Engineering short peptide sequences for uranyl binding.

Peptides are interesting tools to rationalize uranyl-protein interactions, which are relevant to uranium toxicity in vivo. Structured cyclic peptide scaffolds were chosen as promising candidates to coordinate uranyl thanks to four amino acid side chains pre-oriented towards the dioxo cation equatorial plane. The binding of uranyl by a series of decapeptides has been investigated with complementary analytical and spectroscopic methods to determine the key parameters for the formation of stable uranyl-peptide complexes. The molar ellipticity of the uranyl complex at 195 nm is directly correlated to its stability, which demonstrates that the β-sheet structure is optimal for high stability in the peptide series. Cyclodecapeptides with four glutamate residues exhibit the highest affinities for uranyl with log KC =8.0-8.4 and, therefore, appear as good starting points for the design of high-affinity uranyl-chelating peptides.

[1]  C. Gateau,et al.  Design of intrahepatocyte copper(I) chelators as drug candidates for Wilson's disease , 2014, Annals of the New York Academy of Sciences.

[2]  D. Testemale,et al.  D-Penicillamine tripodal derivatives as efficient copper(I) chelators. , 2014, Inorganic chemistry.

[3]  Luhua Lai,et al.  A protein engineered to bind uranyl selectively and with femtomolar affinity. , 2014, Nature chemistry.

[4]  C. Vidaud,et al.  Characterization of UO2(2+) binding to osteopontin, a highly phosphorylated protein: insights into potential mechanisms of uranyl accumulation in bones. , 2014, Metallomics : integrated biometal science.

[5]  G. Creff,et al.  Osteopontin: a uranium phosphorylated binding-site characterization. , 2013, Chemistry.

[6]  D. Testemale,et al.  X-ray absorption spectroscopy proves the trigonal-planar sulfur-only coordination of copper(I) with high-affinity tripodal pseudopeptides. , 2013, Inorganic chemistry.

[7]  G. Deblonde,et al.  Solution thermodynamic evaluation of hydroxypyridinonate chelators 3,4,3-LI(1,2-HOPO) and 5-LIO(Me-3,2-HOPO) for UO2(VI) and Th(IV) decorporation , 2013 .

[8]  C. Lebrun,et al.  Rational design of lanthanide binding peptides , 2013 .

[9]  C. Vidaud,et al.  Revision of the biodistribution of uranyl in serum: is fetuin-A the major protein target? , 2013, Chemical research in toxicology.

[10]  A. Fragoso,et al.  Copper(II) coordination properties of decapeptides containing three His residues: the impact of cyclization and Asp residue coordination. , 2013, Dalton transactions.

[11]  A. Fragoso,et al.  Harnessing the flexibility of peptidic scaffolds to control their copper(II)-coordination properties: a potentiometric and spectroscopic study. , 2013, Chemistry.

[12]  Fangting Yu,et al.  Designing a functional type 2 copper center that has nitrite reductase activity within α-helical coiled coils , 2012, Proceedings of the National Academy of Sciences.

[13]  C. Soares,et al.  Design of a peptidic turn with high affinity for Hg(II). , 2012, Inorganic chemistry.

[14]  C. Berthomieu,et al.  Modulating Uranium Binding Affinity in Engineered Calmodulin EF-Hand Peptides: Effect of Phosphorylation , 2012, PloS one.

[15]  A. Manceau,et al.  Mercury-Sequestering Pseudopeptides with a Tris(cysteine) Environment in Water , 2012 .

[16]  D. Cassio,et al.  A sulfur tripod glycoconjugate that releases a high-affinity copper chelator in hepatocytes. , 2012, Angewandte Chemie.

[17]  C. Lebrun,et al.  Femtomolar Ln(III) affinity in peptide-based ligands containing unnatural chelating amino acids. , 2012, Inorganic chemistry.

[18]  C. Lebrun,et al.  Lanthanide-binding peptides with two pendant aminodiacetate arms: impact of the sequence on chelation. , 2012, Dalton transactions.

[19]  L. Hemmingsen,et al.  Towards the role of metal ions in the structural variability of proteins: CdII speciation of a metal ion binding loop motif. , 2011, Metallomics : integrated biometal science.

[20]  C. Lebrun,et al.  A series of tripodal cysteine derivatives as water-soluble chelators that are highly selective for copper(I). , 2011, Chemistry.

[21]  D. Boturyn,et al.  Access to biomolecular assemblies through one-pot triple orthogonal chemoselective ligations. , 2011, Angewandte Chemie.

[22]  O. Renaudet,et al.  Hepatocyte targeting and intracellular copper chelation by a thiol-containing glycocyclopeptide. , 2011, Journal of the American Chemical Society.

[23]  C. Vidaud,et al.  Surface plasmon resonance for rapid screening of uranyl affine proteins. , 2010, Analytical chemistry.

[24]  J. Pellequer,et al.  Predicting the disruption by UO22+ of a protein‐ligand interaction , 2010, Protein science : a publication of the Protein Society.

[25]  Deborah I. Bunin,et al.  Biomimetic actinide chelators: an update on the preclinical development of the orally active hydroxypyridonate decorporation agents 3,4,3-LI(1,2-HOPO) and 5-LIO(Me-3,2-HOPO). , 2010, Health physics.

[26]  P. Fries,et al.  Outer-sphere investigation of MRI relaxation contrast agents. Example of a cyclodecapeptide gadolinium complex with second-sphere water. , 2010, The journal of physical chemistry. B.

[27]  P. Labbé,et al.  Template-assembled synthetic G-quadruplex (TASQ): a useful system for investigating the interactions of ligands with constrained quadruplex topologies. , 2010, Chemistry.

[28]  C. Lebrun,et al.  A lanthanide binding peptide with short chelating side-chains: structural impact of the backbone coordination. , 2010, Dalton transactions.

[29]  C. Garnier,et al.  Determinations of Uranium(VI) Binding Properties with some Metalloproteins (Transferrin, Albumin, Metallothionein and Ferritin) by Fluorescence Quenching , 2010, Journal of Fluorescence.

[30]  C. Apostolidis,et al.  Spectroscopic study of the interaction of U(VI) with transferrin and albumin for speciation of U(VI) under blood serum conditions. , 2009, Journal of inorganic biochemistry.

[31]  C. Lebrun,et al.  Lanthanide(III) complexes with two hexapeptides incorporating unnatural chelating amino acids: secondary structure and stability. , 2009, Chemistry.

[32]  D. Boturyn,et al.  A gadolinium-binding cyclodecapeptide with a large high-field relaxivity involving second-sphere water. , 2009, Chemistry.

[33]  C. Vidaud,et al.  Identification of uranyl binding proteins from human kidney-2 cell extracts by immobilized uranyl affinity chromatography and mass spectrometry. , 2009, Journal of chromatography. A.

[34]  V. Pecoraro,et al.  Understanding the biological chemistry of mercury using a de novo protein design strategy , 2009 .

[35]  C. Lebrun,et al.  A cysteine-based tripodal chelator with a high affinity and selectivity for copper(I). , 2009, Journal of the American Chemical Society.

[36]  Chuan He,et al.  Engineering a uranyl-specific binding protein from NikR. , 2009, Angewandte Chemie.

[37]  C. Vidaud,et al.  Specific capture of uranyl protein targets by metal affinity chromatography. , 2008, Journal of chromatography. A.

[38]  C. Vidaud,et al.  High-affinity uranyl-specific antibodies suitable for cellular imaging. , 2008, Chemical research in toxicology.

[39]  P. Durbin.  Actinides in Animals and Man , 2008 .

[40]  C. Auwer,et al.  Review of actinide decorporation with chelating agents , 2007 .

[41]  L. Rao,et al.  Complexation of UVI with 1-hydroxyethane-1,1-diphosphonic acid in acidic to basic solutions. , 2007, Inorganic chemistry.

[42]  C. Vidaud,et al.  Structural consequences of binding of UO2(2+) to apotransferrin: can this protein account for entry of uranium into human cells? , 2007, Biochemistry.

[43]  J. Pellequer,et al.  Structural insights into protein-uranyl interaction: towards an in silico detection method. , 2006, Biochimie.

[44]  M. Carrière,et al.  Actinide speciation in relation to biological processes. , 2006, Biochimie.

[45]  M. Ferrand,et al.  Model peptides based on the binding loop of the copper metallochaperone Atx1: selectivity of the consensus sequence MxCxxC for metal ions Hg(II), Cu(I), Cd(II), Pb(II), and Zn(II). , 2006, Inorganic chemistry.

[46]  P. Dumy,et al.  Control of amyloid beta-peptide protofibril formation by a designed template assembly. , 2006, Angewandte Chemie.

[47]  Huan Huang,et al.  Uranium(VI) bio-coordination chemistry from biochemical, solution and protein structural data , 2006 .

[48]  C. Vita,et al.  Selective binding of uranyl cation by a novel calmodulin peptide , 2006 .

[49]  S. Chierici,et al.  Chemoselective assembly and immunological evaluation of multiepitopic glycoconjugates bearing clustered Tn antigen as synthetic anticancer vaccines. , 2005, Bioconjugate chemistry.

[50]  F. Taran,et al.  Discovery of powerful uranyl ligands from efficient synthesis and screening. , 2005, Chemistry.

[51]  C. Vidaud,et al.  Screening of human serum proteins for uranium binding. , 2005, Chemical research in toxicology.

[52]  J. V. Van Horn,et al.  Uranyl-peptide interactions in carbonate solution with DAHK and derivatives. , 2005, Inorganic chemistry.

[53]  J. Covès,et al.  Is the cytoplasmic loop of MerT, the mercuric ion transport protein, involved in mercury transfer to the mercuric reductase? , 2004, FEBS letters.

[54]  Jean-Luc Coll,et al.  Template assembled cyclopeptides as multimeric system for integrin targeting and endocytosis. , 2004, Journal of the American Chemical Society.

[55]  M. Ferrand,et al.  Novel model peptide for Atx1-like metallochaperones. , 2004, Chemical communications.

[56]  Robert M. Smith,et al.  NIST standard reference database 46 version 8.0: NIST critically selected stability constants of metal complexes , 2004 .

[57]  Robert M. Smith,et al.  NIST Critically Selected Stability Constants of Metal Complexes Database , 2004 .

[58]  Jide Xu,et al.  Rational design of sequestering agents for plutonium and other actinides. , 2003, Chemical reviews.

[59]  J. Renshaw,et al.  Synthesis and characterization of uranyl compounds with iminodiacetate and oxydiacetate displaying variable denticity. , 2002, Inorganic chemistry.

[60]  M. Crisma,et al.  Crystal Structure of a Synthetic Cyclodecapeptide for Template‐Assembled Synthetic Protein Design , 2001, Chembiochem : a European journal of chemical biology.

[61]  C. Madic,et al.  Uranium (VI)-Transferrin System Studied by Time-Resolved Laser-Induced Fluorescence , 1998 .

[62]  D. Taylor,et al.  Environmental Uranium and Human Health , 1997, Reviews on environmental health.

[63]  M. Mutter,et al.  Solution structure of regioselectively addressable functionalized templates: an NMR and restrained molecular dynamics investigation. , 1998, Biopolymers.

[64]  B. Imperiali,et al.  A conformational study of peptides with the general structure Ac-L-Xaa-Pro-D-Xaa-L-Xaa-NH2: spectroscopic evidence for a peptide with significant .beta.-turn character in water and in dimethyl sulfoxide , 1992 .

[65]  K. Kopple,et al.  Reverse Turns in Peptides and Protein , 1980 .

[66]  G. Choppin,et al.  The complexation of lanthanides by aminocarboxylate ligands—I: Stability constants , 1977 .