Molecular Dynamics Simulation of the Effect of Carbon Space Lengths

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Molecular Dynamics Simulation of Effect of Carbon Space Lengths on Antifouling Properties of Hydroxyalkyl Acrylamides Yonglan Liu, Yanxian Zhang, Baiping Ren, Yan Sun, Yi He, Fang Cheng, Jianxiong Xu, and Jie Zheng Langmuir, Just Accepted Manuscript • DOI: 10.1021/acs.langmuir.8b04229 • Publication Date (Web): 05 Feb 2019 Downloaded from http://pubs.acs.org on February 9, 2019

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Molecular Dynamics Simulation of Effect of Carbon Space Lengths on Antifouling Properties of Hydroxyalkyl Acrylamides

Yonglan Liu1,5¶, Yanxian Zhang5¶, Baiping Ren5, Yan Sun2, Yi He3, Fang Cheng4, Jianxiong Xu1*, and Jie Zheng5* 1Hunan

Key Laboratory of Biomedical Nanomaterials and Devices College of Life Science and Chemistry Hunan University of Technology, Zhuzhou 412007, P. R. China

2Department

of Biochemical Engineering and Key Laboratory of Systems Bioengineering of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300354, China 3College

of Chemical and Biological Engineering Zhejiang University, Hangzhou, Zhejiang 310027, China 4State

Key Laboratory of Fine Chemicals Dalian University of Technology, Dalian, 116024, China 5Department

of Chemical & Biomolecular Engineering The University of Akron, Ohio 44325, USA

¶

The authors contribute equally to this work. *Corresponding Author: J.X. [email protected]; J.Z. [email protected]

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Abstract Surface hydration has been proposed as the key antifouling mechanism of antifouling materials. However, molecular-level details of the structure, dynamic, and interaction of interfacial water around antifouling polymers still remains elusive. In this work, using all-atom molecular dynamics (MD) simulations, we studied the four different acrylamides (AMs) for their interfacial water behaviors and their interactions with a protein, with special attention to the effect of carbon spacer lengths (CSLs) on hydration properties of AMs. Collective MD simulation data revealed that while all four AMs displayed strong hydration, N-hydroxymethyl acrylamide (HMAA) and N-(2-hydroxyethyl)acrylamide (HEAA) with the shorter CSLs displayed the longer residence time, the slower self-diffusion, the less coordination number of interfacial water molecules than N-(3-hydroxypropyl)acrylamide (HPAA), and N-(5hydroxypentyl)-acrylamide (HPenAA) with the longer CSLs. The shorter CSLs allows water molecules to form bridging hydrogen bonds with different hydrophilic groups in the same AM chain, thus enhancing AMs hydration capacity. Consequently, different from HPenAA that had weak but detectable interaction with a protein, HMAA, HEAA, and HPAA had almost zero interactions with a protein. This computational work provides a better fundamental understanding of surface hydration and protein interaction of different AMs with subtle structural changes from structural, dynamic, and energy aspects at atomic level, which hopefully will guide the design of new and effective nonfouling materials. Keywords: antifouling materials; acrylamide; surface hydration; protein resistance; molecular dynamics Introduction 2 ACS Paragon Plus Environment

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Development of antifouling polymers is of great significance for many fundamental research and industrial applications,1-4 including biosensors, implanted devices, marine coatings, membrane separation, and drug/gene delivery. Extensive experimental studies have observed that hydrophilic polymers always possess much better and stronger antifouling properties against unwanted proteins/cells/bacterial adsorptions than hydrophobic ones. Thus, it is generally accepted that strong surface hydration around hydrophilic polymers is considered to be the key contributors to their antifouling property. The tightly bound water layer will act as physical and energy barrier against the attachment of biomolecules, because the replacement of water molecules around both polymers and biomolecules will cost significant free energy penalty. Based on the surface hydration mechanisms, antifouling polymers can be classified into the two groups: hydrophilic-based polymers [e.g. poly(ethylene glycol) (PEG),5-6 poly(acrylamide),7 polysaccharides,8 polypeptoids,9 and poly(hydroxyethyl methacrylate)10] and

zwitterionic

polymers

[poly(sulfobetaine

methacrylate),11

poly(carboxybetaine

methacrylate),12 2-methacryloyloxylethyl phosphorycholine,13 oleophobicity materials14-15, and polyampholytes with equally mixed positive and negative charged groups of NH2/CA, DM/CA, DE/CA, TM/CA16]. While hydrophilic and zwitterionic polymers possess significant differences in structure and chemistry, they are all known to bind strongly to water molecules via different binding forces, i.e. hydrophilic polymers achieve strong surface hydration via hydrogen bonds by hydrophilic groups (e.g. hydroxyl, amide, ether, and/or ethylene glycol groups),16-22 while zwitterionic polymers via electrostatic-induced hydration by zwitterionic groups (e.g. carboxylic, sulfonate, sulfate, and quaternary/tertiary/secondary/primary ammonium groups).23-25 3 ACS Paragon Plus Environment

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The nonfouling behavior of a polymer and its surface hydration appears to be a straightforward correlation. However, from a nanoscopic viewpoint, the structure, dynamics, and interaction of interfacial water molecules around antifouling polymers still remain largely unknown, simply because much less efforts have been done to computationally examine the surface hydration-antifouling property relationship. A number of molecular dynamics (MD) simulations have been reported to study and compare the structure of surface hydration of zwitterionic carboxybetaine (CB) and sulfobetaine (SB) polymers26. While both CB- and SBbased polymers exhibited almost identical, superlow fouling properties to resist nonspecific protein adsorption ( HMAA > HPAA>HPenAA. It is generally accepted that the water molecules near hydrophilic polymer surfaces should diffuse more slowly due to the strong interaction with polymers, leading to prolonged residence time around polymers. So, we calculated the selfdiffusion coefficient of water molecule near the 1st and 2nd hydration layers of AMs by measuring the mean square displacement (MSD) of water molecules and the results were shown in Figure 6b. The self-diffusion coefficients (Ds) of the first/second water layers around HMAA, HEAA, HPAA, HPenAA were 1.82×10-5/1.84×10-5 cm2/s, 1.81×10-5/1.84×10-5 cm2/s, 1.82×10-5/1.83×10-5 cm2/s, and 2.10×10–5/2.56×10-5 cm2/s, respectively. Overall, in the cases of HMAA-CI2, HEAA-CI2, HPAA-CI2, Ds in the first water layer (Ds1) was almost identical to Ds2 in the second water layer. As CSLs of AM ≤3, all Ds values both in the first and second water layers were smaller than Ds of bulk water (2.54×105 cm2/s), confirming the tightly bound water molecules around AMs. However, in the case of HPenAA, the self-diffusion coefficient gradually increased from 2.10×10-5 cm2/s in the first hydration layer to 2.56×10-5 cm-2/s in the second hydration layer, and both values were close to that of bulk water. This indicates that water molecules diffuse more freely around HPenAA. Due to strong hydrophilic nature of AMs, it was observed that interfacial waters near HMAA and HEAA with shorter CSLs have longer τs and smaller Ds than those near HPAA and HPenAA with longer CSLs, indicating that HMAA and HEAA interact more strongly with water than HPAA and HPenAA, particularly via hydrogen bonds. So, we calculated the average number of hydrogen bonds between water molecules and AMs, as normalized by the number of AMs. We define strong, moderate, weak hydrogen bonds based on the donor-acceptor 17 ACS Paragon Plus Environment

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distance of HPAA > HPenAA in terms of their strong hydration and protein resistance capacity. This computational work provides a better understanding of the similarity and difference between these four AMs in terms of hydration and protein interaction, which hopefully will lay down a good foundation to the rational design of new and effective antifouling materials beyond AMs or PEG materials for a wide variety of fundamental and industrial applications. Acknowledgement. J.Z. thanks financial supports from NSF (DMR-1806138 and CMMI1825122). We also thank Kairui Liang (Chongqing No. Middle School) for his participation and assistance in this project during the summer. Supporting Information. Protein stability data by RMSD; Force field parameters for AMs.


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Content of Figure


Molecular Dynamics Simulation of the Effect of Carbon Space Lengths

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