Secondary structure propensity and chirality of the amyloidophilic peptide p5 and its analogues impacts ligand binding - In vitro characterization

Wall, Jonathan S.; Williams, Angela; Wooliver, Craig; Martin, Emily B.; Cheng, Xiaolin; Heidel, R. Eric; Kennel, Stephen J.

doi:10.1016/j.bbrep.2016.08.007

Secondary structure propensity and chirality of the amyloidophilic peptide p5 and its analogues impacts ligand binding - In vitro characterization

Journal Article · Thu Aug 11 00:00:00 EDT 2016 · Biochemistry and Biophysics Reports

DOI:https://doi.org/10.1016/j.bbrep.2016.08.007· OSTI ID:1327690

Wall, Jonathan S. ^[1]; Williams, Angela ^[1]; Wooliver, Craig ^[1]; Martin, Emily B. ^[1]; Cheng, Xiaolin ^[2]; Heidel, R. Eric ^[1]; Kennel, Stephen J. ^[1]

Univ. of Tennessee, Knoxville, TN (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Here, polybasic helical peptides, such as peptide p5, bind human amyloid extracts and synthetic amyloid fibrils. When radio labeled, peptide p5 has been shown to specifically bind amyloid in vivo thereby allowing imaging of the disease. Structural requirements for heparin and amyloid binding have been studied using analogues of p5 that modify helicity and chirality.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: ME USDOE - Office of Management, Budget, and Evaluation; ORNL work for others

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1327690

Journal Information:: Biochemistry and Biophysics Reports, Journal Name: Biochemistry and Biophysics Reports Journal Issue: C Vol. 8; ISSN 2405-5808

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (39)

Binding of small basic peptides to membranes containing acidic lipids: theoretical models and experimental results Ben-Tal, N.; Honig, B.; Peitzsch, R. M. Biophysical Journal, Vol. 71, Issue 2 https://doi.org/10.1016/s0006-3495(96)79280-9	journal	August 1996
Binding of a de novo designed peptide to specific glycosaminoglycans Jayaraman, G.; Wu, C. W.; Liu, Y. J. FEBS Letters, Vol. 482, Issue 1-2 https://doi.org/10.1016/s0014-5793(00)01964-5	journal	September 2000
Interaction of Heparin with Two Synthetic Peptides that Neutralize the Anticoagulant Activity of Heparin ^† Wang, Jing; Rabenstein, Dallas L. Biochemistry, Vol. 45, Issue 51 https://doi.org/10.1021/bi061346a	journal	December 2006
In vivo molecular imaging of peripheral amyloidosis using heparin-binding peptides Wall, J. S.; Richey, T.; Stuckey, A. Proceedings of the National Academy of Sciences, Vol. 108, Issue 34 https://doi.org/10.1073/pnas.1103247108	journal	August 2011
Amyloidogenesis: historical and modern observations point to heparan sulfate proteoglycans as a major culprit Ancsin, John B. Amyloid, Vol. 10, Issue 2 https://doi.org/10.3109/13506120309041728	journal	January 2003
Preclinical Validation of the Heparin-Reactive Peptide p5+14 as a Molecular Imaging Agent for Visceral Amyloidosis Wall, Jonathan; Martin, Emily; Richey, Tina Molecules, Vol. 20, Issue 5 https://doi.org/10.3390/molecules20057657	journal	April 2015
Development of the multiple sequence approximation within the AGADIR model of α-helix formation: Comparison with Zimm-Bragg and Lifson-Roig formalisms Muñoz, Victor; Serrano, Luis Biopolymers, Vol. 41, Issue 5 https://doi.org/10.1002/(SICI)1097-0282(19970415)41:5<495::AID-BIP2>3.0.CO;2-H	journal	April 1997
Importance of the spatial display of charged residues in heparinâpeptide interactions Rullo, Anthony; Nitz, Mark Biopolymers, Vol. 93, Issue 3 https://doi.org/10.1002/bip.21339	journal	March 2010
Heparin Dependent Coiled‐Coil Formation Nitz, Mark; Rullo, Anthony; Ding, Matias Xiao Yue ChemBioChem, Vol. 9, Issue 10 https://doi.org/10.1002/cbic.200800056	journal	July 2008
Scalable molecular dynamics with NAMD Phillips, James C.; Braun, Rosemary; Wang, Wei Journal of Computational Chemistry, Vol. 26, Issue 16, p. 1781-1802 https://doi.org/10.1002/jcc.20289	journal	January 2005
Bioenergetic impact of tissue-specific regulation of iodothyronine deiodinases during nutritional imbalance Araujo, Renata L.; Carvalho, Denise P. Journal of Bioenergetics and Biomembranes, Vol. 43, Issue 1 https://doi.org/10.1007/s10863-011-9327-x	journal	January 2011
Comparative Analysis of Peptide p5 and Serum Amyloid P Component for Imaging AA Amyloid in Mice Using Dual-Isotope SPECT Wall, Jonathan S.; Richey, Tina; Williams, Angela Molecular Imaging and Biology, Vol. 14, Issue 4 https://doi.org/10.1007/s11307-011-0524-0	journal	October 2011
Binding of small basic peptides to membranes containing acidic lipids: theoretical models and experimental results Ben-Tal, N.; Honig, B.; Peitzsch, R. M. Biophysical Journal, Vol. 71, Issue 2 https://doi.org/10.1016/S0006-3495(96)79280-9	journal	August 1996
A Helix Propensity Scale Based on Experimental Studies of Peptides and Proteins Nick Pace, C.; Martin Scholtz, J. Biophysical Journal, Vol. 75, Issue 1 https://doi.org/10.1016/S0006-3495(98)77529-0	journal	July 1998
Binding of a de novo designed peptide to specific glycosaminoglycans Jayaraman, G.; Wu, C. W.; Liu, Y. J. FEBS Letters, Vol. 482, Issue 1-2 https://doi.org/10.1016/S0014-5793(00)01964-5	journal	September 2000
Localization of type I iodothyronine 5'-deiodinase to the basolateral plasma membrane in renal cortical epithelial cells Leonard, J. L.; Ekenbarger, D. M.; Frank, S. J. Journal of Biological Chemistry, Vol. 266, Issue 17 https://doi.org/10.1016/S0021-9258(18)99157-X	journal	June 1991
Micro‐Imaging of Amyloid in Mice Wall, Jonathan S.; Paulus, Michael J.; Gleason, Shaun Methods in Enzymology https://doi.org/10.1016/S0076-6879(06)12011-X	book	January 2006
Heparan Sulfate Proteoglycans in Amyloidosis Zhang, Xiao; Li, Jin-Ping Progress in Molecular Biology and Translational Science https://doi.org/10.1016/S1877-1173(10)93013-5	book	January 2010
Peptide p5 binds both heparinase-sensitive glycosaminoglycans and fibrils in patient-derived AL amyloid extracts Martin, Emily B.; Williams, Angela; Heidel, Eric Biochemical and Biophysical Research Communications, Vol. 436, Issue 1 https://doi.org/10.1016/j.bbrc.2013.05.063	journal	June 2013
Dynamic PET and SPECT imaging with radioiodinated, amyloid-reactive peptide p5 in mice: A positive role for peptide dehalogenation Martin, Emily B.; Kennel, Stephen J.; Richey, Tina Peptides, Vol. 60 https://doi.org/10.1016/j.peptides.2014.07.024	journal	October 2014
Calculating Structures and Free Energies of Complex Molecules: Combining Molecular Mechanics and Continuum Models Kollman, Peter A.; Massova, Irina; Reyes, Carolina Accounts of Chemical Research, Vol. 33, Issue 12 https://doi.org/10.1021/ar000033j	journal	December 2000
Minimum FGF2 Binding Structural Requirements of Heparin and Heparan Sulfate Oligosaccharides As Determined by NMR Spectroscopy Guglieri, Sara; Hricovíni, Miloš; Raman, Rahul Biochemistry, Vol. 47, Issue 52 https://doi.org/10.1021/bi801007p	journal	December 2008
Thermodynamic Instability of Human λ6 Light Chains: Correlation with Fibrillogenicity ^† Wall, Jonathan; Schell, Maria; Murphy, Charles Biochemistry, Vol. 38, Issue 42 https://doi.org/10.1021/bi991131j	journal	October 1999
Impact of Resistance Mutations on Inhibitor Binding to HIV-1 Integrase Chen, Qi; Buolamwini, John K.; Smith, Jeremy C. Journal of Chemical Information and Modeling, Vol. 53, Issue 12 https://doi.org/10.1021/ci400537n	journal	November 2013
All-Atom Empirical Potential for Molecular Modeling and Dynamics Studies of Proteins ^† MacKerell, A. D.; Bashford, D.; Bellott, M. The Journal of Physical Chemistry B, Vol. 102, Issue 18 https://doi.org/10.1021/jp973084f	journal	April 1998
I-TASSER: a unified platform for automated protein structure and function prediction Roy, Ambrish; Kucukural, Alper; Zhang, Yang Nature Protocols, Vol. 5, Issue 4 https://doi.org/10.1038/nprot.2010.5	journal	March 2010
Elucidating the folding problem of helical peptides using empirical parameters Muñoz, Victor; Serrano, Luis Nature Structural & Molecular Biology, Vol. 1, Issue 6 https://doi.org/10.1038/nsb0694-399	journal	June 1994
Comparative evaluation of p5+14 with SAP and peptide p5 by dual-energy SPECT imaging of mice with AA amyloidosis Martin, Emily B.; Williams, Angela; Richey, Tina Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep22695	journal	March 2016
Particle mesh Ewald: An N ⋅log( N ) method for Ewald sums in large systems Darden, Tom; York, Darrin; Pedersen, Lee The Journal of Chemical Physics, Vol. 98, Issue 12 https://doi.org/10.1063/1.464397	journal	June 1993
3D structure of Alzheimer's amyloid- (1-42) fibrils Luhrs, T.; Ritter, C.; Adrian, M. Proceedings of the National Academy of Sciences, Vol. 102, Issue 48 https://doi.org/10.1073/pnas.0506723102	journal	November 2005
Amyloid-specific Heparan Sulfate from Human Liver and Spleen Lindahl, Birgitta; Lindahl, Ulf Journal of Biological Chemistry, Vol. 272, Issue 42 https://doi.org/10.1074/jbc.272.42.26091	journal	October 1997
Characterization of the Subunit Structure of the Catalytically Active Type I Iodothyronine Deiodinase Leonard, Jack L.; Visser, Theo J.; Leonard, Deborah M. Journal of Biological Chemistry, Vol. 276, Issue 4 https://doi.org/10.1074/jbc.M006973200	journal	January 2001
The Heparan Sulfate Motif (GlcNS6S-IdoA2S) ₃ , Common in Heparin, Has a Strict Topography and Is Involved in Cell Behavior and Disease Smits, Nicole C.; Kurup, Sindhulakshmi; Rops, Angelique L. Journal of Biological Chemistry, Vol. 285, Issue 52 https://doi.org/10.1074/jbc.M110.153791	journal	September 2010
Systemic Amyloidoses Blancas-Mejía, Luis M.; Ramirez-Alvarado, Marina Annual Review of Biochemistry, Vol. 82, Issue 1 https://doi.org/10.1146/annurev-biochem-072611-130030	journal	June 2013
The characterization of soluble amyloid prepared in water Schubert, M. Pras, M.; Zucker-Franklin, D.; Rimon, A. Journal of Clinical Investigation, Vol. 47, Issue 4 https://doi.org/10.1172/JCI105784	journal	April 1968
I-TASSER server for protein 3D structure prediction Zhang, Yang BMC Bioinformatics, Vol. 9, Issue 1 https://doi.org/10.1186/1471-2105-9-40	journal	January 2008
Amyloidosis Pinney, Jennifer H.; Hawkins, Philip N. Annals of Clinical Biochemistry: International Journal of Laboratory Medicine, Vol. 49, Issue 3 https://doi.org/10.1258/acb.2011.011225	journal	March 2012
A Binding-Site Barrier Affects Imaging Efficiency of High Affinity Amyloid-Reactive Peptide Radiotracers In Vivo Wall, Jonathan S.; Williams, Angela; Richey, Tina PLoS ONE, Vol. 8, Issue 6 https://doi.org/10.1371/journal.pone.0066181	journal	June 2013
Light Chain Amyloid Fibrils Cause Metabolic Dysfunction in Human Cardiomyocytes McWilliams-Koeppen, Helen P.; Foster, James S.; Hackenbrack, Nicole PLOS ONE, Vol. 10, Issue 9 https://doi.org/10.1371/journal.pone.0137716	journal	September 2015

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Secondary structure propensity and chirality of the amyloidophilic peptide p5 and its analogues impacts ligand binding - In vitro characterization

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