Difference of carboxybetaine and oligo(ethylene glycol) moieties in altering hydrophobic interactions: a molecular simulation study.

Polycarboxybetaine and poly(ethylene glycol) materials resist nonspecific protein adsorption but differ in influencing biological functions such as enzymatic activity. To investigate this difference, we studied the influence of carboxybetaine and oligo(ethylene glycol) moieties on hydrophobic interactions using molecular simulations. We employed a model system composed of two non-polar plates and studied the potential of mean force of plate-plate association in carboxybetaine, (ethylene glycol)4, and (ethylene glycol)2 solutions using well-tempered metadynamics simulations. Water, trimethylamine N-oxide, and urea solutions were used as reference systems. We analyzed the variation of the potential of mean force in various solutions to study how carboxybetaine and oligo(ethylene glycol) moieties influence the hydrophobic interactions. To study the origin of their influence, we analyzed the normalized distributions of moieties and water molecules using molecular dynamics simulations. The simulation results showed that oligo(ethylene glycol) moieties repel water molecules away from the non-polar plates and weaken the hydrophobic interactions. Carboxybetaine moieties do not repel water molecules away from the plates and therefore do not influence the hydrophobic interactions.

[1]  Shaoyi Jiang,et al.  Zwitterionic hydrogels implanted in mice resist the foreign-body reaction , 2013, Nature Biotechnology.

[2]  Ruth Nussinov,et al.  Molecular insights into the reversible formation of tau protein fibrils. , 2013, Chemical communications.

[3]  Shaoyi Jiang,et al.  Effect of carbon spacer length on zwitterionic carboxybetaines. , 2013, The journal of physical chemistry. B.

[4]  Michael Thompson,et al.  Surface chemistry to minimize fouling from blood-based fluids. , 2012, Chemical Society reviews.

[5]  Shaoyi Jiang,et al.  Different effects of zwitterion and ethylene glycol on proteins. , 2012, The Journal of chemical physics.

[6]  Jeremy L. England,et al.  Role of solvation effects in protein denaturation: from thermodynamics to single molecules and back. , 2011, Annual review of physical chemistry.

[7]  Shaoyi Jiang,et al.  Local and bulk hydration of zwitterionic glycine and its analogues through molecular simulations. , 2011, The journal of physical chemistry. B.

[8]  Shaoyi Jiang,et al.  Zwitterionic poly(carboxybetaine) hydrogels for glucose biosensors in complex media. , 2011, Biosensors & bioelectronics.

[9]  Shaoyi Jiang,et al.  Poly(zwitterionic)protein conjugates offer increased stability without sacrificing binding affinity or bioactivity. , 2011, Nature chemistry.

[10]  Shaoyi Jiang,et al.  Difference in hydration between carboxybetaine and sulfobetaine. , 2010, The journal of physical chemistry. B.

[11]  B. Berne,et al.  Dewetting and hydrophobic interaction in physical and biological systems. , 2009, Annual review of physical chemistry.

[12]  K. Dill,et al.  Theory for protein folding cooperativity: helix bundles. , 2009, Journal of the American Chemical Society.

[13]  Massimiliano Bonomi,et al.  PLUMED: A portable plugin for free-energy calculations with molecular dynamics , 2009, Comput. Phys. Commun..

[14]  B. Berne,et al.  Urea's action on hydrophobic interactions. , 2009, Journal of the American Chemical Society.

[15]  Carsten Kutzner,et al.  GROMACS 4:  Algorithms for Highly Efficient, Load-Balanced, and Scalable Molecular Simulation. , 2008, Journal of chemical theory and computation.

[16]  G. Meer,et al.  Membrane lipids: where they are and how they behave , 2008, Nature Reviews Molecular Cell Biology.

[17]  M. Parrinello,et al.  Well-tempered metadynamics: a smoothly converging and tunable free-energy method. , 2008, Physical review letters.

[18]  Berk Hess,et al.  P-LINCS:  A Parallel Linear Constraint Solver for Molecular Simulation. , 2008, Journal of chemical theory and computation.

[19]  S. Fatima,et al.  Effect of polyethylene glycols on the function and structure of thiol proteases. , 2007, Journal of biochemistry.

[20]  B. Berne,et al.  Effect of ions on the hydrophobic interaction between two plates. , 2007, Journal of the American Chemical Society.

[21]  H. Scheraga,et al.  The role of hydrophobic interactions in initiation and propagation of protein folding , 2006, Proceedings of the National Academy of Sciences.

[22]  N. V. D. van der Vegt,et al.  Does urea denature hydrophobic interactions? , 2006, Journal of the American Chemical Society.

[23]  A. Plückthun,et al.  Protein PEGylation Decreases Observed Target Association Rates via a Dual Blocking Mechanisms⃞ , 2005, Molecular Pharmacology.

[24]  D. Chandler.  Interfaces and the driving force of hydrophobic assembly , 2005, Nature.

[25]  S. Garde,et al.  Osmolyte trimethylamine-N-oxide does not affect the strength of hydrophobic interactions: origin of osmolyte compatibility. , 2005, Biophysical journal.

[26]  Anna Marabotti,et al.  Free energy of ligand binding to protein: evaluation of the contribution of water molecules by computational methods. , 2004, Current medicinal chemistry.

[27]  Shaoyi Jiang,et al.  Molecular simulation study of water interactions with oligo (ethylene glycol)-terminated alkanethiol self-assembled monolayers. , 2004, Langmuir : the ACS journal of surfaces and colloids.

[28]  J. Brickmann,et al.  Binary phases of aliphatic N-oxides and water: Force field development and molecular dynamics simulation , 2003 .

[29]  A. Laio,et al.  Escaping free-energy minima , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[30]  K. Dill,et al.  A View of the Hydrophobic Effect , 2002 .

[31]  D. Chandler,et al.  The hydrophobic effect and the influence of solute-solvent attractions , 2002 .

[32]  H. C. van der Mei,et al.  Bacterial adhesion to surface hydrophilic and hydrophobic contact lenses. , 2001, Biomaterials.

[33]  J. Israelachvili.  The different faces of poly(ethylene glycol). , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[34]  W. L. Jorgensen,et al.  Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids , 1996 .

[35]  T. Darden,et al.  A smooth particle mesh Ewald method , 1995 .

[36]  Hoover,et al.  Canonical dynamics: Equilibrium phase-space distributions. , 1985, Physical review. A, General physics.

[37]  H. Berendsen,et al.  Molecular dynamics with coupling to an external bath , 1984 .

[38]  S. Nosé.  A unified formulation of the constant temperature molecular dynamics methods , 1984 .

[39]  W. L. Jorgensen,et al.  Comparison of simple potential functions for simulating liquid water , 1983 .