Recent advances in the development of anti-infective peptoids

Bicker, Kevin L.; Cobb, Steven L.

doi:10.1039/d0cc04704j

Cited by 44 publications

(49 citation statements)

References 66 publications

(109 reference statements)

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“…Surprisingly, a total loss of activity was observed with a free acid at the C ‐terminus instead of the ethyl ester (hexamer 19 versus hexamer 17 ). It should be noted that antibacterial peptoids developed to date are oligomers with primary amide at the C ‐terminus obtained by solid‐phase synthesis and variation of the C ‐terminal group was to our knowledge never studied contrary to the N ‐terminal group influence [11c] . Therefore, we have no point of comparison with previous work but it is noticeable from this study that C ‐terminal free acid has a deleterious effect on the antibacterial activity of short cationic peptoids.…”

Section: Resultsmentioning

confidence: 71%

Solution‐Phase Synthesis of Backbone‐Constrained Cationic Peptoid Hexamers with Antibacterial and Anti‐Biofilm Activities

et al. 2021

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Submonomer synthesis in solution and block‐coupling protocols were combined to prepare amphiphilic peptoid hexamers. The amphipathic character arises from the use of hydrophobic aliphatic tert‐butyl side‐chains imposing the cis‐amide backbone conformation and various cationic side‐chains periodically introduced each three residues. Evaluation of the effect on Gram‐positive and Gram‐negative bacterial strains as well as the capacity to impair biofilm formation and the toxicity of one selected compound allowed to highlight the potential of a short constrained peptoid carrying triazolium‐type cationic pendant groups.

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Section: Resultsmentioning

confidence: 71%

Solution‐Phase Synthesis of Backbone‐Constrained Cationic Peptoid Hexamers with Antibacterial and Anti‐Biofilm Activities

et al. 2021

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“…[28] Thus the polypeptoids exhibit biocompatibility, potential biological activity and excellent stability upon proteolysis. [29][30][31][32][33][34] In addition, the properties of polypeptoids are mainly dominated by the side-chain motifs as a result of lack of hydrogen bonding and chirality in the backbone. This offers great convenience for preparation of polypeptoids with versatile and tunable properties.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Copolypeptoids with Potent Activity against Drug Resistant Bacteria and Biofilms, Excellent Stability, and Recycling Property

Zhang

Lin

et al. 2022

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The preparation of a type of innovative cationic copolypeptoid antimicrobials containing various hydrophobic moieties that resemble both structure and membrane‐lytic antibacterial mechanism of natural antimicrobial peptides (AMPs) is reported. By finely tuning the hydrophilic/hydrophobic balance, the polypeptoids exhibit a wide spectrum of antibacterial activity against both Gram‐positive bacteria and Gram‐negative bacteria with the lowest minimum inhibitory concentration (MIC) at only 2 µg mL−1, whereas they also show low haemolytic properties. In particular, high selectivity (>128) is achieved from the polymers with butyl moieties. Moreover, the polypeptoids can readily inhibit the formation of biofilms and effectively eradicate the bacteria embedded in the mature biofilms, which is superior to many natural AMPs and vancomycin. Unlike conventional antibiotics, the polypeptoids possess potent activity against drug‐resistant bacteria without visible resistance development after repeated usage. Notably, the polypeptoid antimicrobials not only have inherently fast bactericidal properties and excellent stability against incubation with human plasma, but also show excellent in vivo antibacterial effect. The prepared antimicrobials, coated onto magnetic nanospheres show recycling properties and enhanced antibacterial activity as combined with near‐infrared (NIR)‐induced photothermal antibacterial therapy.

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“…Their progress to clinical use has been languid and hampered by several constraints, including their inhibition by physiological concentrations of salts and anionic polymers, such as glycosaminoglycans; their susceptibility to proteases and peptidases that abound at infection sites; and (largely unknown) toxicity at higher concentrations as well as their cost and issues with large-scale production [44,45]. For this reason, several mimics of HDPs have been proposed and developed to address these shortcomings, such as all-D amino acid peptides [46,47], β-peptides [48], peptoids [48,49], peptide-mimicking polymers [50], and others [51], which were to some extent successful in reproducing biological properties similar to those of HDPs. This review explicitly discusses HDP-inspired antimicrobial polymers and addresses their design principles, recent developments, limitations, and future development.…”

Section: Introductionmentioning

confidence: 99%

Host Defense Peptide-Mimicking Polymers and Polymeric-Brush-Tethered Host Defense Peptides: Recent Developments, Limitations, and Potential Success

Etayash

Hancock

2021

Pharmaceutics

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Amphiphilic antimicrobial polymers have attracted considerable interest as structural mimics of host defense peptides (HDPs) that provide a broad spectrum of activity and do not induce bacterial-drug resistance. Likewise, surface engineered polymeric-brush-tethered HDP is considered a promising coating strategy that prevents infections and endows implantable materials and medical devices with antifouling and antibacterial properties. While each strategy takes a different approach, both aim to circumvent limitations of HDPs, enhance physicochemical properties, therapeutic performance, and enable solutions to unmet therapeutic needs. In this review, we discuss the recent advances in each approach, spotlight the fundamental principles, describe current developments with examples, discuss benefits and limitations, and highlight potential success. The review intends to summarize our knowledge in this research area and stimulate further work on antimicrobial polymers and functionalized polymeric biomaterials as strategies to fight infectious diseases.

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Recent advances in the development of anti-infective peptoids

Abstract: This feature article highlights the progress that has been made towards the development of novel anti-infective peptoids and the key areas for future development within this field.

Cited by 44 publications

References 66 publications

Solution‐Phase Synthesis of Backbone‐Constrained Cationic Peptoid Hexamers with Antibacterial and Anti‐Biofilm Activities

Solution‐Phase Synthesis of Backbone‐Constrained Cationic Peptoid Hexamers with Antibacterial and Anti‐Biofilm Activities

Antibacterial Copolypeptoids with Potent Activity against Drug Resistant Bacteria and Biofilms, Excellent Stability, and Recycling Property

Host Defense Peptide-Mimicking Polymers and Polymeric-Brush-Tethered Host Defense Peptides: Recent Developments, Limitations, and Potential Success

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