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1.
This review treats the biological properties of the various anionic calix[n]arenes, both as soluble forms and in the colloidal state. The complexation of these molecules with amino-acids, peptides and proteins is discussed, as is their interaction with model membranes. The complexations with various Active Pharmaceutical Ingredients as complexes, for tamoxifen as solid state and colloidal structures, are treated in depth. Two sections deal with the direct biological action of the calix[n]arenes and their use as biosensors. A final section deals with the toxicity, in reality the lack of toxicity of the calix[n]arenes. 相似文献
2.
The complexation-induced critical aggregation concentrations of 1-pyrenemethylaminium by mono-p-sulfonatocalix[n]arenes and bis-p-sulfonatocalix[n]arenes (n=4, 5) were systemically measured by fluorescence spectroscopy. In all cases, the complexation-induced critical aggregation concentration decreases by about 3 times upon addition of p-sulfonatocalix[n]arenes. However, the optimal molar ratios for the aggregation of 1-pyrenemethylaminium by mono-p-sulfonatocalix[n]arenes and bis-p-sulfonatocalix[n]arenes are distinctly different: For mono-p-sulfonatocalix[n]arenes, the optimum mixing ratio for the aggregation of 1-pyrenemethylaminium is 1:4 mono-p-sulfonatocalix[n]arenes/1-pyrenemethylaminium, whereas only 2.5 molecules of 1-pyrenemethylaminium can be bound by one cavity of bis-p-sulfonatocalix[n]arenes. The intermolecular complexation of mono-p-sulfonatocalix[n]arenes and bis-p-sulfonatocalix[n]arenes with 1-pyrenemethylaminium led to the formation of two distinctly different nanoarchitectures, which were shown to be nanoscale vesicle and rod aggregates, respectively, by using dynamic laser scattering, TEM, and SEM. This behavior is also different from the fiber-like aggregates with lengths of several micrometers that were formed by 1-pyrenemethylaminium itself above its critical aggregation concentration. Furthermore, the obtained nanoaggregates exhibit benign water solubility, self-labeled fluorescence, and, more importantly, temperature responsiveness. 相似文献
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4.
Joice Thomas Liliana Dobrzańska Mahendra Punjaji Sonawane Mario Smet Wouter Maes 《Supramolecular chemistry》2014,26(7-8):591-596
Synthetic procedures towards homodithiacalix[n]arenes are developed, starting from simple and readily available bifunctional aryl building blocks, by a dynamic covalent chemistry approach. Reaction of 1,3-bis(mercaptomethyl)-5-tert-butyl-2-methoxybenzene under basic conditions leads to a mixture of trimeric, tetrameric and pentameric dimethylenedithia-bridged cyclooligomers, whereas reaction of 5-tert-butyl-2-methoxy-1,3-bis(thiocyanatomethyl) benzene under reducing conditions (and subsequent oxidation) affords the homodithiacalix[4]arene macrocycle in a very selective fashion through efficient disulphide exchange chemistry. 相似文献
5.
E. Da. Silva D. Ficheux A. W. Coleman 《Journal of inclusion phenomena and macrocyclic chemistry》2005,52(3):201-206
The parent p-sulfonato-calix[n]arenes and six O-monosubstituted derivatives were investigated in vitro for anticoagulant activity. Different concentrations of calixarenes were tested, showing that the compound 49-mono-(2-carboxymethoxy)-5,11,17,23,29,35,41,47-octa-sulfonato-calix[8]arene (C8SMA) has a significantly strong prolongation on the activated partial thromboplastin time (APTT) and on the thrombin time (TT) than the other calixarenes. Secondly, investigation of whether the anticoagulant behaviour was via interaction with antithrombin or Heparin Cofactor II was determined. Thrombin inhibition mediated by antithrombin (AT) and Heparin Cofactor II (HCII) activation was investigated in comparison to the biological activators, Heparin (Hep) and Dermatan sulfate (DS). The results show that the 49-mono-(2-carboxymethoxy)-5,11,17,23,29,35,41,47-octa-sulfonato-calix[8]arene (C8SMA) and 5,11,17,23,29,35-hexa-sulfonato-calix[6]arene (C6S) produce activation of HCII at 500 μM comparable to that induced by DS at 100 μM. However, activation of AT by all of the investigated calixarenes is between 10 and 50 times lower than that observed in the presence of heparin. The mechanism of the anticoagulant effect of these calixarenes is as activators of HCII and not as activators of AT. 相似文献
6.
The parent p-sulfonato-calix[n]arenes and six O-monosubstituted derivatives were investigated in vitro for anticoagulant activity. Different concentrations of calixarenes were tested, showing that the compound 49-mono-(2-carboxymethoxy)-5,11,17,23,29,35,41,47-octa-sulfonato-calix[8]arene (C8SMA) has a significantly strong prolongation on the activated partial thromboplastin time (APTT) and on the thrombin time (TT) than the other calixarenes. Secondly, investigation of whether the anticoagulant behaviour was via interaction with antithrombin or Heparin Cofactor II was determined. Thrombin inhibition mediated by antithrombin (AT) and Heparin Cofactor II (HCII) activation was investigated in comparison to the biological activators, Heparin (Hep) and Dermatan sulfate (DS). The results show that the 49-mono-(2-carboxymethoxy)-5,11,17,23,29,35,41,47-octa-sulfonato-calix[8]arene (C8SMA) and 5,11,17,23,29,35-hexa-sulfonato-calix[6]arene (C6S) produce activation of HCII at 500 μM comparable to that induced by DS at 100 μM. However, activation of AT by all of the investigated calixarenes is between 10 and 50 times lower than that observed in the presence of heparin. The mechanism of the anticoagulant effect of these calixarenes is as activators of HCII and not as activators of AT.in final form: 24 November 2004This revised version was published online in July 2005 with a corrected issue number. 相似文献
7.
Hiroyuki Takemura Teruo Shinmyozu Hirokazu Miura Islam Ullah Khan Takahiko Inazu 《Journal of inclusion phenomena and macrocyclic chemistry》1994,19(1-4):193-206
Side arm modifications of hexahomotriazacalix[3]arene (1) were achieved by simple synthetic methods. Compound5 has picolyl side arms and liquid-liquid extraction experiments showed that the alkali cation affinity of5 is much stronger than that of1. A chiral group was also introduced into the azacalixarene structure. Calix[4]arene was converted into dihomoazacalix[4]arene (2) in 8% yield. Clathrate formation of2 with various solvents is described. MM3 calculations were carried out onp-substituted analogs of2. The self-filled structure, in which the benzyl side arm is placed in its cavity, is the most stable structure when thep-positions of the aromatic rings carry small substituents. Strong hydrogen bonds between nitrogen and phenolic hydroxyl groups in dihomoazacalix[4]arene (2) were observed at low temperatures. The1H-NMR signals of phenolic hydroxyl groups appeared as six singlets in the range of 9.817.1 ppm at –70°C.This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes. 相似文献
8.
W. Abraham 《Journal of inclusion phenomena and macrocyclic chemistry》2002,43(3-4):159-174
Calix[n]arenes represent an interestingclass of preorganized aromatic hostsexhibiting an enhanced ability forcation- interaction. Recent resultsobtained with the complexation of variouscalix[n]arenes and five structural typesof organic cations, namely ammonium ions,quaternary ammonium ions, phosphonium ions,iminium ions and tropylium ions are reviewed.The influence of both the guest structure and theshape and flexibility of the hosts on the complexstability in the gas phase and (mainly) in solutionis considered. 相似文献
9.
Yuhui Kou Derong Cao Hongqi Tao Lingyun Wang Jianquan Liang Zhizhao Chen Herbert Meier 《Journal of inclusion phenomena and macrocyclic chemistry》2013,77(1-4):279-289
A detailed study of the reaction conditions revealed that a quantitative cyclocondensation of 1,4-dialkoxy-2,5-bis(alkoxymethyl)-benzenes to pillar[n]arenes can be achieved by catalysis of p-toluenesulfonic acid in CH2Cl2. Major product of this new reaction is in each case a cyclopentamer (n = 5), but small amounts of the pillar[n]arenes with n = 6, 7 and 10 can be obtained as well. Different alkoxy groups in 1- and 4-position lead to regioisomers. All cyclooligomers exist in pillar structures as pair of enantiomers, which show a racemisation at room temperature, which is fast in terms of the NMR time scale. The racemisation process occurs by rotation of the 1,4-phenylene segments in the macrocyclic rings. Pillar[n]arenes exhibit novel host–guest behavior. 相似文献
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Bhattacharya S Nayak SK Chattopadhyay S Banerjee M Mukherjee AK 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2005,61(1-2):321-329
[60]- and [70]fullerenes have been shown to form 1:1 supramolecular complexes with (i) 24,26-dimethoxy-25,27-dihydroxy-5,11,17,23-tetra(4-tert-butyl)calix[4]arene (1) and (ii) 37,39,41-trimethoxy-38,40,42-trihydroxy-5,11,17,23,29,35-hexa(4-tert-butyl)calix[6]arene (2) in CCl(4) medium by absorption spectroscopy. Charge transfer absorption bands of the complexes have been located in each of the cases (except [70]fullerene-2 complex) studied from which the vertical ionisation potential of 1 has been obtained. Formation constants of the complexes have been determined at four different temperatures from which the enthalpies and entropies of formation of the complexes have been obtained. Moreover, the formation constant of [70]fullerene-2 complex is higher than that of the [60]fullerene-1 and [60]fullerene-2 complexes at all the four temperatures studied. This has been accounted in terms of greater cavity size of 2 which is a calix[6]arene compared to 1 which is a calix[4]arene and also by the fact that a high degree of preorganisation takes place in case of 2 through intramolecular H-bonding at its lower rim. 相似文献
12.
Ziqing Xi Zhenshan Yang Xuecheng Zhang He Yuan Wanting Wang Prof. Maoxia He Dr. Ju Xie 《Chemphyschem》2023,24(24):e202300527
Despite the widespread use in industrial production, benzene derivatives are harmful to both human beings and the environment. The control of these substances has become an important subject of scientific research. This study introduces a new approach for adsorption and separation of benzene derivatives utilizing pagoda[n]arene based supramolecular materials. Density functional theory calculations were employed to investigate the molecular recognition mechanism of benzene derivatives by pagoda[4]arenes and pagoda[5]arenes (Pa[4]As and Pa[5]As). Results indicate that Pa[4]As and Pa[5]As can effectively accommodate benzene derivatives through non-covalent interactions, leading to the formation of stable host-guest complexes. Additionally, molecular dynamics simulations revealed that both crystalline and non-crystalline supramolecular aggregates of Pa[4]As and Pa[5]As possess the ability to adsorb benzene derivatives and maintain the stability of the adsorption. Moreover, increasing the temperature causes benzene derivatives to desorb from the adsorbing aggregates, and thus the material can be reutilized. 相似文献
13.
《中国化学快报》2022,33(5):2451-2454
Reported here is the comprehensive investigation on the formation of biphen[n]arenes by tailoring reaction modules. Five new macrocyclic arenes and four oligomers were synthesized by the condensation of monomers possessing different multimethoxyphenyl reaction modules and paraformaldehyde. We proved that the number and sites of methoxy on reaction modules greatly affected the reaction activity, shape, and connection mode of macrocycles. Moreover, the triangular and saddle-shaped configuration of macrocycles were revealed by single crystal structures. The results provided a typical and fundamental guidance in designing new macrocyclic arenes. 相似文献
14.
The CE separation of p-sulfonated calix[n]arenes, where n=4,6 and 8, was investigated. Under positive potential conditions optimum separation was found to be borate buffer modified with sodium dodecyl sulfate. Under these conditions separation was achieved in less than 10 min. The effect on the separation of the addition of divalent cations: Mg(2+), Ca(2+) and Ba(2+) was studied. p-Sulfonatedcalixarenes were detected in the anodic side of the capillary. There was an improvement in the reproducibility and analysis time although efficiency did not improve significantly. 相似文献
15.
Background Pillar[n]arene(PA[n])contains a symmetrical structures,where para-bridge connection between the units looks like a column-like or pillar shape and polygonal structure from side and top views,respectively.The attached groups to the PA[n]are pointing towards the opposite directions along the columnar axis. 相似文献
16.
Coleman AW Jebors S Shahgaldian P Ananchenko GS Ripmeester JA 《Chemical communications (Cambridge, England)》2008,(20):2291-2303
The para-acylcalix[n]arenes possess a very rich capacity to self-assemble into a wide variety of structures and sizes ranging from molecular assemblies through dimeric capsules, molecular sheets to nanoparticles. All these assemblies are capable of taking guest molecules and in the process of this inclusion discrete nanoscopic reaction vessels may be formed for photochemistry. Interestingly this uptake of quite large organic molecules occurs in the bulk in non-porous crystals without loss of crystallinity. At the air-water interface either as Langmuir monolayers or as colloidal suspensions the para-acylcalix[n]arenes show interaction with ionic species. The extension from para-acylcalix[4]arenes to para-acylcalix[8]arenes is in its infancy but already there is much promise for novel assemblies to be found. 相似文献
17.
《Tetrahedron: Asymmetry》1999,10(1):177-182
The synthesis of new chiral calix[n]arenes, related to Corey's phenyl-menthol, is described. Starting from enantiomerically pure (R)-(+)-pulegone, calix[n]arenes with different ring sizes could be obtained in reasonable yield. 相似文献
18.
Jianbin Chao Kailun Song Huijuan Wang Zhiqiang Guo Bingtai Zhang Ting Zhang 《Physics and Chemistry of Liquids》2017,55(5):579-588
The inclusion complexes of norfloxacin (NFX) with p-sulfonatocalix[n]arenes (SCXn) were studied. The characteristics of host–guest (HG) complexation between p-sulfonatocalix[n]arenes with NFX were investigated by fluorescence spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, fourier transform infrared spectroscopy (FT-IR) and differential scanning calorimetry (DSC). Stoichiometry and association constants (K) of the inclusion complexes were determined by the non-linear fitting method. An interesting 1:1 stochiometric of HG complexes were formed at different pH values (pH = 3.00, 6.00, 8.00) The inclusion mode of NFX with p-sulfonatocalix[n]arenes was confirmed by NMR spectroscopy. 相似文献
19.
Marie-Hélène Paclet Cécile F. Rousseau Campion Yannick Françoise Morel Anthony W. Coleman 《Journal of inclusion phenomena and macrocyclic chemistry》2006,55(3-4):353-357
The effects of para-Sulphonato-calix[4]arene, para-Sulphonato-calix[6]arene and para-Sulphonato-calix[8]arene on the activation of NADPH oxidase in neutrophils has been studied. All three molecules do not induce NADPH oxidase activation, and hence do not stimulate neutrophils. Measurement of cell viability demonstrates that these three water-soluble calix[n]arene derivatives are not cytotoxic. 相似文献
20.
H. M. Chawla S. Kumar N. Pant A. Santra K. Sriniwas N. Kumar David StC. Black 《Journal of inclusion phenomena and macrocyclic chemistry》2011,71(1-2):169-178
A series of deep cavity diphenyl imidazolyl calix[n]arenes (4, 6, 8) have been obtained from readily available starting materials through a five step synthetic methodology involving appropriate alkylation of lower rim of preformed calixarene, formylation of the upper rim and subsequent condensation with aryl diketones in the presence of ammonium acetate and glacial acetic acid. Optimized reaction conditions for obtaining the titled derivatives in their cone configuration and their characterization by spectroscopic methods (IR, UV, NMR and FAB mass) have been delineated. The synthesized imidazolyl calixarenes have preliminarily been examined for selective recognition of monovalent metal ions (Li+, Na+, K+, Cs+, Ag+). 相似文献