Kenichi Kuroda

University of Michigan, Ann Arbor, Michigan, United States

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Publications (25)115.53 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: Dentin hypersensitivity (DH) is a prevalent problem. This study aimed to formulate a paste using fluorhydroxyapatite (FA) crystals dispersed in different carriers to treat DH. The ability to occlude patent dentinal tubules and to release ions was investigated. Twenty percent FA/sodium alginate, 40 % FA/poly(hydroxyethyl methacylate(HEMA)), and 40 % FA/poly(DMA-co-MEA) were applied to etched dentin samples and examined with scanning electron microscopy (SEM) to determine the degree of tubule occlusion. Fluoride electrode was used to measure F release and spectroscopy to evaluate Ca and PO4 release. The cytotoxicity of the synthesized poly(DMA-co-MEA) gel was tested. Kruskall-Wallis test was used to test the differences in ion release between the groups. FA/poly(DMA-co-MEA) paste obstructed up to 80 % of the dentinal tubules, while the coverage was up to 70 % for FA/poly(HEMA) and less than 50 % for FA/sodium alginate. Fluoride and Ca release was the highest for FA/P(HEMA), 7.2 ± 0.7 and 139.8 ± 32.5 ppm, respectively. The highest concentration of PO4 was 46.2 ± 16.4 ppm for FA/Sodium alginate. No statistical significance was found. FA/Poly(DMA-co-MEA) and FA/poly(HEMA) pastes may offer immediate short-term relief of DH because of their ability to occlude the tubules and adhere to wet dentin surfaces. The release of the F, Ca, and PO4 ions may offer long-term relief by forming a mineral barrier both within the dentinal tubules and on the dentin surface. The tested materials may offer a long-term treatment for DH.
    Clinical Oral Investigations 02/2015; · 2.20 Impact Factor
  • Kazuma Yasuhara, Kenichi Kuroda
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    ABSTRACT: To gain an understanding of the toxicity of antimicrobial polymers to human cells, their hemolytic action was investigated using human red blood cells (RBCs). We examined the hemolysis induced by cationic amphiphilic methacrylate random copolymers, which have amino ethyl sidechains as cationic units and either butyl or methyl methacrylate as hydrophobic units. The polymer with 30 mol% butyl sidechains (B30) displayed higher hemolytic toxicity than the polymer with 59 mol% methyl sidechains (M59). B30 also induced faster release of hemoglobin from RBCs than M59. A new theoretical model is proposed based on two consecutive steps to form active polymer species on the RBC membranes, which are associated to RBC lysis. This model takes the all-or-none release of hemoglobin by the rupture of RBCs into account, providing new insight into the polymer-induced hemolysis regarding how individual or collective cells respond to the polymers.
    Chinese Chemical Letters 02/2015; · 1.18 Impact Factor
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    Upayan Baul, Kenichi Kuroda, Satyavani Vemparala
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    ABSTRACT: Using atomistic molecular dynamics simulations, interaction of multiple synthetic random copolymers based on methacrylates on prototypical bacterial membranes is investigated. The simulations show that the cationic polymers form a micellar aggregate in water phase and the aggregate, when interacting with the bacterial membrane, induces clustering of oppositely charged anionic lipid molecules to form clusters and enhances ordering of lipid chains. The model bacterial membrane, consequently, develops lateral inhomogeneity in membrane thickness profile compared to polymer-free system. The individual polymers in the aggregate are released into the bacterial membrane in a phased manner and the simulations suggest that the most probable location of the partitioned polymers is near the 1-palmitoyl-2-oleoyl-phosphatidylglycerol (POPG) clusters. The partitioned polymers preferentially adopt facially amphiphilic conformations at lipid-water interface, despite lacking intrinsic secondary structures such as α-helix or β-sheet found in naturally occurring antimicrobial peptides.
    The Journal of Chemical Physics 08/2014; 141(8):084902. · 3.12 Impact Factor
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    ABSTRACT: We demonstrate utilization of star-shaped polymers as high-density polymer brush coatings and their effectiveness to inhibit the adhesion of platelets and bacteria. Star polymers consisting of poly(2-hydroxyethyl methacrylate) (PHEMA) and/or poly(methyl methacrylate) (PMMA) were synthesized using living radical polymerization with a ruthenium catalyst. The polymer coatings were prepared by simple drop casting of the polymer solution onto poly(ethylene terephthalate) (PET) surfaces and then dried. Among the star polymers prepared in this study, the PHEMA star polymer (star-PHEMA) and the PHEMA/PMMA (mol. ratio of 71/29) heteroarm star polymer (star-H71M29) coatings showed the highest percentage of inhibition against platelet adhesion (78–88% relative to the non-coated PET surface) and Escherichia coli (94–97%). These coatings also showed anti-adhesion activity against platelets after incubation in Dulbecco's phosphate buffered saline or surfactant solution for 7 days. In addition, the PMMA component of the star polymers increased the scratch resistance of the coating. These results indicate that the star-polymer architecture provides high polymer chain density on PET surfaces to prevent adhesion of platelets and bacteria, as well as coating stability and physical durability to prevent exposure of bare PET surfaces. The star polymers provide a simple and effective approach to preparing anti-adhesion polymer coatings on biomedical materials against the adhesion of platelets and bacteria.
    Biomater. Sci. 07/2014; 2(9).
  • Laura M Thoma, Blaise R Boles, Kenichi Kuroda
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    ABSTRACT: The in vitro and in vivo antimicrobial activity of primary ammonium ethyl methacrylate homopolymers (AEMPs) was investigated. AEMPs with different degrees of polymerization (DP = 7.7 to 12) were prepared by reversible addition-fragmentation chain-transfer (RAFT) polymerization. The AEMPs showed higher inhibitory effects against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), than Gram-negative bacteria. The AEMPs also showed potent anti-S. aureus activity in the presence of fetal bovine serum, while the activity of antibiotic mupirocin was reduced under the same condition. The AEMPs showed very little or no hemolytic activity. The cytotoxicity of AEMPs against mammalian cells HEp-2 and COS-7 was concentration dependent, and the cell viabilities significantly decreased at higher polymer concentrations. The AEMPs significantly reduced the number of viable S. aureus cells in the nasal environment of cotton rats when compared to the control. This study demonstrates that AEMPs have potential for use in treating topical S. aureus infections.
    Biomacromolecules 07/2014; · 5.79 Impact Factor
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    ABSTRACT: The function and mode of action of curcumin in modulating the formation of lipid raft domains were investigated by microscopic observation using model membranes. Curcumin induces fusion of lipid raft domains at extremely low concentrations through the alteration of the boundary between the ordered and disordered phases.
    Chemical Communications 01/2014; · 6.38 Impact Factor
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    ABSTRACT: Back Cover: The search for more effective antibiotics is addressed on page 1285, where K. Kuroda and colleagues design and develop antimicrobial copolymers which mimic naturally occurring antimicrobial peptides. These polymers exhibit powerful activity against a broad spectrum of bacteria without the onset of adverse effects or resistance. The flexible synthesis of such polymers show promise in the development of highly efficient antimicrobial materials.
    Macromolecular Bioscience 10/2013; 13(10):1456. · 3.65 Impact Factor
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    ABSTRACT: There is an urgent need for new antibiotics which are effective against drug-resistant bacteria without contributing to resistance development. We have designed and developed antimicrobial copolymers with cationic amphiphilic structures based on the mimicry of naturally occurring antimicrobial peptides. These copolymers exhibit potent antimicrobial activity against a broad spectrum of bacteria including methicillin-resistant Staphylococcus aureus with no adverse hemolytic activity. Notably, these polymers also did not result in any measurable resistance development in E. coli. The peptide-mimetic design principle offers significant flexibility and diversity in the creation of new antimicrobial materials and their potential biomedical applications.
    Macromolecular Bioscience 07/2013; · 3.65 Impact Factor
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    ABSTRACT: Polymeric synthetic mimics of antimicrobial peptides (SMAMPs) have recently demonstrated similar antimicrobial activity as natural antimicrobial peptides (AMPs) from innate immunity. This is surprising, since polymeric SMAMPs are heterogeneous in terms of chemical structure (random sequence) and conformation (random coil), in contrast to defined amino acid sequence and intrinsic secondary structure. To understand this better, we compare AMPs with a 'minimal' mimic, a well characterized family of polydisperse cationic methacrylate-based random copolymer SMAMPs. Specifically, we focus on a comparison between the quantifiable membrane curvature generating capacity, charge density, and hydrophobicity of the polymeric SMAMPs and AMPs. Synchrotron small angle x-ray scattering (SAXS) results indicate that typical AMPs and these methacrylate SMAMPs generate similar amounts of membrane negative Gaussian curvature (NGC), which is topologically necessary for a variety of membrane-destabilizing processes. Moreover, the curvature generating ability of SMAMPs is more tolerant of changes in the lipid composition than that of natural AMPs with similar chemical groups, consistent with the lower specificity of SMAMPs. We find that, although the amount of NGC generated by these SMAMPs and AMPs are similar, the SMAMPs require significantly higher levels of hydrophobicity and cationic charge to achieve the same level of membrane deformation. We propose an explanation for these differences, which has implications for new synthetic strategies aimed at improved mimesis of AMPs.
    Macromolecules 03/2013; 46(5):1908-1915. · 5.93 Impact Factor
  • Kenichi Kuroda, Gregory A Caputo
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    ABSTRACT: Antibiotic-resistant bacteria 'superbugs' are an emerging threat to public health due to the decrease in effective antibiotics as well as the slowed pace of development of new antibiotics to replace those that become ineffective. The need for new antimicrobial agents is a well-documented issue relating to world health. Tremendous efforts have been given to developing compounds that not only show high efficacy, but also those that are less susceptible to resistance development in the bacteria. However, the development of newer, stronger antibiotics which can overcome these acquired resistances is still a scientific challenge because a new mode of antimicrobial action is likely required. To that end, amphiphilic, cationic polymers have emerged as a promising candidate for further development as an antimicrobial agent with decreased potential for resistance development. These polymers are designed to mimic naturally occurring host-defense antimicrobial peptides which act on bacterial cell walls or membranes. Antimicrobial-peptide mimetic polymers display antibacterial activity against a broad spectrum of bacteria including drug-resistant strains and are less susceptible to resistance development in bacteria. These polymers also showed selective activity to bacteria over mammalian cells. Antimicrobial polymers provide a new molecular framework for chemical modification and adaptation to tune their biological functions. The peptide-mimetic design of antimicrobial polymers will be versatile, generating a new generation of antibiotics toward implementation of polymers in biomedical applications. WIREs Nanomed Nanobiotechnol 2012. doi: 10.1002/wnan.1199 Conflict of interest: K. K. is a coinventor on a patent application filed by the University of Pennsylvania covering 'Antimicrobial Copolymers and Uses Thereof'. The patent application has been licensed to PolyMedix Inc. (Radnor, PA). PolyMedix did not play a role in the design and conduct of this study; in the collection, analysis, or interpretation of the data; or in the preparation, review, or approval of the article. For further resources related to this article, please visit the WIREs website.
    Wiley Interdisciplinary Reviews Nanomedicine and Nanobiotechnology 10/2012; · 5.68 Impact Factor
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    ABSTRACT: We report the structure-activity relationship in the antimicrobial activity of linear and branched poly(ethylene imine)s (L- and B-PEIs) with a range of molecular weights (MWs) (500-12 000). Both L- and B-PEIs displayed enhanced activity against Staphylococcus aureus over Escherichia coli. Both B- and L-PEIs did not cause any significant permeabilization of E. coli cytoplasmic membrane. L-PEIs induced depolarization of S. aureus membrane although B-PEIs did not. The low MW B-PEIs caused little or no hemolysis while L-PEIs are hemolytic. The low MW B-PEIs are less cytotoxic to human HEp-2 cells than other PEIs. However, they induced significant cell viability reduction after 24 h incubation. The results presented here highlight the interplay between polymer size and structure on activity.
    Macromolecular Bioscience 08/2012; 12(9):1279-89. · 3.65 Impact Factor
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    ABSTRACT: Self-degradable antimicrobial copolymers bearing cationic side chains and main-chain ester linkages were synthesized using the simultaneous chain- and step-growth radical polymerization of t-butyl acrylate and 3-butenyl 2-chloropropionate, followed by the transformation of t-butyl groups into primary ammonium salts. We prepared a series of copolymers with different structural features in terms of molecular weight, monomer composition, amine functionality, and side chain structures to examine the effect of polymer properties on their antimicrobial and hemolytic activities. The acrylate copolymers containing primary amine side chains displayed moderate antimicrobial activity against E. coli but were relatively hemolytic. The acrylate copolymer with quaternary ammonium groups and the acrylamide copolymers showed low or no antimicrobial and hemolytic activities. An acrylate copolymer with primary amine side chains degraded to lower molecular weight oligomers with lower antimicrobial activity in aqueous solution. This degradation was due to amidation of the ester groups of the polymer chains by the nucleophilic addition of primary amine groups in the side chains resulting in cleavage of the polymer main chain. The degradation mechanism was studied in detail by model reactions between amine compounds and precursor copolymers.
    Biomacromolecules 04/2012; 13(5):1554-63. · 5.79 Impact Factor
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    ABSTRACT: Antimicrobial and hemolytic activities of amphiphilic random copolymers were modulated by the structure of the cationic side chain spacer arms, including 2-aminoethylene, 4-aminobutylene, and 6-aminohexylene groups. Cationic amphiphilic random copolymers with ethyl methacrylate (EMA) comonomer were prepared with a range of comonomer fractions, and the library of copolymers was screened for antimicrobial and hemolytic activities. Copolymers with 4-aminobutylene cationic side chains showed an order of magnitude enhancement in their antimicrobial activity relative to those with 2-aminoethylene spacer arms, without causing adverse hemolysis. When the spacer arms were further elongated to hexylene, the copolymers displayed potent antimicrobial and hemolytic activities. The 4-aminobutylene side chain appears to be the optimal spacer arm length for maximal antimicrobial potency and minimal hemolysis, when combined with hydrophobic ethylmethacrylate in a roughly 70/30 ratio. The copolymers displayed relatively rapid bactericidal kinetics and broad-spectrum activity against a panel of Gram-positive and Gram-negative bacteria. The effect of the spacer arms on the polymer conformation in the membrane-bound state was investigated by molecular dynamics simulations. The polymer backbones adopt an extended chain conformation, parallel to the membrane surface. A facially amphiphilic conformation at the membrane surface was observed, with the primary ammonium groups localized at the lipid phoshophate region and the nonpolar side chains of EMA comonomers buried in the hydrophobic membrane environment. This study demonstrates that the antimicrobial activity and molecular conformation of amphiphilic methacrylate random copolymers can be modulated by adjustment of cationic side chain spacer arms.
    Biomacromolecules 04/2012; 13(5):1632-41. · 5.79 Impact Factor
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    ABSTRACT: Cationic amphiphilic polymethacrylate derivatives (PMAs) have shown potential as a novel class of synthetic antimicrobials. A panel of PMAs with varied ratios of hydrophobic and cationic side chains were synthesized and tested for antimicrobial activity and mechanism of action. The PMAs are shown to be active against a panel of pathogenic bacteria, including a drug-resistant Staphylococcus aureus, compared to the natural antimicrobial peptide magainin which did not display any activity against the same strain. The selected PMAs with 47–63% of methyl groups in the side chains showed minimum inhibitory concentrations of ≤2–31 µg/mL, but cause only minimal harm to human red blood cells. The PMAs also exhibit rapid bactericidal kinetics. Culturing Escherichia coli in the presence of the PMAs did not exhibit any potential to develop resistance against the PMAs. The antibacterial activities of PMAs against E. coli and S. aureus were slightly reduced in the presence of physiological salts. The activity of PMAs showed bactericidal effects against E. coli and S. aureus in both exponential and stationary growth phases. These results demonstrate that PMAs are a new antimicrobial platform with no observed development of resistance in bacteria. In addition, the PMAs OPEN ACCESS Polymers 2011, 3 1513 permeabilized the E. coli outer membrane at polymer concentrations lower than their MIC values, but they did not show any effect on the bacterial inner membrane. This indicates that mechanisms other than membrane permeabilization may be the primary factors determining their antimicrobial activity.
    Polymers 12/2011; 3:1512-1532. · 2.51 Impact Factor
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    ABSTRACT: We examined the antibacterial and hemolytic activities in a series of amphiphilic block and random copolymers of poly(vinyl ether) derivatives prepared by base-assisting living cationic polymerization. Block and random amphiphilic copolymers with similar monomer compositions showed the same level of activity against Escherichia coli . However, the block copolymers are much less hemolytic compared to the highly hemolytic random copolymers. These results indicate that the amphiphilic copolymer structure is a key determinant of activity. Furthermore, the block copolymers induced dye leakage from lipid vesicles consisting of E. coli -type lipids, but not mammalian lipids, while the random copolymers disrupted both types of vesicles. In addition, both copolymers displayed bactericidal and hemolytic activities at concentrations 1 or 2 orders of magnitude lower than their critical (intermolecular) aggregation concentrations (CACs), as determined by light scattering measurements. This suggests that polymer aggregation or macromolecular assembly is not a requisite for the antibacterial activity and selectivity against bacteria over human red blood cells (RBCs). We speculate that different single-chain conformations between the block and random copolymers play an important role in the antibacterial action and underlying antibacterial mechanisms.
    Biomacromolecules 08/2011; 12(10):3581-91. · 5.79 Impact Factor
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    ABSTRACT: A simple homogeneous assay for the detection of membrane permeabilization by antimicrobial peptides and synthetic copolymers is described. Liposomes encapsulating pyrroloquinoline quinone (PQQ), the prosthetic group of the apoenzyme glucose dehydrogenase (GDH), are used to detect membrane permeabilization by the antimicrobial peptides MSI-594 and MSI-78 as well as various synthetic antimicrobial copolymers in an optical microwell assay. PQQ-loaded liposomes and the peptide or copolymer are added to wells of a 96-well microtiter plate. If the integrity of the liposome is compromised, the PQQ encapsulated in the liposomes is released and available for activating the apoenzyme. The release of PQQ catalyzes a color change in the presence of apo-GDH, glucose, and the redox dye 1,6-dichlorophenol indophenol (DCPIP) that can be evaluated through a visual color change. For more quantitative measurements, the absorbance change over a 30min period was measured. The absorbance change is related to the activity and concentration for a given antimicrobial agent. Furthermore, by varying liposome compositions to include cholesterol, the potential toxicity of the peptide or polymer toward mammalian cells can be readily evaluated. The assay is simple and sensitive and will be useful for analyzing the membrane permeation/disruption properties of a host of antimicrobial peptides and synthetic polymers.
    Analytical Biochemistry 04/2011; 411(2):194-9. · 2.31 Impact Factor
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    ABSTRACT: A new strategy for preparing antimicrobial surfaces by a simple dip-coating procedure is reported. Amphiphilic polycations with different mole ratios of monomers containing dodecyl quaternary ammonium, methoxyethyl, and catechol groups were synthesized by free-radical polymerization. The polymer coatings were prepared by immersing glass slides into a polymer solution and subsequent drying and heating. The quaternary ammonium side chains endow the coatings with potent antibacterial activity, the methoxyethyl side chains enable tuning the hydrophobic/hydrophilic balance, and the catachol groups promote immobilization of the polymers into films. The polymer-coated surfaces displayed bactericidal activity against Escherichia coli and Staphylococcus aureus in a dynamic contact assay and prevented the accumulation of viable E. coli, S. aureus, and Acinetobacter baumannii for up to 96 h. Atomic force microscopy (AFM) images of coating surfaces indicated that the surfaces exhibit virtually the same smoothness for all polymers except the most hydrophobic. The hydrophobic polymer without methoxyethyl side chains showed clear structuring into polymer domains, causing high surface roughness. Sum-frequency generation (SFG) vibrational spectroscopy characterization of the surface structures demonstrated that the dodecyl chains are predominantly localized at the surface-air interface of the coatings. SFG also showed that the phenyl groups of the catechols are oriented on the substrate surface. These results support our hypothesis that the adhesive or cross-linking functionality of catechol groups discourages polymer leaching, allowing the tuning of the amphiphilic balance by incorporating hydrophilic components into the polymer chains to gain potent biocidal activity.
    Langmuir 03/2011; 27(7):4010-9. · 4.38 Impact Factor
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    ABSTRACT: Sum frequency generation (SFG) vibrational spectroscopy was used to analyze interactions between solid-supported lipid bilayers acting as models for cellular membranes and several membrane-active random copolymers with different lipophilic side chains, named 0R (no group), 33Me (methyl group), 11Bz (benzyl group), and 33Bu (butyl group), according to both the identity and percentage of the side chains within the polymer. Biological tests of the minimum inhibitory concentration (MIC) and hemolytic concentration were performed. The inherent surface sensitivity of SFG allowed for independent monitoring of isotopically labeled lipid bilayer leaflets as a function of concentration to study polymer-bilayer interaction mechanisms. Concentrations at which each bilayer leaflet was disrupted were quantitatively determined for each copolymer. Spectroscopic evidence of interaction with the bilayer below the critical concentrations was observed for the 11Bz polymer. The lipophilic butyl side chain of the 33Bu polymer was found to be oriented parallel to the surface normal. This research shows that SFG is a useful analytical technique which provides unique details regarding the interaction mechanisms of these membrane-active copolymers and lipid bilayers.
    Analytical Chemistry 02/2011; 83(4):1342-9. · 5.83 Impact Factor
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    ABSTRACT: Cationic, amphiphilic polymers are currently being used as antimicrobial agents that disrupt biomembranes, although their mechanisms remain poorly understood. Herein, membrane association and disruption by amphiphilic polymers bearing primary, tertiary, or quaternary ammonium salt groups reveal the role of cationic group structure in the polymer-membrane interaction. The dissociation constants of polymers to liposomes of POPC were obtained by a fluorometric assay, exploiting the environmental sensitivity of dansyl moieties in the polymer end groups. Dye leakage from liposomes and solid-state NMR provided further insights into the polymer-induced membrane disruption. Interestingly, the polymers with primary amine groups induced reorganization of the bilayer structure to align lipid headgroups perpendicular to the membrane. The results showed that polymers bearing primary amines exceed the tertiary and quaternary ammonium counterparts in membrane binding and disrupting abilities. This is likely due to enhanced complexation of primary amines to the phosphate groups in the lipids, through a combination of hydrogen bonding and electrostatic interactions.
    The Journal of Physical Chemistry B 01/2011; 115(2):366-75. · 3.38 Impact Factor
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    ABSTRACT: Hemolysis induced by antimicrobial polymers was examined to gain an understanding of the mechanism of polymer toxicity to human cells. A series of cationic amphiphilic methacrylate random copolymers containing primary ammonium groups as the cationic functionality and either butyl or methyl groups as hydrophobic side chains have been prepared by radical copolymerization. Polymers with 0-47 mol % methyl groups in the side chains, relative to the total number of monomeric units, showed antimicrobial activity but no hemolysis. The polymers with 65 mol % methyl groups or 27 mol % butyl groups displayed both antimicrobial and hemolytic activity. These polymers induced leakage of the fluorescent dye calcein trapped in human red blood cells (RBCs), exhibiting the same dose-response curves as for hemoglobin leakage. The percentage of disappeared RBCs after hemolysis increased in direct proportion to the hemolysis percentage, indicating complete release of hemoglobin from fractions of RBCs (all-or-none leakage) rather than partial release from all cells (graded leakage). An osmoprotection assay using poly(ethylene glycol)s (PEGs) as osmolytes indicated that the PEGs with MW > 600 provided protection against hemolysis while low molecular weight PEGs and sucrose had no significant effect on the hemolytic activity of polymers. Accordingly, we propose the mechanism of polymer-induced hemolysis is that the polymers produce nanosized pores in the cell membranes of RBCs, causing an influx of small solutes into the cells and leading to colloid-osmotic lysis.
    Biomacromolecules 01/2011; 12(1):260-8. · 5.79 Impact Factor

Publication Stats

386 Citations
115.53 Total Impact Points


  • 2009–2014
    • University of Michigan
      • • Department of Biologic and Materials Sciences
      • • School of Dentistry
      • • Department of Chemistry
      • • Department of Macromolecular Science And Engineering
      Ann Arbor, Michigan, United States
    • Concordia University–Ann Arbor
      Ann Arbor, Michigan, United States
  • 2012
    • Nagoya University
      • Graduate School of Engineering
      Nagoya-shi, Aichi-ken, Japan
  • 2011
    • Seoul National University of Science and Technology
      Sŏul, Seoul, South Korea
    • Osaka University
      • Department of Macromolecular Science
      Ōsaka-shi, Osaka-fu, Japan