calixarenes

Summary

Summary: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.

Top Publications

  1. Sansone F, Dudic M, Donofrio G, Rivetti C, Baldini L, Casnati A, et al. DNA condensation and cell transfection properties of guanidinium calixarenes: dependence on macrocycle lipophilicity, size, and conformation. J Am Chem Soc. 2006;128:14528-36 pubmed
    ..Furthermore, hexyl and octyl chains confer to these calixarenes cell transfection capabilities...
  2. Shahgaldian P, Quattrocchi L, Gualbert J, Coleman A, Goreloff P. AFM imaging of calixarene based solid lipid nanoparticles in gel matrices. Eur J Pharm Biopharm. 2003;55:107-13 pubmed
    ..2020, hyaluronic acid and xanthan containing dispersions of solid lipid nanoparticles (SLNs) of amphiphilic calixarenes. Imaging shows that the SLNs are dispersed within the gels as discrete particles of 150nm in diameter and show ..
  3. Shahgaldian P, Gualbert J, Aïssa K, Coleman A. A study of the freeze-drying conditions of calixarene based solid lipid nanoparticles. Eur J Pharm Biopharm. 2003;55:181-4 pubmed
    ..All carbohydrates tested showed excellent cryoprotection and redispersion properties with the calixarene based SLNs. ..
  4. Gualbert J, Shahgaldian P, Coleman A. Interactions of amphiphilic calix[4]arene-based Solid Lipid Nanoparticles with bovine serum albumin. Int J Pharm. 2003;257:69-73 pubmed
    ..The carrier systems have shown the ability to interact with bovine serum albumin (BSA), which forms a capping layer up to 17nm in depth. AFM imaging revealed that the SLNs are protected by this layer against flattening on surfaces. ..
  5. Baldini L, Casnati A, Sansone F, Ungaro R. Calixarene-based multivalent ligands. Chem Soc Rev. 2007;36:254-66 pubmed
    ..The phenol-formaldehyde cyclic oligomers, called calixarenes, have been used as scaffolds for the synthesis of multivalent ligands thanks to the fact that they have a ..
  6. Hu W, Blecking C, Kralj M, Suman L, Piantanida I, Schrader T. Dimeric calixarenes: a new family of major-groove binders. Chemistry. 2012;18:3589-97 pubmed publisher
    ..The orientation of the ligands can be deduced from NMR titrations and is reproduced in Monte-Carlo simulations on 1:1 complexes in water. ..
  7. Rodik R, Klymchenko A, Jain N, Miroshnichenko S, Richert L, Kalchenko V, et al. Virus-sized DNA nanoparticles for gene delivery based on micelles of cationic calixarenes. Chemistry. 2011;17:5526-38 pubmed publisher
    ..In the present work, we synthesized new amphiphilic calixarenes bearing cationic groups at the upper rim and alkyl chains at the lower rim...
  8. Jebors S, Leydier A, Wu Q, Bertino Ghera B, Malbouyre M, Coleman A. Solid lipid nanoparticles (SLNs) derived from para-acyl-calix[9]-arene: preparation and stability. J Microencapsul. 2010;27:561-71 pubmed publisher
    ..Encapsulation was shown using acridine as a fluorescent probe. ..
  9. Peters M, Li M, Schrader T. Interactions of calix[n]arenes with nucleic acids. Nat Prod Commun. 2012;7:409-17 pubmed
    ..b>Calixarenes have not received so much attention, although they consist of a compact aromatic core tuneable in size, and ..

More Information

Publications62

  1. Ananchenko G, Udachin K, Ripmeester J, Perrier T, Coleman A. Phototransformation of stilbene in van der Waals nanocapsules. Chemistry. 2006;12:2441-7 pubmed
  2. Perret F, Nishihara M, Takeuchi T, Futaki S, Lazar A, Coleman A, et al. Anionic fullerenes, calixarenes, coronenes, and pyrenes as activators of oligo/polyarginines in model membranes and live cells. J Am Chem Soc. 2005;127:1114-5 pubmed
    ..Applied to HeLa cells, pyrenebutyrate is shown to significantly increase the uptake of a fluorescently labeled octaarginine in a concentration-dependent manner. ..
  3. Korbakov N, Timmerman P, Lidich N, Urbach B, Sa ar A, Yitzchaik S. Acetylcholine detection at micromolar concentrations with the use of an artificial receptor-based fluorescence switch. Langmuir. 2008;24:2580-7 pubmed publisher
    ..The unique [Cn.D] complex optical switching paves the way for application in ACh imaging and optoelectronic sensing. ..
  4. Shahgaldian P, Sciotti M, Pieles U. Amino-substituted amphiphilic calixarenes: self-assembly and interactions with DNA. Langmuir. 2008;24:8522-6 pubmed publisher
    ..2 mV. The interaction of these SLNs with double-stranded DNA is demonstrated. ..
  5. Bagnacani V, Sansone F, Donofrio G, Baldini L, Casnati A, Ungaro R. Macrocyclic nonviral vectors: high cell transfection efficiency and low toxicity in a lower rim guanidinium calix[4]arene. Org Lett. 2008;10:3953-6 pubmed publisher
    ..New multivalent cationic lipids, one of them showing high efficiency and low toxicity in cell transfection, have been obtained by attaching guanidinium groups at the lower rim of calix[4]arenes. ..
  6. Jebors S, Fache F, Balme S, Devoge F, Monachino M, Cecillon S, et al. Designer amphiphiles based on para-acyl-calix[8]arenes. Org Biomol Chem. 2008;6:319-29 pubmed publisher
    ..The anionic derivatives O-4-sulfonatobutoxy-para-ocatanoylcalix[8]arene and O-carboxymethoxy-para-ocatanoylcalix[8]arene have been shown to possess anticoagulant properties but to have no haemolytic toxicity. ..
  7. Shahgaldian P, Da Silva E, Coleman A, Rather B, Zaworotko M. Para-acyl-calix-arene based solid lipid nanoparticles (SLNs): a detailed study of preparation and stability parameters. Int J Pharm. 2003;253:23-38 pubmed
    ..1H NMR, X-ray powder diffraction (XPD) and AFM have also been carried out on the calix-arene based SLNs and demonstrate the presence of a semi-organised matrix structure for the SLNs. ..
  8. Li N, English C, Eaton A, Gillespie A, Ence T, Christensen T, et al. Cation separation and preconcentration using columns containing cyclen and cyclen-resorcinarene derivatives. J Chromatogr A. 2012;1245:83-9 pubmed publisher
    ..A retention mechanism is proposed for the latter system in which the protonated cyclen units attract negatively charged HC?O?? ions that cooperate with cyclen sites in retaining transition metal ions. ..
  9. Cecioni S, Lalor R, Blanchard B, Praly J, Imberty A, Matthews S, et al. Achieving high affinity towards a bacterial lectin through multivalent topological isomers of calix[4]arene glycoconjugates. Chemistry. 2009;15:13232-40 pubmed publisher
    ..Surface plasmon resonance (SPR) experiments confirmed that this glycoconjugate is the strongest inhibitor for binding of PA-IL to galactosylated surfaces for potential applications as an anti-adhesive agent. ..
  10. Mehta V, Athar M, Jha P, Panchal M, Modi K, Jain V. Efficiently functionalized oxacalix[4]arenes: Synthesis, characterization and exploration of their biological profile as novel HDAC inhibitors. Bioorg Med Chem Lett. 2016;26:1005-1010 pubmed publisher
    ..The compounds were theoretically evaluated by docking studies as potential histone deacetylase inhibitors (HDACi). The study indicates that compounds bound adequately with HDAC, and hence complemented the experimental findings. ..
  11. Korchowiec B, Gorczyca M, Rogalska E, Regnouf de Vains J, Mourer M, Korchowiec J. The selective interactions of cationic tetra-p-guanidinoethylcalix[4]arene with lipid membranes: theoretical and experimental model studies. Soft Matter. 2016;12:181-90 pubmed publisher
    ..The latter effect, which is possible due to a flip-flop inversion of the CX1 orientation in the lipid layer compared to the aqueous phase, may be responsible for its antibacterial activity. ..
  12. Ansari S, Mohapatra P, Iqbal M, Huskens J, Verboom W. Two novel extraction chromatography resins containing multiple diglycolamide-functionalized ligands: preparation, characterization and actinide uptake properties. J Chromatogr A. 2014;1334:79-86 pubmed publisher
    ..Column studies on breakthrough indicated 0.76 and 0.37mg/g as the breakthrough capacities of the T-DGA and the C4DGA resins, respectively. It was possible to quantitatively elute the loaded metal ion using EDTA solutions. ..
  13. Rezayi M, Alias Y, Abdi M, Saeedfar K, Saadati N. Conductance studies on complex formation between c-methylcalix[4]resorcinarene and titanium (III) in acetonitrile-H?O binary solutions. Molecules. 2013;18:12041-50 pubmed publisher
  14. Sokkalingam P, Hong S, Aydogan A, Sessler J, Lee C. Decoration of gold nanoparticles by a double-armed calix[4]pyrrole: a receptor-decorated nanoensemble for anion sensing and extraction. Chemistry. 2013;19:5860-7 pubmed publisher
    ..Control experiments revealed that this extraction is not possible when using the analogous monomeric receptor. ..
  15. Geller C, Fontanay S, Mourer M, Dibama H, Regnouf de Vains J, Finance C, et al. Antiseptic properties of two calix[4]arenes derivatives on the human coronavirus 229E. Antiviral Res. 2010;88:343-6 pubmed publisher
    ..Comparing these results with some obtained previously with chlorhexidine and hexamidine, (i) these two calixarenes did not show any cytotoxicity contrary to chlorhexidine and hexamidine, (ii) C[4]S showed as did hexamidine, a ..
  16. Mourer M, Psychogios N, Laumond G, Aubertin A, Regnouf de Vains J. Synthesis and anti-HIV evaluation of water-soluble calixarene-based bithiazolyl podands. Bioorg Med Chem. 2010;18:36-45 pubmed publisher
    ..Most of the compounds have an antiviral activity in a 10-50 microM range, and one of them, sulfonylated, displays its activity, whatever the tropism of the virus, at a micromolar concentration. ..
  17. Jung S, van Paauwe J, Boyd P, Shin S. Noncovalent endo-binding of fullerenes to diprotonated bisporphyrins. Phys Chem Chem Phys. 2011;13:20248-54 pubmed publisher
    ..The side-on binding of C(70) is favored over the end-on binding because the former exerts less steric strain to the lower rim of calixarene. ..
  18. Halder A, Bhatt S, Nayak S, Chattopadhyay S, Bhattacharya S. UV-Vis, fluorescence and NMR spectroscopic investigations on inclusion properties of a designed tetrahomocalix[8]arene with fullerenes C60 and C70 in solution. Spectrochim Acta A Mol Biomol Spectrosc. 2011;84:25-31 pubmed publisher
    ..18. (1)H NMR analysis provides very good support in favor of strong binding between C(60) and 1. The high value of K value for C(60)-1 complex indicates that 1 forms an inclusion complex with C(60). ..
  19. Thiampanya P, Muangsin N, Pulpoka B. Azocalix[4]arene strapped calix[4]pyrrole: a confirmable fluoride sensor. Org Lett. 2012;14:4050-3 pubmed publisher
    ..However, from these ions the highly specific sensing of F(-) is achieved by the addition of Ca(2+) which leads to a color change from light sky blue (of 1·F(-)) back to the original light orange color of 1. ..
  20. Zvereva E, Katsyuba S, Vandyukov A, Chernova A, Kovalenko V, Solovieva S, et al. IR and NMR spectra, intramolecular hydrogen bonding and conformations of para-tert-butyl-aminothiacalix[4]arene in solid state and chloroform solution. Spectrochim Acta A Mol Biomol Spectrosc. 2010;75:872-9 pubmed publisher
  21. Trush V, Cherenok S, Tanchuk V, Kukhar V, Kalchenko V, Vovk A. Calix[4]arene methylenebisphosphonic acids as inhibitors of protein tyrosine phosphatase 1B. Bioorg Med Chem Lett. 2013;23:5619-23 pubmed publisher
    ..Based on molecular docking results, the binding modes of the macrocyclic bisphosphonates in the active centre of PTP1B are discussed. ..
  22. Wang Y, Ping G, Li C. Efficient complexation between pillar[5]arenes and neutral guests: from host-guest chemistry to functional materials. Chem Commun (Camb). 2016;52:9858-72 pubmed publisher
    ..P5As) towards neutral guests in organic media, which is unfeasible for classic crown ethers and calixarenes. The intriguing properties have found extensive applications in many fields from supramolecular chemistry to ..
  23. Palmeira T, Miranda A, Marcos P, Berberan Santos M. Calixarenes as High Temperature Matrices for Thermally Activated Delayed Fluorescence: C70 in Dihomooxacalix[4]arene. Molecules. 2018;23: pubmed publisher
    ..b>Calixarenes are proposed to be suitable matrices for high temperature TADF studies and applications.
  24. Zheng X, Wang X, Shen K, Wang N, Peng Y. Molecular design of a "molecular syringe" mimic for metal cations using a 1,3-alternate calix[4]arene cavity. J Comput Chem. 2010;31:2143-56 pubmed publisher
    ..It is believed that this prototype of a "molecular syringe" is a novel molecular architecture for the action of metal cations. ..
  25. Spagnul A, Bouvier Capely C, Adam M, Phan G, Rebière F, Fattal E. Quick and efficient extraction of uranium from a contaminated solution by a calixarene nanoemulsion. Int J Pharm. 2010;398:179-84 pubmed publisher
    ..The obtained results reveal that the calixarene nanoemulsion could represent a promising system for the emergency treatment of uranium cutaneous contamination. ..
  26. Khutia A, Sanz Miguel P, Lippert B. Isomerism with metallacalix[4]arenes of the nonsymmetrical pyrimidine nucleobase cytosine: how connectivity and rotamer state determine the topology of multinuclear derivatives. Inorg Chem. 2010;49:7635-7 pubmed publisher
  27. Sharma N, Ojha H, Pathak D, Goel R, Sharma R. Ex-vivo complexation, skin permeation, interaction and cytodermal toxicity studies of p-tertbutylcalix[4]arene nanoemulsion for radiation decontamination. Life Sci. 2017;168:65-76 pubmed publisher
    ..Taken together, data indicate that p-tertbutylcalix[4]arene nanoemulsion is both effective and safe formulation to use on skin for radio-decontamination. ..
  28. Mareeswaran P, Babu E, Rajagopal S. Optical recognition of anions by ruthenium(II)-bipyridine-calix[4]arene system. J Fluoresc. 2013;23:997-1006 pubmed publisher
    ..The excited state lifetime and transient absorption studies were carried out the AcO(-) facilitates non radiative pathway. The other anions stabilize the excited state and facilitate the radiative pathway. ..
  29. Acharya A, Ramanujam B, Chinta J, Rao C. 1,3-Diamido-calix[4]arene conjugates of amino acids: recognition of -COOH side chain present in amino acids, peptides, and proteins by experimental and computational studies. J Org Chem. 2011;76:127-37 pubmed publisher
  30. Xue M, Chen C. Aromatic single-walled organic nanotubes self-assembled from NH-bridged azacalix[2]triptycene[2]pyridine. Chem Commun (Camb). 2011;47:2318-20 pubmed publisher
    ..A novel triptycene-derived NH-bridged azacalixarene can self-assemble into an aromatic single-walled organic nanotube with large dimensions by four one-dimensional hydrogen bond chains. ..
  31. Viola S, Merlo S, Consoli G, Drago F, Geraci C, Sortino M. Modulation of C6 Glioma Cell Proliferation by Ureido-Calix[8]arenes. Pharmacology. 2010;86:182-8 pubmed publisher
    b>Calixarenes are synthetic macrocyclic compounds that may serve as scaffolds for biologically active molecules and have been proposed as potential anticancer agents...
  32. Torvinen M, Kalenius E, Sansone F, Casnati A, Jänis J. Noncovalent complexation of glucosylthioureidocalix[4]arenes with carboxylates and their gas-phase characteristics: an ESI-FTICR mass spectrometric study. J Mass Spectrom. 2011;46:787-93 pubmed publisher
    ..dissociation and gas-phase H/D-exchange experiments were performed to obtain information on selectivity of calixarenes towards carboxylates and characteristics of their complexes...
  33. Basilio N, Piñeiro A, Da Silva J, Garcia Rio L. Cooperative assembly of discrete stacked aggregates driven by supramolecular host-guest complexation. J Org Chem. 2013;78:9113-9 pubmed publisher
    ..Moreover, the development of a quantitative analytical model enables the possibility of using this type of system for water-soluble sensing assays, as is also exemplified in the present work. ..
  34. Shu C, Sidhu K, Zhang L, Wang X, Krishnamurthy D, Senanayake C. Palladium-catalyzed cross-coupling of cyclopropylmagnesium bromide with aryl bromides mediated by zinc halide additives. J Org Chem. 2010;75:6677-80 pubmed publisher
    ..The cross-coupling of other alkyl, cycloalkyl, and aryl Grignard reagents with aryl bromides under the same conditions gives the corresponding substituted arenes in good yields. ..
  35. Menon S, Modi N, Patel B, Patel M. Azo calix[4]arene based neodymium(III)-selective PVC membrane sensor. Talanta. 2011;83:1329-34 pubmed publisher
    ..Concerning its applications, it was effectively employed for the determination of neodymium ions in industrial waste water as well as in lake water. ..
  36. Yang L, Ran X, Cai L, Li Y, Zhao H, Li C. Calix[8]arene functionalized single-walled carbon nanohorns for dual-signalling electrochemical sensing of aconitine based on competitive host-guest recognition. Biosens Bioelectron. 2016;83:347-52 pubmed publisher
    ..This dual-signalling sensor can provide more sensitive target recognition and will have important applications in the sensitive and selective electrochemical detection of aconitine. ..
  37. Park Y, Park J, Paek K. Versatile self-assembled molecular capsule formation of a resorcin[4]arene-based benzamidoiminocavitand. Chem Commun (Camb). 2013;49:6316-8 pubmed publisher
    ..Benzamido-iminocavitand efficiently self-assembled into thermally inert molecular capsules in the presence of suitable guests via the eight intermolecular N-H···O=C hydrogen bonds. ..
  38. Mochizuki S, Nishina K, Fujii S, Sakurai K. The transfection efficiency of calix[4]arene-based lipids: the role of the alkyl chain length. Biomater Sci. 2015;3:317-22 pubmed publisher
    ..Thus, the alkyl chain length of cationic lipids is related to their interaction with the endosomal compartment and can provide a basis for the design of novel transfection reagents. ..
  39. Alberto M, Mazzone G, Russo N, Sicilia E. The mutual influence of non-covalent interactions in pi-electron deficient cavities: the case of anion recognition by tetraoxacalix[2]arene[2]triazine. Chem Commun (Camb). 2010;46:5894-6 pubmed publisher
    ..Results show that their combination leads to a cooperativity effect. ..
  40. James E, Eggers P, Harvey A, Dunlop S, Fitzgerald M, Stubbs K, et al. Antioxidant phospholipid calix[4]arene mimics as micellular delivery systems. Org Biomol Chem. 2013;11:6108-12 pubmed publisher
    ..The calix[4]arenes appear to be potent synthetic antioxidants that could be used as nano-carriers for drug delivery. ..
  41. Gaeta C, Talotta C, Mirra S, Margarucci L, Casapullo A, Neri P. Catenation of calixarene annulus. Org Lett. 2013;15:116-9 pubmed publisher
    Through-the-annulus-catenated calixarenes have been obtained, for the first time, by exploiting the "superweak anion" approach that allows the threading of the calix cavity with functionalized dialkylammonium axles...
  42. Colasson B, Le Poul N, Le Mest Y, Reinaud O. Tris(triazolyl) calix[6]arene-based zinc and copper funnel complexes: imidazole-like or pyridine-like? A comparative study. Inorg Chem. 2011;50:10985-93 pubmed publisher
    ..The ease of preparation and the versatility of 1,4-disubstituted-1,2,3-triazoles with tunable steric and electronic properties make them promising candidates for further applications from biology to materials. ..
  43. Martin A, Boulos R, Stubbs K, Raston C. Phosphonated calix[4]arene-based amphiphiles as scaffolds for fluorescent nano-fibres. Chem Commun (Camb). 2011;47:7329-31 pubmed publisher
    ..Molecular simulations support a micelle-like arrangement of calixarenes with the alkyl chains directed inwards, and they form a composite material with a fluorescent molecule.
  44. Zhao W, Hu K, Wang C, Liang S, Niu B, He L, et al. New oxo-bridged calix[2]arene[2]triazine stationary phase for high performance liquid chromatography. J Chromatogr A. 2012;1223:72-8 pubmed publisher
    ..The OCATS column was successfully employed for the analysis of melamine in infant formula. ..
  45. Chui J, Fyles T. Ionic conductance of synthetic channels: analysis, lessons, and recommendations. Chem Soc Rev. 2012;41:148-75 pubmed publisher
  46. Qazi M, Ocak U, Ocak M, Memon S, Solangi I. Bifunctional calix[4]arene sensor for Pb(II) and Cr2O7(2-) ions. J Fluoresc. 2013;23:575-90 pubmed publisher
    ..The complexation phenomenon has been confirmed by FTIR spectroscopy that favors the selective nature of HCC4 with Pb(II) and Cr2O7(2-). Thermal gravimetric analysis (TGA) also supports its utility in drastic conditions. ..
  47. Mummidivarapu V, Nehra A, Hinge V, Rao C. Triazole linked picolylimine conjugate of calix[6]arene as a sequential sensor for La3+ followed by F-. Org Lett. 2012;14:2968-71 pubmed publisher
    ..The in situ complex of L with La(3+) recognizes F(-) via fluorescence quenching. The reversible response of sensing La(3+) and F(-) sequentially by L has been demonstrated. ..
  48. Talotta C, Gaeta C, Pierro T, Neri P. Sequence stereoisomerism in calixarene-based pseudo[3]rotaxanes. Org Lett. 2011;13:2098-101 pubmed publisher
    ..These stereoisomeric pseudo[3]rotaxanes can be considered as a minimal "informational system" because the "written information" on the thread is transferred to a specific sequence stereoisomer. ..
  49. Hu K, Zhao W, Wen F, Liu J, Zhao X, Xu Z, et al. Investigation on the preparation and chromatographic behavior of a new para-tert-butylcalix[4]arene-1,2-crown-4 stationary phase for high performance liquid chromatography. Talanta. 2011;85:317-24 pubmed publisher
    ..The CBS4-4 column has been successfully employed for the analysis of benzoic acid in Sprite drink. ..
  50. Schneider C, Menyes U, Jira T. Characterization of calixarene-bonded stationary phases. J Sep Sci. 2010;33:2930-42 pubmed publisher
    ..interaction shows differences since adsorption and partition interactions on or in a bonded layer of calixarenes are not similar to those of alkyl-bonded layers...
  51. Sestito S, Facchini F, Morbioli I, Billod J, Martin Santamaria S, Casnati A, et al. Amphiphilic Guanidinocalixarenes Inhibit Lipopolysaccharide (LPS)- and Lectin-Stimulated Toll-like Receptor 4 (TLR4) Signaling. J Med Chem. 2017;60:4882-4892 pubmed publisher
    ..Some of these calixarenes were active in inhibiting, in a dose-dependent way, the LPS-stimulated TLR4 activation and TLR4-dependent ..
  52. Boudebbouze S, Coleman A, Tauran Y, Mkaouar H, Perret F, Garnier A, et al. Discriminatory antibacterial effects of calix[n]arene capped silver nanoparticles with regard to gram positive and gram negative bacteria. Chem Commun (Camb). 2013;49:7150-2 pubmed publisher
    ..The calix[6]arene derivative with only O-alkyl sulphonate groups shows bactericidal activity. ..
  53. Miao F, Zhou J, Tian D, Li H. Enantioselective recognition of mandelic acid with (R)-1,1-bi-2-naphthol-linked calix[4]arene via fluorescence and dynamic light scattering. Org Lett. 2012;14:3572-5 pubmed publisher
    ..Using this dynamic light-scattering technique, the detection sensitivity was improved almost 100-fold, with a detection limit of 2.0 × 10(-7) M, compared with fluorescent methods. ..