{"title":"A new amino functionalized thio-modified β-cyclodextrin based ligand and its Fe(III) complex with physico‑chemical and antibacterial activity: an integrated experimental and computational investigation","authors":"Pritika Gurung, Ananya Das, Sudarshan Pradhan, Anmol Chettri, Tanmoy Dutta, Biswajit Sinha","doi":"10.1007/s10847-024-01247-z","DOIUrl":"10.1007/s10847-024-01247-z","url":null,"abstract":"<div><p><i>β</i>-Cyclodextrin plays a crucial role in augmenting the activity of metal complexes by ameliorating their solubility, stability, and reactivity, therefore the thio-functionalized <i>β</i>-cyclodextrin based amino ligand mono-6-deoxy-(<i>o</i>-aminobenzylthio)-<i>β</i>-cyclodextrin (4) was synthesized and analyzed by elemental analyses, AAS, UV–visible, FTIR, and <sup>1</sup>H NMR spectroscopy. The newly synthesized Fe III) complex was soluble in water. The Fe(III) complex's spectral analysis using FTIR confirmed that the ligand aided the metal ion coordinate by way of the sulfur atom of the <i>β</i>-cyclodextrin moiety and the nitrogen atoms of the two ligand molecules, with two H<sub>2</sub>O occupying the fifth and sixth coordination sites. Additionally, the mass spectrometry verifies that the intended Fe(III) complex has synthesized. Density functional theory (DFT) was used to calculate different electronic parameters of the optimized structure of Fe(III) complex to reveal its stability. Antimicrobial metal complexes that are suitable for therapeutic application are known to be more stable and bioavailable when <i>β</i>-cyclodextrin is introduced, therefore studies have been done to inquire into the possible comparative in vitro antibacterial activity of the Fe(III) complex and free ligand against two gram positive (<i>Bacillus subtilis</i>, and <i>Staphylococcus aureus</i>) and two gram negative bacteria (<i>Escherichia coli</i>, <i>Klebsiella pneumoniae</i>) strains. Molecular docking was used to further corroborate these capabilities.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-024-01247-z.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141360523","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}
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":"10.1007/s10847-024-01246-0","url":null,"abstract":"<div><p>The effective binding of Rhodamine B (RhB), a xanthene dye, in solutions of amphiphilic sulfobetaine tetrapentylcalix[4]resorcinarene (C<sub>5</sub>-SB) at millimolar concentrations has been found. Using the FT-PGSE NMR technique, it was determined that the binding fraction (<i>P</i><sub><i>b</i></sub>) of RhB in the solution with a <i>С</i>(RhB)/<i>С</i>(С<sub>5</sub>-SB) ratio of 3.75 mM/5 mM was 0.57, whereas in a solution with an order of magnitude lower concentration, the <i>P</i><sub><i>b</i></sub> was only 0.12. This significant difference in interaction is also supported by 2D NOESY and <sup>1</sup>H NMR spectra. Based on fluorimetry data, it appears that the influence of C<sub>5</sub>-SB on the spectral properties of RhB increases as the C<sub>5</sub>-SB/RhB molar ratio increases, but decreases as the concentration of C<sub>5</sub>-SB and RhB decreases. By comparing the spectral properties of RhB in the presence of C<sub>5</sub>-SB and tetrapentylcalix[4]resorcinarene with carboxylic (C<sub>5</sub>-COO<sup>−</sup>) and trimethylammonium (C5-N<sup>+</sup>Me<sub>3</sub>) 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.</p></div>","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}
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":"10.1007/s10847-024-01245-1","url":null,"abstract":"<div><p>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 <sup>1</sup>HNMR, <sup>13</sup>CNMR, FT-IR and SEM spectroscopic methods.</p></div>","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}
{"title":"Trans-to-cis isomerization of a platinum(II) complex with two triphosphine ligands via coordination with gold(I) ions","authors":"Kazuki Nagasato, Taichi Baba, Hayato Soma, Nobuto Yoshinari","doi":"10.1007/s10847-024-01228-2","DOIUrl":"10.1007/s10847-024-01228-2","url":null,"abstract":"<div><p>The reaction of a square-planar platinum(II) complex containing two bis(2-diphenylphosphinoethyl)phenylphosphine (triphos), [Pt(triphos)<sub>2</sub>](NO<sub>3</sub>)<sub>2</sub>, with [Au(tu)<sub>2</sub>]Cl (tu = thiourea) gave a new trinuclear Au<sup>I</sup><sub>2</sub>Pt<sup>II</sup> complex, [Pt(triphos)<sub>2</sub>{Au(tu)}<sub>2</sub>]Cl<sub>2</sub>(NO<sub>3</sub>)<sub>2</sub>, through Au-P coordination. While the [Pt(triphos)<sub>2</sub>]<sup>2+</sup> unit in [Pt(triphos)<sub>2</sub>](NO<sub>3</sub>)<sub>2</sub> adopted the trans-meso configuration, only the cis-racemic isomer was observed for [Pt(triphos)<sub>2</sub>{Au(tu)}<sub>2</sub>]Cl<sub>2</sub>(NO<sub>3</sub>)<sub>2</sub>. <sup>31</sup>P NMR spectroscopy indicated rapid equilibrium among the possible isomers of [Pt(triphos)<sub>2</sub>]<sup>2+</sup>, which facilitated the trans-to-cis transformation at the Pt<sup>II</sup> center in this system. Additionally, we observed that this structural transformation led to an increase in the emission intensity.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-024-01228-2.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140939868","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}
Yara Luiza Coelho, Hauster Maximiler Campos de Paula, Lívia Neves Santa Rosa, Isabela Araujo Marques, Nícolas Glanzmann, Camilla Fonseca Silva, Adilson David da Silva, Clebio Soares Nascimento Jr., Ana Clarissa dos Santos Pires, Luis Henrique Mendes da Silva
{"title":"Kinetics and thermodynamics of β-cyclodextrin-NH2/β-carotene complexation: how much energy is required to include a hydrophobic group in the macrocycle cavity?","authors":"Yara Luiza Coelho, Hauster Maximiler Campos de Paula, Lívia Neves Santa Rosa, Isabela Araujo Marques, Nícolas Glanzmann, Camilla Fonseca Silva, Adilson David da Silva, Clebio Soares Nascimento Jr., Ana Clarissa dos Santos Pires, Luis Henrique Mendes da Silva","doi":"10.1007/s10847-024-01240-6","DOIUrl":"10.1007/s10847-024-01240-6","url":null,"abstract":"<div><p>To improve the efficiency of cyclodextrins as carotenoid carriers, the kinetics and thermodynamics of the inclusion complex formation between modified β-cyclodextrin (βCD-NH<sub>2</sub>) and β-carotene (βCT) were studied using surface plasmon resonance (SPR) at pH 7.4 and theoretical calculations. The observed dissociation rate of the [βCD-NH<sub>2</sub>/βCT]° inclusion complex is small <span>((2.59times 1{0}^{-1} {text{s}}^{-1})</span>), indicating that βCD-NH<sub>2</sub> only interacted with the βCT ionone group to form inclusion complex. The βCD-NH<sub>2</sub>/βCT binding constant is <span>(2.80times 1{0}^{4} text{L} {text{m}text{o}text{l}}^{-1})</span> (at 298.15 <i>K</i>), and its temperature dependence indicates that the [βCD-NH<sub>2</sub>/βCT]° formation is driven by hydrophobic interactions (<span>({Delta }H^circ = 28.83 text{k}text{J} text{m}text{o}{text{l}}^{-1})</span> and <span>(T{Delta }S^circ = 54.21 text{k}text{J} text{m}text{o}{text{l}}^{-1})</span>) caused mainly by the βCT end group desolvation. In contrast, the formation of the [βCD-NH<sub>2</sub>/βCT]<sup>‡</sup> activated complex via association between free molecules and dissociation of [βCD-NH<sub>2</sub>/βCT]° occurred with the overcoming of an energy barrier (<span>(E_{a}^{ddag } = 40.77~{text{kJ mol}}^{{ - 1}} ~)</span> and <span>({E}_{d}^{ddag}=11.94 text{k}text{J} text{m}text{o}{text{l}}^{-1})</span>) and decrease in entropy (<span>(T{varDelta S}_{a}^{ddag}=-11.70 text{k}text{J} text{m}text{o}{text{l}}^{-1})</span> and <span>(T{varDelta S}_{d}^{ddag}=- 65.92 text{k}text{J} text{m}text{o}{text{l}}^{-1})</span>).</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140889001","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":"Fabrication of a novel bone adhesive (crosslinked phytic acid-gelatin coordinated with magnesium phosphate and calcined dolomite, and montmorillonite) for enhancing adhesion strength and biocompatibility","authors":"Man-Na Hu, Xue-Jing Qu, Xiao-Lan Chen, Dan He, Guo-Ya Wang, Jia-Hui Liu, Tania Roy, Alfin Kurniawan, Chun-Hui Zhou","doi":"10.1007/s10847-024-01234-4","DOIUrl":"10.1007/s10847-024-01234-4","url":null,"abstract":"<div><p>Bone adhesives are known as a promising fracture treatment material because they can quickly heal broken bones. However, the existing bone adhesives have the disadvantages of weak binding ability to bone tissue, non-absorption, or difficulty in curing under wet conditions, which limits their wide application in the field of bone tissue engineering. In this study, the raw material of magnesium phosphate bone adhesive was modified, and the composite material of magnesium phosphate bone repair was prepared by the method of solid–liquid blending crosslinking. Mineral-organic composite, a new type of bone adhesive was prepared using calcined dolomite and montmorillonite as mineral components, phytic acid and gelatin as organic components. The compressive strength, porosity and bonding strength of the magnesium phosphate-based bone adhesive were analyzed by Fourier transform infrared spectroscopy, X-ray diffraction and scanning electron microscopy. When the dosage of dolomite is 8 wt% and the concentration of gelatin is 9 wt%, the adhesion strength of the bone adhesive is 2.04 MPa after 168 h placement. And the compressive strength of the bone adhesive was 6.66 MPa after 168 h placement. After the prepared bone adhesives were immersed in SBF solution for 14 and 21 days, EDS analysis showed that the accumulated material was bone-like hydroxyapatite, indicating that the prepared bone adhesives had good osteogenic activity. In addition, it was also found that the bone adhesive had fluid absorption ability and no cytotoxicity. So, conclusively it can be stated that such newly synthesized bone adhesive has significant medical potential.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140662588","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":"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":null,"pages":null},"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":null,"pages":null},"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":null,"pages":null},"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}