Journal of Inclusion Phenomena and Macrocyclic Chemistry最新文献

Development and characterization of a cyclodextrin-based delivery system for enhanced pharmacokinetic and safety profile of oseltamivir 开发基于环糊精的给药系统并确定其特性，以增强奥司他韦的药代动力学和安全性特征

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-09-09 DOI: 10.1007/s10847-024-01258-w

Andreea Alexandra Olteanu, Flavian Ștefan Rădulescu, Coralia Bleotu, Corina-Cristina Aramă

{"title":"Development and characterization of a cyclodextrin-based delivery system for enhanced pharmacokinetic and safety profile of oseltamivir","authors":"Andreea Alexandra Olteanu, Flavian Ștefan Rădulescu, Coralia Bleotu, Corina-Cristina Aramă","doi":"10.1007/s10847-024-01258-w","DOIUrl":"https://doi.org/10.1007/s10847-024-01258-w","url":null,"abstract":"Oseltamivir (OST) phosphate is a prodrug, metabolized by hepatic carboxylesterase to its active metabolite (oseltamivir carboxylate). OST is efficient in treatment of influenza, in both children and adults. The protein bonding of the prodrug and its active metabolite is low (42% and 3%, respectively). It has a short half-life 1–3 h but its active metabolite has a half-life of 6–10 h, permitting twice daily administration. The most common side effect is gastrointestinal disturbances that are usually nausea and vomiting and can be reduced when taken simultaneously with food. OST phosphate is a white powder with bitter taste and the marketed oral suspension uses sorbitol for masking it. Cross-linked cyclodextrin polymers are known for their ability to increase the dissolution rate, solubility, stability, and permeability of insoluble drugs and provide prolonged release. Therefore, they are promising drug delivery systems that could improve its pharmacokinetic properties and patient adherence. In this study we focused on developing a therapeutic system of OST using cyclodextrin polymer crosslinked with pyromellitic dianhydride (PMDA CD) to enhance its pharmacokinetic properties and to improve its compliance. PMDA CD polymer and PMDA CD polymer complex with OST were prepared. Physicochemical characterization by FTIR spectra, thermal analysis, DLS, SEM and EDX confirmed the existence of interaction between the two components. The prepared complex has a different pharmaceutical profile compared to OST, with higher stability and a controlled dissolution profile. Toxicity studies showed that the polymer complex has lower toxicity than OST, suggesting the protective effect of the polymer.","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210026","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}

引用次数: 0

The host behaviour of 9-phenyl-9 H-xanthene derivatives in mixtures of cyclohexanone and the methylcyclohexanone isomers 环己酮和甲基环己酮异构体混合物中 9-苯基-9H-呫吨衍生物的宿主行为

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-26 DOI: 10.1007/s10847-024-01256-y

Brandon Barnardo, Benita Barton, Eric C Hosten

{"title":"The host behaviour of 9-phenyl-9 H-xanthene derivatives in mixtures of cyclohexanone and the methylcyclohexanone isomers","authors":"Brandon Barnardo, Benita Barton, Eric C Hosten","doi":"10.1007/s10847-024-01256-y","DOIUrl":"https://doi.org/10.1007/s10847-024-01256-y","url":null,"abstract":"Here we report on the host behaviour of compounds N, N’-bis(9-phenyl-9-xanthenyl)propane-1,3-diamine (H1) and N, N’-bis(9-phenyl-9-xanthenyl)butane-1,4-diamine (H2) in the presence of potential guest species cyclohexanone (CYC) and 2-, 3- and 4-methylcyclohexanone (2MeCYC, 3MeCYC and 4MeCYC). H1 only formed a complex with CYC, whilst all four guest solvents were enclathrated by H2. Thermal analyses in conjunction with SCXRD experiments revealed that more energy was required to remove guest species from the crystals of their complexes when they were housed in discrete cavities compared with guest molecules retained in channels. Only in H1·CYC was identified an intramolecular (host)N‒H···N(host) hydrogen bond, while complexes H2·2(CYC), H2·2(3MeCYC) and H2·4MeCYC all experienced strong (host)N‒H···O(guest) hydrogen bonds which assisted in retention of the guests in the complexes; this interaction type was absent in both H1·CYC and H2·2(2MeCYC). Hirshfeld surface analyses demonstrated that the amounts of (guest)O···H(host) interatomic interactions were comparable and ranged between 11.1 and 13.9%. Guest competition experiments showed that H2 possessed an affinity for, more usually, 3MeCYC, despite the complex H2·2(3MeCYC) being the least thermally stable one. Finally, it was established that H1 and H2 would not be appropriate host compounds for separations of mixed cyclohexanones through supramolecular chemistry strategies.","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141772151","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}

引用次数: 0

Pillar[5]arene-based thiazole NHC/Pd(II) supramolecular coordinated polymer: synthesis, structure and catalytic activity in Suzuki–Miyaura reaction 柱状[5]炔基噻唑 NHC/钯(II)超分子配位聚合物：合成、结构和在铃木-宫浦反应中的催化活性

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-21 DOI: 10.1007/s10847-024-01254-0

Linqian Tang, Kaijie Lai, Xiyun Lan, Haibo Wang

{"title":"Pillar[5]arene-based thiazole NHC/Pd(II) supramolecular coordinated polymer: synthesis, structure and catalytic activity in Suzuki–Miyaura reaction","authors":"Linqian Tang, Kaijie Lai, Xiyun Lan, Haibo Wang","doi":"10.1007/s10847-024-01254-0","DOIUrl":"https://doi.org/10.1007/s10847-024-01254-0","url":null,"abstract":"As a booming research theme, heterogeneous catalysts have demonstrated significant advantages over homogeneous catalysts in terms of stability, recyclability, and separability from the reactant mixture. In this study, a supramolecular coordinated polymer (P[5]-SCP) was synthesized by complexing thiazole-derived pillar[5]arene (P[5]) with Pd(II), which was obtained by nucleophilic substitution between 1,4-bis(2-Bromoethoxy) pillar[5]arene and 4-methyl-5-(β-hydroxyethyl) thiazole. The chemical component and structure of the P[5]-SCP were confirmed by NMR, EA, FI-IR, XPS, XRD, SEM, TEM, HR MS. In the Suzuki–Miyaura coupling reaction, the catalytic activity, stability, and recyclability were thoroughly evaluated. The P[5]-SCP had excellent catalytic activity in mild reaction conditions (up to 81% yield) and exhibited little loss of activity after at least five recycles. Furthermore, catalyst P[5]-SCP was easily synthesized from simple raw materials and low-cost, thereby a novel pillar[5]arene based-NHC catalyst was developed in green heterogeneous catalysis.<h3 data-test=\"abstract-sub-heading\">Graphical abstract</h3>\u0000","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141745368","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}

引用次数: 0

Prediction of the free energy of binding for cyclodextrin-steroid complexes: phase solubility and molecular dynamics studies 环糊精-类固醇复合物结合自由能的预测：相溶性和分子动力学研究

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-20 DOI: 10.1007/s10847-024-01255-z

Parisa Fereidounpour, Casper Steinmann, Kim Lambertsen Larsen

{"title":"Prediction of the free energy of binding for cyclodextrin-steroid complexes: phase solubility and molecular dynamics studies","authors":"Parisa Fereidounpour, Casper Steinmann, Kim Lambertsen Larsen","doi":"10.1007/s10847-024-01255-z","DOIUrl":"https://doi.org/10.1007/s10847-024-01255-z","url":null,"abstract":"Steroid hormones play a crucial role in the body by acting as chemical messengers. They are, however, poorly soluble in water, and cyclodextrins can increase their solubility thus leading to increased bioavailability when used in drug formulations. Accuracy in the prediction of the free energy of binding of cyclodextrin/steroid inclusion complexes with simulation is important because of the potential value it brings by providing low-cost predictions of the real-life behavior of the cyclodextrin/steroid inclusion complex and the potential for high-through-put screening. Many computational methods exist, and it is therefore important to understand the ability of current theoretical models to accurately predict the free energy of binding for these inclusion complexes. We focused specifically on the estimation of the free energy of binding of inclusion complexes of four steroids: Hydrocortisone, dexamethasone, prednisolone, and 6α-methylprednisolone with native α-CD, β-CD, γ-CD, (2-hydroxy)propyl-β-CD, and sulfobutylether-β-CD by phase solubility as well as with α, β, and γ-CD by simulations. The simulations were assessed with both docking and the molecular mechanics combined with the generalized Born and surface area (MM/GBSA) continuum solvation approach. Considering the phase solubility diagram, (2-hydroxy)propyl-β-CD and sulfobutylether-β-CD dissolved more steroids in the higher concentration range as expected. The assessment of the free energy of binding obtained from the phase solubility and theory showed that the MM/GBSA method has shown promise in reliably generating accurate predictions in the field of calculating the free energy of binding of steroids/cyclodextrins with a correlation coefficient (R2) = 0.94.","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-07-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141745367","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}

引用次数: 0

Solid-state structures of some fluorescent macrocyclic complexes of alkali metal ions studied by single-crystal X-ray diffraction studies, vibrational spectroscopy and NMR spectroscopy: a review 通过单晶 X 射线衍射研究、振动光谱和核磁共振光谱研究碱金属离子的一些荧光大环配合物的固态结构：综述

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-18 DOI: 10.1007/s10847-024-01253-1

Namrata Ghildiyal

{"title":"Solid-state structures of some fluorescent macrocyclic complexes of alkali metal ions studied by single-crystal X-ray diffraction studies, vibrational spectroscopy and NMR spectroscopy: a review","authors":"Namrata Ghildiyal","doi":"10.1007/s10847-024-01253-1","DOIUrl":"https://doi.org/10.1007/s10847-024-01253-1","url":null,"abstract":"The aim of this review is to compile important results of single-crystal X-ray diffraction method, vibrational and NMR studies conducted on alkali metal ion complexes of some small ring benzo-crown ethers namely benzo-15-crown-5, dibenzo-15-crown-5 and benzo-12-crown-4 to determine their structure, stoichiometry and conformation in the solid-state. This review focuses on solid-state architectural diversity of alkali metal ion complexes studied by single-crystal X-ray diffraction method. Investigations of these complexes are significant as the interactions of alkali metal ions with these crown ethers mimic those present in nature between univalent ions and several bioligands. The benzo group in the macrocycle allows to monitor the complexation event by fluorescence studies and extends the applications of these crown ethers to fluorescent ion sensors. The selected small ring benzo oxa-crown ethers have cavities that match the size of the alkali metal ions and give stable complexes with them. The review presents results related to variation in infrared and Raman spectra of the ligands with changes in their crystal structure and conformation on complexation with alkali salts. Single-crystal X-ray diffraction studies of these complexes help to confirm the chemical structure, stoichiometry, stable conformation and presence of associated solvent molecules in the solid state. As noncovalent interactions are involved in the formation of these complexes, they are capable of forming supramolecular assemblies for building smart functional materials.<h3 data-test=\"abstract-sub-heading\">Graphical Abstract</h3>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141745369","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}

引用次数: 0

Structure, stability, and dynamics of inclusion complexes formed from auranofin derivatives and hydroxypropyl-β-cyclodextrin 呋喃丹衍生物与羟丙基-β-环糊精形成的包合物的结构、稳定性和动力学特性

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-12 DOI: 10.1007/s10847-024-01252-2

Hélio F. Dos Santos, Cleber P. A. Anconi

{"title":"Structure, stability, and dynamics of inclusion complexes formed from auranofin derivatives and hydroxypropyl-β-cyclodextrin","authors":"Hélio F. Dos Santos, Cleber P. A. Anconi","doi":"10.1007/s10847-024-01252-2","DOIUrl":"https://doi.org/10.1007/s10847-024-01252-2","url":null,"abstract":"The inclusion compounds of auranofin (AF) and its iodide derivative (AF-I) with HP-β-CD were recently identified and characterized experimentally. In the present work, classical molecular dynamics and the quantum computational GFN2-xTB method were applied to investigate the inclusion processes. As a result, both approaches identified AF-I@HP-β-CD as the most favourable system, as observed experimentally. The higher stability of AF-I@HP-β-CD was explained by entropy and solvation factors, with the GFN2-xTB method providing a stability constant (logK1:1) in good agreement with the experimental results: 0.21–1.21 for AF@HP-β-CD and 1.31–2.33 for AF-I@HP-β-CD (the experimental values are 1.48 and 2.52, respectively). The preferred inclusion mode for AF-I@HP-β-CD has a triethylphosphine (-PEt3) group pointed towards the head portion of the HP-β-CD where the HP groups are attached (labelled P2). The P2 mode showed short contacts between -CH2CH3 groups (-PEt3) and -H-3 only (inside the CD cavity), which is also supported by ROESY experiments.","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141611176","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}

引用次数: 0

NMR methods for studying inclusion complexes focused on chiral hosts 研究以手性宿主为重点的包涵复合物的核磁共振方法

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-04 DOI: 10.1007/s10847-024-01251-3

Sylwia Jopa, Jacek Wójcik, Andrzej Ejchart, Michał Nowakowski

引用次数: 0

Encapsulation investigation of molnupiravir drug guest using cucurbituril hosts through the DFT approach 通过 DFT 方法研究使用葫芦素宿主包囊莫仑比拉韦药物客体的情况

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-02 DOI: 10.1007/s10847-024-01250-4

Wandee Rakrai, Butsayamat Rattanadon, Chanukorn Tabtimsai, Chatthai Kaewtong, Banchob Wanno

引用次数: 0

The interaction of rhodamine B with sulfobetaine tetrapentylcalix[4]resorcinarene in the range of millimolar concentrations 罗丹明 B 在毫摩尔浓度范围内与磺基甜菜碱四戊基钙[4]间苯二酚的相互作用

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-06-04 DOI: 10.1007/s10847-024-01246-0

Zuchra R. Gilmullina, Victor V. Syakaev, Julia E. Morozova, Albina Yu. Ziganshina, Igor S. Antipin

{"title":"The interaction of rhodamine B with sulfobetaine tetrapentylcalix[4]resorcinarene in the range of millimolar concentrations","authors":"Zuchra R. Gilmullina, Victor V. Syakaev, Julia E. Morozova, Albina Yu. Ziganshina, Igor S. Antipin","doi":"10.1007/s10847-024-01246-0","DOIUrl":"https://doi.org/10.1007/s10847-024-01246-0","url":null,"abstract":"The effective binding of Rhodamine B (RhB), a xanthene dye, in solutions of amphiphilic sulfobetaine tetrapentylcalix[4]resorcinarene (C5-SB) at millimolar concentrations has been found. Using the FT-PGSE NMR technique, it was determined that the binding fraction (Pb) of RhB in the solution with a С(RhB)/С(С5-SB) ratio of 3.75 mM/5 mM was 0.57, whereas in a solution with an order of magnitude lower concentration, the Pb was only 0.12. This significant difference in interaction is also supported by 2D NOESY and 1H NMR spectra. Based on fluorimetry data, it appears that the influence of C5-SB on the spectral properties of RhB increases as the C5-SB/RhB molar ratio increases, but decreases as the concentration of C5-SB and RhB decreases. By comparing the spectral properties of RhB in the presence of C5-SB and tetrapentylcalix[4]resorcinarene with carboxylic (C5-COO−) and trimethylammonium (C5-N+Me3) peripheral groups, an assumption about the driving forces behind RhB, which led to an enhancement of the emission properties of the dye, was made. The study demonstrates the possibility of controlling the emissive properties of a xanthene dye by binding it to a supramolecular associate with amphiphilic calix [4] resorcinarene.","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141253927","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}

引用次数: 0

Synthesis and characterization of new rotaxanes from related crown compounds 从相关冠化合物中合成新的轮烷并确定其特性

IF 2.3 4区化学

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-05-28 DOI: 10.1007/s10847-024-01245-1

Abdullah Najdhashemi, Samad Bavili Tabrizi, Mirzaagha Babazadeh

{"title":"Synthesis and characterization of new rotaxanes from related crown compounds","authors":"Abdullah Najdhashemi, Samad Bavili Tabrizi, Mirzaagha Babazadeh","doi":"10.1007/s10847-024-01245-1","DOIUrl":"https://doi.org/10.1007/s10847-024-01245-1","url":null,"abstract":"Physical manipulation can be carried out on molecules and cells through the utilization of nanomachines which are machines with nano dimensions. There are different types of nanomachines. Among them, rotaxanes stand out as the most well-known. The term of rotaxane originates from the combination of the Latin words wheel and axis. The application of nanomachines is identifying and measuring the concentration of toxic substances in the environment, targeted drug delivery and cancer diagnosis. The objective of this study is to synthesize and identify several new nanomachines in the form of rotaxanes (internally locked molecules) with nanopharmaceutical properties from the corresponding crown compounds. In the first step, 2,2-dimethylphenol was converted into bisphenol compound (1) in reaction with thionyl chloride. Bisphenol compound (1) was converted into methyl diester compound (2) in reaction with methyl chloroacetate. The methyl diester compound (2) reacts with the appropriate diamine to form the diamide macrocycle compound (3). Rod (4) is prepared from the reaction of diethylene glycol ditosylate, 4,4-bipyridine and a bulk phenol such as 4-tert-butylphenol in DMF. Each of the rings in the presence of the prepared rod leads to the corresponding rotaxane compound (5). Chemical structure of the obtained compounds were established by 1HNMR, 13CNMR, FT-IR and SEM spectroscopic methods.","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141169051","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}

引用次数: 0