Poly(sulfur ylides): a new class of zwitterionic polymers with distinct thermal and solution behaviour

Poulladofonou, Georgia; Neumann, Kevin

doi:10.1039/d2py00851c

“…Here, we demonstrate that sulfur ylides, a recently reported new class of zwitterionic polymers, [27] display strong antifouling properties. Our results indicate that the antifouling behaviour is caused by a synergistic effect from induced hydration layers and inhibition of bacterial growth.…”

Section: Introductionmentioning

confidence: 66%

Zwitterionic Polymeric Sulfur Ylides with Minimal Charge Separation Open a New Generation of Antifouling and Bactericidal Materials**

Berking,

Poulladofonou,

Karagrigoriou

et al. 2023

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Zwitterionic polymers are widely employed hydrophilic building blocks for antifouling coatings with numerous applications across a wide range of fields, including but not limited to biomedical science, drug delivery and nanotechnology. Zwitterionic polymers are considered as an attractive alternative to polyethylene glycol because of their biocompatibility and effectiveness to prevent formation of biofilms. To this end, zwitterionic polymers are classified in two categories, namely polybetaines and polyampholytes. Yet, despite a fundamental interest to drive the development of new antifouling materials, the chemical composition of zwitterionic polymer remains severely limited. Here, we show that poly(sulfur ylides) that belong to the largely overlooked class of poly(ylides), effectively prevent the formation of biofilms from pathogenic bacteria. While surface energy analysis reveals strong hydrogen‐bond acceptor capabilities of poly(sulfur ylide), membrane damage of pathogenic bacteria induced by poly(sulfur ylides) indicates toxicity towards bacteria while not affecting eucaryotic cells. Such synergistic effect of poly(sulfur ylides) offers distinct advantages over polyethylene glycol when designing new antifouling materials. We expect that our findings will pave the way for the development of a range of ylide‐based materials with antifouling properties that have yet to be explored, opening up new directions at the interface of chemistry, biology, and material science.

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“…Yet, the restricted structural diversity and chemical space of N -oxides hamper further advancements. Our group explored the use of sulfur ylides as the zwitterionic residue for antifouling materials, where the negative charge is localized on a carbon and the positive charge on a sulfonium residue. , Our results indicated that coatings from poly(sulfur ylides) not only induce a strong hydration layer but also provide a hostile environment selectively to bacteria. Consequently, we observed that those bacteria that overcome the physical barrier of hydration experience a bactericidal environment.…”

mentioning

confidence: 99%

“…Recently, our group and the group of S. Jiang have independently reported poly(ylides) as a new class of unexplored zwitterionic materials (Figure ). − This long-overlooked class of polymers features some distinct structural properties, namely, a positive charge directly adjacent to a negative charge, thereby being in strong contrast to polybetaines that typically have a carbon spacer between the charges. The Jiang group disclosed N -oxides and demonstrated their ultralow antifouling properties in mice models …”

mentioning

confidence: 99%

Unveiling the Antifouling Potential of Stabilized Poly(phosphorus ylides)

Karagrigoriou,

Berking,

Wang

et al. 2023

ACS Macro Lett.

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Zwitterionic polymers have emerged as highly attractive building blocks for antifouling coatings in biomedical applications. Notably, these polymers offer effective alternatives to the widely used poly(ethylene glycol) (PEG), which has raised concerns regarding its immunotoxicity and the development of PEGspecific antibodies. Polymeric ylides, a largely overlooked class of zwitterionic polymers, have been reported as effective antifouling scaffolds. However, the reported subclasses, poly(sulfur ylides) and N-oxides, lack structural diversity and chemical variability. In this study, we present the synthesis and characterization of polymeric phosphorus ylides as an unexplored class of poly(ylides) with significantly increased structural diversity, which is of high value when designing future ylide-based antifouling materials. Our findings demonstrate that, owing to their low dipole moments and hydration layers, these polymeric phosphorus ylides significantly reduce bacterial attachment. Furthermore, we observe selective toxicity toward bacteria rather than mammalian cells. The bactericidal nature of poly(phosphorus ylides), coupled with their expanded chemical space, provides a distinct advantage over existing materials, including zwitterionic polymers from betaine scaffolds. We anticipate that these unexplored structures will broaden the scope of antifouling applications for poly(ylides).

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Zwitterionic Polymeric Sulfur Ylides with Minimal Charge Separation Open a New Generation of Antifouling and Bactericidal Materials**

Berking,

Poulladofonou,

Karagrigoriou

et al. 2023

Angewandte Chemie

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Zwitterionic polymers are widely employed hydrophilic building blocks for antifouling coatings with numerous applications across a wide range of fields, including but not limited to biomedical science, drug delivery and nanotechnology. Zwitterionic polymers are considered as an attractive alternative to polyethylene glycol because of their biocompatibility and effectiveness to prevent formation of biofilms. To this end, zwitterionic polymers are classified in two categories, namely polybetaines and polyampholytes. Yet, despite a fundamental interest to drive the development of new antifouling materials, the chemical composition of zwitterionic polymer remains severely limited. Here, we show that poly(sulfur ylides) that belong to the largely overlooked class of poly(ylides), effectively prevent the formation of biofilms from pathogenic bacteria. While surface energy analysis reveals strong hydrogen‐bond acceptor capabilities of poly(sulfur ylide), membrane damage of pathogenic bacteria induced by poly(sulfur ylides) indicates toxicity towards bacteria while not affecting eucaryotic cells. Such synergistic effect of poly(sulfur ylides) offers distinct advantages over polyethylene glycol when designing new antifouling materials. We expect that our findings will pave the way for the development of a range of ylide‐based materials with antifouling properties that have yet to be explored, opening up new directions at the interface of chemistry, biology, and material science.

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Poly(sulfur ylides): a new class of zwitterionic polymers with distinct thermal and solution behaviour

Abstract: Zwitterionic polymers have emerged as an important class of hydrophilic polymers and found widespread applications not only in biomedical science but also in nanotechnology as antifouling coatings, drug delivery vesicles...

Cited by 8 publications

References 23 publications

Zwitterionic Polymeric Sulfur Ylides with Minimal Charge Separation Open a New Generation of Antifouling and Bactericidal Materials**

Zwitterionic Polymeric Sulfur Ylides with Minimal Charge Separation Open a New Generation of Antifouling and Bactericidal Materials**

Unveiling the Antifouling Potential of Stabilized Poly(phosphorus ylides)

Zwitterionic Polymeric Sulfur Ylides with Minimal Charge Separation Open a New Generation of Antifouling and Bactericidal Materials**

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