Polycationic pillar[5]arene derivatives: interaction with DNA and biological applications.

Dendritic pillar[5]arene derivatives have been efficiently prepared by grafting dendrons with peripheral Boc-protected amine subunits onto a preconstructed pillar[5]arene scaffold. Upon cleavage of the Boc-protected groups, water-soluble pillar[5]arene derivatives with 20 (13) and 40 (14) peripheral ammonium groups have been obtained. The capability of these compounds to form stable nanoparticles with plasmid DNA has been demonstrated by gel electrophoresis, transmission electron microscopy (TEM), and dynamic light scattering (DLS) investigations. Transfection efficiencies of the self-assembled 13/pCMV-Luc and 14/pCMV-Luc polyplexes have been evaluated in vitro with HeLa cells. The transfection efficiencies found for both compounds are good, and pillar[5]arenes 13 and 14 show very low toxicity if any.

[1]  A. Caminade,et al.  Positively charged phosphorus dendrimers. An overview of their properties , 2013 .

[2]  Feihe Huang,et al.  Responsive reverse giant vesicles and gel from self-organization of a bolaamphiphilic pillar[5]arene , 2013 .

[3]  Feihe Huang,et al.  A sugar-functionalized amphiphilic pillar[5]arene: synthesis, self-assembly in water, and application in bacterial cell agglutination. , 2013, Journal of the American Chemical Society.

[4]  J. Nierengarten,et al.  Macrocyclic Effects in the Mesomorphic Properties of Liquid‐Crystalline Pillar[5]‐ and Pillar[6]arenes , 2013 .

[5]  A. M. Brouwer,et al.  Förster resonance energy transfer by formation of a mechanically interlocked [2]rotaxane. , 2013, Chemical communications.

[6]  J. Nierengarten,et al.  A mannosylated pillar[5]arene derivative: Chiral information transfer and antiadhesive properties against uropathogenic bacteria , 2013 .

[7]  T. Ogoshi,et al.  Pillararenes: Versatile Synthetic Receptors for Supramolecular Chemistry , 2013 .

[8]  V. Franceschi,et al.  Arginine clustering on calix[4]arene macrocycles for improved cell penetration and DNA delivery , 2013, Nature Communications.

[9]  Zhan-Ting Li,et al.  Chiral selective transmembrane transport of amino acids through artificial channels. , 2013, Journal of the American Chemical Society.

[10]  S. Fujinami,et al.  Clickable di- and tetrafunctionalized pillar[n]arenes (n = 5, 6) by oxidation-reduction of pillar[n]arene units. , 2012, The Journal of organic chemistry.

[11]  Feihe Huang,et al.  Pillar[6]arene/paraquat molecular recognition in water: high binding strength, pH-responsiveness, and application in controllable self-assembly, controlled release, and treatment of paraquat poisoning. , 2012, Journal of the American Chemical Society.

[12]  Feihe Huang,et al.  Novel [2]rotaxanes based on the recognition of pillar[5]arenes to an alkane functionalized with triazole moieties , 2012 .

[13]  Feihe Huang,et al.  Cavity‐Extended Pillar[5]arenes: Syntheses and Host–Guest Complexation with Paraquat and Bispyridinium Derivatives , 2012 .

[14]  Xiaoshi Hu,et al.  Synthesis of a fully functionalized pillar[5]arene by ‘click chemistry’ and its effective binding toward neutral alkanediamines , 2012 .

[15]  Feihe Huang,et al.  A water-soluble pillar[6]arene: synthesis, host-guest chemistry, and its application in dispersion of multiwalled carbon nanotubes in water. , 2012, Journal of the American Chemical Society.

[16]  J. Nierengarten,et al.  Building liquid crystals from the 5-fold symmetrical pillar[5]arene core. , 2012, Chemical communications.

[17]  Feihe Huang,et al.  Preparation of two new [2]rotaxanes based on the pillar[5]arene/alkane recognition motif , 2012 .

[18]  J. L. Jiménez Blanco,et al.  Polycationic amphiphilic cyclodextrins as gene vectors: effect of the macrocyclic ring size on the DNA complexing and delivery properties. , 2012, Organic & biomolecular chemistry.

[19]  S. Kawauchi,et al.  High-yield diastereoselective synthesis of planar chiral [2]- and [3]rotaxanes constructed from per-ethylated pillar[5]arene and pyridinium derivatives. , 2012, Chemistry.

[20]  Jun-Li Hou,et al.  Single-molecular artificial transmembrane water channels. , 2012, Journal of the American Chemical Society.

[21]  Yong Yang,et al.  Pillararenes, a new class of macrocycles for supramolecular chemistry. , 2012, Accounts of chemical research.

[22]  T. Ogoshi,et al.  Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials , 2012, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[23]  T. Ogoshi,et al.  Reversibly tunable lower critical solution temperature utilizing host-guest complexation of pillar[5]arene with triethylene oxide substituents. , 2012, Journal of the American Chemical Society.

[24]  J. F. Stoddart,et al.  A self-complexing and self-assembling pillar[5]arene. , 2012, Chemical communications.

[25]  J. Nierengarten,et al.  The inhibition of liposaccharide heptosyltransferase WaaC with multivalent glycosylated fullerenes: a new mode of glycosyltransferase inhibition. , 2012, Chemistry.

[26]  K. Sharma,et al.  Pillar[5]arenes: fascinating cyclophanes with a bright future. , 2012, Chemical Society reviews.

[27]  Wen Si,et al.  Selective artificial transmembrane channels for protons by formation of water wires. , 2011, Angewandte Chemie.

[28]  Jiuming He,et al.  A cationic water-soluble pillar[5]arene: synthesis and host-guest complexation with sodium 1-octanesulfonate. , 2011, Chemical communications.

[29]  J. F. Stoddart,et al.  Dynamic clicked surfaces based on functionalised pillar[5]arene. , 2011, Chemical communications.

[30]  Y. Yu,et al.  Complexation of 1,4-bis(pyridinium)butanes by negatively charged carboxylatopillar[5]arene. , 2011, The Journal of organic chemistry.

[31]  T. Ogoshi,et al.  "Clickable" pillar[5]arenes. , 2011, Chemical communications.

[32]  Y. Mély,et al.  Virus-sized DNA nanoparticles for gene delivery based on micelles of cationic calixarenes. , 2011, Chemistry.

[33]  M. Nothisen,et al.  Gene delivery with polycationic fullerene hexakis-adducts. , 2011, Chemical communications.

[34]  J. F. Stoddart,et al.  Monofunctionalized pillar[5]arene as a host for alkanediamines. , 2011, Journal of the American Chemical Society.

[35]  A. Imberty,et al.  Synthesis of dodecavalent fullerene-based glycoclusters and evaluation of their binding properties towards a bacterial lectin. , 2011, Chemistry.

[36]  J. Bouckaert,et al.  The functional valency of dodecamannosylated fullerenes with Escherichia coli FimH--towards novel bacterial antiadhesives. , 2011, Chemical communications.

[37]  S. Fujinami,et al.  Facile, rapid, and high-yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure. , 2011, The Journal of organic chemistry.

[38]  Philippe Compain,et al.  Glycosidase inhibition with fullerene iminosugar balls: a dramatic multivalent effect. , 2010, Angewandte Chemie.

[39]  J. M. Benito,et al.  Preorganized, macromolecular, gene-delivery systems. , 2010, Chemistry.

[40]  M. Sánchez‐Navarro,et al.  Fullerene sugar balls. , 2010, Chemical communications.

[41]  J. Nierengarten,et al.  Sequential copper catalyzed alkyne-azide and thiol-ene click reactions for the multiple functionalization of fullerene hexaadducts. , 2010, Chemical communications.

[42]  T. Ogoshi,et al.  Synthesis, conformational and host-guest properties of water-soluble pillar[5]arene. , 2010, Chemical communications.

[43]  T. Ogoshi,et al.  Polypseudorotaxane Constructed from Pillar[5]arene and Viologen Polymer , 2010 .

[44]  Nicolas Guilloteau,et al.  Polycationic amphiphilic cyclodextrins for gene delivery: synthesis and effect of structural modifications on plasmid DNA complex stability, cytotoxicity, and gene expression. , 2009, Chemistry.

[45]  T. Ogoshi,et al.  Through-space pi-delocalized Pillar[5]arene. , 2009, Chemical communications.

[46]  J. Nierengarten,et al.  A click-click approach for the preparation of functionalized [5:1]-hexaadducts of C60. , 2009, Chemistry.

[47]  U. Schubert,et al.  Klick-Chemie jenseits von metallkatalysierten Cycloadditionen , 2009 .

[48]  Richard Hoogenboom,et al.  Click chemistry beyond metal-catalyzed cycloaddition. , 2009, Angewandte Chemie.

[49]  F. Santoyo-González,et al.  Preorganized macromolecular gene delivery systems: amphiphilic beta-cyclodextrin "click clusters". , 2009, Organic & biomolecular chemistry.

[50]  A. Caminade,et al.  Dendrimers and DNA: combinations of two special topologies for nanomaterials and biology. , 2008, Chemistry.

[51]  G. Donofrio,et al.  Macrocyclic nonviral vectors: high cell transfection efficiency and low toxicity in a lower rim guanidinium calix[4]arene. , 2008, Organic letters.

[52]  Konstantina Yannakopoulou,et al.  Synthesis, characterization, and remarkable biological properties of cyclodextrins bearing guanidinoalkylamino and aminoalkylamino groups on their primary side. , 2008, Chemistry.

[53]  Yoshiaki Nakamoto,et al.  para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property. , 2008, Journal of the American Chemical Society.

[54]  Sathya Srinivasachari,et al.  Polycationic beta-cyclodextrin "click clusters": monodisperse and versatile scaffolds for nucleic acid delivery. , 2008, Journal of the American Chemical Society.

[55]  S. E. Matthews,et al.  Efficient gene transfection with functionalised multicalixarenes. , 2007, Chemical communications.

[56]  F. Diederich,et al.  Dendritic vectors for gene transfection , 2007 .

[57]  C. Rivetti,et al.  DNA condensation and cell transfection properties of guanidinium calixarenes: dependence on macrocycle lipophilicity, size, and conformation. , 2006, Journal of the American Chemical Society.

[58]  H. Okayama,et al.  Gene delivery by aminofullerenes: structural requirements for efficient transfection. , 2006, Chemistry, an Asian journal.

[59]  R. Darcy,et al.  Cell transfection with polycationic cyclodextrin vectors. , 2004, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[60]  K. Sharpless,et al.  Click-Chemie: diverse chemische Funktionalität mit einer Handvoll guter Reaktionen , 2001 .

[61]  Arwin J. Brouwer,et al.  Convergent Synthesis and Diversity of Amino Acid Based Dendrimers , 2001 .

[62]  G. Levi,et al.  Size, diffusibility and transfection performance of linear PEI/DNA complexes in the mouse central nervous system , 1998, Gene Therapy.

[63]  P. Cullis,et al.  Nomenclature for synthetic gene delivery systems. , 1997, Human gene therapy.

[64]  H. Shim,et al.  Synthesis and characterization of poly(2,5-dipropargyloxy-1,4-phenylenevinylene) and its copolymers with 1,4-phenylenevinylene , 1996 .

[65]  C. Hawker,et al.  Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules , 1990 .

[66]  Yanli Zhao,et al.  Thermo-responsive fluorescent vesicles assembled by fluorescein-functionalized pillar[5]arene , 2013 .

[67]  R. Darcy,et al.  Cationic cyclodextrin amphiphiles as gene delivery vectors , 2004 .

[68]  C. Hawker,et al.  A new convergent approach to monodisperse dendritic macromolecules , 1990 .