Journal of Inclusion Phenomena and Macrocyclic Chemistry最新文献

{"title":"Size-complementary effects of PEG diamine 1,1’-disubstituted ferrocene on incorporations of β- and γ-cyclodextrins and syntheses of poly(pseudo)rotaxanes with lower coverages therefrom","authors":"Rong-hao Song,&nbsp;Ming Gao,&nbsp;Xue Geng,&nbsp;Lin Ye,&nbsp;Ai-ying Zhang,&nbsp;Zeng-guo Feng","doi":"10.1007/s10847-021-01104-3","DOIUrl":"10.1007/s10847-021-01104-3","url":null,"abstract":"<p>Poly(ethylene glycol) diamine 1,1’-disubstituted ferrocene was utilized as a size-com-plementary site to synthesize lower coverage pseudopolyrotaxanes (pPRs) from self-assemblies with β- and γ-cyclodextrins (CDs). After end-capping β-CD pPRs using N-(triphenylmethyl)glycine (Trt-Gly-OH), an exact β-CD [3]polyrotaxane (PR) was created. However, an unexpected γ-CD [2]PR and a predictive chain folded stranded γ-CD pPR were identified from end-capped γ-CD pPRs.</p>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4400092","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Additional information","authors":"","doi":"10.1007/s10847-021-01105-2","DOIUrl":"10.1007/s10847-021-01105-2","url":null,"abstract":"","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4058261","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"trans-α,α,α′,α′-Tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol and its tetra(p-chlorophenyl) derivative: roof-shaped host compounds for the purification of aromatic C8H10 isomeric guest mixtures","authors":"Benita Barton,&nbsp;Ulrich Senekal,&nbsp;Eric C. Hosten","doi":"10.1007/s10847-021-01102-5","DOIUrl":"10.1007/s10847-021-01102-5","url":null,"abstract":"<div><p>Roof-shaped host compounds <i>trans</i>-α,α,α′,α′-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol <b>H3</b> and <i>trans</i>-α,α,α′,α′-tetra(<i>p</i>-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol <b>H6</b> were assessed for their host potential and selectivity behaviour when presented with single or mixed guest solvents comprising <i>o</i>-xylene, <i>m</i>-xylene, <i>p</i>-xylene and ethylbenzene (<i>o</i>-Xy, <i>m</i>-Xy, <i>p</i>-Xy and EB). <b>H3</b> included each solvent with 3:1 host:guest ratios, while the ratios preferred by <b>H6</b> were more varied (4:3, 1:1 and 3:2). More importantly, the selectivity behaviour of these two host compounds was observed to be entirely different: <b>H3</b> possessed only a very modest preference for <i>o</i>-Xy (37.9–68.2%) when recrystallized from various equimolar binary, ternary and quaternary guest mixtures, while <b>H6</b> was considerably more selective, preferring <i>m</i>-Xy (the least favoured guest of <b>H3</b>) with selectivities ranging from 57.7 to 91.4% in analogous conditions. The latter result was obtained in <i>o</i>-Xy/<i>m</i>-Xy mixtures and demonstrates that <b>H6</b> may be employed as a purification tool for mixtures of these two xylenes via host–guest chemistry protocols. A single crystal diffraction experiment on 3(<b>H3</b>)·<i>o</i>-Xy (containing the preferred guest of <b>H3</b>) revealed that the guest was retained in the host crystal by means of a singular (host)<i>m</i>-Ar–H···π(guest) interaction that measured 2.73 Å (148°) as well as numerous other host···guest interactions involving only the aromatic protons of the free host phenyl groups and the guest methyl protons or aromatic carbons and protons (2.20–2.54 Å, 121–125°). Thermal analyses explained the preference of <b>H3</b> for <i>o</i>-Xy, while these were less informative for the complexes of <b>H6</b>.\u0000</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-021-01102-5.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4368852","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Beta-carotene/cyclodextrin-based inclusion complex: improved loading, solubility, stability, and cytotoxicity","authors":"Mahsa Yazdani,&nbsp;Omid Tavakoli,&nbsp;Mehdi Khoobi,&nbsp;Yi Shuan Wu,&nbsp;Mohammad Ali Faramarzi,&nbsp;Elham Gholibegloo,&nbsp;Shabnam Farkhondeh","doi":"10.1007/s10847-021-01100-7","DOIUrl":"10.1007/s10847-021-01100-7","url":null,"abstract":"<div><p>Beta-carotene (BC) is a vitamin A precursor and has potential anticancer benefits, but the delivery of BC is hindered by its low solubility and storage instability. To overcome these challenges, this study investigated the use of fabricated cyclodextrin-based nanosponges (CDNS) using different ratios of two cross-linkers, epiclon (EPI) and hexamethylene diisocyanate (HMDI) to form inclusion complex with BC. The ratios of crosslinkers to βCD for two most optimaly encapsulated CDNSs-BC were determined to be 2:1 for EPI and 4:1 for HMDI with loading efficiency of 61.46% and 59.61%, respectively. The charachterization tests were carefully done for two optimal CDNSs. Encapsulation significantly improved the solubility by ~ 10 folds, 30-day storage stability by 40% compared to BCs. The in vitro release of the two encapsulated products showed no burst release. The MTT assay revealed a variable increase in cytotoxic effect in both normal and cancer cells compared to free BC. Overall, the CDNSs appear to be promising carriers for the delivery of BCs.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-021-01100-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4958591","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"CdO nanoparticles: robust inorganic additive for cadmium selective polymeric electrode based on N-phenylaza-15-crown-5","authors":"Anis Golab Ghadaksaz,&nbsp;Arezoo Ghaemi,&nbsp;Roya Mohammadzadeh Kakhki","doi":"10.1007/s10847-021-01098-y","DOIUrl":"10.1007/s10847-021-01098-y","url":null,"abstract":"<div><p>This study presents the development of a new and sensitive polyvinyl chloride electrode based on cadmium oxide (CdO) nanoparticles and <i>N</i>-phenylaza-15-crown-5 for the selective determination of cadmium cations. To this end, synthesized cadmium oxide nanoparticles were characterized through XRD, FT-IR and FESEM analysis. Then, CdO nanoparticles were applied as a modifier for the fabrication of the proposed electrode. The optimum membrane composition to construct the electrode comprised poly(vinyl chloride) (30%), nitrobenzene (61%), cadmium oxide nanoparticle (3%) and <i>N</i>-phenylaza-15-crown-5 (6%). The Nernstian slope of the electrode was obtained 27.3 ± 0.3 mV/decade in the 1.0 × 10^–8 to 1.0 × 10^–1 M concentration range, and the detection limit was obtained as 9.8 × 10^–9 M. The response time of the electrode was short (5 s), while its reversibility and lifetime were high. It was revealed that the operation pH range of the electrode ranged between 2 and 9, and the electrode had a very good selectivity to cadmium cations among the other interfering ions. Further, the electrode was successfully used as a potentiometric sensor in complexometric titrations and the measurement of cadmium cations in the environmental waters.</p><h3>Graphic abstract</h3>\u0000 <figure><div><div><div><picture><img></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4285462","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Cyclodextrin-based Pickering emulsions: functional properties and drug delivery applications","authors":"Mario Jug,&nbsp;Bo Kyeong Yoon,&nbsp;Joshua A. Jackman","doi":"10.1007/s10847-021-01097-z","DOIUrl":"10.1007/s10847-021-01097-z","url":null,"abstract":"<div><p>Cyclodextrins (CDs) are biocompatible, cyclic oligosaccharides that are widely used in various industrial applications and have intriguing interfacial science properties. While CD molecules typically have low surface activity, they are capable of stabilizing emulsions by inclusion complexation of oil-phase components at the oil/water interface, which results in Pickering emulsion formation. Such surfactant-free formulations have gained considerable attention in recent years, owing to their enhanced physical stability, improved tolerability, and superior environmental compatibility compared to conventional, surfactant-based emulsions. In this review, we critically describe the latest insights into the molecular mechanisms involved in CD stabilization of Pickering emulsions, including covering practical aspects such as methods to prepare CD-based Pickering emulsions, lipid encapsulation, and relevant stability issues. In addition, the rheological and textural features of CD-based Pickering emulsions are discussed and particular attention is focused on promising examples for drug delivery, cosmetic, and nutraceutical applications. The functionality of currently developed CD-based Pickering emulsions is also summarised, including examples such as antifungal uses, and we close by discussing emerging possibilities to utilize the molecular encapsulation of CD-based emulsions for translational medicine applications in the antiviral and antibacterial spaces.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-021-01097-z","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4112525","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Comparative host–guest complex formation of the Alzheimer’s drug memantine with para-sulfonatocalix[n]arenes (n = 4 or 8)","authors":"Nial J. Wheate","doi":"10.1007/s10847-021-01096-0","DOIUrl":"10.1007/s10847-021-01096-0","url":null,"abstract":"<div><p>The comparative encapsulation of the Alzheimer’s drug memantine (3,5-dimethyladamantan-1-amine), used as its hydrochloride salt, within the cavity of two different sized <i>para</i>-sulfonatocalix[<i>n</i>]arenes (sCX[<i>n</i>]; <i>n</i> = 4 or 8) was analysed by ¹H NMR spectroscopy. Addition of either macrocycle to memantine results in selective upfield shifts of all drug proton resonances of between 0.50 and 1.72 ppm for sCX[4] and between 0.80 and 1.53 ppm for sCX[8]. Memantine binding results in the observation of an extra sCX[4] resonance for the macrocycle’s methylene protons, which is not observed for the larger sCX[8], indicating a potential change in shape of the sCX[4] upon host–guest formation. Difference in changes to the chemical shift of the memantine doublet-of-doublets resonance for both macrocycles indicates a potential change in shape of memantine upon host–guest formation. From Job Plots, memantine binds to sCX[4] in a 1:1 ratio with a binding constant of 6.6 × 10⁶ M⁻¹, whereas binding to sCX[8] is in a 1:2 host–guest ratio. Overall, the results indicate that memantine forms subtly different host–guest complexes with different sized sCX[<i>n</i>] homologues, which could be used to tune the drug delivery potential of the macrocycle for different pharmaceutical applications.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-021-01096-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4495813","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Gaussian processes regression for cyclodextrin host-guest binding prediction","authors":"Ruan M. Carvalho,&nbsp;Iago G. L. Rosa,&nbsp;Diego E. B. Gomes,&nbsp;Priscila V. Z. C. Goliatt,&nbsp;Leonardo Goliatt","doi":"10.1007/s10847-021-01092-4","DOIUrl":"10.1007/s10847-021-01092-4","url":null,"abstract":"<div><p>Machine Learning (ML) techniques are becoming an integral part of rational drug design and discovery. Data-driven modeling regularly outperforms physics-based models for predicting molecular binding affinities, placing ML as a promising tool. Cyclodextrins are nano-cages used to improve the delivery of insoluble or toxic drugs. Due to chemical similarity to proteins, ML approaches could vastly profit to improve affinity prediction and enhance their carriable drug portfolio. Here we evaluate the performance of three well-known ML methods—Support Vector Regression (SVR), Gaussian Process Regression (GPR), and eXtreme Gradient Boosting (XGB)—to predict the binding affinity of cyclodextrin and known ligands. We perform hyperparameter tuning through Random Search. The results were compatible with the presented literature. We increased our previous prediction performance and present a GPR model to adjust to the data (<span>(R^2)</span> = 0.803) with low prediction errors (RMSE = 1.811 kJ/mol and MAE = 1.201 kJ/mol).</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-021-01092-4","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4498864","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Improved solubility and stability of rifampicin as an inclusion complex of acyclic cucurbit[n]uril","authors":"Hui Liu,&nbsp;Zu-Zheng He,&nbsp;Lei Yu,&nbsp;Jun Ma,&nbsp;Xue-Pin Jin","doi":"10.1007/s10847-021-01093-3","DOIUrl":"10.1007/s10847-021-01093-3","url":null,"abstract":"<div><p>The poor solubility and low stability of rifampicin limited its therapeutic efficacy. One of the common strategies is to form an inclusion complex to address the problems. In this study, acyclic cucurbit[n]uril was used for encapsulation of rifampicin to form an inclusion complex. The inclusion complex was prepared by the kneading method and characterized by DSC, SEM, FT-IR, NMR, PXRD, and UV-Vis spectroscopy. The results confirmed the formation of 1:1 inclusion complex. The drug content was calculated to be 27.35 ± 0.54%. The aqueous solubility of rifampicin was increased 20-fold by complexation with acyclic cucurbit[n]uril. Moreover, the thermo-stability and photo-stability of free rifampicin and inclusion complex were investigated by HPLC. Rifampicin was stabilized by encapsulating the piperazine ring in the cavity of acyclic cucurbit[n]uril. In addition, the MIC of free RIF and RIF‧ACB were determined by using in vitro experiments. It was found that rifampicin complexed by acyclic cucurbit[n]uril exhibited similar antibacterial activities against strain H37Rv to rifampicin alone.</p><h3>Graphic abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 <dl><dt><dfn>•:</dfn></dt><dd>\u0000 <p>Acyclic cucurbit[n]uril was used to encapsulate rifampicin to form an inclusion complex.</p>\u0000 </dd><dt><dfn>•:</dfn></dt><dd>\u0000 <p>The aqueous solubility of rifampicin was increased 20-fold by encapsulation with acyclic\u0000cucurbit[n]uril.</p>\u0000 </dd><dt><dfn>•:</dfn></dt><dd>\u0000 <p>The thermo-stability and photo-stability of rifampicin was improved by formation of\u0000inclusion complex.</p>\u0000 </dd><dt><dfn>•:</dfn></dt><dd>\u0000 <p>The antibiotic potency of rifampicin complexed by acyclic cucurbit[n]uril was close to that\u0000of rifampicin alone.</p>\u0000 </dd></dl>\u0000 </div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-021-01093-3","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4021361","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of branched cyclodextrins using activated carbon as a catalyst","authors":"Kandai Ishikura,&nbsp;Kazunori Yanagihara,&nbsp;Hiroki Takagi","doi":"10.1007/s10847-021-01089-z","DOIUrl":"10.1007/s10847-021-01089-z","url":null,"abstract":"<div><p>Activated carbon has been reported to act as a catalyst for condensation reactions between glucose molecules. The present study describes the use of activated carbon as a new catalyst for the synthesis of branched cyclodextrins (CDs). Two main methods have been used to synthesize branched CDs: a method using an enzymatic condensation or transfer reaction, and a method using a chemical reaction. However, these methods have problems such as a limited number of the types of branched CDs that can be synthesized that depend on the characteristics of the enzyme, the long reaction time required (several days or more), difficulty in synthesizing branched CD with a high degree of substitution (DS), the need for large quantities of environmentally harmful solvents, and a complicated and costly reaction. Using activated carbon as a catalyst, branched CDs with a high DS could be synthesized within a relatively short time (a few hours), regardless of the type of saccharide in the branched portion. Furthermore, since the reaction was conducted under solvent-free conditions using activated carbon, the amount of solvent used in the production of branched CD could be reduced. The branched β-CDs prepared using the activated carbon catalyst showed high solubility, high solubilization capacity, and low hemolytic activity, similar to the 2-hydroxypropyl-β-CD used for pharmaceuticals. These results indicate that activated carbon is an industrially and environmentally useful catalyst for branched CD syntheses.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-06-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-021-01089-z","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4862153","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}