Self-Assembly of Catecholic Moiety-Containing Cationic Random Acrylic Copolymers

Journal of Physical Chemistry B

Volumn 119, Issue 26, 2015, Pages 8369-8379

  Taresco, Vincenzo ^a   Gontrani, Lorenzo ^a   Crisante, Fernanda ^a   Francolini, Iolanda ^a   Martinelli, Andrea ^a   D'Ilario, Lucio ^a   Bordi, Federico ^a   Piozzi, Antonella ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ASSOCIATION REACTIONS; CARBON; CHAINS; DISTRIBUTION FUNCTIONS; DYNAMIC LIGHT SCATTERING; HYDROPHOBICITY; LIGHT SCATTERING; MICELLES; MOLECULAR DYNAMICS; MONOMERS; POLYELECTROLYTES; SELF ASSEMBLY;

AMPHIPHILIC POLYELECTROLYTES; ANTI-MICROBIAL ACTIVITY; ATOMISTIC MOLECULAR DYNAMICS; ELECTRICAL CONDUCTIVITY MEASUREMENTS; MINIMUM INHIBITORY CONCENTRATION; RADIAL DISTRIBUTION FUNCTIONS; SELF-ASSOCIATION PROPERTIES; ZETA POTENTIAL MEASUREMENTS;

ACRYLIC MONOMERS;

EID: 84947287006     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b05022     Document Type: Article

References (61)

1. Varadaraj, R.; Branham, K. D.; McCormick, C. L.; Bock, J. In Macromolecular Complexes In Chemistry and Biology; Dubin, P. L., Bock, J., Davies, R. M., Schulz, D. N., Thies, C., Eds; Springer Verlag: Berlin, 1994; pp 15-31.
2. Pal, S.; Roy, S. G.; De, P. Synthesis via RAFT Polymerization of Thermo- and pH-responsive Random Copolymers Containing Cholic Acid Moieties and their Self-assembly in Water Polym. Chem. 2014, 5, 1275-1284
3. Holder, S. J.; Sommerdijk, N. A. J. M. New Micellar Morphologies From Amphiphilic Block Copolymers: Disks, Toroids and Bicontinuous Micelles Polym. Chem. 2011, 2, 1018-1028
4. Lodge, T. P.; Rasdal, A.; Li, Z.; Hillmyer, M. A. Simultaneous, Segregated Storage of Two Agents in a Multicompartment Micelle J. Am. Chem. Soc. 2005, 127, 17608-17609
5. McCormick, C. L. Stimuli-Responsive Water Soluble and Amphiphilic Polymers; ACS Symposium Series 780; American Chemical Society: Washington, DC, 2001.
6. Glass, J. E. Hydrophilic Polymer, Performance with Environmental Acceptability; ACS Advanced in Chemistry Series 248; American Chemical Society: Washington, DC, 1996.
7. Goddard, E. D.; Gruber, J. V. Principles of Polymer Science and Technology in Cosmetics and Personal Care; CRC Press, Marcel Dekker, Inc.: New York, 1999.
8. Du, J.; O'Reilly, R. K. Advances and Challenges in Smart and Functional Polymer Vesicles Soft Matter 2009, 5, 3544-3561
9. Blanazs, A.; Armes, S. P.; Ryan, A. J. Self-Assembled Block Copolymer Aggregates: from Micelles to Vesicles and their Biological Applications Macromol. Rapid Commun. 2009, 30, 267-277
10. Liu, R. C. W.; Marc Brestaz, A. P.; Pantoustier, N.; Tribet, C. Impact of Polymer Microstructure on the Self-Assembly of Amphiphilic Polymers in Aqueous Solutions Macromolecules 2007, 40, 4276-4286
11. Fuks, G.; Talom, R. M.; Gauffre, F. Biohybrid Block Copolymers: Towards Functional Micelles and Vesicles Chem. Soc. Rev. 2011, 40, 2475-2493
12. Förster, S.; Abetz, V.; Müller, A. H. E. Polyelectrolyte Block Copolymer Micelles, in Polyelectrolytes with Defined Molecular Architecture II; Schmidt, M., Ed.; Advanced Polymer Science 166; Springer: Berlin, 2004; pp 173-210.
13. Kumar, S.; Acharya, R.; Chatterji, U.; De, P. Side-Chain Amino-Acid-Based pH-Responsive Self-Assembled Block Copolymers for Drug Delivery and Gene Transfer Langmuir 2013, 29, 15375-15385
14. Mori, T.; Hashidzume, A.; Sato, T. Micellization Behavior of an Amphiphilic Statistical Copolymer in Water-Methanol Mixtures Polym. J. 2009, 41, 189-194
15. Forster, S.; Antonietti, M. Amphiphilic Block Copolymers in Structure-Controlled Nanomaterial Hybrids Adv. Mater. 1998, 10, 195-217
16. Qin, A.; Tian, M.; Ramireddy, C.; Webber, S. E.; Munk, P.; Tuzar, Z. Polystyrene-Poly(methacry1ic acid) Block Copolymer Micelles Macromolecules 1994, 27, 120-126
17. Riess, G. Micellization of Block Copolymers Prog. Polym. Sci. 2003, 28, 1107-1170
18. Mikhail, A. S.; Allen, C. Block Copolymer Micelles for Delivery of Cancer Therapy: Transport at the Whole Body, Tissue and Cellular Levels J. Controlled Release 2009, 138, 214-223
19. Yoon, H. J.; Jang, W. D. Polymeric Supramolecular Systems for Drug Delivery J. Mater. Chem. 2010, 20, 211-222
20. Dan, K.; Rajdev, P.; Deb, J.; Jana, S. S.; Ghosh, S. Remarkably Stable Amphiphilic Random Copolymer Assemblies: A Structure-Property Relationship Study J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4932-4943
21. Kramer, M. C.; Welch, C. G.; Steger, J. R.; McCormik, C. L. Water-Soluble Copolymers. 63. Rheological and Photophysical Studies on the Associative Properties of Pyrene-Labeled Poly[acrylamide-co-sodium-1,1-(acrylamido)undecanoate Macromolecules 1995, 28, 5248-5254
22. Morishima, Y.; Nomura, S.; Ikeda, T.; Seki, M.; Kamachi, M. Characterization of Unimolecular Micelles of Random Copolymers of Sodium 2-(Acrylamido)-2-methylpropanesulfonate and Methacrylamides Bearing Bulky Hydrophobic Substituents Macromolecules 1995, 28, 2874-2881
23. Suwa, M.; Hashidzume, A.; Morishima, Y.; Nakato, T.; Tomida, M. Self-Association Behavior of Hydrophobically Modified Poly(aspartic acid) in Water Studied by Fluorescence and Dynamic Light Scattering Techniques Macromolecules 2000, 33, 7884-7892
24. Branham, K. D.; Snowden, H. S.; McCormick, C. L. Water-Soluble Copolymers. 64. Effects of pH and Composition on Associative Properties of Amphiphilic Acrylamide/Acrylic Acid Terpolymers Macromolecules 1996, 29, 254-262
25. Hashidzume, A.; Kawaguchi, A.; Tagawa, A.; Hyoda, K.; Sato, T. Synthesis and Structural Analysis of Self-Associating Amphiphilic Statistical Copolymers in Aqueous Media Macromolecules 2006, 39, 1135-1143
26. Yamamoto, H.; Tomatsu, I.; Hashidzume, A.; Morishima, Y. Associative Properties in Water of Copolymers of Sodium 2-(Acrylamido)-2-methylpropanesulfonate and Methacrylamides Substituted with Alkyl Groups of Varying Lengths Macromolecules 2000, 33, 7852-7861
27. Noda, T.; Hashidzume, A.; Morishima, Y. Effects of Spacer Length on the Side-Chain Micellization in Random Copolymers of Sodium 2-(Acrylamido)-2-methylpropanesulfonate and Methacrylates Substituted with Ethylene Oxide-Based Surfactant Moieties Macromolecules 2001, 34, 1308-1317
28. Gohon, Y.; Giusti, F.; Prata, C.; Charvolin, D.; Timmins, P.; Ebel, C.; Tribet, C.; Popot, J. L. Well-defined Nanoparticles Formed by Hydrophobic Assembly of a Short and Polydisperse Random Terpolymer, Amphipol A8-35 Langmuir 2006, 22, 1281-1290
29. Perlmutter, J. D.; Drasler, W. J., II; Xie, W.; Gao, J.; Popot, J. L.; Sachs, J. N. All-Atom and Coarse-Grained Molecular Dynamics Simulation of a Membrane Protein Stabilizing Polymer Langmuir 2011, 27, 10523-10537
30. Kawata, T.; Hashidzume, A.; Sato, T. Micellar Structure of Amphiphilic Statistical Copolymers Bearing Dodecyl Hydrophobes in Aqueous Media Macromolecules 2007, 40, 1174-1180
31. Tominaga, Y.; Mizuse, M.; Hashidzume, A.; Morishima, Y.; Sato, T. Flower Micelle of Amphiphilic Random Copolymers in Aqueous Media J. Phys. Chem. B 2010, 114, 11403-11408
32. Carmona-Ribeiro, A. M.; Dias de Melo Carrasco, L. Cationic Antimicrobial Polymers and their Assemblies Int. J. Mol. Sci. 2013, 14, 9906-9946
33. Munoz-Bonilla, A.; Fernàndez-Garcìa, M. Polymeric Materials with Antimicrobial Activity Prog. Polym. Sci. 2012, 37, 281-339
34. Kuroda, K.; Caputo, G. A. Antimicrobial Polymers as Synthetic Mimics of Host Defense Peptides WIREs Nanomed. Nanobiotechnol. 2013, 5, 49-66
35. Palermo, E. F.; Kuroda, K. Structural Determinants of Antimicrobial Activity in Polymers which Mimic Host Defense Peptides Appl. Microbiol. Biotechnol. 2010, 87, 1605-1615
36. Palermo, E. F.; Vemparala, S.; Kuroda, K. Cationic Spacer Arm Design Strategy for Control of Antimicrobial Activity and Conformation of Amphiphilic Methacrylate Random Copolymers Biomacromolecules 2012, 13, 1632-1641
37. Mowery, B. P.; Lee, S. E.; Kissounko, D. A.; Epand, R. F.; Epand, R. M.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Mimicry of Antimicrobial Host-Defense Peptides by Random Copolymers J. Am. Chem. Soc. 2007, 129, 15474-15476
38. Vieira, D. B.; Carmona-Ribeiro, A. M. Cationic Lipids and Surfactants as Antifungal Agents: Mode of Action J. Antimicrob. Chemother. 2006, 58, 760-767
39. Chu, B. Structure and Dynamics of Block Copolymer Colloids Langmuir 1995, 11, 414-421
40. Taresco, V.; Crisante, F.; Francolini, I.; Martinelli, A.; D'Ilario, L.; Ricci-Vitiani, L.; Buccarelli, M.; Pietrelli, L.; Piozzi, A. Antimicrobial and Antioxidant Amphiphilic Random Copolymers to Address Medical Device-Centered Infections Acta Biomater. 2015, 22, 131-140
41. Oda, Y.; Kanaoka, S.; Sato, T.; Aoshima, S.; Kuroda, K. Block Versus Random Amphiphilic Copolymers as Antibacterial Agents Biomacromolecules 2011, 12, 3581-3591
42. Mincione, E.; Barontini, M.; Crisante, F. Università degli Studi della Tuscia. Method for Preparing Hydroxytyrosol and Hydroxytyrosol Derivatives. PCT/IB2008/000598, IPN: WO2008/110908 A1, 2008.
43. Bernini, R.; Mincione, E.; Barontini, M.; Crisante, F. Convenient Synthesis of Hydroxytyrosol and its Lipophilic Derivatives from Tyrosol or Homovanillyl Alcohol J. Agric. Food Chem. 2008, 56, 8897-8904
44. Francolini, I.; Taresco, V.; Crisante, F.; Martinelli, A.; D'Ilario, L.; Piozzi, A. Water Soluble Usnic Acid-Polyacrylamide Complexes with Enhanced Antimicrobial Activity against Staphylococcus epidermidis Int. J. Mol. Sci. 2013, 14, 7356-7369
45. Zhang, L.; Wang, X.; Wang, J.; Grinberg, N.; Krishnamurthy, D.; Senanayake, C. H. An Improved Method of Amide Synthesis Using Acyl Chlorides Tetrahedron Lett. 2009, 50, 2964-2966
46. Weininger, D. SMILES. 3. DEPICT. Graphical Depiction of Chemical Structures J. Chem. Inf. Model. 1980, 30, 237-243
47. O'Boyle, N. M.; Banck, M.; James, C. A.; Morley, C.; Vandermeersch, T.; Hutchison, G. R. Open Babel: An Open Chemical Toolbox J. Cheminform. 2011, 3, 33
48. Wang, J.; Caldwell, W. J. W.; Kollman, P. A.; Case, D. A. Development and Testing of a General Amber Force Field J. Comput. Chem. 2004, 25, 1157-1174
49. Gasteiger, J.; Marsili, M. Iterative Partial Equalization of Orbital Electronegativity-A Rapid Access to Atomic Charges Tetrahedron 1980, 36, 3219-3228
50. Martínez, L.; Andrade, R.; Birgin, E. G.; Martínez, J. M. Packmol: A Package for Building Initial Configurations for Molecular Dynamics Simulations J. Comput. Chem. 2009, 30, 2157-2164
51. Case, D. A.; Darden, T. A.; Cheatham, T. E., III; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Walker, R. C.; Zhang, W.; Merz, K. M. et al., AMBER 12; University of California, San Francisco, 2012.
52. Van Der Spoel, D.; Lindahl, E.; Hess, B.; Groenhof, G.; Mark, A. E.; Berendsen, H. J. C. GROMACS: Fast, Flexible, and Free J. Comput. Chem. 2005, 26, 1701-1718
53. Brehm, M.; Kirchner, B. TRAVIS-A Free Analyzer and Visualizer for Monte Carlo and Molecular Dynamics Trajectories J. Chem. Inf. Model. 2011, 51, 2007-2023
54. Gedde, U. W. Polymer Physics; Springer 1995.
55. Bergman, D. L.; Laaksonen, L.; Laaksonen, A. Visualization of Solvation Structures in Liquid Mixtures J. Mol. Graph. Model. 1997, 15, 301-306
56. Bütün, V.; Armes, S. P.; Billingham, N. C. Selective Quaternization of 2-(Dimethylamino)ethylMethacrylate Residues in Tertiary Amine Methacrylate Diblock Copolymers Macromolecules 2001, 34, 1148-1159
57. Jeong, Y. I.; Nah, J. W.; Lee, H. C.; Kim, S. H.; Cho, C. S. Adriamycin Release from Flower-Type Polymeric Micelle Based on Star-Block Copolymer Composed of Poly(G-Benzyl L-Glutamate) as the Hydrophobic Part and Poly(Ethylene Oxide) as the Hydrophilic Part Int. J. Pharm. 1999, 188, 49-58
58. Lee, E. S.; Oh, K. T.; Kim, D.; Youn, Y. S.; Bae, Y. H. Tumor pH-Responsive Flower-Like Micelles of Poly(L-Lactic Acid)-B-Poly(Ethylene Glycol)-B-Poly(L-Histidine) J. Controlled Release 2007, 123, 19-26
59. Ilker, M. F.; Nüsslein, K.; Tew, G. N.; Coughlin, E. B. Tuning the Hemolytic and Antibacterial Activities of Amphiphilic Polynorbornene Derivatives J. Am. Chem. Soc. 2004, 126, 15870-15875
60. Mowery, B. P.; Lee, S. E.; Kissounko, D. A.; Epand, R. F.; Epand, R. M.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Mimicry of Antimicrobial Host-Defense Peptides by Random Copolymers J. Am. Chem. Soc. 2007, 129, 15474-15476
61. Kuroda, K.; Caputo, G. A.; DeGrado, W. F. The Role of Hydrophobicity in the Antimicrobial and Hemolytic Activities of Polymethylacrylate Derivatives Chem.-Eur. J. 2009, 15, 1123-1133