Journal of Inclusion Phenomena and Macrocyclic Chemistry最新文献

{"title":"Calixarenes: recent progress in supramolecular chemistry for application in cancer therapy","authors":"Aysen Isik,&nbsp;Mehmet Oguz,&nbsp;Ahmet Kocak,&nbsp;Mustafa Yilmaz","doi":"10.1007/s10847-022-01134-5","DOIUrl":"10.1007/s10847-022-01134-5","url":null,"abstract":"<div><p>Cancer is one of the leading causes of death worldwide, and the limited success of currently used anticancer drugs is a driving force for the search for new compounds with anticancer potential. Calixarenes make up a fascinating class of macrocycles that find a wide range of biological applications in supramolecular chemistry. Especially in recent years, the anticancer activity of various calixarene derivatives has been reported by many researchers. The aim of this review article is to find relatively simple, efficient, and synthetic methods for the preparation of macrocyclic compounds containing various pharmacophoric groups to produce new and effective anticancer materials in cancer research and to investigate the usability of calixarene-based supramolecular in cancer research.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-03-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4094268","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":"Three 18-membered macrocyclic diamides with differing donor atoms and backbone substituents","authors":"Gary L. N. Smith,&nbsp;Douglas R. Powell,&nbsp;Michelle D. Moser,&nbsp;Richard W. Taylor","doi":"10.1007/s10847-022-01133-6","DOIUrl":"10.1007/s10847-022-01133-6","url":null,"abstract":"<div><p>The crystal structures are reported for 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-6,17-dione, (C₁₂H₂₂N₂O₆), (<b>I</b>), dibenzo[e,q][1,4,10,13,7,16] tetraoxadiazacyclooctadecine-6,13-dione, (C₂₀H₂₂N₂O₆), (<b>II</b>) and 1,4-dioxa-10,13-dithia-7,16-diazacyclooctadecane-8,15-dione, (C₁₂H₂₂N₂O₄S₂), (<b>III</b>). Solid-state structures show different types of hydrogen bonding for all three structures. In <b>I</b>, there are two intermolecular hydrogen bonds between an amide and carbonyl [N–H···O = 2.8206(11) Å and 2.8637(11) Å] and two intermolecular hydrogen bonds between an amide and ether [N–H···O = 2.9570(11) Å and 3.0067(11) Å]. There are two intramolecular hydrogen bonds between amide and ether oxygens [N–H···O = 2.589(3) Å and 2.623(4) Å] in <b>II</b>. Molecule <b>III</b> has a mixture of intramolecular hydrogen bonds between an amide and thioether [N–H···S = 3.0501(18) Å] and intermolecular hydrogen bonds between an amide and carbonyl [N–H···O = 2.835(2) Å].</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4856652","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 aromatic ethers as solvents for a calix[6]arene derivative and extraction of amino acids and proteins","authors":"Tatsuya Oshima,&nbsp;Tokiya Asano,&nbsp;Asuka Inada,&nbsp;Keisuke Ohto,&nbsp; Jumina","doi":"10.1007/s10847-022-01132-7","DOIUrl":"10.1007/s10847-022-01132-7","url":null,"abstract":"<div><p>Calixarene derivatives are excellent host compounds for ionic species in liquid–liquid extraction. However, many studies using calixarene derivatives have been conducted using highly toxic chloroform as a solvent because of their poor solubility in typical hydrocarbons. In the present study, aromatic ethers were developed as solvents for calixarene derivatives to enhance their industrial applicability. The solubility of the calix[6]arene carboxylic acid derivative ^tOct[6]CH₂COOH in 1-octoxybenzene (OB) and 1-butoxybenzene (BB) was 11.3 mM and 24.9 mM, respectively. The cationic guest molecule tryptophan methyl ester was extracted using the ^tOct[6]CH₂COOH host in OB and BB. The cationic lysine-rich protein cytochrome <i>c</i> was also extracted using ^tOct[6]CH₂COOH in BB as shown for ^tOct[6]CH₂COOH in chloroform in previous studies. However, cytochrome <i>c</i> was not extracted using ^tOct[6]CH₂COOH in OB and instead, precipitated. As ^tOct[6]CH₂COOH stabilizes the ammonium group of biomolecules because of its suitable cavity size, the extraction of the tryptophan ester and cytochrome <i>c</i> using ^tOct[6]CH₂COOH was much higher than those using the corresponding calix[4]arene and calix[8]arene derivatives. These results confirm that aromatic ethers are potential solvents for calixarene derivatives for the extraction of biomolecules.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-022-01132-7.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5119248","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":"CoIIIcorrole: versatile synthetic methods and wide range of applications","authors":"Tingting Gu,&nbsp;Zhen Zhang,&nbsp;Shengyu Zhang,&nbsp;Weihua Zhu,&nbsp;Xu Liang","doi":"10.1007/s10847-021-01127-w","DOIUrl":"10.1007/s10847-021-01127-w","url":null,"abstract":"<div><p>This review introduces the synthesis, properties and applications of Co^IIIcorroles. The synthesis methods are containing A₂B type, A₃ type, ABC type, Hangman H₃corrole and H₃biscorrole synthesis and their metal-inserting reactions. Also, the spectroscopic and electrochemical properties of Co^IIIcorroles were also described. However, the most important part of this paper is about the application of Co^IIIcorroles, including the development of sustainable and pollution-free chemical energy sources, the degradation of environmentally harmful organochlorides, and the oxidation of alkanes.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4159658","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":"Organic porous solid as promising iodine capture materials","authors":"Ya-Nan Yu,&nbsp;Zheng Yin,&nbsp;Li-Hui Cao,&nbsp;Yang-Min Ma","doi":"10.1007/s10847-022-01128-3","DOIUrl":"10.1007/s10847-022-01128-3","url":null,"abstract":"<div><p>Facing the dual pressure of increasing global energy demand and heavy task in carbon emission reduction on schedule, nuclear renaissance is being seriously discussed as transitive choice before full renewable energy supply, yet there is a crucial concern about radioactive safety. The treatment of radioactive iodine is particularly important and challenging because of its high ratio in fission product, extremely long radioactive periods up to several millions of years, as well as easy diffusion in the whole ecosystem. Given that several challenge including easy sublimation, high water solubility, diverse existing species of I₂, I⁻, I_2n+1⁻ and organic iodine, biocompatibility and strong aggregation in thyroid, rapid capture and permanent storage of iodine is requested. Comparing to inorganic adsorbents of zeolite and inorganic–organic hybrid MOFs, pure organic porous solid are emerging as new and promising iodine capture material. Their high iodine affinity and adsorption capacity, good stability in various environments, facile modification and functionalization, intrinsic structural flexibility guaranteed the outstanding performance in iodine capture. Four main categories of organic cages, supramolecular framework connected by weak interaction, covalent organic frameworks and polymers with intrinsic microporosity were summarized and discussed, from the viewpoints of design principles, iodine capture performance, and adsorbent-iodine interactions. As the main prospect, we hope this work will attracting more researchers to study porous organic materials and address the challenge of effective capture of radioactive iodine.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-022-01128-3.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4892753","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":"Preparation and recognition property of an acyclic cucurbit[n]uril dimer","authors":"Fang Zhou,&nbsp;Da Ma,&nbsp;Yamin Liu","doi":"10.1007/s10847-022-01130-9","DOIUrl":"10.1007/s10847-022-01130-9","url":null,"abstract":"<div><p>A new acyclic cucurbit[<i>n</i>]uril (CB[<i>n</i>]) dimer is synthesized by copper-catalyzed azide-alkyne cycloaddition or “click” reaction. The acyclic CB[<i>n</i>] dimer possesses two cavities, and is able to encapsulate two guest molecules simultaneously. This dimer is discovered to be high affinity host molecule for a wide variety of dyes, pharmaceutical drugs and guest molecules.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4819807","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":"Spectral studies of protonated and anionic forms of porphyrins with an asymmetric substitution system","authors":"Yulia B. Ivanova,&nbsp;Svetlana G. Pukhovskaya,&nbsp;Alexey V. Lyubimtsev,&nbsp;Anna O. Plotnikova,&nbsp;Sergei A. Syrbu","doi":"10.1007/s10847-022-01131-8","DOIUrl":"10.1007/s10847-022-01131-8","url":null,"abstract":"<div><p>The directed synthesis of asymmetrically substituted porphyrins—tetraphenylporphyrine derivatives containing amino acid residues as a functional group, which can be used as “anchor” groups, for incorporation into the structure of a protein molecule, was carried out. The obtained compounds were characterized by a number of spectral methods confirming their structure and purity. Their base and acid ionization constants in the AN–HClO₄ and DMSO–potassium cryptate (KOH[222])—systems were measured by spectrophotometric titration. It was found that the asymmetric substitution architecture contributed to the stabilization of the protonated forms of porphyrins. This allowed, for the first time, to extract and spectrally characterize the mono- and doubly-protonated forms (H₃P⁺ and H₄P²⁺) of each ligands in the AN–HClO₄ system. The analysis of the spectral changes of the monoamino derivative led to identify three stages of the protonation, which first involves the nitrogen atom of the periphery substituent (p<i>K</i>_b = 13.26) and then the central nitrogen atoms of the macrocycle (p<i>K</i>_b1 = 11.50; p<i>K</i>_b2 = 9.65; p<i>K</i>_b1,2 = 21.15). The relative stability of the first intermediate is assumed to be caused by charge delocalization. The electron-donor nature of the solvent in the DMSO–KOH [222] system led to the leveling of the ionization constants for the first and second stages, which allowed us to determine only the total values for the porphyrins studied. The successive stages of acid–base interactions were analyzed in the article.</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":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4822038","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":"Recent advances in therapeutical applications of the versatile hydroxypyridinone chelators","authors":"Shailza Sharma,&nbsp;Minati Baral,&nbsp;B. K. Kanungo","doi":"10.1007/s10847-021-01114-1","DOIUrl":"10.1007/s10847-021-01114-1","url":null,"abstract":"<div><p>Hydroxypyridinones (HOPOs) are excellent class of chelators that have been gaining attention in the field of pharmaceutical drugs by their high chelating efficacy and specificity with different metal ions. Among all the metal ions, they exhibit a high binding affinity towards iron (III) and are clinically used as iron chelators nowadays. The HOPO family has different isomers, out of which 3,4-HOPO possesses applicability for designing drugs. The effect of methyl substitution on different positions of pyridinone ring also plays an essential role in deciding the pM values, thus describing the metal affinity. Several metal ions like Fe, Al, Cu, Zn, and some actinides are found to exhibit good chelation efficacy with HOPOs. In terms of denticity, there are various forms of HOPO. Among these, discussion on bidentate, tetradentate, hexadentate, octadentate, and dendrimers will be done here. This review systematically summarizes the various literature reports on the design and pharmacological activities of the newly developed HOPOs and their derivatives, including antibiotics, anticancer, and antineurodegeneratives.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2022-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4648974","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":"Lanthanide complexes with polyaminopolycarboxylates as prospective NMR/MRI diagnostic probes: peculiarities of molecular structure, dynamics and paramagnetic properties","authors":"Eugeny N. Zapolotsky,&nbsp;Yanyang Qu,&nbsp;Sergey P. Babailov","doi":"10.1007/s10847-021-01112-3","DOIUrl":"10.1007/s10847-021-01112-3","url":null,"abstract":"<div><p>The paramagnetic lanthanide complexes with polyaminopolycarboxylate (PAPC) ligands attract considerable attention from the standpoint of potential applications thereof as relaxation agents used in medical magnetic resonance imaging (MRI) and in luminescent materials, as well as owing to promising use thereof as paramagnetic labels for studying the properties of biopolymers since they exhibit thermodynamic stability, good solubility in aqueous media and moderate toxicity. For the last decades, the NMR methods have been used to determine the physical and chemical properties of paramagnetic Ln compounds. The studies concerning paramagnetic NMR lanthanide-induced shifts (LISs) in dissolved Ln complexes, as well as the analysis of band shape as a function of temperature make it possible to obtain valuable information on the structure, intra- and intermolecular dynamics and paramagnetic properties thereof. This review is devoted solely to the following features: firstly, the processes of intramolecular dynamics of lanthanide complexes with polyamino-polycarboxylate ligands such as DOTA, EDTA and DTPA and their derivatives studied by NMR; secondly, the LISs of lanthanide complexes with EDTA, DOTA, DTPA and some of their derivatives depending on temperature and pH. Moreover, in this review, for the first time, the dependence of the activation energy of molecular dynamics in complexes with polydentate ligands on the atomic number of the lanthanide cation is analyzed and a monotonic change in energy is detected, which is due to the effect of lanthanide contraction. It should be noted that this phenomenon is quite general and may also appear in the future in many other series of lanthanide complexes with both other multidentate ligands and with bidentate and monodentate ligands. In the future, it is possible to predict the dependence of the properties of certain lanthanide complexes on the ionic radius of the lanthanide cation based on the approaches presented in the review. In this review, we have also presented the dynamic NMR as the main research method widely used to analyze the processes of molecular dynamics, and the structural studies based on the NMR relaxation spectroscopy and LIS analysis.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4473487","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":"Studies on cobalt(III) complexes of a cyanoethyl derivative of an isomeric hexamethyl tetraazamacrocyclic ligand","authors":"Mohammad Abu Sayed,&nbsp;Saswata Rabi,&nbsp;Pradip Paul,&nbsp;Lucky Dey,&nbsp;Benu Kumar Dey,&nbsp;Zinnat A. Begum,&nbsp;Ismail M. M. Rahman,&nbsp;Tapashi Ghosh Roy","doi":"10.1007/s10847-021-01110-5","DOIUrl":"10.1007/s10847-021-01110-5","url":null,"abstract":"<div><p>A 14-membered hexamethyl-tetraazamacrocycle, viz. Me₆[14]diene.2HClO₄ (L.2HClO₄), afforded a mixture of isomeric ligands, Me₆[14]anes, upon reduction with NaBH₄ and extraction by CHCl₃ at pH &gt; 12. These ligands were separated by fractional crystallization from xylene and were designated as ‘tet-a’ and ‘tet-b.’ The interaction of ‘tet-b’ with excess acrylonitrile was fairly stereoselective and formed an <i>N</i>-pendent derivative, ‘tet-bx’, in which two cyano-ethyl groups were attached to trans <i>N</i>-atoms that are sterically less crowded. Aeration of ‘tet-bx’ and cobalt(II) acetate salt in methanol, followed by its treatment with HCl, yielded a bluish-green product, viz. <i>trans</i>-[Co(‘tet-bx’)Cl₂]Cl. <i>trans</i>-[Co(‘tet-bx’)Cl₂]Cl underwent axial substitution reactions with KSCN and KNO₃ and subsequent axial substitution and anion exchange reactions with NaNO₂, KBr, and KI to produce six-coordinated octahedral complexes, viz. bluish-green <i>trans</i>-[Co(‘tet-bx’)(NCS)₂]Cl, light-blue <i>trans</i>-[Co(‘tet-bx’)(NO₃)₂]Cl, yellow <i>trans</i>-[Co(‘tet-bx’)(NO₂)₂]NO₂, green <i>trans</i>-[Co(‘tet-bx’)Br₂]Br, and red <i>trans</i>-[Co(‘tet-bx’)I₂]I. These complexes were characterized using different modern analytical and spectroscopic techniques. The antibacterial activities of the <i>N</i>-pendent ligand and its cobalt(III) complexes on four types of selected bacteria were investigated.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2021-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4225754","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}