Journal of Inclusion Phenomena and Macrocyclic Chemistry最新文献

{"title":"Synthesis of tris- and pentakis(tetra-armed cyclen) and their complexing properties towards silver(I) ions","authors":"Hiroki Horita,&nbsp;Fumika Nemoto,&nbsp;Izumi Sato,&nbsp;Mari Ikeda,&nbsp;Shunsuke Kuwahara,&nbsp;Yoichi Habata","doi":"10.1007/s10847-023-01189-y","DOIUrl":"10.1007/s10847-023-01189-y","url":null,"abstract":"<div><p>Tris(tetra-armed cyclen) with three cyclens linearly linked (<b>1a</b>) and pentakis(tetra-armed cyclen) with four cyclens linked to the central cyclen (<b>1b</b>) have been prepared. These structures of the ligands were confirmed by ¹H and ¹³C{¹H} NMR, CSI-MS, and elemental analysis. Upon addition of Ag⁺ to these novel ligands, we observed the formation of 1:1 to 1:3 (= <b>1a</b>:Ag⁺) complexes and 1:1 to 1:5 (= <b>1b</b>:Ag⁺) complexes, respectively, according to stoichiometry. The association constants for <b>1a</b> and <b>1b</b> with Ag⁺ using titration experiments with UV–vis spectroscopy were also estimated. Log<i>β</i>₁, log<i>β</i>₂, and log<i>β</i>₃ of <b>1a</b> were 6.4, 14, and 21, respectively, while log<i>β</i>₁, log<i>β</i>₂, log<i>β</i>₃, log<i>β</i>₄, and log<i>β</i>₅ of <b>1b</b> were 6.8, 13, 19, 24, and 29, respectively. The association constants obtained from experiments revealed that all cyclen units within the molecules formed complexes with Ag⁺ that exhibited nearly identical association constants. The result suggests that the ligands have a uniform binding affinity for Ag⁺ throughout their structures.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"103 5-6","pages":"223 - 233"},"PeriodicalIF":2.3,"publicationDate":"2023-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4215699","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":"Play of molecular host: guest assembly on a G-quadruplex binder","authors":"Aleyamma Alexander,&nbsp;Archana Sumohan Pillai,&nbsp;Sudhaker Raboni Grace,&nbsp;Nallamuthu Ananthi,&nbsp;Haridas Pal,&nbsp;Israel Vijayaraj Muthu Vijayan Enoch,&nbsp;Mhejabeen Sayed","doi":"10.1007/s10847-023-01185-2","DOIUrl":"10.1007/s10847-023-01185-2","url":null,"abstract":"<div><p>Benzimidazoles are known G-quadruplex binding molecules. G-quadruplex-selective binding is relevant in the target-based design of the molecules for treating certain diseases, including cancer. Herein, we present the synthesis of a new benzimidazolyl guanidine and its binding association with various nucleic acids viz., calf thymus DNA (duplex), kit22, myc22, and telo (G-quadruplexes). The synthesized compound is characterized by IR, NMR, and mass spectrometric techniques. The binding titration is carried out utilizing UV–vis and fluorescence spectroscopy. The conformational changes of DNAs on the ligand binding are monitored using circular dichroism. Further, the compound inclusion complex with a porphyrin-β-cyclodextrin host molecule. The binding strengths of the guanidine and its Ppy-CD inclusion complex are compared. The inclusion complexes bind stronger to G-quadruplexes than CT-DNA. The binding constants value is the largest for the interaction of the guanidine: porphyrin-β-cyclodextrin inclusion complex with the G-quadruplex kit22, which possesses a parallel conformation. The difference in the binding strengths is articulated and compared between duplex and G-quadruplex bindings.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"103 3-4","pages":"147 - 159"},"PeriodicalIF":2.3,"publicationDate":"2023-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-023-01185-2.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4443938","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":"Advancement in supramolecular control of organic reactivity induced by cucurbit[n]urils","authors":"Kevin Droguett,&nbsp;Guillermo E. Quintero,&nbsp;José G. Santos,&nbsp;Margarita E. Aliaga","doi":"10.1007/s10847-022-01172-z","DOIUrl":"10.1007/s10847-022-01172-z","url":null,"abstract":"<div><p>This Review Article covers advances over the past two decades in the field of the organic modulation reactivity by supramolecular hosts. Specifically, the scope of this review is focused on some members of the cucurbit[<i>n</i>]urils (CB[<i>n</i>]) family. As we will show with different examples, the use of CB [6], CB [7] and CB [8] enables modification of the reactivity on a wide variety of reactions by their exceptional recognition properties in aqueous medium, adequate size, hydrophobic cavity and polarity portals. The first part of this review gives a brief discussion of the chemical properties of CB[<i>n</i>] relevant to understanding their effect on the reactivity of organic guests. Then, this article highlights two opposite effects: catalysis and inhibition processes based on the ability of CB[<i>n</i>] to modulate the chemical reactivity of representatives guests. Some examples of organic reactions, such as solvolysis, oxidation, isomerization, cicloaddition, among others, are discussed from a kinetic and thermodynamic point of view.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"103 1-2","pages":"1 - 20"},"PeriodicalIF":2.3,"publicationDate":"2022-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5577223","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":"Structural and physico-chemical properties of clathrate hydrates of tetraisoamylammonium polyacrylates","authors":"Irina S. Terekhova,&nbsp;Andrey Yu. Manakov,&nbsp;Galina V. Villevald,&nbsp;Tamara D. Karpova","doi":"10.1007/s10847-022-01171-0","DOIUrl":"10.1007/s10847-022-01171-0","url":null,"abstract":"<div><p>Physico-chemical and structural characteristics have been studied of ionic clathrate hydrates of cross-linked (<i>n</i> = 1%) tetraisoamylammonium (TiAA) polyacrylates with different extent of substitution of proton-ions of the carboxylic groups for TiAA cations (<i>x</i> = 77%, 60%, 40%) in the polyacrylate. Powder X-ray diffraction studies have been carried out. All hydrates are isostructural to the earlier studied clathrate hydrate of cross-linked TiAA polyacrylate with <i>x</i> = 100%. The hexagonal structure with the space group <i>P</i>6<i>/mmm</i> and slightly different unit cell parameters (<i>a</i> ~ 12.24 Å, <i>c</i> ~ 12.70 Å) is related to the idealized Hexagonal Structure I of clathrate hydrates. Compositions, phase transition temperatures and decomposition enthalpies of the hydrates have been determined using differential thermal analysis and differential scanning calorimetry. The stability of the hydrates structure decreases with lessening of the content of TiAA cations in the polymeric molecule. The hydrates decomposition temperatures go down from + 14.6 to + 9.8 °C (for <i>x</i> = 100–40%) and the decomposition enthalpies—from 189.1 kJ/mol of hydrate to 84.0 kJ/mol of hydrate (for the same interval of <i>x</i>). The comparison has been made of physico-chemical characteristics of the ionic clathrate hydrates of cross-linked TiAA polyacrylates with those of the hydrates of tetrabutylammonium (TBA) polyacrylates and also of the ionic clathrate hydrates of TBA salts with monomeric anions.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 11-12","pages":"905 - 915"},"PeriodicalIF":2.3,"publicationDate":"2022-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-022-01171-0.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4100222","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":"Construction of unique pseudo[1]rotaxanes and [1]rotaxanes based on mono-functionalized pillar[5]arene Schiff bases","authors":"Dan Li,&nbsp;Ying Han,&nbsp;Jing Sun,&nbsp;Chao-Guo Yan","doi":"10.1007/s10847-022-01165-y","DOIUrl":"10.1007/s10847-022-01165-y","url":null,"abstract":"<div><p>A series of mono-functionalized pillar[5]arene Schiff bases were successfully synthesized by amidation reaction of pillar[5]arene mono-<i>O</i>-butyrate with various diaminoalkanes and sequential condensation reaction of monoaminoalkyl-functionalized pillar[5]arenes with substituted salicylaldehydes. ¹H NMR and 2D NOESY spectra clearly showed that all monoaminoalkyl-functionalized pillar[5]arenes could form pseudo[1]rotaxanes by self-sorting of aminoalkyl chain into the cavity of pillar[5]arene, while pillars[5]arene Schiff bases with longer than butylene chain (n ≥ 4) could form stable [1]rotaxane. The fluorescence spectrophotometry indicated that pillar[5]arene Schiff bases coordinated with Zn²⁺ ion to form interesting complexes with 2:1 coordination ratio and with significant enhance of the fluorescence intensity.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 9-10","pages":"819 - 829"},"PeriodicalIF":2.3,"publicationDate":"2022-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4954493","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":"Multi-functionalized single-walled carbon nanotubes as delivery carriers: promote the targeting uptake and antitumor efficacy of doxorubicin","authors":"Shuoye Yang,&nbsp;Jiaxin Liu,&nbsp;Yahong Ping,&nbsp;Zhenwei Wang,&nbsp;Jiaying Zhang,&nbsp;Lu Zhang,&nbsp;Lan Cui,&nbsp;Yongmei Xiao,&nbsp;Lingbo Qu","doi":"10.1007/s10847-022-01163-0","DOIUrl":"10.1007/s10847-022-01163-0","url":null,"abstract":"<div><p>As one of carbon-based nanomaterials, single-walled carbon nanotubes (SWCNTs) are widely regarded as potentially potent drug delivery carriers on account of their prominent properties. Nevertheless, their biomedical application, particularly in the drug delivery field has been seriously restricted by some inherent defects. In this study, SWCNTs materials were functionalized by covalent and non-covalent approaches, respectively. In short, the pristine SWCNTs were first purified with strong oxidizing acids (H₂SO₄/HNO₃), and the resulting carboxylated ones (CNTs) were attached sequentially by different modification agents, including polyethylene glycol (PEG), polyethyleneimine (PEI), folic acid (FA) and chitosan (CS). Various nanocarriers were then systematically characterized and comparatively evaluated. The results illustrated that all CNTs samples could act as drug delivery carriers since they had high drug loading efficiency, good biocompatibility and responsive drug release. In comparison with other CNTs, multi-functionalized ones (CNTs-PPFC) exhibited more excellent performance, such as rapid drug release at low pH condition, higher cell internalization efficiency, and enhanced antitumor activity toward MCF-7 cells. These advantages should be attributed to their better dispersion state and comparably higher affinity with tumor cells, which favor the more efficient selective cellular uptake and subsequent drug accumulation. Moreover, further pharmacological mechanism analysis also revealed that CNTs-PPFC/DOX could induce the apoptosis of MCF-7 cells most effectively, by triggering ROS overproduction and affecting cell cycle distribution. In conclusion, the multi-functionalized CNTs-PPFC can be utilized as promising nanocarriers, and the findings will contribute to the rational design of novel delivery vehicles for anticancer drugs.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 9-10","pages":"801 - 817"},"PeriodicalIF":2.3,"publicationDate":"2022-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-022-01163-0.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4876887","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":"Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex","authors":"Ryosuke Hiroshige,&nbsp;Satoru Goto,&nbsp;Chihiro Tsunoda,&nbsp;Risa Ichii,&nbsp;Shota Shimizu,&nbsp;Yuta Otsuka,&nbsp;Kosho Makino,&nbsp;Hideyo Takahashi,&nbsp;Hideshi Yokoyama","doi":"10.1007/s10847-022-01160-3","DOIUrl":"10.1007/s10847-022-01160-3","url":null,"abstract":"<div><p>Ketoprofen is a nonsteroidal anti-inflammatory drug used as mohrus tape which causes unwanted photosensitivity due to UV irradiation. In addition, photodegradation of ketoprofen induces its decarboxylation. Here, we aim to determine the effect of cyclodextrin on the photolysis of ketoprofen. Separation technique using HPLC confirmed that UV irradiation of ketoprofen produced multiple products. A unique reaction proceeded in the presence of β-cyclodextrin. Furthermore, characterization by UV spectroscopy was performed, and the obtained spectra were analyzed using singular value decomposition. By analyzing the trajectory of the singular vector space, we were able to reflect the difference in the reaction pathway of ketoprofen with and without cyclodextrin. This study uses a singular value decomposition analysis, which is useful as a novel approach for solutions of radical reactions and a promising technique for analysis of radical reactions in the future.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 9-10","pages":"791 - 800"},"PeriodicalIF":2.3,"publicationDate":"2022-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4278227","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, antimicrobial and thermal studies of nitropyridine-substituted double armed benzo-15-crown-5 ligands; alkali (Na+ and K+) and transition metal (Ag+) complexes; reduction of nitro compounds","authors":"Serhat Koçoğlu,&nbsp;Zeliha Hayvalı,&nbsp;Hatice Ogutcu,&nbsp;Orhan Atakol","doi":"10.1007/s10847-022-01157-y","DOIUrl":"10.1007/s10847-022-01157-y","url":null,"abstract":"<div><p>Nitropyridine substituted double-armed benzo 15-crown-5 compounds (<b>1–4</b>) were synthesized by the reactions of 4′,5′-bis(bromomethyl)benzo-15-crown-5 with hydroxypyridine derivatives. Na⁺ and K⁺ complexes (<b>1a–4a, 1b–4b</b>) of crown ether compounds (<b>1–4</b>) were prepared with sodium picrate and potassium picrate, respectively. Transition metal complexes (<b>1c–4c</b>) of the synthesized ligands (<b>1–4</b>) were prepared from Ag⁺ cation. In addition, nitro compounds (<b>1, 2</b> and <b>4</b>) were reduced by using Pd/C and hydrazine hydrate and new amine compounds (<b>5, 6</b> and <b>8</b>) were obtained. The structures of new double-armed crown ether compounds (<b>2–4</b>), their metal complexes (<b>1a–4a, 1b–4b, 2c–4c</b>) and amine compounds (<b>5</b>, <b>6</b> and <b>8</b>) were elucidated by FTIR, HRMS, ¹H–NMR, ¹³C–NMR spectroscopic methods. The thermal behaviors of these nitro group containing ligands (<b>1–4</b>) were compared with the resulting silver complexes (<b>1c–4c</b>) and amine compounds (<b>5</b>, <b>6</b> and <b>8</b>). All synthesized compounds were examined for antibacterial activity against pathogenic strains <i>Listeria monocytogenes</i>, <i>Salmonella typhi H</i>, <i>Bacillus cereus</i>, <i>Staphylococcus aureus</i>, <i>Staphylococcus epidermidis</i>, <i>Micrococcus luteus</i>, <i>Escherichia coli</i>, <i>Klebsiella pneumonia</i>, <i>Proteus vulgaris</i>, <i>Serratia marcescens</i>, <i>Shigella dysenteria</i> and antifungal activity against <i>Candida albicans</i>.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 9-10","pages":"763 - 780"},"PeriodicalIF":2.3,"publicationDate":"2022-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5000377","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":"Acyclic cucurbiturils and their applications","authors":"Hui Liu,&nbsp;You-Jia Guo","doi":"10.1007/s10847-022-01159-w","DOIUrl":"10.1007/s10847-022-01159-w","url":null,"abstract":"<div><p>Acyclic cucurbit[n]urils are a novel type of cucurbituril derivatives, consisting of a central glycoluril tetramer skeleton, two substituted terminal aromatic rings, and four linkers bearing solubilizing groups. Due to flexible conformation and facile functionalization, acyclic cucurbit[n]urils are tailored to exhibit high binding affinity and selectivity toward a variety of guests. In this review, we focus on the relationship between structure and property of acyclic cucurbit[n]urils. The recent development of acyclic cucurbit[n]urils has paved the way for practical applications in pharmaceutical and biochemical areas.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 9-10","pages":"723 - 733"},"PeriodicalIF":2.3,"publicationDate":"2022-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4885076","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":"Crystalline γ-cyclodextrin metal organic framework nano-containers for encapsulation of benzaldehyde and their host–guest interactions","authors":"Ajay Kathuria,&nbsp;Youn Suk Lee,&nbsp;Joongmin Shin,&nbsp;Mohsen Kivy","doi":"10.1007/s10847-022-01158-x","DOIUrl":"10.1007/s10847-022-01158-x","url":null,"abstract":"<div><p>The nano-porous crystals of γ-cyclodextrin MOF (CDMOF) were synthesized and encapsulated with benzaldehyde. The host–guest interactions between CDMOF and benzaldehyde were analyzed using fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and molecular docking calculations. We observed that around 13% benzaldehyde was adsorbed by the CDMOF crystals, which was supported by TGA, FTIR, DSC and XRD. The preferred inclusion geometry was identified, and the strength of these interactions was recorded. A polar carbonyl group was identified as a docking site which leads to stabilization and complex formation with glucopyranose unit of CDMOF. It was observed that the binding energy for the complex is—4.04 kcal mol⁻¹, which indicates that complex formation is thermodynamically favorable.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 9-10","pages":"781 - 790"},"PeriodicalIF":2.3,"publicationDate":"2022-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-022-01158-x.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4640771","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}