{"title":"Employing supramolecular chemistry strategies for the separation of mixtures of anisole and bromoanisole isomers","authors":"Benita Barton, Ulrich Senekal","doi":"10.1007/s10847-024-01242-4","DOIUrl":"10.1007/s10847-024-01242-4","url":null,"abstract":"<div><p>In the present work, host compounds <i>trans</i>-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate (<b>H1</b>), <i>trans</i>-α,α,α’,α’-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (<b>H2</b>) and <i>trans</i>-α,α,α’,α’-tetra(<i>p</i>-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (<b>H3</b>) were assessed for their host ability for anisole (ANI) and 2-, 3- and 4-bromoanisole (2-, 3- and 4-BA). It was demonstrated that <b>H3</b> formed complexes with each of these guest species, while <b>H1</b> and <b>H2</b> only possessed the ability to enclathrate ANI. When <b>H3</b> was crystallized from equimolar binary guest solutions, a significantly enhanced host affinity was observed for ANI and 3-BA. As examples, equimolar binary ANI/2-BA and 2-BA/3-BA solutions afforded complexes that demonstrated a near-complete <b>H3</b> selectivity towards ANI (97.5%) and 3-BA (94.5%), respectively. Furthermore, from <b>H3</b> crystallization experiments in binary ANI/2-BA, ANI/4-BA, 3-BA/2-BA and 3-BA/4-BA mixtures, where the molar guest amounts were varied sequentially, were calculated significant selectivity coefficients (K values), so much so that <b>H3</b> may be used to separate very many of the guest anisole mixtures prepared in this work, through supramolecular chemistry strategies, which serves as a greener separation protocol compared with tedious and energy intensive fractional distillations. Thermal analyses were also used to investigate the relative stabilities of each of the single solvent complexes.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 7-8","pages":"439 - 446"},"PeriodicalIF":2.3,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-024-01242-4.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140670923","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":"Probing the interaction of ciprofol and human serum albumin using multiple spectroscopies","authors":"Qiao Pan, Chengfeng Yao, Yulin Zhu, Shujun Shang","doi":"10.1007/s10847-024-01241-5","DOIUrl":"10.1007/s10847-024-01241-5","url":null,"abstract":"<div><p>The interaction between ciprofol and human serum albumin (HSA) was studied using spectroscopy-based approaches at different temperatures under simulated physiological conditions <i>in vitro</i>. Quenching of intrinsic Trp fluorescence of HSA with increasing ciprofol concentration is the actuating tool in the analysis. Experimental results proved that ciprofol quenched the intrinsic fluorescence of HSA through a static quenching mechanism. The thermodynamic parameters (Δ<i>G</i> = -2.35 × 10<sup>4</sup> J·mol<sup>−1</sup>, Δ<i>S</i> = -131 J·mol<sup>−1</sup>·K<sup>−1</sup>, and Δ<i>H</i> = -6.39 × 10<sup>4</sup> J·mol<sup>−1</sup> at 310 K), binding sites (<i>n</i> = 0.83), and binding constant (<i>K</i><sub>A</sub> = 9.12 × 10<sup>3</sup> M<sup>−1</sup>) indicated that hydrogen bond and van der Waals forces played a major role in the HSA-ciprofol association with weak binding force. Furthermore, the circular dichroism, synchronous, and three-dimensional fluorescence spectral results indicated adaptive structural changes of HSA in the presence of ciprofol. In addition, the effect of some common metal ions on the binding between ciprofol and HSA was examined, and Fe<sup>3+</sup> and Hg<sup>2+</sup> were proven to help prolong the storage time and improve the drug efficacy. The study provides accurate and full basic data for clarifying the binding mechanisms of ciprofol with HSA and helps understand its effect on protein function during the blood transportation process and activity in vivo.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 7-8","pages":"407 - 414"},"PeriodicalIF":2.3,"publicationDate":"2024-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140609056","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":"Li-selective calix[4]arene with trialkyl-monoacetic acid groups: effect of three alkyl branches and t-octyl groups at p-position on selectivity for Li extraction","authors":"Keisuke Ohto, Hirotoshi Sadamatsu, Takuya Hanada, Shintaro Morisada, Hidetaka Kawakita","doi":"10.1007/s10847-024-01233-5","DOIUrl":"10.1007/s10847-024-01233-5","url":null,"abstract":"<div><p>Trialkyl-monoacetic acid derivatives of <i>p</i>–t-octylcalix[4]arene and calix[4]arene were prepared to investigate the effect of the alkyl branches attached to the phenoxy oxygen atoms and the <i>p</i>-position on the selective extraction of Li<sup>+</sup> over Na<sup>+</sup>. Alkyl branches on the phenoxy oxygen atoms remarkably affected the Li<sup>+</sup> selectivity, whereas those at the <i>p</i>-position had less effect. The former can contribute to excluding Na<sup>+</sup> extraction while enabling Li<sup>+</sup> extraction. Optimal selection of the alkyl branch improves the Li<sup>+</sup> selectivity of calix[4]arene. However, sterically-hindered <i>p</i>–t-octylcalix[4]arene with three 2-ethylbutyl branches exhibited opposite selectivity.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 5-6","pages":"185 - 197"},"PeriodicalIF":2.3,"publicationDate":"2024-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140609025","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":"Coordination competency of a flexible polyfunctional tripodal framework: an insight on solution thermodynamics and DFT studies","authors":"Shalini Singh, B. K. Kanungo, Minati Baral","doi":"10.1007/s10847-024-01229-1","DOIUrl":"10.1007/s10847-024-01229-1","url":null,"abstract":"<div><p>Chelation and solution thermodynamic stability of a tripodal hydroxypyranone-based chelator (tris[(5-hydroxy-4-oxo-pyran-2-yl)methyl]benzene-1,3,5-tricarboxylate), TBHPY, towards biologically relevant divalent metal ions:Cu(II), Fe(II), Ni(II), Co(II) and Zn(II) were studied by potentiometric and spectroscopic methods in 9:1 (H<sub>2</sub>O:DMSO) medium. The metal ions formed ML, MLH<sub>2,</sub> MLH, MLH<sub>-2</sub>, and MLH<sub>-1</sub> type complexes with high formation constants. The ligand was explored for its application as a potential fluorimetric sensor and examined in the presence of various cations. Nearly twofold quenching was observed upon addition of Gd(III) to TBHPY. The experimental, spectroscopic and thermodynamic stability results were validated with the theoretical quantum mechanical calculations using density functional theory (DFT). The geometrical structures, electronic properties,and bonding behavior of the complexes are described in detail.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 5-6","pages":"219 - 231"},"PeriodicalIF":2.3,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140585072","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}
Sotaro Kusumoto, Youssef Atoini, Yoshihiro Koide, Shinya Hayami, Yang Kim, Jack Harrowfield, Pierre Thuéry
{"title":"Perrhenate anion encapsulation in a uranyl ion–zwitterionic dicarboxylate coordination polymer","authors":"Sotaro Kusumoto, Youssef Atoini, Yoshihiro Koide, Shinya Hayami, Yang Kim, Jack Harrowfield, Pierre Thuéry","doi":"10.1007/s10847-024-01238-0","DOIUrl":"10.1007/s10847-024-01238-0","url":null,"abstract":"<div><p>The zwitterionic dicarboxylate 1,1′-[(2,3,5,6-tetramethylbenzene-1,4-diyl)bis(methylene)]bis(pyridin-1-ium-4-carboxylate) (L) has been reacted with uranyl nitrate under solvo-hydrothermal conditions and in the presence of KReO<sub>4</sub> to give the complex [UO<sub>2</sub>(L)(OH)(H<sub>2</sub>O)](ReO<sub>4</sub>) (<b>1</b>). This compound crystallizes as a cationic, monoperiodic coordination polymer with ReO<sub>4</sub><sup>–</sup> as a simple counterion. The daisy-chain polymer is based on dinuclear rings built by the convergent zwitterionic ligands, these rings being linked to one another by double hydroxide bridges. In addition to a Coulombic interaction with a pyridinium ring, ReO<sub>4</sub><sup>–</sup> is involved in one OH(water)⋅⋅⋅O and four CH⋅⋅⋅O interactions, and it is thus nestled in a cavity formed by three chains, seemingly with some selectivity over nitrate and chloride anions also present in the reaction mixture. This result illustrates the interest of zwitterionic dicarboxylates in building cationic assemblies able to trap ReO<sub>4</sub><sup>–</sup>, a surrogate for the radioactive TcO<sub>4</sub><sup>–</sup>, an anion of environmental relevance.</p><h3>Graphical abstract</h3><p>A zwitterionic dicarboxylate ligand was reacted with the uranyl ion to generate a cationic, daisychain coordination polymer including perrhenate as counterion. Examination of the Hirshfeld surface of the anion allows for an analysis of the weak interactions involved.</p>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 5-6","pages":"209 - 217"},"PeriodicalIF":2.3,"publicationDate":"2024-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140585185","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}
Neha Kumari, Minati Baral, Dinesh Kumar, B. K. Kanungo
{"title":"Thermodynamics, optical properties, and coordination of lanthanoids with hydroxyquinolate functionalised receptor","authors":"Neha Kumari, Minati Baral, Dinesh Kumar, B. K. Kanungo","doi":"10.1007/s10847-024-01230-8","DOIUrl":"10.1007/s10847-024-01230-8","url":null,"abstract":"<div><p>Two new lanthanide complexes with the general formula [Ln(hqtsc)<sub>2</sub>Cl], where Ln = Eu<sup>3+</sup>/Tb<sup>3+</sup> and hqtsc is (E)-2-((8-hydroxyquinolin-2-yl)methylene)hydrazine-1-carbothioamide have been synthesized. The structures of the complexes have been elucidated through IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR and HR-mass spectroscopy. The coordination behavior of the ligand was investigated with proton and two trivalent lanthanides, Eu(III) and Tb(III), by potentiometric and spectrophotometric methods in a highly aqueous medium. The studies reveal that the two lanthanides form complexes of the type ML<sub>2</sub>H<sub>2</sub>, ML<sub>2</sub>H<sub>1</sub>, ML<sub>2</sub>, ML<sub>2</sub>H<sub>−1,</sub> and ML<sub>2</sub>H<sub>−2</sub>. The high formation constants of ML with log β = 26.55 and 27.13 indicate that these complexes will become promising candidates for chelation therapy, radioimmunotherapy, and other biomedical applications. Further, the change in colour and electronic spectra of the complexes in the presence of anions showed the selective colorimetric sensing ability towards H<sub>2</sub>PO<sub>4</sub><sup>−</sup> (orange/yellow→, colorless) and CN<sup>−</sup> (orange/yellow → red). The DFT studies were also carried out to establish the structure, bonding, and sensing mechanism of the complexes.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 5-6","pages":"233 - 255"},"PeriodicalIF":2.3,"publicationDate":"2024-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140585270","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}
Kyoungha Jang, Dong Gil Shin, Wooseop Seong, Seunghyeon Kim, Tae Nam Kim, Jeong Zoo Lee, Yangkyu Park, Hyeon Woo Kim
{"title":"Factors affecting the effectiveness of intravesical injection of botulinum toxin A in females with overactive bladder","authors":"Kyoungha Jang, Dong Gil Shin, Wooseop Seong, Seunghyeon Kim, Tae Nam Kim, Jeong Zoo Lee, Yangkyu Park, Hyeon Woo Kim","doi":"10.1007/s10847-024-01236-2","DOIUrl":"10.1007/s10847-024-01236-2","url":null,"abstract":"<div><p>The objective of this study is to examine the determinants influencing the efficacy of intravesical administration of botulinum toxin A (BoNT-A) in patients suffering from overactive bladder (OAB). The study included 32 females diagnosed with OAB, with or without urge urinary incontinence. All participants underwent BoNT-A injections (100 units) at the posterior bladder wall (20 points) from our institution between March 2017 and June 2020. Clinical data was gathered, and the severity of OAB was evaluated both before and four weeks following the procedure utilizing the International Consultation on Incontinence Modular Questionnaire-Urinary Incontinence (ICIG-UI) and the Overactive Bladder Symptom Score (OABSS). The study also looked into the status of medication for OAB four weeks after the procedure. Total mean ICIQ-UI and OABSS were significantly improved four weeks after BoNT-A injection (14.00 ± 3.46 to 7.00 ± 6.82, p < 0.001 and 11.40 ± 5.01 to 6.40 ± 1.25, p = 0.009, respectively). Younger age, longer OAB duration, and ongoing OAB medication were the factors that significantly improved the effectiveness of BoNT-A injection.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 5-6","pages":"343 - 348"},"PeriodicalIF":2.3,"publicationDate":"2024-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140585377","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}
Wooseop Seong, Dong Gil Shin, Seunghyeon Kim, Tae Nam Kim, Jeong Zoo Lee, Yangkyu Park, Kyoungha Jang, Hyeon Woo Kim
{"title":"Predictors for symptom improvement in overactive bladder patients treated with imidafenacin","authors":"Wooseop Seong, Dong Gil Shin, Seunghyeon Kim, Tae Nam Kim, Jeong Zoo Lee, Yangkyu Park, Kyoungha Jang, Hyeon Woo Kim","doi":"10.1007/s10847-024-01237-1","DOIUrl":"10.1007/s10847-024-01237-1","url":null,"abstract":"<div><p>The objective of this investigation is to ascertain the determinants associated with the amelioration of symptoms in female patients suffering from overactive bladder (OAB) following treatment with 0.2 mg of imidafenacin. The study included 66 female OAB patients who had been prescribed a daily dose of 0.2 mg imidafenacin for a minimum of 3 months, spanning from March 2018 to June 2020. Various clinical parameters including age, coexistence of additional voiding symptoms, prior history of urological surgeries, and responses to the Overactive Bladder Symptom Score questionnaire (OABSS), both pre- and post-initiation of imidafenacin therapy, were evaluated. The mean total OABSS scores recorded before and 3 months subsequent to imidafenacin therapy were 8.36 ± 3.65 and 5.15 ± 3.22, respectively. Following the 3-month course of imidafenacin treatment, there was a statistically significant improvement in both the total OABSS score and the severity of OAB symptoms (p < 0.001 for both). Prior to treatment initiation, Group B (n = 38) exhibited significantly higher total OABSS scores and subscores compared to Group A (n = 28) (p < 0.05). Multivariable analysis identified the OABSS subscores for items 1 and 3 prior to treatment as significant predictors for the improvement of OAB severity subsequent to imidafenacin therapy (p = 0.046, OR 3.10, 95% CI 1.019–9.440 and p < 0.001, OR 2.77, 95% CI 1.671–4.587, respectively). Consequently, imidafenacin emerges as an efficacious therapeutic agent for alleviating OAB severity in female patients, with the OABSS subscores for items 1 and 3 prior to treatment initiation holding potential utility in predicting the efficacy of imidafenacin in managing OAB.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 5-6","pages":"335 - 341"},"PeriodicalIF":2.3,"publicationDate":"2024-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140585376","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":"Development of a highly selective and sensitive fluorescent chemosensory for zinc ion detection in aqueous ethanol solution: synthesis of a new aza-oxo macrocycle using high-dilution condition method","authors":"Reza Azadbakht, Hasti Moshiri, Mostafa Koolivand","doi":"10.1007/s10847-024-01223-7","DOIUrl":"10.1007/s10847-024-01223-7","url":null,"abstract":"<div><p>Utilizing a high-dilution condition method, a new aza-oxo macrocycle, referred to as L, was synthesized as a chemosensor. The chemosensing capabilities of L were thoroughly investigated using fluorescence studies. The obtained results demonstrate that L effectively responds to the presence of zinc ions, leading to a significant increase in fluorescence intensity. Comparative studies were conducted to investigate the impact of various metal cations, including Cr(III), Mn(II), Fe(II), Fe(III), Co(II), Ni(II), Cu(I), Cu(II), Zn(II), Cd(II), Gd(III), Na(I), K(I), Ba(II), Mg(II), Al(III), Pb(II), Sn(II), Hg(II), and Ag(I), on the fluorescence of L in an aqueous ethanol environment. During our investigations, a binding constant value of 7.81 × 105 M<sup>−1</sup>, with a 1:1 stoichiometry for Zn<sup>2+</sup>–L interactions, was established. Additionally, a low detection limit of 2.51 × 10<sup>−8</sup> M and a rapid response time were observed. Furthermore, the chemical inputs of Zn<sup>2+</sup> and Cu<sup>2+</sup> ions meet the conditions of an INHIBIT molecular logic gate.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"104 7-8","pages":"371 - 381"},"PeriodicalIF":2.3,"publicationDate":"2024-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140585339","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}