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2014
Lamanna Giuseppe, Grillaud Maxime, Macri Christophe, Chaloin Olivier, Muller Sylviane, Bianco Alberto
Adamantane-based dendrons for trimerization of the therapeutic P140 peptide Article de journal
Dans: Biomaterials, vol. 35, non 26, p. 7553–7561, 2014, ISSN: 1878-5905.
Résumé | Liens | BibTeX | Étiquettes: Adamantane, Animals, Biotin, C3-symmetry, Dendrimers, Dendrons, Drug Carriers, Female, HSC70 Heat-Shock Proteins, HSPA8 protein, Humans, I2CT, Inbred MRL lpr, Lupus Erythematosus, Mice, P140 peptide, Peptide Fragments, Systemic, Team-Bianco
@article{lamanna_adamantane-based_2014,
title = {Adamantane-based dendrons for trimerization of the therapeutic P140 peptide},
author = {Giuseppe Lamanna and Maxime Grillaud and Christophe Macri and Olivier Chaloin and Sylviane Muller and Alberto Bianco},
doi = {10.1016/j.biomaterials.2014.05.017},
issn = {1878-5905},
year = {2014},
date = {2014-01-01},
journal = {Biomaterials},
volume = {35},
number = {26},
pages = {7553--7561},
abstract = {Dendrons constituted of an adamantane core, a focal point and three arms, were synthetized starting from a multifunctional adamantane derivative. Maleimido groups at the periphery of the scaffold were used to covalently attach the peptide called P140, a therapeutic phosphopeptide controlling disease activity in systemic lupus, both in mice and patients. Biotinylation of the trimers at the focal point was performed using click chemistry and the conjugates were studied in terms of solubility, binding affinity to its receptor, the HSPA8/HSC70 chaperone protein, effect on HSPA8 folding property and in vivo activity. The results showed that the trimerization of P140 peptide does not trigger aggregation or steric hindrances during the interaction with HSPA8 protein. Compared to the monomeric cognate peptide, the trivalent P140 peptide displayed the same capacity, in vitro, to down-regulate HSPA8 activity and, in vivo in MRL/lpr lupus-prone mice, to reduce abnormal blood hypercellularity. The control trimer synthesized with the same scaffold and a scrambled sequence of P140 showed no effect in vivo. This work reveals that adamantane-based scaffolds with a well-defined spatial conformation are promising trivalent systems for molecular recognition and for biomedical applications.},
keywords = {Adamantane, Animals, Biotin, C3-symmetry, Dendrimers, Dendrons, Drug Carriers, Female, HSC70 Heat-Shock Proteins, HSPA8 protein, Humans, I2CT, Inbred MRL lpr, Lupus Erythematosus, Mice, P140 peptide, Peptide Fragments, Systemic, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Dendrons constituted of an adamantane core, a focal point and three arms, were synthetized starting from a multifunctional adamantane derivative. Maleimido groups at the periphery of the scaffold were used to covalently attach the peptide called P140, a therapeutic phosphopeptide controlling disease activity in systemic lupus, both in mice and patients. Biotinylation of the trimers at the focal point was performed using click chemistry and the conjugates were studied in terms of solubility, binding affinity to its receptor, the HSPA8/HSC70 chaperone protein, effect on HSPA8 folding property and in vivo activity. The results showed that the trimerization of P140 peptide does not trigger aggregation or steric hindrances during the interaction with HSPA8 protein. Compared to the monomeric cognate peptide, the trivalent P140 peptide displayed the same capacity, in vitro, to down-regulate HSPA8 activity and, in vivo in MRL/lpr lupus-prone mice, to reduce abnormal blood hypercellularity. The control trimer synthesized with the same scaffold and a scrambled sequence of P140 showed no effect in vivo. This work reveals that adamantane-based scaffolds with a well-defined spatial conformation are promising trivalent systems for molecular recognition and for biomedical applications.
2012
Lamanna Giuseppe, Russier Julie, Dumortier Hélène, Bianco Alberto
Enhancement of anti-inflammatory drug activity by multivalent adamantane-based dendrons Article de journal
Dans: Biomaterials, vol. 33, non 22, p. 5610–5617, 2012, ISSN: 1878-5905.
Résumé | Liens | BibTeX | Étiquettes: Animals, Anti-Inflammatory Agents, Cell Line, Cell Survival, Dendrimers, Drug Synergism, Dumortier, I2CT, Ibuprofen, Macrophages, Mice, Team-Bianco, Team-Dumortier
@article{lamanna_enhancement_2012,
title = {Enhancement of anti-inflammatory drug activity by multivalent adamantane-based dendrons},
author = {Giuseppe Lamanna and Julie Russier and Hélène Dumortier and Alberto Bianco},
doi = {10.1016/j.biomaterials.2012.03.072},
issn = {1878-5905},
year = {2012},
date = {2012-01-01},
journal = {Biomaterials},
volume = {33},
number = {22},
pages = {5610--5617},
abstract = {We have developed a straightforward method to prepare 1(st) and 2(nd) generation adamantane-based dendrons, previously called HYDRAmers, bearing at the periphery the anti-inflammatory drug, ibuprofen. The multivalency effect on the drug activity was studied, demonstrating that our multivalent ibuprofen-dendron conjugates exert an enhanced anti-inflammatory activity compared to free ibuprofen, in vitro. These results provide insights into the effect of HYDRAmer multivalency on biological interactions for therapeutic applications.},
keywords = {Animals, Anti-Inflammatory Agents, Cell Line, Cell Survival, Dendrimers, Drug Synergism, Dumortier, I2CT, Ibuprofen, Macrophages, Mice, Team-Bianco, Team-Dumortier},
pubstate = {published},
tppubtype = {article}
}
We have developed a straightforward method to prepare 1(st) and 2(nd) generation adamantane-based dendrons, previously called HYDRAmers, bearing at the periphery the anti-inflammatory drug, ibuprofen. The multivalency effect on the drug activity was studied, demonstrating that our multivalent ibuprofen-dendron conjugates exert an enhanced anti-inflammatory activity compared to free ibuprofen, in vitro. These results provide insights into the effect of HYDRAmer multivalency on biological interactions for therapeutic applications.
2011
Lamanna Giuseppe, Russier Julie, Ménard-Moyon Cécilia, Bianco Alberto
HYDRAmers: design, synthesis and characterization of different generation novel Hydra-like dendrons based on multifunctionalized adamantane Article de journal
Dans: Chemical Communications (Cambridge, England), vol. 47, non 31, p. 8955–8957, 2011, ISSN: 1364-548X.
Résumé | Liens | BibTeX | Étiquettes: Adamantane, Animals, Cell Line, Dendrimers, Drug Design, Humans, I2CT, L-Lactate Dehydrogenase, Magnetic Resonance Spectroscopy, Mice, Team-Bianco, tumor
@article{lamanna_hydramers_2011,
title = {HYDRAmers: design, synthesis and characterization of different generation novel Hydra-like dendrons based on multifunctionalized adamantane},
author = {Giuseppe Lamanna and Julie Russier and Cécilia Ménard-Moyon and Alberto Bianco},
doi = {10.1039/c1cc11689d},
issn = {1364-548X},
year = {2011},
date = {2011-08-01},
journal = {Chemical Communications (Cambridge, England)},
volume = {47},
number = {31},
pages = {8955--8957},
abstract = {In this communication we present a new synthetic strategy to different generation Hydra-like dendrons based on tetrafunctionalized adamantane as a building block. The novel dendrons, which we termed HYDRAmers, possess at the periphery and at the central core orthogonal protections that can be exploited for conjugation of targeting ligands, drugs and/or imaging probes.},
keywords = {Adamantane, Animals, Cell Line, Dendrimers, Drug Design, Humans, I2CT, L-Lactate Dehydrogenase, Magnetic Resonance Spectroscopy, Mice, Team-Bianco, tumor},
pubstate = {published},
tppubtype = {article}
}
In this communication we present a new synthetic strategy to different generation Hydra-like dendrons based on tetrafunctionalized adamantane as a building block. The novel dendrons, which we termed HYDRAmers, possess at the periphery and at the central core orthogonal protections that can be exploited for conjugation of targeting ligands, drugs and/or imaging probes.
2009
Herrero Antonia M, Toma Francesca M, Al-Jamal Khuloud T, Kostarelos Kostas, Bianco Alberto, Ros Tatiana Da, Bano Fouzia, Casalis Loredana, Scoles Giacinto, Prato Maurizio
Synthesis and characterization of a carbon nanotube-dendron series for efficient siRNA delivery Article de journal
Dans: Journal of the American Chemical Society, vol. 131, non 28, p. 9843–9848, 2009, ISSN: 1520-5126.
Résumé | Liens | BibTeX | Étiquettes: Acrylates, Animals, Azo Compounds, Biological Transport, carbon, Cytoplasm, Dendrimers, Drug Carriers, Ethylenediamines, Gene Silencing, HeLa Cells, Humans, I2CT, Nanotubes, Polyamines, RNA, Small Interfering, Solubility, Team-Bianco, Thiosemicarbazones, Transfection, water
@article{herrero_synthesis_2009,
title = {Synthesis and characterization of a carbon nanotube-dendron series for efficient siRNA delivery},
author = {Antonia M Herrero and Francesca M Toma and Khuloud T Al-Jamal and Kostas Kostarelos and Alberto Bianco and Tatiana Da Ros and Fouzia Bano and Loredana Casalis and Giacinto Scoles and Maurizio Prato},
doi = {10.1021/ja903316z},
issn = {1520-5126},
year = {2009},
date = {2009-07-01},
journal = {Journal of the American Chemical Society},
volume = {131},
number = {28},
pages = {9843--9848},
abstract = {A new series of dendron-functionalized multiwalled carbon nanotube (MWNT) derivatives, characterized by the presence of numerous positively charged tetraalkyl ammonium salts at the periphery of the dendron, has been synthesized. The positive charges on the MWNT surface, coupled with the unique ability of carbon nanotubes (CNTs) to penetrate cell membranes, make the new derivatives potentially ideal vectors for siRNA delivery. Using a fluorescently labeled, noncoding siRNA sequence, we demonstrate that cytoplasmic delivery of the nucleic acid is remarkably increased throughout the different dendron generations. The work reported here highlights the fact that dendron-functionalized CNTs can be rationally designed as efficient carriers of siRNA that can eventually lead to gene silencing.},
keywords = {Acrylates, Animals, Azo Compounds, Biological Transport, carbon, Cytoplasm, Dendrimers, Drug Carriers, Ethylenediamines, Gene Silencing, HeLa Cells, Humans, I2CT, Nanotubes, Polyamines, RNA, Small Interfering, Solubility, Team-Bianco, Thiosemicarbazones, Transfection, water},
pubstate = {published},
tppubtype = {article}
}
A new series of dendron-functionalized multiwalled carbon nanotube (MWNT) derivatives, characterized by the presence of numerous positively charged tetraalkyl ammonium salts at the periphery of the dendron, has been synthesized. The positive charges on the MWNT surface, coupled with the unique ability of carbon nanotubes (CNTs) to penetrate cell membranes, make the new derivatives potentially ideal vectors for siRNA delivery. Using a fluorescently labeled, noncoding siRNA sequence, we demonstrate that cytoplasmic delivery of the nucleic acid is remarkably increased throughout the different dendron generations. The work reported here highlights the fact that dendron-functionalized CNTs can be rationally designed as efficient carriers of siRNA that can eventually lead to gene silencing.
