenzene linker in dilute aqueous solution. β-Cyclodextrin was immobilized onto silica nanoparticles either by nucleophilic substitution or by thiol-ene click chemistry. Azobenzene has two isomers which can be converted into each other by alternating irradiation with visible light (λ = 465 nm) and UV light (λ = 350 nm). When using visible light, the trans isomer of the azobenzene moieties on the linker bind to the β-cyclodextrin cavities on the nanoparticle surface leading to aggregation of the nanoparticles. The aggregation is reversible, since irradiation with UV light leads to the formation of the cis isomer of the azobenzene linker, dissociation of the azobenzene and the cyclodextrin, and subsequent dispersion of the nanoparticles. The light-responsive supramolecular system is investigated by using optical density measurements (OD600), DLS and TEM measurements. This journal is the Partner Organisations 2014.