Schaeffer Evelyne, Sánchez-Fernández Elena M, Gonçalves-Pereira Rita, Flacher Vincent, Lamon Delphine, Duval Monique, Fauny Jean-Daniel, Fernández José M García, Mueller Christopher G, Mellet Carmen Ortiz
In: European Journal of Medicinal Chemistry, vol. 169, pp. 111–120, 2019, ISSN: 1768-3254.
Abstract | Links | BibTeX | Tags: Activation, Acute Disease, Animals, antagonists & inhibitors, CD14, Cells, chemical synthesis, Chemistry, CO-RECEPTOR, Cultured, Dendritic cell, Dendritic Cells, Dose-Response Relationship, Drug, drug effects, drug therapy, Glycolipid, Glycolipids, Human, Humans, Iminosugar, immunopathology, IN VITRO, In vivo, Inbred C57BL, inflammation, Interleukin-6, lipopolysaccharide, Lipopolysaccharides, LPS, Male, Maturation, metabolism, Mice, MICROGLIA, Molecular Structure, mouse, pathology, Pharmacology, PRODUCTION, Receptor, signaling, Structure-Activity Relationship, Sulfone, Sulfoxide, Tail, target, Team-Mueller
@article{schaeffer_sp2-iminosugar_2019,
title = {sp2-Iminosugar glycolipids as inhibitors of lipopolysaccharide-mediated human dendritic cell activation in vitro and of acute inflammation in mice in vivo},
author = {Evelyne Schaeffer and Elena M Sánchez-Fernández and Rita Gonçalves-Pereira and Vincent Flacher and Delphine Lamon and Monique Duval and Jean-Daniel Fauny and José M García Fernández and Christopher G Mueller and Carmen Ortiz Mellet},
doi = {10.1016/j.ejmech.2019.02.078},
issn = {1768-3254},
year = {2019},
date = {2019-05-01},
journal = {European Journal of Medicinal Chemistry},
volume = {169},
pages = {111--120},
abstract = {Glycolipid mimetics consisting of a bicyclic polyhydroxypiperidine-cyclic carbamate core and a pseudoanomeric hydrophobic tail, termed sp2-iminosugar glycolipids (sp2-IGLs), target microglia during neuroinflammatory processes. Here we have synthesized and investigated new variants of sp2-IGLs for their ability to suppress the activation of human monocyte-derived dendritic cells (DCs) by lipopolysaccharide (LPS) signaling through Toll-like receptor 4. We report that the best lead was (1R)-1-dodecylsulfonyl-5N,6O-oxomethylidenenojirimycin (DSO2-ONJ), able to inhibit LPS-induced TNFα production and maturation of DCs. Immunovisualization experiments, using a mannoside glycolipid conjugate (MGC) that also suppress LPS-mediated DC activation as control, evidenced a distinct mode of action for the sp2-IGLs: unlike MGCs, DSO2-ONJ did not elicit internalization of the LPS co-receptor CD14 or induce its co-localization with the Toll-like receptor 4. In a mouse model of LPS-induced acute inflammation, DSO2-ONJ demonstrated anti-inflammatory activity by inhibiting the production of the pro-inflammatory interleukin-6. The ensemble of the data highlights sp2-IGLs as a promising new class of molecules against inflammation by interfering in Toll-like receptor intracellular signaling.},
keywords = {Activation, Acute Disease, Animals, antagonists & inhibitors, CD14, Cells, chemical synthesis, Chemistry, CO-RECEPTOR, Cultured, Dendritic cell, Dendritic Cells, Dose-Response Relationship, Drug, drug effects, drug therapy, Glycolipid, Glycolipids, Human, Humans, Iminosugar, immunopathology, IN VITRO, In vivo, Inbred C57BL, inflammation, Interleukin-6, lipopolysaccharide, Lipopolysaccharides, LPS, Male, Maturation, metabolism, Mice, MICROGLIA, Molecular Structure, mouse, pathology, Pharmacology, PRODUCTION, Receptor, signaling, Structure-Activity Relationship, Sulfone, Sulfoxide, Tail, target, Team-Mueller},
pubstate = {published},
tppubtype = {article}
}
Chypre Mélanie, Madel Maria-Bernadette, Chaloin Olivier, Blin-Wakkach Claudine, Morice Christophe, Mueller Christopher G
Porphyrin Derivatives Inhibit the Interaction between Receptor Activator of NF-κB and Its Ligand Journal Article
In: ChemMedChem, vol. 12, no. 20, pp. 1697–1702, 2017, ISSN: 1860-7187.
Abstract | Links | BibTeX | Tags: Animals, Cell Survival, cell-based assays, ELISA, Humans, Jurkat Cells, Mice, Molecular Structure, Osteoclasts, Osteogenesis, porphyrins, Protein Binding, RANK ligand, receptor activator of NF-κB, Receptor Activator of Nuclear Factor-kappa B, Structure-Activity Relationship, Team-Mueller
@article{chypre_porphyrin_2017,
title = {Porphyrin Derivatives Inhibit the Interaction between Receptor Activator of NF-κB and Its Ligand},
author = {Mélanie Chypre and Maria-Bernadette Madel and Olivier Chaloin and Claudine Blin-Wakkach and Christophe Morice and Christopher G Mueller},
doi = {10.1002/cmdc.201700462},
issn = {1860-7187},
year = {2017},
date = {2017-10-01},
journal = {ChemMedChem},
volume = {12},
number = {20},
pages = {1697--1702},
abstract = {Receptor activator of NF-κB (RANK), a member of the TNF-receptor superfamily, plays an important role in bone resorption and stimulates immune and epithelial cell activation. Denosumab, a human monoclonal antibody that blocks the RANK ligand (RANKL), is approved for the treatment of osteoporosis and bone metastasis. However, a small molecule that inhibits the RANK-RANKL interaction would be beneficial to decrease cost and to facilitate treatments with orally available therapeutic agents. Herein we report the discovery of the first nonpeptidic inhibitors of RANK-RANKL interactions. In screening a chemical library by competitive ELISA, the porphyrin verteporfin was identified as a hit. Derivatives were screened, and the chlorin-macrocycle-containing pheophorbide A and purpurin 18 were found to bind recombinant RANKL, to inhibit RANK-RANKL interactions in the ELISA, and to suppress the RANKL-dependent activation of model cells and the differentiation of RANK-expressing precursors into osteoclasts. This discovery of a family of small molecules that inhibit RANK activation presents an initial basis for further development of nonpeptidic therapeutic agents targeting the interaction between RANK and RANKL.},
keywords = {Animals, Cell Survival, cell-based assays, ELISA, Humans, Jurkat Cells, Mice, Molecular Structure, Osteoclasts, Osteogenesis, porphyrins, Protein Binding, RANK ligand, receptor activator of NF-κB, Receptor Activator of Nuclear Factor-kappa B, Structure-Activity Relationship, Team-Mueller},
pubstate = {published},
tppubtype = {article}
}
Schaeffer Evelyne, Dehuyser Laure, Sigwalt David, Flacher Vincent, Bernacchi Serena, Chaloin Olivier, Remy Jean-Serge, Mueller Christopher G, Baati Rachid, Wagner Alain
Dynamic micelles of mannoside glycolipids are more efficient than polymers for inhibiting HIV-1 trans-infection Journal Article
In: Bioconjugate Chemistry, vol. 24, no. 11, pp. 1813–1823, 2013, ISSN: 1520-4812.
Abstract | Links | BibTeX | Tags: Anti-HIV Agents, Calcium, Cells, Chemistry, Cultured, Dendritic Cells, Dose-Response Relationship, Drug, Electron, fluorescence, Glycolipids, HIV, HIV Infections, HIV-1, Human, Humans, immunodeficiency, immunopathology, inhibition, LECTIN, Lectins, lipid, Mannosides, Micelles, Microbial Sensitivity Tests, Microscopy, Models, Molecular, Molecular Structure, Polymers, prophylaxis, Spectrometry, Structure-Activity Relationship, Surface Plasmon Resonance, target, Team-Mueller, Thermodynamics, Transmission, virus
@article{schaeffer_dynamic_2013,
title = {Dynamic micelles of mannoside glycolipids are more efficient than polymers for inhibiting HIV-1 trans-infection},
author = {Evelyne Schaeffer and Laure Dehuyser and David Sigwalt and Vincent Flacher and Serena Bernacchi and Olivier Chaloin and Jean-Serge Remy and Christopher G Mueller and Rachid Baati and Alain Wagner},
doi = {10.1021/bc4000806},
issn = {1520-4812},
year = {2013},
date = {2013-11-01},
journal = {Bioconjugate Chemistry},
volume = {24},
number = {11},
pages = {1813--1823},
abstract = {Mannoside glycolipid conjugates are able to inhibit human immunodeficiency virus type 1 (HIV-1) trans-infection mediated by human dendritic cells (DCs). The conjugates are formed by three building blocks: a linear or branched mannose head, a hydrophilic linker, and a 24-carbon lipid chain. We have shown that, even as single molecules, these compounds efficiently target mannose-binding lectins, such as DC-specific ICAM-3-grabbing nonintegrin (DC-SIGN) important for HIV-1 transmission. With the goal to optimize their inhibitory activity by supramolecular structure formation, we have compared saturated and unsaturated conjugates, as single molecules, self-assemblies of dynamic micelles, and photopolymerized cross-linked polymers. Surface plasmon resonance showed that, unexpectedly, polymers of trivalent conjugates did not display a higher binding affinity for DC-SIGN than single molecules. Interactions on a chip or in solution were independent of calcium; however, binding to DCs was inhibited by a calcium chelator. Moreover, HIV-1 trans-infection was mostly inhibited by dynamic micelles and not by rigid polymers. The inhibition data revealed a clear correlation between the structure and molecular assembly of a conjugate and its biological antiviral activity. We present an interaction model between DC-SIGN and conjugates-either single molecules, micelles, or polymers-that highlights that the most effective interactions by dynamic micelles involve both mannose heads and lipid chains. Our data reveal that trivalent glycolipid conjugates display the highest microbicide potential for HIV prophylaxis, as dynamic micelles conjugates and not as rigid polymers.},
keywords = {Anti-HIV Agents, Calcium, Cells, Chemistry, Cultured, Dendritic Cells, Dose-Response Relationship, Drug, Electron, fluorescence, Glycolipids, HIV, HIV Infections, HIV-1, Human, Humans, immunodeficiency, immunopathology, inhibition, LECTIN, Lectins, lipid, Mannosides, Micelles, Microbial Sensitivity Tests, Microscopy, Models, Molecular, Molecular Structure, Polymers, prophylaxis, Spectrometry, Structure-Activity Relationship, Surface Plasmon Resonance, target, Team-Mueller, Thermodynamics, Transmission, virus},
pubstate = {published},
tppubtype = {article}
}
Singh Prabhpreet, Lamanna Giuseppe, Ménard-Moyon Cécilia, Toma Francesca Maria, Magnano Elena, Bondino Federica, Prato Maurizio, Verma Sandeep, Bianco Alberto
Formation of efficient catalytic silver nanoparticles on carbon nanotubes by adenine functionalization Journal Article
In: Angewandte Chemie (International Ed. in English), vol. 50, no. 42, pp. 9893–9897, 2011, ISSN: 1521-3773.
Abstract | Links | BibTeX | Tags: Adenine, carbon, Catalysis, I2CT, Metal Nanoparticles, Molecular Structure, Nanotubes, Silver, Surface Properties, Team-Bianco
@article{singh_formation_2011,
title = {Formation of efficient catalytic silver nanoparticles on carbon nanotubes by adenine functionalization},
author = {Prabhpreet Singh and Giuseppe Lamanna and Cécilia Ménard-Moyon and Francesca Maria Toma and Elena Magnano and Federica Bondino and Maurizio Prato and Sandeep Verma and Alberto Bianco},
doi = {10.1002/anie.201102976},
issn = {1521-3773},
year = {2011},
date = {2011-10-01},
journal = {Angewandte Chemie (International Ed. in English)},
volume = {50},
number = {42},
pages = {9893--9897},
abstract = {Stuck together: adenine/carbon nanotube hybrids trigger the formation of controlled-size catalytic silver nanoparticles on the nanotube surface. The catalytic efficiency of the resulting species was assessed in the oxidation of 2-methylhydroquinone to its corresponding benzoquinone, with complete recovery and without loss of activity of the catalyst.},
keywords = {Adenine, carbon, Catalysis, I2CT, Metal Nanoparticles, Molecular Structure, Nanotubes, Silver, Surface Properties, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Singh Prabhpreet, Toma Francesca Maria, Kumar Jitendra, Venkatesh V, Raya Jesus, Prato Maurizio, Verma Sandeep, Bianco Alberto
Carbon nanotube-nucleobase hybrids: nanorings from uracil-modified single-walled carbon nanotubes Journal Article
In: Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 17, no. 24, pp. 6772–6780, 2011, ISSN: 1521-3765.
Abstract | Links | BibTeX | Tags: carbon, I2CT, Magnetic Resonance Spectroscopy, Molecular Structure, Nanotubes, Team-Bianco, Uracil
@article{singh_carbon_2011,
title = {Carbon nanotube-nucleobase hybrids: nanorings from uracil-modified single-walled carbon nanotubes},
author = {Prabhpreet Singh and Francesca Maria Toma and Jitendra Kumar and V Venkatesh and Jesus Raya and Maurizio Prato and Sandeep Verma and Alberto Bianco},
doi = {10.1002/chem.201100312},
issn = {1521-3765},
year = {2011},
date = {2011-06-01},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
volume = {17},
number = {24},
pages = {6772--6780},
abstract = {Single-walled carbon nanotubes (SWCNTs) have been covalently functionalized with uracil nucleobase. The hybrids have been characterized by using complementary spectroscopic and microscopic techniques including solid-state NMR spectroscopy. The uracil-functionalized SWCNTs are able to self-assemble into regular nanorings with a diameter of 50-70 nm, as observed by AFM and TEM. AFM shows that the rings do not have a consistent height and thickness, which indicates that they may be formed by separate bundles of CNTs. The simplest model for the nanoring formation likely involves two bundles of CNTs interacting with each other via uracil-uracil base-pairing at both CNT ends. These nanorings can be envisaged for the development of advanced electronic circuits.},
keywords = {carbon, I2CT, Magnetic Resonance Spectroscopy, Molecular Structure, Nanotubes, Team-Bianco, Uracil},
pubstate = {published},
tppubtype = {article}
}
Violette Aude, Lancelot Nathalie, Poschalko Alexander, Piotto Martial, Briand Jean-Paul, Raya Jesus, Elbayed Karim, Bianco Alberto, Guichard Gilles
Exploring helical folding of oligoureas during chain elongation by high-resolution magic-angle-spinning (HRMAS) NMR spectroscopy Journal Article
In: Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 14, no. 13, pp. 3874–3882, 2008, ISSN: 0947-6539.
Abstract | Links | BibTeX | Tags: I2CT, Magnetic Resonance Spectroscopy, Molecular Structure, Solvents, Team-Bianco, Urea
@article{violette_exploring_2008,
title = {Exploring helical folding of oligoureas during chain elongation by high-resolution magic-angle-spinning (HRMAS) NMR spectroscopy},
author = {Aude Violette and Nathalie Lancelot and Alexander Poschalko and Martial Piotto and Jean-Paul Briand and Jesus Raya and Karim Elbayed and Alberto Bianco and Gilles Guichard},
doi = {10.1002/chem.200701923},
issn = {0947-6539},
year = {2008},
date = {2008-01-01},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
volume = {14},
number = {13},
pages = {3874--3882},
abstract = {The development of novel folding oligomers (foldamers) for biological and biomedical applications requires both precise structural information and appropriate methods to detect folding propensity. However, the synthesis and the systematic conformational investigation of large arrays of oligomers to determine the influence of factors, such as chain length, side chains, and surrounding environment, on secondary structure can be quite tedious. Herein, we show for 2.5-helical N,N'-linked oligoureas (gamma-peptide lineage) that the whole process of foldamer characterization can be accelerated by using high-resolution magic-angle-spinning (HRMAS) NMR spectroscopy. This was achieved by monitoring a simple descriptor of conformational homogeneity (e.g., chemical shift difference between diastereotopic main chain CH2 protons) at different stages of oligourea chain growth on a solid support. HRMAS NMR experiments were conducted on two sets of oligoureas, ranging from dimer to hexamer, immobilized on DEUSS, a perdeuterated poly(oxyethylene)-based solid support swollen in solvents of low to high polarity. One evident advantage of the method is that only minute amount of material is required. In addition, the resonance of the deuterated resin is almost negligeable. On-bead NOESY spectra of high quality and with resolution comparable to that of liquid samples were obtained for longer oligomers, thus allowing detailed structural characterization.},
keywords = {I2CT, Magnetic Resonance Spectroscopy, Molecular Structure, Solvents, Team-Bianco, Urea},
pubstate = {published},
tppubtype = {article}
}
Klumpp Cédric, Lacerda Lara, Chaloin Olivier, Ros Tatiana Da, Kostarelos Kostas, Prato Maurizio, Bianco Alberto
Multifunctionalised cationic fullerene adducts for gene transfer: design, synthesis and DNA complexation Journal Article
In: Chemical Communications (Cambridge, England), no. 36, pp. 3762–3764, 2007, ISSN: 1359-7345.
Abstract | Links | BibTeX | Tags: DNA, Electrophoresis, Fullerenes, Gene Transfer Techniques, I2CT, Molecular Structure, Plasmids, Team-Bianco
@article{klumpp_multifunctionalised_2007,
title = {Multifunctionalised cationic fullerene adducts for gene transfer: design, synthesis and DNA complexation},
author = {Cédric Klumpp and Lara Lacerda and Olivier Chaloin and Tatiana Da Ros and Kostas Kostarelos and Maurizio Prato and Alberto Bianco},
doi = {10.1039/b708435h},
issn = {1359-7345},
year = {2007},
date = {2007-01-01},
journal = {Chemical Communications (Cambridge, England)},
number = {36},
pages = {3762--3764},
abstract = {Cationic poly-N,N-dimethylfulleropyrrolidinium derivatives have been designed and synthesised to complex plasmid DNA for gene delivery.},
keywords = {DNA, Electrophoresis, Fullerenes, Gene Transfer Techniques, I2CT, Molecular Structure, Plasmids, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Dumortier Hélène, Lacotte Stéphanie, Pastorin Giorgia, Marega Riccardo, Wu Wei, Bonifazi Davide, Briand Jean-Paul, Prato Maurizio, Muller Sylviane, Bianco Alberto
Functionalized carbon nanotubes are non-cytotoxic and preserve the functionality of primary immune cells Journal Article
In: Nano Letters, vol. 6, no. 7, pp. 1522–1528, 2006, ISSN: 1530-6984.
Abstract | Links | BibTeX | Tags: Amides, B-Lymphocytes, Biotechnology, carbon, Cell Survival, Cytokines, Dumortier, I2CT, Macrophages, Molecular Structure, Nanotubes, Oxidation-Reduction, T-Lymphocytes, Team-Bianco, Team-Dumortier
@article{dumortier_functionalized_2006,
title = {Functionalized carbon nanotubes are non-cytotoxic and preserve the functionality of primary immune cells},
author = {Hélène Dumortier and Stéphanie Lacotte and Giorgia Pastorin and Riccardo Marega and Wei Wu and Davide Bonifazi and Jean-Paul Briand and Maurizio Prato and Sylviane Muller and Alberto Bianco},
doi = {10.1021/nl061160x},
issn = {1530-6984},
year = {2006},
date = {2006-07-01},
journal = {Nano Letters},
volume = {6},
number = {7},
pages = {1522--1528},
abstract = {Carbon nanotubes are emerging as innovative tools in nanobiotechnology. However, their toxic effects on environment and health have become an issue of strong concern. In the present study, we address the impact of functionalized carbon nanotubes (f-CNTs) on cells of the immune system. We have prepared two types of f-CNTs, following the 1,3-dipolar cycloaddition reaction (f-CNTs 1 and 2) and the oxidation/amidation treatment (f-CNTs 3 and 4), respectively. We have found that both types of f-CNTs are uptaken by B and T lymphocytes as well as macrophages in vitro, without affecting cell viability. Subsequently, the functionality of the different cells was analyzed carefully. We discovered that f-CNT 1, which is highly water soluble, did not influence the functional activity of immunoregulatory cells. f-CNT 3, which instead possesses reduced solubility and forms mainly stable water suspensions, preserved lymphocytes' functionality while provoking secretion of proinflammatory cytokines by macrophages.},
keywords = {Amides, B-Lymphocytes, Biotechnology, carbon, Cell Survival, Cytokines, Dumortier, I2CT, Macrophages, Molecular Structure, Nanotubes, Oxidation-Reduction, T-Lymphocytes, Team-Bianco, Team-Dumortier},
pubstate = {published},
tppubtype = {article}
}
Dumortier Hélène, Lacotte Stéphanie, Pastorin Giorgia, Marega Riccardo, Wu Wei, Bonifazi Davide, Briand Jean-Paul, Prato Maurizio, Muller Sylviane, Bianco Alberto
Functionalized carbon nanotubes are non-cytotoxic and preserve the functionality of primary immune cells Journal Article
In: Nano Letters, vol. 6, no. 7, pp. 1522–1528, 2006, ISSN: 1530-6984.
Abstract | Links | BibTeX | Tags: Amides, B-Lymphocytes, Biotechnology, carbon, Cell Survival, Cytokines, I2CT, Macrophages, Molecular Structure, Nanotubes, Oxidation-Reduction, T-Lymphocytes, Team-Bianco
@article{dumortier_functionalized_2006b,
title = {Functionalized carbon nanotubes are non-cytotoxic and preserve the functionality of primary immune cells},
author = {Hélène Dumortier and Stéphanie Lacotte and Giorgia Pastorin and Riccardo Marega and Wei Wu and Davide Bonifazi and Jean-Paul Briand and Maurizio Prato and Sylviane Muller and Alberto Bianco},
doi = {10.1021/nl061160x},
issn = {1530-6984},
year = {2006},
date = {2006-07-01},
journal = {Nano Letters},
volume = {6},
number = {7},
pages = {1522--1528},
abstract = {Carbon nanotubes are emerging as innovative tools in nanobiotechnology. However, their toxic effects on environment and health have become an issue of strong concern. In the present study, we address the impact of functionalized carbon nanotubes (f-CNTs) on cells of the immune system. We have prepared two types of f-CNTs, following the 1,3-dipolar cycloaddition reaction (f-CNTs 1 and 2) and the oxidation/amidation treatment (f-CNTs 3 and 4), respectively. We have found that both types of f-CNTs are uptaken by B and T lymphocytes as well as macrophages in vitro, without affecting cell viability. Subsequently, the functionality of the different cells was analyzed carefully. We discovered that f-CNT 1, which is highly water soluble, did not influence the functional activity of immunoregulatory cells. f-CNT 3, which instead possesses reduced solubility and forms mainly stable water suspensions, preserved lymphocytes' functionality while provoking secretion of proinflammatory cytokines by macrophages.},
keywords = {Amides, B-Lymphocytes, Biotechnology, carbon, Cell Survival, Cytokines, I2CT, Macrophages, Molecular Structure, Nanotubes, Oxidation-Reduction, T-Lymphocytes, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Bianco Alberto, Fournel Sylvie, Wieckowski Sébastien, Hoebeke Johan, Guichard Gilles
Solid-phase synthesis of CD40L mimetics Journal Article
In: Organic & Biomolecular Chemistry, vol. 4, no. 8, pp. 1461–1463, 2006, ISSN: 1477-0520.
Abstract | Links | BibTeX | Tags: Apoptosis, CD40 Ligand, Cell Line, Chromatography, Combinatorial Chemistry Techniques, High Pressure Liquid, Humans, I2CT, Molecular Mimicry, Molecular Structure, Protein Binding, Team-Bianco, tumor
@article{bianco_solid-phase_2006,
title = {Solid-phase synthesis of CD40L mimetics},
author = {Alberto Bianco and Sylvie Fournel and Sébastien Wieckowski and Johan Hoebeke and Gilles Guichard},
doi = {10.1039/b601528j},
issn = {1477-0520},
year = {2006},
date = {2006-04-01},
journal = {Organic & Biomolecular Chemistry},
volume = {4},
number = {8},
pages = {1461--1463},
abstract = {The C3-symmetric molecule has been previously shown to mimic CD40 ligand (CD40L) homotrimers and to display effector functions. This molecule consists of a cyclic hexapeptide core containing the repetition of the D-Ala-L-Lys motif. The side chains of the lysine residues have been modified by appending the CD40L-derived sequence 143Lys-Gly-Tyr-Tyr146 via a 6-aminohexanoic acid residue as a spacer. The present report describes a general solid-phase synthesis approach to and related trimeric architectures. In addition, their CD40 binding properties as well as their effector functions have been evaluated.},
keywords = {Apoptosis, CD40 Ligand, Cell Line, Chromatography, Combinatorial Chemistry Techniques, High Pressure Liquid, Humans, I2CT, Molecular Mimicry, Molecular Structure, Protein Binding, Team-Bianco, tumor},
pubstate = {published},
tppubtype = {article}
}
Tasis Dimitrios, Tagmatarchis Nikos, Bianco Alberto, Prato Maurizio
Chemistry of carbon nanotubes Journal Article
In: Chemical Reviews, vol. 106, no. 3, pp. 1105–1136, 2006, ISSN: 0009-2665.
Links | BibTeX | Tags: Animals, Biopolymers, carbon, Chemical Phenomena, Chemistry, I2CT, Molecular Structure, Nanotubes, Solubility, Surface Properties, Team-Bianco
@article{tasis_chemistry_2006,
title = {Chemistry of carbon nanotubes},
author = {Dimitrios Tasis and Nikos Tagmatarchis and Alberto Bianco and Maurizio Prato},
doi = {10.1021/cr050569o},
issn = {0009-2665},
year = {2006},
date = {2006-03-01},
journal = {Chemical Reviews},
volume = {106},
number = {3},
pages = {1105--1136},
keywords = {Animals, Biopolymers, carbon, Chemical Phenomena, Chemistry, I2CT, Molecular Structure, Nanotubes, Solubility, Surface Properties, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Singh Ravi, Pantarotto Davide, Lacerda Lara, Pastorin Giorgia, Klumpp Cédric, Prato Maurizio, Bianco Alberto, Kostarelos Kostas
Tissue biodistribution and blood clearance rates of intravenously administered carbon nanotube radiotracers Journal Article
In: Proceedings of the National Academy of Sciences of the United States of America, vol. 103, no. 9, pp. 3357–3362, 2006, ISSN: 0027-8424.
Abstract | Links | BibTeX | Tags: Animals, carbon, Electron, Female, Half-Life, I2CT, Inbred BALB C, Indium Radioisotopes, Injections, Intravenous, Mice, Microscopy, Molecular Structure, Nanotubes, Pentetic Acid, Team-Bianco, Tissue Distribution, Transmission
@article{singh_tissue_2006,
title = {Tissue biodistribution and blood clearance rates of intravenously administered carbon nanotube radiotracers},
author = {Ravi Singh and Davide Pantarotto and Lara Lacerda and Giorgia Pastorin and Cédric Klumpp and Maurizio Prato and Alberto Bianco and Kostas Kostarelos},
doi = {10.1073/pnas.0509009103},
issn = {0027-8424},
year = {2006},
date = {2006-02-01},
journal = {Proceedings of the National Academy of Sciences of the United States of America},
volume = {103},
number = {9},
pages = {3357--3362},
abstract = {Carbon nanotubes (CNT) are intensively being developed for biomedical applications including drug and gene delivery. Although all possible clinical applications will require compatibility of CNT with the biological milieu, their in vivo capabilities and limitations have not yet been explored. In this work, water-soluble, single-walled CNT (SWNT) have been functionalized with the chelating molecule diethylentriaminepentaacetic (DTPA) and labeled with indium ((111)In) for imaging purposes. Intravenous (i.v.) administration of these functionalized SWNT (f-SWNT) followed by radioactivity tracing using gamma scintigraphy indicated that f-SWNT are not retained in any of the reticuloendothelial system organs (liver or spleen) and are rapidly cleared from systemic blood circulation through the renal excretion route. The observed rapid blood clearance and half-life (3 h) of f-SWNT has major implications for all potential clinical uses of CNT. Moreover, urine excretion studies using both f-SWNT and functionalized multiwalled CNT followed by electron microscopy analysis of urine samples revealed that both types of nanotubes were excreted as intact nanotubes. This work describes the pharmacokinetic parameters of i.v. administered functionalized CNT relevant for various therapeutic and diagnostic applications.},
keywords = {Animals, carbon, Electron, Female, Half-Life, I2CT, Inbred BALB C, Indium Radioisotopes, Injections, Intravenous, Mice, Microscopy, Molecular Structure, Nanotubes, Pentetic Acid, Team-Bianco, Tissue Distribution, Transmission},
pubstate = {published},
tppubtype = {article}
}
Fournel Sylvie, Wieckowski Sébastien, Sun Weimin, Trouche Nathalie, Dumortier Hélène, Bianco Alberto, Chaloin Olivier, Habib Mohammed, Peter Jean-Christophe, Schneider Pascal, Vray Bernard, Toes René E, Offringa Rienk, Melief Cornelis J M, Hoebeke Johan, Guichard Gilles
C3-symmetric peptide scaffolds are functional mimetics of trimeric CD40L Journal Article
In: Nature Chemical Biology, vol. 1, no. 7, pp. 377–382, 2005, ISSN: 1552-4450.
Abstract | Links | BibTeX | Tags: Animals, Apoptosis, Biological, CD40 Antigens, CD40 Ligand, Cell Line, Dumortier, Humans, I2CT, Inbred BALB C, Mice, Models, Molecular Mimicry, Molecular Structure, Peptides, Protein Conformation, Protein Structure, Quaternary, Structure-Activity Relationship, Team-Bianco, Team-Dumortier, Time Factors, tumor
@article{fournel_c3-symmetric_2005,
title = {C3-symmetric peptide scaffolds are functional mimetics of trimeric CD40L},
author = {Sylvie Fournel and Sébastien Wieckowski and Weimin Sun and Nathalie Trouche and Hélène Dumortier and Alberto Bianco and Olivier Chaloin and Mohammed Habib and Jean-Christophe Peter and Pascal Schneider and Bernard Vray and René E Toes and Rienk Offringa and Cornelis J M Melief and Johan Hoebeke and Gilles Guichard},
doi = {10.1038/nchembio746},
issn = {1552-4450},
year = {2005},
date = {2005-12-01},
journal = {Nature Chemical Biology},
volume = {1},
number = {7},
pages = {377--382},
abstract = {Interaction between CD40, a member of the tumor necrosis factor receptor (TNFR) superfamily, and its ligand CD40L, a 39-kDa glycoprotein, is essential for the development of humoral and cellular immune responses. Selective blockade or activation of this pathway provides the ground for the development of new treatments against immunologically based diseases and malignancies. Like other members of the TNF superfamily, CD40L monomers self-assemble around a threefold symmetry axis to form noncovalent homotrimers that can each bind three receptor molecules. Here, we report on the structure-based design of small synthetic molecules with C3 symmetry that can mimic CD40L homotrimers. These molecules interact with CD40, compete with the binding of CD40L to CD40, and reproduce, to a certain extent, the functional properties of the much larger homotrimeric soluble CD40L. Architectures based on rigid C3-symmetric cores may thus represent a general approach to mimicking homotrimers of the TNF superfamily.},
keywords = {Animals, Apoptosis, Biological, CD40 Antigens, CD40 Ligand, Cell Line, Dumortier, Humans, I2CT, Inbred BALB C, Mice, Models, Molecular Mimicry, Molecular Structure, Peptides, Protein Conformation, Protein Structure, Quaternary, Structure-Activity Relationship, Team-Bianco, Team-Dumortier, Time Factors, tumor},
pubstate = {published},
tppubtype = {article}
}
Wu Wei, Wieckowski Sébastien, Pastorin Giorgia, Benincasa Monica, Klumpp Cédric, Briand Jean-Paul, Gennaro Renato, Prato Maurizio, Bianco Alberto
Targeted delivery of amphotericin B to cells by using functionalized carbon nanotubes Journal Article
In: Angewandte Chemie (International Ed. in English), vol. 44, no. 39, pp. 6358–6362, 2005, ISSN: 1433-7851.
Links | BibTeX | Tags: Amphotericin B, Antifungal Agents, carbon, Drug Carriers, Drug Delivery Systems, Fungi, Humans, I2CT, Jurkat Cells, Molecular Structure, Nanotubes, Particle Size, Solubility, Surface Properties, Team-Bianco
@article{wu_targeted_2005,
title = {Targeted delivery of amphotericin B to cells by using functionalized carbon nanotubes},
author = {Wei Wu and Sébastien Wieckowski and Giorgia Pastorin and Monica Benincasa and Cédric Klumpp and Jean-Paul Briand and Renato Gennaro and Maurizio Prato and Alberto Bianco},
doi = {10.1002/anie.200501613},
issn = {1433-7851},
year = {2005},
date = {2005-10-01},
journal = {Angewandte Chemie (International Ed. in English)},
volume = {44},
number = {39},
pages = {6358--6362},
keywords = {Amphotericin B, Antifungal Agents, carbon, Drug Carriers, Drug Delivery Systems, Fungi, Humans, I2CT, Jurkat Cells, Molecular Structure, Nanotubes, Particle Size, Solubility, Surface Properties, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Imler Jean-Luc, Bulet Philippe
Antimicrobial peptides in Drosophila: structures, activities and gene regulation Journal Article
In: Chemical Immunology and Allergy, vol. 86, pp. 1–21, 2005, ISSN: 1660-2242.
Abstract | Links | BibTeX | Tags: Animals, Antimicrobial Cationic Peptides, Defensins, Gene Expression Regulation, Genes, Glycopeptides, imler, Immunity, Innate, Insect, Insect Proteins, M3i, Molecular Structure, Signal Transduction
@article{imler_antimicrobial_2005,
title = {Antimicrobial peptides in Drosophila: structures, activities and gene regulation},
author = {Jean-Luc Imler and Philippe Bulet},
doi = {10.1159/000086648},
issn = {1660-2242},
year = {2005},
date = {2005-01-01},
journal = {Chemical Immunology and Allergy},
volume = {86},
pages = {1--21},
abstract = {The production of antimicrobial peptides (AMPs) is an important aspect of host-defence in multicellular organisms. Biochemical analysis of the hemolymph of the fruit-fly Drosophila melanogaster and other Diptera has led to the discovery of eight classes of AMPs. These peptides can be grouped into three families based on their main biological targets, gram-positive bacteria (defensin), gram-negative bacteria (cecropins, drosocin, attacins, diptericin, MPAC), or fungi (drosomycin, metchnikowin). Drosophila AMPs are synthesized by the fat body in response to infection, and secreted into the blood. Most of them can also be induced in surface epithelia in a tissue-specific manner. Finally, some of them are constitutively expressed in defined tissues, such as the salivary glands or the reproductive tract. We review here the structures and activities of these AMPs, as well as the signalling cascades, which lead to their induction upon detection of infectious non-self.},
keywords = {Animals, Antimicrobial Cationic Peptides, Defensins, Gene Expression Regulation, Genes, Glycopeptides, imler, Immunity, Innate, Insect, Insect Proteins, M3i, Molecular Structure, Signal Transduction},
pubstate = {published},
tppubtype = {article}
}
Fournel Sylvie, Wieckowski Sébastien, Sun Weimin, Trouche Nathalie, Dumortier Hélène, Bianco Alberto, Chaloin Olivier, Habib Mohammed, Peter Jean-Christophe, Schneider Pascal, Vray Bernard, Toes René E, Offringa Rienk, Melief Cornelis J M, Hoebeke Johan, Guichard Gilles
C3-symmetric peptide scaffolds are functional mimetics of trimeric CD40L Journal Article
In: Nature Chemical Biology, vol. 1, no. 7, pp. 377–382, 2005, ISSN: 1552-4450.
Abstract | Links | BibTeX | Tags: Animals, Apoptosis, Biological, CD40 Antigens, CD40 Ligand, Cell Line, Humans, I2CT, Inbred BALB C, Mice, Models, Molecular Mimicry, Molecular Structure, Peptides, Protein Conformation, Protein Structure, Quaternary, Structure-Activity Relationship, Team-Bianco, Time Factors, tumor
@article{fournel_c3-symmetric_2005b,
title = {C3-symmetric peptide scaffolds are functional mimetics of trimeric CD40L},
author = {Sylvie Fournel and Sébastien Wieckowski and Weimin Sun and Nathalie Trouche and Hélène Dumortier and Alberto Bianco and Olivier Chaloin and Mohammed Habib and Jean-Christophe Peter and Pascal Schneider and Bernard Vray and René E Toes and Rienk Offringa and Cornelis J M Melief and Johan Hoebeke and Gilles Guichard},
doi = {10.1038/nchembio746},
issn = {1552-4450},
year = {2005},
date = {2005-01-01},
journal = {Nature Chemical Biology},
volume = {1},
number = {7},
pages = {377--382},
abstract = {Interaction between CD40, a member of the tumor necrosis factor receptor (TNFR) superfamily, and its ligand CD40L, a 39-kDa glycoprotein, is essential for the development of humoral and cellular immune responses. Selective blockade or activation of this pathway provides the ground for the development of new treatments against immunologically based diseases and malignancies. Like other members of the TNF superfamily, CD40L monomers self-assemble around a threefold symmetry axis to form noncovalent homotrimers that can each bind three receptor molecules. Here, we report on the structure-based design of small synthetic molecules with C3 symmetry that can mimic CD40L homotrimers. These molecules interact with CD40, compete with the binding of CD40L to CD40, and reproduce, to a certain extent, the functional properties of the much larger homotrimeric soluble CD40L. Architectures based on rigid C3-symmetric cores may thus represent a general approach to mimicking homotrimers of the TNF superfamily.},
keywords = {Animals, Apoptosis, Biological, CD40 Antigens, CD40 Ligand, Cell Line, Humans, I2CT, Inbred BALB C, Mice, Models, Molecular Mimicry, Molecular Structure, Peptides, Protein Conformation, Protein Structure, Quaternary, Structure-Activity Relationship, Team-Bianco, Time Factors, tumor},
pubstate = {published},
tppubtype = {article}
}
Bianco Alberto, Kostarelos Kostas, Partidos Charalambos D, Prato Maurizio
Biomedical applications of functionalised carbon nanotubes Journal Article
In: Chemical Communications (Cambridge, England), no. 5, pp. 571–577, 2005, ISSN: 1359-7345.
Abstract | Links | BibTeX | Tags: Antigens, carbon, Chemical, Drug Delivery Systems, Gene Transfer Techniques, Humans, I2CT, Models, Molecular Structure, nanotechnology, Nanotubes, Team-Bianco, Vaccines
@article{bianco_biomedical_2005,
title = {Biomedical applications of functionalised carbon nanotubes},
author = {Alberto Bianco and Kostas Kostarelos and Charalambos D Partidos and Maurizio Prato},
doi = {10.1039/b410943k},
issn = {1359-7345},
year = {2005},
date = {2005-01-01},
journal = {Chemical Communications (Cambridge, England)},
number = {5},
pages = {571--577},
abstract = {The organic functionalisation of carbon nanotubes can improve substantially their solubility and biocompatibility profile; as a consequence, their manipulation and integration into biological systems has become possible so that functionalised carbon nanotubes hold currently strong promise as novel systems for the delivery of drugs, antigens and genes.},
keywords = {Antigens, carbon, Chemical, Drug Delivery Systems, Gene Transfer Techniques, Humans, I2CT, Models, Molecular Structure, nanotechnology, Nanotubes, Team-Bianco, Vaccines},
pubstate = {published},
tppubtype = {article}
}
Pantarotto Davide, Tagmatarchis Nikos, Bianco Alberto, Prato Maurizio
Synthesis and biological properties of fullerene-containing amino acids and peptides Journal Article
In: Mini Reviews in Medicinal Chemistry, vol. 4, no. 7, pp. 805–814, 2004, ISSN: 1389-5575.
Abstract | BibTeX | Tags: Amino Acids, Animals, Fullerenes, Humans, I2CT, Molecular Structure, Peptides, Solubility, Team-Bianco
@article{pantarotto_synthesis_2004,
title = {Synthesis and biological properties of fullerene-containing amino acids and peptides},
author = {Davide Pantarotto and Nikos Tagmatarchis and Alberto Bianco and Maurizio Prato},
issn = {1389-5575},
year = {2004},
date = {2004-09-01},
journal = {Mini Reviews in Medicinal Chemistry},
volume = {4},
number = {7},
pages = {805--814},
abstract = {Organofullerene derivatives have shown a great potential in a wide variety of biological activities such as DNA photocleavage, HIV-protease inhibition, neuroprotection and apoptosis. Among the plethora of functionalized organofullerenes that have been synthesized, fullerene-based amino acids are particularly appealing for structural studies and biological applications. When the fullerene-framework is incorporated into peptides, its original properties can be substantially modified. In addition, the water-solubility of the fullerene derivatives is enhanced, which makes such molecules amenable to biological studies. In this review, recent advances in the growing field of medicinal chemistry of fullerene derivatives will be discussed. Emphasis will be given to the synthesis of the biggest unnatural amino acid 3,4-fulleroproline (Fpr) and its derivatives. For example, Fpr derivatives have been found to interact with different hydrolytic enzymes and selectively discriminate between rationally designed peptides. Fullerene-based peptides have been found to substantially activate enzymes involved in the oxidative deamination of biogenic amines. In addition, their membranotropic properties and effects on the structure and permeability of the lipid bilayer of phosphatidylcholine liposomes as well as the transmembrane transport of bivalent metal ions have been studied. Finally, applications in medicinal chemistry of such types of amino acids and peptides will be highlighted.},
keywords = {Amino Acids, Animals, Fullerenes, Humans, I2CT, Molecular Structure, Peptides, Solubility, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Bianco Alberto, Pantarotto Davide, Hoebeke Johan, Briand Jean-Paul, Prato Maurizio
Solid-phase synthesis and characterization of a novel fullerene-peptide derived from histone H3 Journal Article
In: Organic & Biomolecular Chemistry, vol. 1, no. 23, pp. 4141–4143, 2003, ISSN: 1477-0520.
Abstract | Links | BibTeX | Tags: Chromatography, Epitopes, Fullerenes, Glutamic Acid, High Pressure Liquid, Histones, I2CT, Models, Molecular, Molecular Structure, Peptides, Protein Structure, Team-Bianco, Tertiary
@article{bianco_solid-phase_2003,
title = {Solid-phase synthesis and characterization of a novel fullerene-peptide derived from histone H3},
author = {Alberto Bianco and Davide Pantarotto and Johan Hoebeke and Jean-Paul Briand and Maurizio Prato},
doi = {10.1039/b311505d},
issn = {1477-0520},
year = {2003},
date = {2003-12-01},
journal = {Organic & Biomolecular Chemistry},
volume = {1},
number = {23},
pages = {4141--4143},
abstract = {A peptide analogue from a histone H3 protein containing the L-fulleropyrrolidino-glutamic acid has been prepared by a solid-phase approach and has been fully characterized. By molecular modelling it was verified that this peptide derivative is able to retain a binding capacity to the MHC (major histocompatibility complex) molecule similar to that of the cognate epitope.},
keywords = {Chromatography, Epitopes, Fullerenes, Glutamic Acid, High Pressure Liquid, Histones, I2CT, Models, Molecular, Molecular Structure, Peptides, Protein Structure, Team-Bianco, Tertiary},
pubstate = {published},
tppubtype = {article}
}
Dimarcq Jean-Luc, Hoffmann Danièle, Meister Marie, Bulet Philippe, Lanot R, Reichhart Jean-Marc, Hoffmann Jules A
Characterization and transcriptional profiles of a Drosophila gene encoding an insect defensin. A study in insect immunity Journal Article
In: Eur. J. Biochem., vol. 221, no. 1, pp. 201–209, 1994, ISSN: 0014-2956.
Abstract | BibTeX | Tags: Animals, Base Sequence, Blood Proteins, Chromosome Mapping, Cloning, Complementary, Defensins, DNA, Gene Expression, Genetic, Gram-Positive Bacteria, hoffmann, Larva, M3i, Molecular, Molecular Structure, Nucleic Acid, Protein Precursors, Regulatory Sequences, reichhart, Transcription
@article{dimarcq_characterization_1994,
title = {Characterization and transcriptional profiles of a Drosophila gene encoding an insect defensin. A study in insect immunity},
author = {Jean-Luc Dimarcq and Danièle Hoffmann and Marie Meister and Philippe Bulet and R Lanot and Jean-Marc Reichhart and Jules A Hoffmann},
issn = {0014-2956},
year = {1994},
date = {1994-04-01},
journal = {Eur. J. Biochem.},
volume = {221},
number = {1},
pages = {201--209},
abstract = {Insect defensins are a family of 4-kDa, cationic, inducible antibacterial peptides which bear six cysteine residues engaged in three intramolecular disulfide bridges. They owe their name to certain sequence similarities with defensins from mammalian neutrophiles and macrophages. We report the characterization of a novel defensin isoform from Drosophila and the cloning of the gene encoding a preprodefensin. The gene, which is intronless and present in a single copy/haploid genome, maps at position 46CD on the right arm of the second chromosome. The analysis of the upstream region of the gene reveals the presence of multiple putative cis-regulatory sequences similar to mammalian regulatory motifs of acute-phase-response genes. Transcriptional profiles indicate that the Drosophila defensin gene is induced by bacterial challenge with acute-phase kinetics. It is also expressed in the absence of immune challenge during metamorphosis. These and other data on the Drosophila defensin gene lead us to suggest that insect and mammalian defensins have evolved independently.},
keywords = {Animals, Base Sequence, Blood Proteins, Chromosome Mapping, Cloning, Complementary, Defensins, DNA, Gene Expression, Genetic, Gram-Positive Bacteria, hoffmann, Larva, M3i, Molecular, Molecular Structure, Nucleic Acid, Protein Precursors, Regulatory Sequences, reichhart, Transcription},
pubstate = {published},
tppubtype = {article}
}