Pub Date : 2021-11-02DOI: 10.1080/10610278.2022.2159824
Paulina Hernández‐Pacheco, Gustavo A. Zelada‐Guillén, M. Flores‐Álamo, Martha V. Escárcega‐Bobadilla
ABSTRACT The synthesis, characterisation, and crystallographic analysis of a novel -OH functionalised Ni-Salphen complex and its hybrid nanomaterial counterparts in the form of the molecule covalently bonded to Edge-Oxidised Graphene Oxide are described. Spectrophotometric titrations of the complex and of the nanomaterial performed against different pyridine-based guests showed a constant stoichiometry of association but different trends in association constants upon grafting. These changes could be ascribed to differences in the supramolecular environment at the binding site upon grafting, which may find cooperativity thanks to additional interactions arising from the graphene component. The spectrofluorimetric emission profile was explored before and upon association to find that emission intensity was affected in a different manner depending on whether the complex was used as a free molecule or in the hybrid nanomaterial, while it also depended on the size and flexibility of the guest used. Graphical Abstract
{"title":"Supramolecular host-guest and fluorescence studies on Ni-Salphen complex as a binding unit on edge oxidised graphene oxide grafted nanomaterial","authors":"Paulina Hernández‐Pacheco, Gustavo A. Zelada‐Guillén, M. Flores‐Álamo, Martha V. Escárcega‐Bobadilla","doi":"10.1080/10610278.2022.2159824","DOIUrl":"https://doi.org/10.1080/10610278.2022.2159824","url":null,"abstract":"ABSTRACT The synthesis, characterisation, and crystallographic analysis of a novel -OH functionalised Ni-Salphen complex and its hybrid nanomaterial counterparts in the form of the molecule covalently bonded to Edge-Oxidised Graphene Oxide are described. Spectrophotometric titrations of the complex and of the nanomaterial performed against different pyridine-based guests showed a constant stoichiometry of association but different trends in association constants upon grafting. These changes could be ascribed to differences in the supramolecular environment at the binding site upon grafting, which may find cooperativity thanks to additional interactions arising from the graphene component. The spectrofluorimetric emission profile was explored before and upon association to find that emission intensity was affected in a different manner depending on whether the complex was used as a free molecule or in the hybrid nanomaterial, while it also depended on the size and flexibility of the guest used. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"45 4 1","pages":"647 - 663"},"PeriodicalIF":3.3,"publicationDate":"2021-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85358641","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}
Pub Date : 2021-10-03DOI: 10.1080/10610278.2022.2117623
Amy V. Hall, D. Yufit, Yingfeng Zhang, O. Musa, J. Steed
ABSTRACT Cocrystallisation of butanoic acid (BA), pentanoic acid (PA), and eicosanoic acid (EA) with 4,4’-azopyridine (azp) and trans-1,2-bis(4-pyridyl)ethylene (bpe) results in 2:1 lamellar cocrystals. All cocrystals display the OH···Npyridyl seven-membered ring supramolecular synthon however, each cocrystal responds differently upon heating. Positive thermal expansion (PTE) occurs along the c-axis due to π···π stacking in the isostructural BA cocrystals, while the PA cocrystals are not isostructural and display a mixture of anti and gauche conformations of the acid chains because of the length mismatch with the coformer. PA2·azp displays negative thermal expansion (NTE) of the intrasynthon C···O hydrogen bond. The two EA cocrystals both display c-axis elongation on warming due to the expansion of the distance between the alkyl chains. The expansion by more than 1 Å in EA2·azp is highly anisotropic, however, there is much less c-axis expansion in EA2·bpe. Graphical Abstract
{"title":"Anisotropic thermal expansion effects in layered n-Alkyl carboxylic acid – bipyridyl cocrystals","authors":"Amy V. Hall, D. Yufit, Yingfeng Zhang, O. Musa, J. Steed","doi":"10.1080/10610278.2022.2117623","DOIUrl":"https://doi.org/10.1080/10610278.2022.2117623","url":null,"abstract":"ABSTRACT Cocrystallisation of butanoic acid (BA), pentanoic acid (PA), and eicosanoic acid (EA) with 4,4’-azopyridine (azp) and trans-1,2-bis(4-pyridyl)ethylene (bpe) results in 2:1 lamellar cocrystals. All cocrystals display the OH···Npyridyl seven-membered ring supramolecular synthon however, each cocrystal responds differently upon heating. Positive thermal expansion (PTE) occurs along the c-axis due to π···π stacking in the isostructural BA cocrystals, while the PA cocrystals are not isostructural and display a mixture of anti and gauche conformations of the acid chains because of the length mismatch with the coformer. PA2·azp displays negative thermal expansion (NTE) of the intrasynthon C···O hydrogen bond. The two EA cocrystals both display c-axis elongation on warming due to the expansion of the distance between the alkyl chains. The expansion by more than 1 Å in EA2·azp is highly anisotropic, however, there is much less c-axis expansion in EA2·bpe. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"126 1","pages":"578 - 585"},"PeriodicalIF":3.3,"publicationDate":"2021-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87784971","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}
Pub Date : 2021-10-03DOI: 10.1080/10610278.2022.2109472
Nika Gazdek, I. Zonjić, I. Nikšić-Franjić, Leo Leo Frkanec, I. Piantanida
ABSTRACT We showed that aristolochic acid toxin (ARI) and its fluorescent analogue form inclusion complexes with various cyclodextrins (CDs), including the clinically used γ-CD: Sugammadex. The binding affinity of ARI towards CDs varied on a CD size and rim modifications, whereby the stability of ARI/Sugammadex complex was 2-fold greater than ARI binding to serum albumin (BSA), blood protein well-known as a transporter of small molecules and similar to the ARI complex with ds-DNA. Molecular modelling supported the formation of ARI/ Sugammadex complex with carboxyl group of ARI exposed to water and ARI-condensed aromatic moiety deeply immersed into CD-cavity. These results are a proof-of-concept that CDs could be used as a first aid upon acute intoxication with ARI by binding larger part of the toxin in competition with serum albumin or ds-DNA and significantly reducing ARI absorption in the organism, similarly as Sugammadex extracts drugs from blood to stop their bioactivity. Graphical abstract
{"title":"Competitive binding of aristolochic acid between various cyclodextrins and serum albumin as a model for acute poisoning detoxification","authors":"Nika Gazdek, I. Zonjić, I. Nikšić-Franjić, Leo Leo Frkanec, I. Piantanida","doi":"10.1080/10610278.2022.2109472","DOIUrl":"https://doi.org/10.1080/10610278.2022.2109472","url":null,"abstract":"ABSTRACT We showed that aristolochic acid toxin (ARI) and its fluorescent analogue form inclusion complexes with various cyclodextrins (CDs), including the clinically used γ-CD: Sugammadex. The binding affinity of ARI towards CDs varied on a CD size and rim modifications, whereby the stability of ARI/Sugammadex complex was 2-fold greater than ARI binding to serum albumin (BSA), blood protein well-known as a transporter of small molecules and similar to the ARI complex with ds-DNA. Molecular modelling supported the formation of ARI/ Sugammadex complex with carboxyl group of ARI exposed to water and ARI-condensed aromatic moiety deeply immersed into CD-cavity. These results are a proof-of-concept that CDs could be used as a first aid upon acute intoxication with ARI by binding larger part of the toxin in competition with serum albumin or ds-DNA and significantly reducing ARI absorption in the organism, similarly as Sugammadex extracts drugs from blood to stop their bioactivity. Graphical abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"16 1","pages":"569 - 577"},"PeriodicalIF":3.3,"publicationDate":"2021-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82813580","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}
Pub Date : 2021-10-03DOI: 10.1080/10610278.2022.2134017
R. Navarro, Yedith Soberanes, M. Inoue
ABSTRACT The complexation of organic electrolytes, like carboxylic acids and amines, is studied usually by spectrometric titration at a constant pH. Obtained stability constants are, however, conditional and dependent on the pH selected, differing from the proper constants. In nuclear magnetic resonance (NMR) titration in D2O, a stability constant determined at a given pD is not directly correlated to other properties observed at a pH in H2O because of difference between acid dissociations in the solvents. To overcome these problems, this report proposes pD-variable NMR spectrometry, which monitors NMR signals of a mixture of the reactants with the variation of pD. This method identifies complexes formed in different pD ranges, and determines the proper stability constants, to yield the species distribution, which can be replotted in pH scale. The usefulness and limitation are examined by simulation of titration curves. An experimental example is presented for complexation of histidine with a cyclophane acid. Excel® files for calculations are available in Supplementary material. Graphical Abstract
{"title":"NMR pD-variation method to determine the proper stabilities of organic electrolyte complexes: case of histidine complexes with a cyclophane acid","authors":"R. Navarro, Yedith Soberanes, M. Inoue","doi":"10.1080/10610278.2022.2134017","DOIUrl":"https://doi.org/10.1080/10610278.2022.2134017","url":null,"abstract":"ABSTRACT The complexation of organic electrolytes, like carboxylic acids and amines, is studied usually by spectrometric titration at a constant pH. Obtained stability constants are, however, conditional and dependent on the pH selected, differing from the proper constants. In nuclear magnetic resonance (NMR) titration in D2O, a stability constant determined at a given pD is not directly correlated to other properties observed at a pH in H2O because of difference between acid dissociations in the solvents. To overcome these problems, this report proposes pD-variable NMR spectrometry, which monitors NMR signals of a mixture of the reactants with the variation of pD. This method identifies complexes formed in different pD ranges, and determines the proper stability constants, to yield the species distribution, which can be replotted in pH scale. The usefulness and limitation are examined by simulation of titration curves. An experimental example is presented for complexation of histidine with a cyclophane acid. Excel® files for calculations are available in Supplementary material. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"26 1","pages":"598 - 604"},"PeriodicalIF":3.3,"publicationDate":"2021-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72746696","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}
Pub Date : 2021-10-03DOI: 10.1080/10610278.2022.2135439
Mou Mandal, Anirban Karak, Satyajit Halder, Shilpita Banerjee, Anwesha Maiti, Kuladip Jana, A. Mahapatra, A. Kar
ABSTRACT A new type of styryl bridging triphenyl amine-indolium conjugated dye has been developed for the colorimetric and ratiometric detection of cyanide. The detection of cyanide is confirmed by means of the fast nucleophilic attack of cyanide by the indolium group of the probe that results a speedy sensing process for cyanide with clear color and fluorescence change of the ICT process. The ratiometric fluorescence changes illustrated a linear response in the range of 0-18 μM with a low LOD value (1.7×10-7 M-1). The as-reported sensor not only function as a colorimetric sensor for “in-the-field” measurement by virtue of a “dip-stick” approach but also interact with a human breast cancer cell (MDA-MB 231) which reveals the realistic value of this probe for tracking cyanide anions in biological systems. Graphical abstract
{"title":"A ratiometric styryl bridging triphenylamine-indolinium based fluorescent dye for detection of cyanide with a large emission shift in human breast cancer cells and test strips","authors":"Mou Mandal, Anirban Karak, Satyajit Halder, Shilpita Banerjee, Anwesha Maiti, Kuladip Jana, A. Mahapatra, A. Kar","doi":"10.1080/10610278.2022.2135439","DOIUrl":"https://doi.org/10.1080/10610278.2022.2135439","url":null,"abstract":"ABSTRACT A new type of styryl bridging triphenyl amine-indolium conjugated dye has been developed for the colorimetric and ratiometric detection of cyanide. The detection of cyanide is confirmed by means of the fast nucleophilic attack of cyanide by the indolium group of the probe that results a speedy sensing process for cyanide with clear color and fluorescence change of the ICT process. The ratiometric fluorescence changes illustrated a linear response in the range of 0-18 μM with a low LOD value (1.7×10-7 M-1). The as-reported sensor not only function as a colorimetric sensor for “in-the-field” measurement by virtue of a “dip-stick” approach but also interact with a human breast cancer cell (MDA-MB 231) which reveals the realistic value of this probe for tracking cyanide anions in biological systems. Graphical abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"46 1","pages":"605 - 615"},"PeriodicalIF":3.3,"publicationDate":"2021-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77318787","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}
Pub Date : 2021-10-03DOI: 10.1080/10610278.2022.2137412
A. Mushtaq, M. Iqbal, Saqib Ali, M. Tahir
ABSTRACT Two copper(II) paddlewheel carboxylate complexes 1 and 2 of the general formula ACuL4CuA, where A is DMSO (1) and meta-bromopyridine (2) and L is meta-chlorophenyl acetate, have been synthesised, isolated quantitatively, crystallised and characterised using FTIR, UV-Visible spectroscopy, electrochemistry and XRD. FTIR spectra contained all the required peaks with the most prominent peaks those of carboxylate moiety indicating the bridging bidentate carboxylate binding mode. Electrochemistry yielded results typical of complexes containing Cu2+ centres. The structures were completely solved by XRD technique assigning square pyramidal geometry to each copper ion of the dinuclear complexes. The square base is formed by four oxygen atoms of the carboxylate moiety while the apical position is occupied by the fifth oxygen (of the DMSO molecule in 1) or nitrogen of the meta-bromopyridine in complex 2. The DNA-binding potency of the complexes was explored by viscometry, cyclic voltammetry, UV-Visible spectrophotometry and spectrofluorimetry. All these techniques provided coincident results and showed that the complexes bonded with DNA via an intercalative-binding mode. Additionally, these complexes were found to scavenge the free radical DPPH effectively. The complexes add interesting and valuable addition to the existing treasury on the copper paddlewheel complexes and their biological relevance. Graphical Abstract
{"title":"Centrosymmetric paddlewheel copper(II) complexes as potent intercalators: synthesis, crystal structure description and DNA-binding studies","authors":"A. Mushtaq, M. Iqbal, Saqib Ali, M. Tahir","doi":"10.1080/10610278.2022.2137412","DOIUrl":"https://doi.org/10.1080/10610278.2022.2137412","url":null,"abstract":"ABSTRACT Two copper(II) paddlewheel carboxylate complexes 1 and 2 of the general formula ACuL4CuA, where A is DMSO (1) and meta-bromopyridine (2) and L is meta-chlorophenyl acetate, have been synthesised, isolated quantitatively, crystallised and characterised using FTIR, UV-Visible spectroscopy, electrochemistry and XRD. FTIR spectra contained all the required peaks with the most prominent peaks those of carboxylate moiety indicating the bridging bidentate carboxylate binding mode. Electrochemistry yielded results typical of complexes containing Cu2+ centres. The structures were completely solved by XRD technique assigning square pyramidal geometry to each copper ion of the dinuclear complexes. The square base is formed by four oxygen atoms of the carboxylate moiety while the apical position is occupied by the fifth oxygen (of the DMSO molecule in 1) or nitrogen of the meta-bromopyridine in complex 2. The DNA-binding potency of the complexes was explored by viscometry, cyclic voltammetry, UV-Visible spectrophotometry and spectrofluorimetry. All these techniques provided coincident results and showed that the complexes bonded with DNA via an intercalative-binding mode. Additionally, these complexes were found to scavenge the free radical DPPH effectively. The complexes add interesting and valuable addition to the existing treasury on the copper paddlewheel complexes and their biological relevance. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"74 2 Pt 1 1","pages":"616 - 623"},"PeriodicalIF":3.3,"publicationDate":"2021-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74560887","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}
Pub Date : 2021-10-03DOI: 10.1080/10610278.2022.2134016
Ranjhan Junejo, Nida Shams Jalbani, S. Kaya, S. Erkan, E. Ebenso
ABSTRACT In this study, silica surface has been coated using pyrrolidinomethylcalix[4]arene through the chemical modification of silanol groups. The pyrrolidinomethylcalix[4]arene-coated silica (PCS) adsorbent was characterized using the Fourier transform infrared and scanning electron microscopic technique. The adsorptive removal efficiency of PCS adsorbent was checked through batch studies with various effective parameters such adsorbent dose, pH, and temperature. During experiments, it has been observed that maximum adsorption was achieved in acidic to neutral pH and 25 mg.L−1 of PCS dose, while the kinetic models demonstrates that the pseudo 2nd order equation was the best fit (R2 0.99). The thermodynamic experiments described that the reaction is exothermic and spontaneous. Furthermore, equilibrium models were applied on experimental data and it has been noticed that the equilibrium data was best-fitted with Langmuir isotherm model (R2 0.99). The DFT analysis of dye molecule is helpful to examine the chemical interaction sites of absorbent and adsorbent using B3LYP/LANL2DZ/6-311++G (d,p) level using G09W software. Graphical Abstract
{"title":"Application of pyrrolidinomethylcalix[4]arene coated silica adsorbent for the removal of Chicago sky blue 6B dye from water samples: Equilibrium and computational modelling studies","authors":"Ranjhan Junejo, Nida Shams Jalbani, S. Kaya, S. Erkan, E. Ebenso","doi":"10.1080/10610278.2022.2134016","DOIUrl":"https://doi.org/10.1080/10610278.2022.2134016","url":null,"abstract":"ABSTRACT In this study, silica surface has been coated using pyrrolidinomethylcalix[4]arene through the chemical modification of silanol groups. The pyrrolidinomethylcalix[4]arene-coated silica (PCS) adsorbent was characterized using the Fourier transform infrared and scanning electron microscopic technique. The adsorptive removal efficiency of PCS adsorbent was checked through batch studies with various effective parameters such adsorbent dose, pH, and temperature. During experiments, it has been observed that maximum adsorption was achieved in acidic to neutral pH and 25 mg.L−1 of PCS dose, while the kinetic models demonstrates that the pseudo 2nd order equation was the best fit (R2 0.99). The thermodynamic experiments described that the reaction is exothermic and spontaneous. Furthermore, equilibrium models were applied on experimental data and it has been noticed that the equilibrium data was best-fitted with Langmuir isotherm model (R2 0.99). The DFT analysis of dye molecule is helpful to examine the chemical interaction sites of absorbent and adsorbent using B3LYP/LANL2DZ/6-311++G (d,p) level using G09W software. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"392 2 1","pages":"586 - 597"},"PeriodicalIF":3.3,"publicationDate":"2021-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73140662","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}
Pub Date : 2021-09-02DOI: 10.1080/10610278.2022.2099277
Sandra Díaz-Cabrera, Israel Carreira-Barral, M. García-Valverde, R. Quesada
ABSTRACT Roseophilin is an alkaloid structurally related to prodiginines . The intriguing pharmacological properties of these derivatives have prompted us to prepare synthetic compounds 1–3 inspired by their structure and to explore their transmembrane anion transport activity. The methoxyfuran heterocycle impacts the anionophoric activity of the compounds as a result of the reduced hydrogen-bonding ability and electrostatic repulsions between the oxygen in the furan ring and the anions. The position of the furan was also found to be crucial for determining their anion transport activity. Overall, replacement of the characteristic methoxypyrrole moiety of prodiginines and tambjamines by the methoxyfuran found in roseophilin is detrimental to their ability as anion carriers, suggesting that the biological activity of roseophilin is likely not related to their potential activity as anion carriers. Compound 2, bearing a furan ring attached to a dipyrromethene moiety, was found to be the most active anion carrier. GRAPHICAL ABSTRACT
{"title":"Roseophilin-inspired derivatives as transmembrane anion carriers","authors":"Sandra Díaz-Cabrera, Israel Carreira-Barral, M. García-Valverde, R. Quesada","doi":"10.1080/10610278.2022.2099277","DOIUrl":"https://doi.org/10.1080/10610278.2022.2099277","url":null,"abstract":"ABSTRACT Roseophilin is an alkaloid structurally related to prodiginines . The intriguing pharmacological properties of these derivatives have prompted us to prepare synthetic compounds 1–3 inspired by their structure and to explore their transmembrane anion transport activity. The methoxyfuran heterocycle impacts the anionophoric activity of the compounds as a result of the reduced hydrogen-bonding ability and electrostatic repulsions between the oxygen in the furan ring and the anions. The position of the furan was also found to be crucial for determining their anion transport activity. Overall, replacement of the characteristic methoxypyrrole moiety of prodiginines and tambjamines by the methoxyfuran found in roseophilin is detrimental to their ability as anion carriers, suggesting that the biological activity of roseophilin is likely not related to their potential activity as anion carriers. Compound 2, bearing a furan ring attached to a dipyrromethene moiety, was found to be the most active anion carrier. GRAPHICAL ABSTRACT","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"51 1","pages":"550 - 558"},"PeriodicalIF":3.3,"publicationDate":"2021-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85127241","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}
Pub Date : 2021-09-02DOI: 10.1080/10610278.2022.2061352
T. Khokhar, Fakhar N. Memon, S. S. Memon, A. Memon, A. A. Bhatti, S. Memon
ABSTRACT This study reports the solubilizing properties of p-sulphonatocalix[4]arene ( p-SCX4) towards Naringenin (NAR) to improve pharmacokinetic characteristics and bioavailability by forming inclusion complex at physiological pH and subsequent release at acid pH values. The complexation of naringenin with p -SCX4 was confirmed through spectroscopic techniques such as UV–visible spectroscopy and Fourier transform infrared spectroscopy. Complex formation was further confirmed through HPLC-DAD analysis by identification of naringenin (1), p-SCX4 (2), and p-SCX4/NAR (3). Job’s plot method and Benesi–Hildebrand equation was used to find the stoichiometry of complex. Solubility of naringenin was determined by Higuchi and Connors method. Results show that there is 1:1 stoichiometry between drug and p-SCX4. The solubility factor was increase up to 10 folds. The drug dissolution/releasing behaviour of the complex was examined at different pH values, and maximum % release amount was observed at pH = 3.5 within time interval up to 220 minutes. Graphical abstract
{"title":"Naringenin solubilizing and pH dependent releasing properties of water soluble p-sulphonatocalix[4]arene","authors":"T. Khokhar, Fakhar N. Memon, S. S. Memon, A. Memon, A. A. Bhatti, S. Memon","doi":"10.1080/10610278.2022.2061352","DOIUrl":"https://doi.org/10.1080/10610278.2022.2061352","url":null,"abstract":"ABSTRACT This study reports the solubilizing properties of p-sulphonatocalix[4]arene ( p-SCX4) towards Naringenin (NAR) to improve pharmacokinetic characteristics and bioavailability by forming inclusion complex at physiological pH and subsequent release at acid pH values. The complexation of naringenin with p -SCX4 was confirmed through spectroscopic techniques such as UV–visible spectroscopy and Fourier transform infrared spectroscopy. Complex formation was further confirmed through HPLC-DAD analysis by identification of naringenin (1), p-SCX4 (2), and p-SCX4/NAR (3). Job’s plot method and Benesi–Hildebrand equation was used to find the stoichiometry of complex. Solubility of naringenin was determined by Higuchi and Connors method. Results show that there is 1:1 stoichiometry between drug and p-SCX4. The solubility factor was increase up to 10 folds. The drug dissolution/releasing behaviour of the complex was examined at different pH values, and maximum % release amount was observed at pH = 3.5 within time interval up to 220 minutes. Graphical abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"435 1","pages":"493 - 503"},"PeriodicalIF":3.3,"publicationDate":"2021-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77815865","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}
ABSTRACT A novel 1:1 supramolecular dye inclusion complex between inverted cucurbit[7]uril (iQ[7]) and Thioflavin T (THT) has been successfully constructed on the basis of host–guest recognition. The obtained results revealed that THT exhibited obvious iQ[7]-induced fluorescence enhancement in this inclusion complex system, and the N-dimethyl and benzene ring moiety of the guest THT were located inside the cavity of iQ[7], whereas the other section of THT remained outside the portal. And THT@iQ[7] was highly stimuli-responsive to competing guests. These results provided a possibility for application in the molecular recognition area. Graphical Abstract
{"title":"Stimuli-responsive supramolecular dye inclusion complex constructed by self-assembly of inverted cucurbit[7]uril and thioflavin T","authors":"Hui Zhao, Wen-Jie Chen, Hao Chen, Jifu Sun, Zhong‐Zheng Gao","doi":"10.1080/10610278.2022.2109471","DOIUrl":"https://doi.org/10.1080/10610278.2022.2109471","url":null,"abstract":"ABSTRACT A novel 1:1 supramolecular dye inclusion complex between inverted cucurbit[7]uril (iQ[7]) and Thioflavin T (THT) has been successfully constructed on the basis of host–guest recognition. The obtained results revealed that THT exhibited obvious iQ[7]-induced fluorescence enhancement in this inclusion complex system, and the N-dimethyl and benzene ring moiety of the guest THT were located inside the cavity of iQ[7], whereas the other section of THT remained outside the portal. And THT@iQ[7] was highly stimuli-responsive to competing guests. These results provided a possibility for application in the molecular recognition area. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"198 1","pages":"559 - 567"},"PeriodicalIF":3.3,"publicationDate":"2021-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78086425","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}
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