Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

Becker, Lisa F.; Schwarz, Dennis H.; Wenz, Gerhard

doi:10.3762/bjoc.10.310

Cited by 11 publications

(7 citation statements)

References 48 publications

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“… CD: cyclodextrin; CRYSMEB: low methylated-β-cyclodextrin; RAMEB: randomly methylated-β-cyclodextrin; HP-β-CD: 2-hydroxypropyl-β-cyclodextrin; SBE-β-CD: sulfobutylether-β-cyclodextrin. a [ 2 ], b [ 45 ], c [ 53 ], d [ 51 ], e [ 54 ], f [ 55 ], g [ 43 ], h [ 49 ], i [ 56 ], j [ 57 ], k [ 44 ], l [ 58 ], m [ 47 ], n [ 50 ], o [ 17 ], p [ 52 ], q [ 49 ], r [ 59 ], s [ 60 ]. …”

Section: Figurementioning

confidence: 99%

Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review

2018

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Cyclodextrins (CDs) are a family of cyclic oligosaccharides that constitute one of the most widely used molecular hosts in supramolecular chemistry. Encapsulation in the hydrophobic cavity of CDs positively affects the physical and chemical characteristics of the guests upon the formation of inclusion complexes. Such a property is interestingly employed to retain volatile guests and reduce their volatility. Within this scope, the starting crucial point for a suitable and careful characterization of an inclusion complex is to assess the value of the formation constant (Kf), also called stability or binding constant. This task requires the application of the appropriate analytical method and technique. Thus, the aim of the present paper is to give a general overview of the main analytical tools used for the determination of Kf values for CD/volatile inclusion complexes. This review emphasizes on the advantages, inconvenients and limits of each applied method. A special attention is also dedicated to the improvement of the current methods and to the development of new techniques. Further, the applicability of each technique is illustrated by a summary of data obtained from the literature.

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Section: Figurementioning

confidence: 99%

Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review

2018

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“…Interlocking multiple β-CDs onto the polymer axis is considered to be an important structural feature of PRXs to exhibit temperature responsivity since the distance of β-CDs shifted to a closer proximity in comparison to that of free β-CDs. However, OEG-modified α- and β-CDs have been reported to exhibit temperature-dependent phase transitions. , For instance, when all hydroxy groups are substituted with TEG-tethered chains, methoxy-terminated TEG-modified β-CDs (TEG-β-CDs) have been reported to exhibit T CP at approximately 35 °C . To verify the contribution of such interlocked PRX structures on the temperature responsivity of the TEG–PRXs, their temperature-dependent transmittance changes were measured after partial and complete degradation.…”

Section: Resultsmentioning

confidence: 99%

Terminal Structure of Triethylene Glycol-Tethered Chains on β-Cyclodextrin-Threaded Polyrotaxanes Dominates Temperature Responsivity and Biointeractions

2021

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Pharmacological and biomedical applications of cyclodextrin (CD)-threaded polyrotaxanes (PRXs) have gained increasing attention. We had previously investigated the therapeutic effects of oligo(ethylene glycol) (OEG)-modified β-CD PRXs in congenital metabolic disorders. Although the chemical modification of PRXs is crucial for these applications, the influences of the chemical structure of OEG modified on PRXs were not completely understood. The current study focuses on the terminal group structures of triethylene glycol (TEG)-tethered chains, wherein three series of TEG-tethered PRXs (TEG−PRXs) with various TEG terminal group structures (hydroxy, methoxy, and ethoxy) were synthesized to investigate their physicochemical properties and biointeractions. The methoxy and ethoxy-terminated TEG−PRXs exhibited temperature-dependent phase transitions in phosphate buffer saline and formed coacervate droplets above their cloud points. A comprehensive analysis revealed that the hydrophobicity of the terminal group structures of the TEG-tethered chains played a dominant role in exhibiting temperature-dependent phase transition. Furthermore, the hydrophobicity of the terminal group structures of TEG-tethered chains on PRXs also affected the interactions with lipids and proteins, with the hydrophobic ethoxy-terminated TEG-tethered chains showing the highest interactions. However, in normal human skin fibroblasts, the moderately hydrophobic methoxy-terminated TEG-modified PRXs showed the highest intracellular uptake levels. As a result, we concluded that methoxy-terminated TEG is a suitable chemical modification for the biomedical applications of PRXs due to the negligible temperature responsivity around physiological temperature and significant intracellular uptake levels. The findings of this study shall contribute significantly to the rational design of PRXs and CD-based materials for future pharmacological and biomedical applications.

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“…• Published procedures for isolating CD derivatives are typically complex, requiring chromatography, lyophilization, and/or centrifugation [35][36][37][38][39] . We wished to use the simpler purification approach of precipitation from DMF with acetone, but our initial attempts failed.…”

Section: Resultsmentioning

confidence: 99%

Facile synthesis of a diverse library of mono-3-substituted β-cyclodextrin analogues

Kellett

Duggan

Gilson

2019

Supramolecular Chemistry

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Substituted cyclodextrins (CDs) have many applications, but synthetic challenges have limited the derivatives that can routinely be accessed. In particular, although there is considerable interest in selective derivatization at the 2-and 3-hydroxyls on the secondary face, since bulky guest molecules are most likely to project through this larger aperture, syntheses of such derivatives have required arduous procedures afforded with poor yields. We address this challenge via synthetic strategies that allow facile creation of diverse libraries of water soluble mono-3-substituted-β-cyclodextrins. The power of these strategies is confirmed through synthesis of twenty water-soluble cyclodextrin analogues with amide, thioureas or urea linkers, using one-pot reactions producing ≥ 55% yields and purifications that do not require chromatography. This work opens new possibilities for the design of selective host molecules for use in supramolecular chemistry, chemical separations, pharmaceutical formulations, and calibration of molecular simulations.

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Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

Cited by 11 publications

References 48 publications

Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review

Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review

Terminal Structure of Triethylene Glycol-Tethered Chains on β-Cyclodextrin-Threaded Polyrotaxanes Dominates Temperature Responsivity and Biointeractions

Facile synthesis of a diverse library of mono-3-substituted β-cyclodextrin analogues

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