2017
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An All-in-One Molecule for the One-Step Synthesis of Functional Hybrid Silica Particles with Tunable Sizes Article de journal J Graffion; D Dems; M Demirelli; T Coradin; N Delsuc; C Aimé European Journal of Inorganic Chemistry, 2017 (43), p. 5047–5051, 2017. @article{Graffion:2017,
title = {An All-in-One Molecule for the One-Step Synthesis of Functional Hybrid Silica Particles with Tunable Sizes},
author = {J Graffion and D Dems and M Demirelli and T Coradin and N Delsuc and C Aim\'{e}},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85035047611&doi=10.1002%2fejic.201701181&partnerID=40&md5=249333f958412776dc6966b033242102},
doi = {10.1002/ejic.201701181},
year = {2017},
date = {2017-01-01},
journal = {European Journal of Inorganic Chemistry},
volume = {2017},
number = {43},
pages = {5047--5051},
abstract = {Spherical particles with well-defined diameters were obtained by self-assembly of trityl-based molecules. Thanks to the robustness of the organic scaffold, a variety of modifications could be covalently introduced into the network so as to stabilize the supramolecular structure by a sol\textendashgel route. Using supramolecular chemistry, we showed that the synthesis of hybrid small molecules allowed engineering nanomaterials with tunable size and functionality. The use of a combination of different characterization techniques, including dynamic light scattering, cryoTEM, and solid-state NMR spectroscopy, provided careful understanding of the relationship between the molecular and supramolecular structures for further chemical engineering of supramolecular hybrid materials. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Spherical particles with well-defined diameters were obtained by self-assembly of trityl-based molecules. Thanks to the robustness of the organic scaffold, a variety of modifications could be covalently introduced into the network so as to stabilize the supramolecular structure by a sol–gel route. Using supramolecular chemistry, we showed that the synthesis of hybrid small molecules allowed engineering nanomaterials with tunable size and functionality. The use of a combination of different characterization techniques, including dynamic light scattering, cryoTEM, and solid-state NMR spectroscopy, provided careful understanding of the relationship between the molecular and supramolecular structures for further chemical engineering of supramolecular hybrid materials. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
2016
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Photophysical properties of single core multimodal probe for imaging (SCoMPI) in a membrane model and in cells Article de journal S Hostachy; J -M Swiecicki; C Sandt; N Delsuc; C Policar Dalton Transactions, 45 (7), p. 2791–2795, 2016. @article{Hostachy:2016,
title = {Photophysical properties of single core multimodal probe for imaging (SCoMPI) in a membrane model and in cells},
author = {S Hostachy and J -M Swiecicki and C Sandt and N Delsuc and C Policar},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84958064177&doi=10.1039%2fc5dt03819g&partnerID=40&md5=fb027086e6424b54b23cc2c11098e273},
doi = {10.1039/c5dt03819g},
year = {2016},
date = {2016-01-01},
journal = {Dalton Transactions},
volume = {45},
number = {7},
pages = {2791--2795},
abstract = {The spectroscopic properties of two luminescent Re(i) tricarbonyl complexes conjugated with two cell-penetrating peptides were examined. Fluorescence experiments and IR quantification in membrane models and in cells showed unexpectedly strong luminescence enhancement for one of the complexes in a lipid environment. © The Royal Society of Chemistry 2016.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The spectroscopic properties of two luminescent Re(i) tricarbonyl complexes conjugated with two cell-penetrating peptides were examined. Fluorescence experiments and IR quantification in membrane models and in cells showed unexpectedly strong luminescence enhancement for one of the complexes in a lipid environment. © The Royal Society of Chemistry 2016. |
New insight into the structural, electrochemical and biological aspects of macroacyclic Cu(II) complexes derived from S-substituted dithiocarbazate schiff bases Article de journal M L Low; L Maigre; M I M Tahir; E R T Tiekink; P Dorlet; R Guillot; T B Ravoof; R Rosli; J -M Pagès; C Policar; N Delsuc; K A Crouse European Journal of Medicinal Chemistry, 120 , p. 1–12, 2016. @article{Low:2016,
title = {New insight into the structural, electrochemical and biological aspects of macroacyclic Cu(II) complexes derived from S-substituted dithiocarbazate schiff bases},
author = {M L Low and L Maigre and M I M Tahir and E R T Tiekink and P Dorlet and R Guillot and T B Ravoof and R Rosli and J -M Pag\`{e}s and C Policar and N Delsuc and K A Crouse},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84967102584&doi=10.1016%2fj.ejmech.2016.04.027&partnerID=40&md5=71cde180942655ac9c57205e82887fcf},
doi = {10.1016/j.ejmech.2016.04.027},
year = {2016},
date = {2016-01-01},
journal = {European Journal of Medicinal Chemistry},
volume = {120},
pages = {1--12},
abstract = {Copper (II) complexes synthesized from the products of condensation of S-methyl- and S-benzyldithiocarbazate with 2,5-hexanedione (SMHDH2 and SBHDH2 respectively) have been characterized using various physicochemical (elemental analysis, molar conductivity, magnetic susceptibility) and spectroscopic (infrared, electronic) methods. The structures of SMHDH2, its copper (II) complex, CuSMHD, and the related CuSBHD complex as well as a pyrrole byproduct, SBPY, have been determined by single crystal X-ray diffraction. In order to provide more insight into the behaviour of the complexes in solution, electron paramagnetic resonance (EPR) and electrochemical experiments were performed. Antibacterial activity and cytotoxicity were evaluated. The compounds, dissolved in 0.5% and 5% DMSO, showed a wide range of antibacterial activity against 10 strains of Gram-positive and Gram-negative bacteria. Investigations of the effects of efflux pumps and membrane penetration on antibacterial activity are reported herein. Antiproliferation activity was observed to be enhanced by complexation with copper. Preliminary screening showed Cu complexes are strongly active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7. © 2016 Published by Elsevier Masson SAS.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Copper (II) complexes synthesized from the products of condensation of S-methyl- and S-benzyldithiocarbazate with 2,5-hexanedione (SMHDH2 and SBHDH2 respectively) have been characterized using various physicochemical (elemental analysis, molar conductivity, magnetic susceptibility) and spectroscopic (infrared, electronic) methods. The structures of SMHDH2, its copper (II) complex, CuSMHD, and the related CuSBHD complex as well as a pyrrole byproduct, SBPY, have been determined by single crystal X-ray diffraction. In order to provide more insight into the behaviour of the complexes in solution, electron paramagnetic resonance (EPR) and electrochemical experiments were performed. Antibacterial activity and cytotoxicity were evaluated. The compounds, dissolved in 0.5% and 5% DMSO, showed a wide range of antibacterial activity against 10 strains of Gram-positive and Gram-negative bacteria. Investigations of the effects of efflux pumps and membrane penetration on antibacterial activity are reported herein. Antiproliferation activity was observed to be enhanced by complexation with copper. Preliminary screening showed Cu complexes are strongly active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7. © 2016 Published by Elsevier Masson SAS. |
Bioinspired superoxide-dismutase mimics: The effects of functionalization with cationic polyarginine peptides Article de journal H Y V Ching; I Kenkel; N Delsuc; E Mathieu; I Ivanović-Burmazović; C Policar Journal of Inorganic Biochemistry, 160 , p. 172–179, 2016. @article{Ching:2016a,
title = {Bioinspired superoxide-dismutase mimics: The effects of functionalization with cationic polyarginine peptides},
author = {H Y V Ching and I Kenkel and N Delsuc and E Mathieu and I Ivanovi\'{c}-Burmazovi\'{c} and C Policar},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84964372716&doi=10.1016%2fj.jinorgbio.2016.01.025&partnerID=40&md5=035d0c2b5ffd4ee0b6fb74df285838da},
doi = {10.1016/j.jinorgbio.2016.01.025},
year = {2016},
date = {2016-01-01},
journal = {Journal of Inorganic Biochemistry},
volume = {160},
pages = {172--179},
abstract = {Continuing a bio-mimetic approach, we have prepared peptide conjugates of a superoxide dismutase (SOD) mimic [MnL]+ (where HL = N-(2-hydroxybenzyl)-N,N'-bis[2-(N-methylimidazolyl)methyl]ethane-1,2-diamine), namely [MnL'-Arg(n-1)]n+ (where n = 2, 4, 7 and 10) and [MnL'-Gly1]+. [MnL'-Arg(n-1)]n+ contained cationic residue(s) that emulate the electrostatic channel of the enzyme. Physicochemical methods showed that functionalization at the secondary amine of HL did not impair coordination to MnII with association constants (Kassoc) between 1.6 and 3.3 × 106 M- 1. The MnIII/MnII redox potential of the conjugates was between 0.27 and 0.30 V vs SCE, slightly higher than [MnL]+ under the same conditions, but remain at a value that facilitates O2•- dismutation. The catalytic rate constant (kcat) of the dismutation for the series was studied using a direct stopped-flow method, which showed that for compounds with the same overall charge, the alkylation of the secondary amine of [MnL]+ (kcat = 5.0 ± 0.1 × 106 M- 1 s- 1) led to a lower value (i.e. for [MnL'Gly]+},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Continuing a bio-mimetic approach, we have prepared peptide conjugates of a superoxide dismutase (SOD) mimic [MnL]+ (where HL = N-(2-hydroxybenzyl)-N,N'-bis[2-(N-methylimidazolyl)methyl]ethane-1,2-diamine), namely [MnL'-Arg(n-1)]n+ (where n = 2, 4, 7 and 10) and [MnL'-Gly1]+. [MnL'-Arg(n-1)]n+ contained cationic residue(s) that emulate the electrostatic channel of the enzyme. Physicochemical methods showed that functionalization at the secondary amine of HL did not impair coordination to MnII with association constants (Kassoc) between 1.6 and 3.3 × 106 M- 1. The MnIII/MnII redox potential of the conjugates was between 0.27 and 0.30 V vs SCE, slightly higher than [MnL]+ under the same conditions, but remain at a value that facilitates O2•- dismutation. The catalytic rate constant (kcat) of the dismutation for the series was studied using a direct stopped-flow method, which showed that for compounds with the same overall charge, the alkylation of the secondary amine of [MnL]+ (kcat = 5.0 ± 0.1 × 106 M- 1 s- 1) led to a lower value (i.e. for [MnL'Gly]+ |
2015
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Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin Article de journal M L Low; G Paulus; P Dorlet; R Guillot; R Rosli; N Delsuc; K A Crouse; C Policar BioMetals, 28 (3), p. 553–566, 2015. @article{Low:2015,
title = {Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin},
author = {M L Low and G Paulus and P Dorlet and R Guillot and R Rosli and N Delsuc and K A Crouse and C Policar},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84939939059&doi=10.1007%2fs10534-015-9831-2&partnerID=40&md5=8d0220a2a88cc9eb122f191d65c87199},
doi = {10.1007/s10534-015-9831-2},
year = {2015},
date = {2015-01-01},
journal = {BioMetals},
volume = {28},
number = {3},
pages = {553--566},
abstract = {Cu(II), Zn(II) and Re(I) complexes have been synthesized with the Schiff base, N′-[1-(2-oxo-2H-chromen-3-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester (SBCM-H) which was prepared by condensation of S-benzyldithiocarbazate and 3-acetylcoumarin. The metal complexes were characterized on the basis of various physico-chemical and spectroscopic techniques including elemental analysis and electrochemical studies, and FT-IR, UV-Vis, NMR, EPR and mass spectroscopy. The Schiff base was found to behave as a bidentate ligand coordinating with Cu(II) and Zn(II) in the thiolate form with 1:2 metal to ligand stoichiometry. Crystals suitable for X-ray diffractometry (XRD) were obtained from the reaction of ReCl(CO)5 with SBCM-H forming a centrosymmetric dimeric complex Re2L2(CO)6 linked by Re-S-Re bridges, where S is the thiolate sulfur of the N,S-bidentate ligand. This Re(I) complex is the first metal carbonyl complex with a bidentate dithiocarbazate ligand to have been characterized by XRD. Cytotoxicity assays revealed enhancement of the bioactivity of SBCM-H upon complexation. Both Cu(II) and Re(I) complexes are found to be active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7. Graphical Abstract: TOC diagram [Figure not available: see fulltext.] © 2015 Springer Science+Business Media New York.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Cu(II), Zn(II) and Re(I) complexes have been synthesized with the Schiff base, N′-[1-(2-oxo-2H-chromen-3-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester (SBCM-H) which was prepared by condensation of S-benzyldithiocarbazate and 3-acetylcoumarin. The metal complexes were characterized on the basis of various physico-chemical and spectroscopic techniques including elemental analysis and electrochemical studies, and FT-IR, UV-Vis, NMR, EPR and mass spectroscopy. The Schiff base was found to behave as a bidentate ligand coordinating with Cu(II) and Zn(II) in the thiolate form with 1:2 metal to ligand stoichiometry. Crystals suitable for X-ray diffractometry (XRD) were obtained from the reaction of ReCl(CO)5 with SBCM-H forming a centrosymmetric dimeric complex Re2L2(CO)6 linked by Re-S-Re bridges, where S is the thiolate sulfur of the N,S-bidentate ligand. This Re(I) complex is the first metal carbonyl complex with a bidentate dithiocarbazate ligand to have been characterized by XRD. Cytotoxicity assays revealed enhancement of the bioactivity of SBCM-H upon complexation. Both Cu(II) and Re(I) complexes are found to be active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7. Graphical Abstract: TOC diagram [Figure not available: see fulltext.] © 2015 Springer Science+Business Media New York. |
An easy-to-detect nona-arginine peptide for epidermal targeting Article de journal S Clède; N Delsuc; C Laugel; F Lambert; C Sandt; A Baillet-Guffroy; C Policar Chemical Communications, 51 (13), p. 2687–2689, 2015. @article{Clede:2015a,
title = {An easy-to-detect nona-arginine peptide for epidermal targeting},
author = {S Cl\`{e}de and N Delsuc and C Laugel and F Lambert and C Sandt and A Baillet-Guffroy and C Policar},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84922637409&doi=10.1039%2fc4cc08737b&partnerID=40&md5=a0e333e8498570e4d4ceb500066d9c1e},
doi = {10.1039/c4cc08737b},
year = {2015},
date = {2015-01-01},
journal = {Chemical Communications},
volume = {51},
number = {13},
pages = {2687--2689},
abstract = {A correlative approach combining synchrotron radiation based IR microscopy and fluorescence microscopy enabled the successful detection and quantification of a nona-arginine peptide labelled with a Single Core Multimodal Probe for Imaging (SCoMPI) in skin biopsies. The topical penetration of the conjugate appeared to be time dependent and occurred most probably via the extracellular matrix. This journal is © The Royal Society of Chemistry 2015.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
A correlative approach combining synchrotron radiation based IR microscopy and fluorescence microscopy enabled the successful detection and quantification of a nona-arginine peptide labelled with a Single Core Multimodal Probe for Imaging (SCoMPI) in skin biopsies. The topical penetration of the conjugate appeared to be time dependent and occurred most probably via the extracellular matrix. This journal is © The Royal Society of Chemistry 2015. |
2014
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Conjugation of a new series of dithiocarbazate schiff base copper(II) complexes with vectors selected to enhance antibacterial activity Article de journal M L Low; L Maigre; P Dorlet; R Guillot; J -M Pagès; K A Crouse; C Policar; N Delsuc Bioconjugate Chemistry, 25 (12), p. 2269–2284, 2014. @article{Low:2014,
title = {Conjugation of a new series of dithiocarbazate schiff base copper(II) complexes with vectors selected to enhance antibacterial activity},
author = {M L Low and L Maigre and P Dorlet and R Guillot and J -M Pag\`{e}s and K A Crouse and C Policar and N Delsuc},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84918505283&doi=10.1021%2fbc5004907&partnerID=40&md5=d51ad81235fa7fd9aec14b7acd2c908a},
doi = {10.1021/bc5004907},
year = {2014},
date = {2014-01-01},
journal = {Bioconjugate Chemistry},
volume = {25},
number = {12},
pages = {2269--2284},
abstract = {A new series of six Schiff bases derived from S-methyldithiocarbazate (SMDTC) and S-benzyldithiocarbazate (SBDTC) with methyl levulinate (SMML, SBML), levulinic acid (SMLA, SBLA), and 4-carboxybenzaldehyde (SM4CB, SB4CB) were reacted with copper(II), producing complexes of general formula MLtextlessinftextgreater2textless/inftextgreater (M = Cu(II)},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
A new series of six Schiff bases derived from S-methyldithiocarbazate (SMDTC) and S-benzyldithiocarbazate (SBDTC) with methyl levulinate (SMML, SBML), levulinic acid (SMLA, SBLA), and 4-carboxybenzaldehyde (SM4CB, SB4CB) were reacted with copper(II), producing complexes of general formula MLtextlessinftextgreater2textless/inftextgreater (M = Cu(II) |
Anti-oxidant Mn-complexes: evaluation in cellular models of oxidative stress Article de journal Clotilde Policar; Anne-Sophie Bernard; Nicolas Delsuc; Geraldine Gazzah; Manon Guille; Frederic Lemaitre; Christian Amatore; Maria Bachelet; Joelle Masliah Journal of Biological Inorganic Chemistry, 19 , p. S739-S740, 2014, (Times Cited: 0
2
12th European Biological Inorganic Chemistry Conference (EuroBIC)
Aug 24-28, 2014
Zurich, SWITZERLAND
Univ Zurich). @article{,
title = {Anti-oxidant Mn-complexes: evaluation in cellular models of oxidative stress},
author = {Clotilde Policar and Anne-Sophie Bernard and Nicolas Delsuc and Geraldine Gazzah and Manon Guille and Frederic Lemaitre and Christian Amatore and Maria Bachelet and Joelle Masliah},
year = {2014},
date = {2014-01-01},
journal = {Journal of Biological Inorganic Chemistry},
volume = {19},
pages = {S739-S740},
note = {Times Cited: 0
2
12th European Biological Inorganic Chemistry Conference (EuroBIC)
Aug 24-28, 2014
Zurich, SWITZERLAND
Univ Zurich},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
From IR-Spectromicroscopy using AFM-IR and SR-FTIR to Bimodal Spectromicroscopy using SCoMPIs - Single Core Multimodal Probe for Imaging Article de journal C Policar; C Sylvain; F Lambert; N Delsuc; C Sandt; P Dumas; M Refregiers; M Plamont; A Vessieres; Z Gueroui; A Dazzi Journal of Biological Inorganic Chemistry, 19 , p. S182-S182, 2014, ISSN: 0949-8257. @article{RN23c,
title = {From IR-Spectromicroscopy using AFM-IR and SR-FTIR to Bimodal Spectromicroscopy using SCoMPIs - Single Core Multimodal Probe for Imaging},
author = {C Policar and C Sylvain and F Lambert and N Delsuc and C Sandt and P Dumas and M Refregiers and M Plamont and A Vessieres and Z Gueroui and A Dazzi},
url = {<Go to ISI>://WOS:000332835300124},
issn = {0949-8257},
year = {2014},
date = {2014-01-01},
journal = {Journal of Biological Inorganic Chemistry},
volume = {19},
pages = {S182-S182},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
2013
|
Synchrotron radiation FTIR detection of a metal-carbonyl tamoxifen analog. Correlation with luminescence microscopy to study its subcellular distribution Article de journal S Clède; F Lambert; C Sandt; Z Gueroui; N Delsuc; P Dumas; A Vessières; C Policar Biotechnology Advances, 31 (3), p. 393–395, 2013. @article{Clede:2013,
title = {Synchrotron radiation FTIR detection of a metal-carbonyl tamoxifen analog. Correlation with luminescence microscopy to study its subcellular distribution},
author = {S Cl\`{e}de and F Lambert and C Sandt and Z Gueroui and N Delsuc and P Dumas and A Vessi\`{e}res and C Policar},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84875055388&doi=10.1016%2fj.biotechadv.2012.01.023&partnerID=40&md5=064b36e2db4e1260e17d3abc8b07bbd6},
doi = {10.1016/j.biotechadv.2012.01.023},
year = {2013},
date = {2013-01-01},
journal = {Biotechnology Advances},
volume = {31},
number = {3},
pages = {393--395},
abstract = {1,1-Di(4-hydroxyphenyl)-2-cyrhetrenylbut-1-ene 1 is an organometallic conjugate where a [(Cp)Re(CO)3] unit is linked to a hydroxytamoxifen-like structure. Its subcellular nuclear distribution was previously observed in a single cell using the near-field technique AFMIR. We show here that synchrotron radiation FTIR spectromicroscopy (SR-FTIR-SM) enabled the mapping of 1 based on its IR-signature (characteristic bands in the 1850-2200cm-1 range) and pointed out the colocalization of 1 with an area of high amide density. Fluorescence microscopy using DAPI staining performed on the same cells confirmed that this area corresponds to the cell nucleus. © 2012 Elsevier Inc.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
1,1-Di(4-hydroxyphenyl)-2-cyrhetrenylbut-1-ene 1 is an organometallic conjugate where a [(Cp)Re(CO)3] unit is linked to a hydroxytamoxifen-like structure. Its subcellular nuclear distribution was previously observed in a single cell using the near-field technique AFMIR. We show here that synchrotron radiation FTIR spectromicroscopy (SR-FTIR-SM) enabled the mapping of 1 based on its IR-signature (characteristic bands in the 1850-2200cm-1 range) and pointed out the colocalization of 1 with an area of high amide density. Fluorescence microscopy using DAPI staining performed on the same cells confirmed that this area corresponds to the cell nucleus. © 2012 Elsevier Inc. |
Homooligomers of substituted prolines and β-prolines: Syntheses and secondary structure investigation Article de journal C Caumes; N Delsuc; R B Azza; I Correia; F Chemla; F Ferreira; L Carlier; A P Luna; R Moumné; O Lequin; P Karoyan New Journal of Chemistry, 37 (5), p. 1312–1319, 2013. @article{Caumes:2013,
title = {Homooligomers of substituted prolines and β-prolines: Syntheses and secondary structure investigation},
author = {C Caumes and N Delsuc and R B Azza and I Correia and F Chemla and F Ferreira and L Carlier and A P Luna and R Moumn\'{e} and O Lequin and P Karoyan},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84876740702&doi=10.1039%2fc3nj00127j&partnerID=40&md5=dbda08d94a12bcb6b260393c90dd6af4},
doi = {10.1039/c3nj00127j},
year = {2013},
date = {2013-01-01},
journal = {New Journal of Chemistry},
volume = {37},
number = {5},
pages = {1312--1319},
abstract = {Homooligomers of enantiomerically pure (2S,3R)-3-methyl-proline, (3R,4R)-4-methyl-β-proline and (3R,4S)-3,4-dimethyl-β-proline were synthesized and studied using circular dichroism (CD) in water, methanol and propanol and using NMR in water. Changes in the far-UV CD spectrum were observed from dimers to hexamers, but little change was observed from hexamers to octa- or nonamers, both in water and methanol. CD and NMR data allowed us to conclude that oligomers of 3-substituted prolines with more than six residues adopt a characteristic PPII secondary structure both in water and aliphatic alcohols. Oligomers of (3R,4R)-4-methyl-β-proline bear the same CD signature as non-substituted β-proline oligomers, suggesting that substitution at position 3 is not sufficient to reduce conformational heterogeneity in β-proline oligomers. In the case of 3,4-disubstituted-β-proline oligomers, an atypical signature with an extra negative band at around 225 nm was observed, together with a concentration dependent CD spectrum indicating association properties. Nevertheless, NMR studies of 13C labelled oligomers of 3,4-disubstituted-β-prolines revealed a complex mixture of cis-trans conformers even for longer oligomers. © 2913 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Homooligomers of enantiomerically pure (2S,3R)-3-methyl-proline, (3R,4R)-4-methyl-β-proline and (3R,4S)-3,4-dimethyl-β-proline were synthesized and studied using circular dichroism (CD) in water, methanol and propanol and using NMR in water. Changes in the far-UV CD spectrum were observed from dimers to hexamers, but little change was observed from hexamers to octa- or nonamers, both in water and methanol. CD and NMR data allowed us to conclude that oligomers of 3-substituted prolines with more than six residues adopt a characteristic PPII secondary structure both in water and aliphatic alcohols. Oligomers of (3R,4R)-4-methyl-β-proline bear the same CD signature as non-substituted β-proline oligomers, suggesting that substitution at position 3 is not sufficient to reduce conformational heterogeneity in β-proline oligomers. In the case of 3,4-disubstituted-β-proline oligomers, an atypical signature with an extra negative band at around 225 nm was observed, together with a concentration dependent CD spectrum indicating association properties. Nevertheless, NMR studies of 13C labelled oligomers of 3,4-disubstituted-β-prolines revealed a complex mixture of cis-trans conformers even for longer oligomers. © 2913 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. |
3-substituted prolines: From synthesis to structural applications, from peptides to foldamers Article de journal C Mothes; C Caumes; A Guez; H Boullet; T Gendrineau; S Darses; N Delsuc; R Moumné; B Oswald; O Lequin; P Karoyan Molecules, 18 (2), p. 2307–2327, 2013. @article{Mothes:2013,
title = {3-substituted prolines: From synthesis to structural applications, from peptides to foldamers},
author = {C Mothes and C Caumes and A Guez and H Boullet and T Gendrineau and S Darses and N Delsuc and R Moumn\'{e} and B Oswald and O Lequin and P Karoyan},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84874605320&doi=10.3390%2fmolecules18022307&partnerID=40&md5=05828aecf601bf07f9a0a6a3fec4e28c},
doi = {10.3390/molecules18022307},
year = {2013},
date = {2013-01-01},
journal = {Molecules},
volume = {18},
number = {2},
pages = {2307--2327},
abstract = {Among the twenty natural proteinogenic amino acids, proline is unique as its secondary amine forms a tertiary amide when incorporated into biopolymers, thus preventing hydrogen bond formation. Despite the lack of hydrogen bonds and thanks to conformational restriction of flexibility linked to the pyrrolidine ring, proline is able to stabilize peptide secondary structures such as -turns or polyproline helices. These unique conformational properties have aroused a great interest in the development of proline analogues. Among them, proline chimeras are tools combining the proline restriction of flexibility together with the information brought by natural amino acids side chains. This review will focus on the chemical syntheses of 3-substituted proline chimeras of potential use for peptide syntheses and as potential use as tools for SAR studies of biologically active peptides and the development of secondary structure mimetics. Their influence on peptide structure will be briefly described. © 2013 by the authors.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Among the twenty natural proteinogenic amino acids, proline is unique as its secondary amine forms a tertiary amide when incorporated into biopolymers, thus preventing hydrogen bond formation. Despite the lack of hydrogen bonds and thanks to conformational restriction of flexibility linked to the pyrrolidine ring, proline is able to stabilize peptide secondary structures such as -turns or polyproline helices. These unique conformational properties have aroused a great interest in the development of proline analogues. Among them, proline chimeras are tools combining the proline restriction of flexibility together with the information brought by natural amino acids side chains. This review will focus on the chemical syntheses of 3-substituted proline chimeras of potential use for peptide syntheses and as potential use as tools for SAR studies of biologically active peptides and the development of secondary structure mimetics. Their influence on peptide structure will be briefly described. © 2013 by the authors. |
2011
|
Relative helix-helix conformations in branched aromatic oligoamide foldamers Article de journal N Delsuc; S Massip; J -M Léger; B Kauffmann; I Huc Journal of the American Chemical Society, 133 (9), p. 3165–3172, 2011. @article{Delsuc:2011,
title = {Relative helix-helix conformations in branched aromatic oligoamide foldamers},
author = {N Delsuc and S Massip and J -M L\'{e}ger and B Kauffmann and I Huc},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-79952263733&doi=10.1021%2fja110677a&partnerID=40&md5=36f1e84ade60bac4aee1c82b34b28b99},
doi = {10.1021/ja110677a},
year = {2011},
date = {2011-01-01},
journal = {Journal of the American Chemical Society},
volume = {133},
number = {9},
pages = {3165--3172},
abstract = {The de novo design and synthesis of large and well-organized, tertiary-like, α-peptidic folded architectures is difficult because it relies on multiple cooperative interactions within and between secondary folded motifs of relatively weak intrinsic stability. The very stable helical structures of oligoamides of 8-amino-2-quinoline carboxylic acid offer a way to circumvent this difficulty thanks to their ability to fold into predictable and stable secondary motifs. Branched architectures comprised of two pairs of tetrameric (1), pentameric (2), or octameric (3) oligomers connected via an ethylene glycol spacer were designed and synthesized. The short spacer holds two helices in close proximity, thus enabling interactions between them. Degrees of freedom allowed in the system are well-defined: the relative P or M handedness of the two helices; the relative orientation of the helix axes; and the gauche or anti conformation of the ethylene spacer. Investigating the structures of 1-3 in the solid state and in solution allowed a detailed picture to be drawn of their conformational preferences and dynamics. The high variability of the solid state structures provides many snapshots of possible solution conformations. Helix-helix handedness communication was evidenced and shown to depend both on solvent and on a defined set of side chains at the helix-helix interface. Interdigitation of the side chains was found to restrict free rotation about the ethylene spacer. One solid state structure shows a high level of symmetry and provides a firm basis to further design specific side chain/side chain directional interactions. © 2011 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The de novo design and synthesis of large and well-organized, tertiary-like, α-peptidic folded architectures is difficult because it relies on multiple cooperative interactions within and between secondary folded motifs of relatively weak intrinsic stability. The very stable helical structures of oligoamides of 8-amino-2-quinoline carboxylic acid offer a way to circumvent this difficulty thanks to their ability to fold into predictable and stable secondary motifs. Branched architectures comprised of two pairs of tetrameric (1), pentameric (2), or octameric (3) oligomers connected via an ethylene glycol spacer were designed and synthesized. The short spacer holds two helices in close proximity, thus enabling interactions between them. Degrees of freedom allowed in the system are well-defined: the relative P or M handedness of the two helices; the relative orientation of the helix axes; and the gauche or anti conformation of the ethylene spacer. Investigating the structures of 1-3 in the solid state and in solution allowed a detailed picture to be drawn of their conformational preferences and dynamics. The high variability of the solid state structures provides many snapshots of possible solution conformations. Helix-helix handedness communication was evidenced and shown to depend both on solvent and on a defined set of side chains at the helix-helix interface. Interdigitation of the side chains was found to restrict free rotation about the ethylene spacer. One solid state structure shows a high level of symmetry and provides a firm basis to further design specific side chain/side chain directional interactions. © 2011 American Chemical Society. |
2010
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Cascading transformations within a dynamic self-assembled system Article de journal Victoria E Campbell; Xavier de Hatten; Nicolas Delsuc; Brice Kauffmann; Ivan Huc; Jonathan R Nitschke Nature Chemistry, 2 (8), p. 684–687, 2010, ISSN: 1755-4349. @article{campbell_cascading_2010,
title = {Cascading transformations within a dynamic self-assembled system},
author = {Victoria E Campbell and Xavier de Hatten and Nicolas Delsuc and Brice Kauffmann and Ivan Huc and Jonathan R Nitschke},
url = {https://www.nature.com/articles/nchem.693},
doi = {10.1038/nchem.693},
issn = {1755-4349},
year = {2010},
date = {2010-01-01},
urldate = {2018-03-06},
journal = {Nature Chemistry},
volume = {2},
number = {8},
pages = {684--687},
abstract = {Molecular subcomponents such as phosphate groups are often passed between biomolecules during complex signalling cascades, the flow of which define the motion of the machinery of life. Here, we show how an abiological system consisting of organic subcomponents knitted together by metal-ion coordination can respond to simple signals in complex ways. A CuI3 helicate transformed into its ZnII2CuI analogue following the addition of zinc(II), and the ejected copper(I) went on to induce the self-assembly of a CuI2 helicate from other free subcomponents present in solution. The addition of an additional subcomponent, 8-aminoquinoline, resulted in the formation of a third, more stable CuI3 helicate, requiring the destruction of both the ZnII2CuI and CuI2 helicates to scavenge sufficient CuI for the new structure. This system thus demonstrates two examples in which the application of one signal provokes two distinct responses involving the creation or destruction of complex assemblies as the system seeks thermodynamic equilibrium following perturbation.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Molecular subcomponents such as phosphate groups are often passed between biomolecules during complex signalling cascades, the flow of which define the motion of the machinery of life. Here, we show how an abiological system consisting of organic subcomponents knitted together by metal-ion coordination can respond to simple signals in complex ways. A CuI3 helicate transformed into its ZnII2CuI analogue following the addition of zinc(II), and the ejected copper(I) went on to induce the self-assembly of a CuI2 helicate from other free subcomponents present in solution. The addition of an additional subcomponent, 8-aminoquinoline, resulted in the formation of a third, more stable CuI3 helicate, requiring the destruction of both the ZnII2CuI and CuI2 helicates to scavenge sufficient CuI for the new structure. This system thus demonstrates two examples in which the application of one signal provokes two distinct responses involving the creation or destruction of complex assemblies as the system seeks thermodynamic equilibrium following perturbation. |
2009
|
Interplay of Interactions Governing the Dynamic Conversions of Acyclic and Macrocyclic Helicates Article de journal Victoria E. Campbell; Xavier de Hatten; Nicolas Delsuc; Brice Kauffmann; Ivan Huc; Jonathan R. Nitschke Chemistry - A European Journal, 15 (25), p. 6138–6142, 2009, ISSN: 09476539, 15213765. @article{campbell_interplay_2009,
title = {Interplay of Interactions Governing the Dynamic Conversions of Acyclic and Macrocyclic Helicates},
author = {Victoria E. Campbell and Xavier de Hatten and Nicolas Delsuc and Brice Kauffmann and Ivan Huc and Jonathan R. Nitschke},
url = {http://doi.wiley.com/10.1002/chem.200900693},
doi = {10.1002/chem.200900693},
issn = {09476539, 15213765},
year = {2009},
date = {2009-01-01},
urldate = {2018-02-18},
journal = {Chemistry - A European Journal},
volume = {15},
number = {25},
pages = {6138--6142},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
Helical Aromatic Oligoamide Foldamers as Organizational Scaffolds for Photoinduced Charge Transfer Article de journal Martin Wolffs; Nicolas Delsuc; Dirk Veldman; Nguyễn Vân Anh; René M Williams; Stefan C J Meskers; René A J Janssen; Ivan Huc; Albertus P H J Schenning Journal of the American Chemical Society, 131 (13), p. 4819–4829, 2009, ISSN: 0002-7863, 1520-5126. @article{wolffs_helical_2009,
title = {Helical Aromatic Oligoamide Foldamers as Organizational Scaffolds for Photoinduced Charge Transfer},
author = {Martin Wolffs and Nicolas Delsuc and Dirk Veldman and Nguyễn V\^{a}n Anh and Ren\'{e} M Williams and Stefan C J Meskers and Ren\'{e} A J Janssen and Ivan Huc and Albertus P H J Schenning},
url = {http://pubs.acs.org/doi/abs/10.1021/ja809367u},
doi = {10.1021/ja809367u},
issn = {0002-7863, 1520-5126},
year = {2009},
date = {2009-01-01},
urldate = {2018-02-18},
journal = {Journal of the American Chemical Society},
volume = {131},
number = {13},
pages = {4819--4829},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
2008
|
Metal-Directed Dynamic Formation of Tertiary Structure in Foldamer Assemblies: Orienting Helices at an Angle Article de journal Nicolas Delsuc; Marie Hutin; Victoria E. Campbell; Brice Kauffmann; Jonathan R. Nitschke; Ivan Huc Chemistry - A European Journal, 14 (24), p. 7140–7143, 2008, ISSN: 09476539, 15213765. @article{delsuc_metal-directed_2008,
title = {Metal-Directed Dynamic Formation of Tertiary Structure in Foldamer Assemblies: Orienting Helices at an Angle},
author = {Nicolas Delsuc and Marie Hutin and Victoria E. Campbell and Brice Kauffmann and Jonathan R. Nitschke and Ivan Huc},
url = {http://doi.wiley.com/10.1002/chem.200800988},
doi = {10.1002/chem.200800988},
issn = {09476539, 15213765},
year = {2008},
date = {2008-01-01},
urldate = {2018-02-18},
journal = {Chemistry - A European Journal},
volume = {14},
number = {24},
pages = {7140--7143},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
Kinetics of Helix-Handedness Inversion: Folding and Unfolding in Aromatic Amide Oligomers Article de journal Nicolas Delsuc; Takahiro Kawanami; Julien Lefeuvre; Atsuomi Shundo; Hirotaka Ihara; Makoto Takafuji; Ivan Huc ChemPhysChem, 9 (13), p. 1882–1890, 2008, ISSN: 14394235, 14397641. @article{delsuc_kinetics_2008,
title = {Kinetics of Helix-Handedness Inversion: Folding and Unfolding in Aromatic Amide Oligomers},
author = {Nicolas Delsuc and Takahiro Kawanami and Julien Lefeuvre and Atsuomi Shundo and Hirotaka Ihara and Makoto Takafuji and Ivan Huc},
url = {http://doi.wiley.com/10.1002/cphc.200800310},
doi = {10.1002/cphc.200800310},
issn = {14394235, 14397641},
year = {2008},
date = {2008-01-01},
urldate = {2018-02-18},
journal = {ChemPhysChem},
volume = {9},
number = {13},
pages = {1882--1890},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
2007
|
Proteomorphous Objects from Abiotic Backbones Article de journal Nicolas Delsuc; Jean-Michel Léger; Stéphane Massip; Ivan Huc Angewandte Chemie International Edition, 46 (1-2), p. 214–217, 2007, ISSN: 14337851, 15213773. @article{delsuc_proteomorphous_2007,
title = {Proteomorphous Objects from Abiotic Backbones},
author = {Nicolas Delsuc and Jean-Michel L\'{e}ger and St\'{e}phane Massip and Ivan Huc},
url = {http://doi.wiley.com/10.1002/anie.200603390},
doi = {10.1002/anie.200603390},
issn = {14337851, 15213773},
year = {2007},
date = {2007-01-01},
urldate = {2018-02-18},
journal = {Angewandte Chemie International Edition},
volume = {46},
number = {1-2},
pages = {214--217},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
The Herringbone Helix: A Noncanonical Folding in Aromatic−Aliphatic Peptides Article de journal Nicolas Delsuc; Frédéric Godde; Brice Kauffmann; Jean-Michel Léger; Ivan Huc Journal of the American Chemical Society, 129 (37), p. 11348–11349, 2007, ISSN: 0002-7863, 1520-5126. @article{delsuc_herringbone_2007,
title = {The Herringbone Helix: A Noncanonical Folding in Aromatic−Aliphatic Peptides},
author = {Nicolas Delsuc and Fr\'{e}d\'{e}ric Godde and Brice Kauffmann and Jean-Michel L\'{e}ger and Ivan Huc},
url = {http://pubs.acs.org/doi/abs/10.1021/ja074285s},
doi = {10.1021/ja074285s},
issn = {0002-7863, 1520-5126},
year = {2007},
date = {2007-01-01},
urldate = {2018-02-18},
journal = {Journal of the American Chemical Society},
volume = {129},
number = {37},
pages = {11348--11349},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
2006
|
Vibrational circular dichroism and ab initio structure elucidation of an aromatic foldamer Article de journal Thierry Buffeteau; Laurent Ducasse; Legiso Poniman; Nicolas Delsuc; Ivan Huc Chemical Communications, (25), p. 2714, 2006, ISSN: 1359-7345, 1364-548X. @article{buffeteau_vibrational_2006,
title = {Vibrational circular dichroism and ab initio structure elucidation of an aromatic foldamer},
author = {Thierry Buffeteau and Laurent Ducasse and Legiso Poniman and Nicolas Delsuc and Ivan Huc},
url = {http://xlink.rsc.org/?DOI=b604462j},
doi = {10.1039/b604462j},
issn = {1359-7345, 1364-548X},
year = {2006},
date = {2006-01-01},
urldate = {2018-02-18},
journal = {Chemical Communications},
number = {25},
pages = {2714},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
2005
|
Probing helix propensity of monomers within a helical oligomer Article de journal Christel Dolain; Jean-Michel Léger; Nicolas Delsuc; Heinz Gornitzka; Ivan Huc Proceedings of the National Academy of Sciences of the United States of America, 102 (45), p. 16146–16151, 2005. @article{dolain_probing_2005,
title = {Probing helix propensity of monomers within a helical oligomer},
author = {Christel Dolain and Jean-Michel L\'{e}ger and Nicolas Delsuc and Heinz Gornitzka and Ivan Huc},
year = {2005},
date = {2005-01-01},
journal = {Proceedings of the National Academy of Sciences of the United States of America},
volume = {102},
number = {45},
pages = {16146--16151},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
