When worlds collide: Interactions at the interface between biological systems and synthetic cationic conjugated polyelectrolytes and oligomers

Langmuir

Volumn 29, Issue 34, 2013, Pages 10635-10647

  Wang, Ying ^a,b   Schanze, Kirk S ^c   Chi, Eva Y ^a   Whitten, David G ^a  

^a University of New Mexico   (United States)

^b UNIVERSITY OF NEW MEXICO   (United States)

^c NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-MICROBIAL EFFECTS; ANTIMICROBIAL MECHANISMS; BIOCIDAL ACTIVITY; CELLULAR TARGETS; CONJUGATED POLYELECTROLYTES; INTERMOLECULAR INTERACTIONS; MAMMALIAN CELLS; SELF-ASSEMBLY BEHAVIORS;

MICROORGANISMS; NUCLEIC ACIDS; OLIGOMERS; POLYELECTROLYTES;

CONJUGATED POLYMERS;

ANTIINFECTIVE AGENT; POLYMER;

ANIMAL; ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; DRUG INTERACTION; HUMAN;

ANIMALS; ANTI-INFECTIVE AGENTS; CIRCULAR DICHROISM; DRUG INTERACTIONS; HUMANS; POLYMERS;

EID: 84883221454     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la4012263     Document Type: Article

References (61)

1. Moellering, R. C. Ndm-1-a Cause for Worldwide Concern N. Engl. J. Med. 2010, 363, 2377-2379
2. Klein, E.; Laxminarayan, R.; Smith, D. L.; Gilligan, C. A. Economic Incentives and Mathematical Models of Disease Environ. Dev. Econ. 2007, 12, 707-732
3. Bunz, U. H. F. Poly(aryleneethynylene)s: Syntheses, Properties, Structures, And Applications Chem. Rev. 2000, 100, 1605-1644
4. Tang, Y. L.; Hill, E. H.; Zhou, Z. J.; Evans, D. G.; Schanze, K. S.; Whitten, D. G. Synthesis, Self-Assembly, and Photophysical Properties of Cationic Oligo(p-phenyleneethynylene)s Langmuir 2011, 27, 4945-4955
5. Zhou, Z. J.; Corbitt, T. S.; Parthasarathy, A.; Tang, Y. L.; Ista, L. F.; Schanze, K. S.; Whitten, D. G. "End-Only" Functionalized Oligo(phenylene ethynylene)s: Synthesis, Photophysical and Biocidal Activity J. Phys. Chem. Lett. 2010, 1, 3207-3212
6. Zhao, X. Y.; Pinto, M. R.; Hardison, L. M.; Mwaura, J.; Muller, J.; Jiang, H.; Witker, D.; Kleiman, V. D.; Reynolds, J. R.; Schanze, K. S. Variable Band Gap Poly(arylene ethynylene) Conjugated Polyelectrolytes Macromolecules 2006, 39, 6355-6366
7. Ji, E.; Corbitt, T. S.; Parthasarathy, A.; Schanzes, K. S.; Whitten, D. G. Light and Dark-Activated Biocidal Activity of Conjugated Polyelectrolytes ACS Appl. Mater. Interfaces 2011, 3, 2820-2829
8. Wang, Y.; Canady, T. D.; Zhou, Z. J.; Tang, Y. L.; Price, D. N.; Bear, D. G.; Chi, E. Y.; Schanze, K. S.; Whitten, D. G. Cationic Phenylene Ethynylene Polymers and Oligomers Exhibit Efficient Antiviral Activity ACS Appl. Mater. Interfaces 2011, 3, 2209-2214
9. Wang, Y.; Chi, E. Y.; Natvig, D. O.; Schanze, K. S.; Whitten, D. G. Antimicrobial Activity of Cationic Conjugated Polyelectrolytes and Oligomers against Saccharomyces cerevisiae Vegetative Cells and Ascospores ACS Appl. Mater. Interfaces 2013, 5, 4555-4561
10. Chemburu, S.; Corbitt, T. S.; Ista, L. K.; Ji, E.; Fulghum, J.; Lopez, G. P.; Ogawa, K.; Schanze, K. S.; Whitten, D. G. Light-Induced Biocidal Action of Conjugated Polyelectrolytes Supported on Colloids Langmuir 2008, 24, 11053-11062
11. Ista, L. K.; Dascier, D.; Ji, E.; Parthasarathy, A.; Corbitt, T. S.; Schanze, K. S.; WhittenII-, D. G. Conjugated-Polyelectrolyte-Grafted Cotton Fibers Act as "Micro Flypaper" for the Removal and Destruction of Bacteria ACS Appl. Mater. Interfaces 2011, 3, 2932-2937
12. Corbitt, T. S.; Sommer, J. R.; Chemburu, S.; Ogawa, K.; Ista, L. K.; Lopez, G. P.; Whitten, D. G.; Schanze, K. S. Conjugated Polyelectrolyte Capsules: Light-Activated Antimicrobial Micro "Roach Motels" ACS Appl. Mater. Interfaces 2009, 1, 48-52
13. Lu, L.; Rininsland, F. H.; Wittenburg, S. K.; Achyuthan, K. E.; McBranch, D. W.; Whitten, D. G. Biocidal Activity of a Light-Absorbing Fluorescent Conjugated Polyelectrolyte Langmuir 2005, 21, 10154-10159
14. Corbitt, T. S.; Ding, L. P.; Ji, E. Y.; Ista, L. K.; Ogawa, K.; Lopez, G. P.; Schanze, K. S.; Whitten, D. G. Light and dark biocidal activity of cationic poly(arylene ethynylene) conjugated polyelectrolytes Photochem. Photobiol. Sci. 2009, 8, 998-1005
15. Tang, Y. L.; Zhou, Z. J.; Ogawa, K.; Lopez, G. P.; Schanze, K. S.; Whitten, D. G. Synthesis, Self-Assembly, and Photophysical Behavior of Oligo Phenylene Ethynylenes: From Molecular to Supramolecular Properties Langmuir 2009, 25, 21-25
16. Wang, Y.; Jones, E. M.; Tang, Y. L.; Ji, E. K.; Lopez, G. P.; Chi, E. Y.; Schanze, K. S.; Whitten, D. G. Effect of Polymer Chain Length on Membrane Perturbation Activity of Cationic Phenylene Ethynylene Oligomers and Polymers Langmuir 2011, 27, 10770-10775
17. Wang, Y.; Zhou, Z. J.; Zhu, J. S.; Tang, Y.; Canady, T. D.; Chi, E. Y.; Schanze, K. S.; Whitten, D. G. Dark Antimicrobial Mechanisms of Cationic Phenylene Ethynylene Polymers and Oligomers against Escherichia coli Polymers 2011, 3, 1199-1214
18. Graham, J. M.; Higgins, J. A. Membrane Analysis; Springer: New York, 1997.
19. Wang, Y.; Chi, E. Y.; Schanze, K. S.; Whitten, D. G. Membrane Activity of Antimicrobial Phenylene Ethynylene Based Polymers and Oligomers Soft Matter 2012, 8, 8547-8558
20. Wang, Y.; Tang, Y. L.; Zhou, Z. J.; Ji, E.; Lopez, G. P.; Chi, E. Y.; Schanze, K. S.; Whitten, D. G. Membrane Perturbation Activity of Cationic Phenylene Ethynylene Oligomers and Polymers: Selectivity against Model Bacterial and Mammalian Membranes Langmuir 2010, 26, 12509-12514
21. Corbitt, T. S.; Ji, E.; Wang, Y.; Parthasarathy, A.; Wilde, K. N.; Hill, E. H.; Dascier, D.; Canavan, H. E.; Chi, E. Y.; Schanze, K. S.; Whitten, D. G. Conjugated Polyelectrolyte-Based Biocide Applications. In Conjugated Polyelectrolytes; Liu, B.; Bazan, G. C., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2012; pp 263-294.
22. Wang, Y.; Corbitt, T. S.; Jett, S. D.; Tang, Y.; Schanze, K. S.; Chi, E. Y.; Whitten, D. G. Direct Visualization of Bactericidal Action of Cationic Conjugated Polyelectrolytes and Oligomers Langmuir 2012, 28, 65-70
23. Wang, Y.; Jett, S. D.; Crum, J.; Schanze, K. S.; Chi, E. Y.; Whitten, D. G. Understanding the Dark and Light-Enhanced Bactericidal Action of Cationic Conjugated Polyelectrolytes and Oligomers Langmuir 2013, 29, 781-792
24. Hill, E. H.; Stratton, K.; Whitten, D. G.; Evans, D. G. Molecular Dynamics Simulation Study of the Interaction of Cationic Biocides with Lipid Bilayers: Aggregation Effects and Bilayer Damage Langmuir 2012, 28, 14849-14854
25. Li, Y. L.; Guo, H. Atomistic Simulations of an Antimicrobial Molecule Interacting with a Model Bacterial Membrane Theor. Chem. Acc. 2013, 132, 1-8
26. Brogden, K. A. Antimicrobial Peptides: Pore Formers or Metabolic Inhibitors in Bacteria? Nat. Rev. Microbiol. 2005, 3, 238-250
27. Wimley, W. C. Describing the Mechanism of Antimicrobial Peptide Action with the Interfacial Activity Model ACS Chem. Biol. 2010, 5, 905-917
28. Wimley, W. C.; Hristova, K. Antimicrobial Peptides: Successes, Challenges and Unanswered Questions J. Membr. Biol. 2011, 239, 27-34
29. Charbonneau, D. M.; Tajmir-Riahi, H. A. Study on the Interaction of Cationic Lipids with Bovine Serum Albumin J. Phys. Chem. B 2010, 114, 1148-1155
30. Razumovsky, L.; Damodaran, S. Surface Activity-Compressibility Relationship of Proteins at the Air-Water Interface Langmuir 1999, 15, 1392-1399
31. White, F. H. Studies on Secondary Structure in Chicken Egg-White Lysozyme after Reductive Cleavage of Disulfide Bonds Biochemistry 1976, 15, 2906-2911
32. Tang, Y. L.; Achyuthan, K. E.; Whitten, D. G. Label-Free and Real-Time Sequence Specific DNA Detection Based on Supramolecular Self-Assembly Langmuir 2010, 26, 6832-6837
33. Cowan, M. K.; Talaro, K. P. Microbiology: A Systems Approach, 2 nd ed.; McGraw-Hill Science: New York, 2008.
34. Tang, Y. L.; Corbitt, T. S.; Parthasarathy, A.; Zhou, Z. J.; Schanze, K. S.; Whitten, D. G. Light-Induced Antibacterial Activity of Symmetrical and Asymmetrical Oligophenylene Ethynylenes Langmuir 2011, 27, 4956-4962
35. Xing, C. F.; Xu, Q. L.; Tang, H. W.; Liu, L. B.; Wang, S. Conjugated Polymer/Porphyrin Complexes for Efficient Energy Transfer and Improving Light-Activated Antibacterial Activity J. Am. Chem. Soc. 2009, 131, 13117-13124
36. Yuan, H. X.; Chong, H.; Wang, B.; Zhu, C. L.; Liu, L. B.; Yang, Q.; Lv, F. T.; Wang, S. Chemical Molecule-Induced Light-Activated System for Anticancer and Antifungal Activities J. Am. Chem. Soc. 2012, 134, 13184-13187
37. Ogilby, P. R. Singlet Oxygen: There Is Indeed Something New under the Sun Chem. Soc. Rev. 2010, 39, 3181-3209
38. Cadet, J.; Ravanat, J. L.; Martinez, G. R.; Medeiros, M. H. G.; Di Mascio, P. Singlet Oxygen Oxidation of Isolated and Cellular DNA: Product Formation and Mechanistic Insights Photochem. Photobiol. 2006, 82, 1219-1225
39. Davies, M. J. Singlet Oxygen-Mediated Damage to Proteins and Its Consequences Biochem. Biophys. Res. Commum. 2003, 305, 761-770
40. Ayuyan, A. G.; Cohen, F. S. Lipid Peroxides Promote Large Rafts: Effects of Excitation of Probes in Fluorescence Microscopy and Electrochemical Reactions during Vesicle Formation Biophys. J. 2006, 91, 2172-2183
41. Rabek, J. F. Photochemistry and Photophysics; CRC Press: Boca Raton, FL, 1991; Vol. 3.
42. Davies, M. J. Reactive Species Formed on Proteins Exposed to Singlet Oxygen Photochem. Photobiol. Sci. 2004, 3, 17-25
43. Luxford, C.; Dean, R. T.; Davies, M. J. Induction of DNA Damage by Oxidised Amino Acids and Proteins Biogerontology 2002, 3, 95-102
44. Kawashima, T.; Ohkubo, K.; Fukuzumi, S. Photoinduced DNA Cleavage by formation of ROS from Oxygen with a Neurotransmitter and Aromatic Amino Acids Org. Biomol. Chem. 2010, 8, 994-996
45. Levy, S. B.; Marshall, B. Antibacterial Resistance Worldwide: Causes, Challenges and Responses Nat. Med. 2004, 10, S122-S129
46. McDonnell, G.; Russell, A. D. Antiseptics and Disinfectants: Activity, Action, And Resistance Clin. Microbiol. Rev. 1999, 12, 147-179
47. Lambert, P. A. Cellular Impermeability and Uptake of Biocides and Antibiotics in Gram-Positive Bacteria and Mycobacteria J. Appl. Microbiol. 2002, 92, 46S-54S
48. Epand, R. M.; Epand, R. F. Lipid Domains in Bacterial Membranes and the Action of Antimicrobial Agents Biochim. Biophys. Acta, Biomembr. 2009, 1788, 289-294
49. Lenoir, S.; Pagnoulle, C.; Galleni, M.; Compere, P.; Jerome, R.; Detrembleur, C. Polyolefin Matrixes with Permanent Antibacterial Activity: Preparation, Antibacterial Activity, and Action Mode of the Active Species Biomacromolecules 2006, 7, 2291-2296
50. Amro, N. A.; Kotra, L. P.; Wadu-Mesthrige, K.; Bulychev, A.; Mobashery, S.; Liu, G. Y. High-Resolution Atomic Force Microscopy Studies of the Escherichia coli Outer Membrane: Structural Basis for Permeability Langmuir 2000, 16, 2789-2796
51. Scherrer, R.; Gerhardt, P. Molecular Sieving by the Bacillus megaterium Cell Wall and Protoplast J. Bacteriol. 1971, 107, 718-735
52. Dahl, T. A.; Midden, W. R.; Hartman, P. E. Comparison of Killing of Gram-Negative and Gram-Positive Bacteria by Pure Singlet Oxygen J. Bacteriol. 1989, 171, 2188-2194
53. Wisplinghoff, H.; Bischoff, T.; Tallent, M.; Seifert, H.; Wenzel, R. P.; Edmond, M. B. Nosocomial Bloodstream Infections in US Hospitals: Analysis of 24,179 Cases from a Prospective Nationwide Surveillance Study Clin. Infect. Dis. 2004, 39, 1093-1093
54. Goldstein, A. L.; McCusker, J. H. Development of Saccharomyces cerevisiae as a Model Pathogen: A System for the Genetic Identification of Gene Products Required for Survival in the Mammalian Host Environment Genetics 2001, 159, 499-513
55. Neiman, A. M. Sporulation in the Budding Yeast Saccharomyces cerevisiae Genetics 2011, 189, 737-765
56. Hoiby, N.; Bjarnsholt, T.; Givskov, M.; Molin, S.; Ciofu, O. Antibiotic Resistance of Bacterial Biofilms Int. J. Antimicrob. Agents 2010, 35, 322-332
57. Dascier, D.; Ji, E.; Parthasarathy, A.; Schanze, K. S.; Whitten, D. G. Efficacy of End-Only-Functionalized Oligo(arylene-ethynylene)s in Killing Bacterial Biofilms Langmuir 2012, 28, 11286-11290
58. Michen, B.; Graule, T. Isoelectric Points of Viruses J. Appl. Microbiol. 2010, 109, 388-397
59. Davies, J. Inactivation of Antibiotics and the Dissemination of Resistance Genes Science 1994, 264, 375-382
60. Zhu, C. L.; Yang, Q. O.; Liu, L. B.; Lv, F. T.; Li, S. Y.; Yang, G. Q.; Wang, S. Multifunctional Cationic Poly(p-phenylene vinylene) Polyelectrolytes for Selective Recognition, Imaging, and Killing of Bacteria Over Mammalian Cells Adv. Mater. 2011, 23, 4805-4810
61. Wang, S.; Wu, Y.; Guo, R.; Huang, Y.; Wen, S.; Shen, M.; Wang, J.; Shi, X. Laponite Nanodisks as an Efficient Platform for Doxorubicin Delivery to Cancer Cells Langmuir 2013, 29, 5030-5036