Lipidated Cyclic γ-AApeptides Display Both Antimicrobial and Anti-inflammatory Activity

Li, Yaqiong; Smith, Clark M.; Wu, Haifan; Padhee, Shruti; Manoj, Namitha; Cardiello, Joseph F; Qiao, Qiao; Cao, Chuanhai; Yin, Hang; Cai, Jianfeng

doi:10.1021/cb4006613

Cited by 63 publications

(89 citation statements)

References 40 publications

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“…In this strategy, alloc-protected γ-AApeptide building blocks ( Figure 2B) are prepared and assembled on solid support to provide the desired γ-AApeptides sequences (Figure 2A) [31][32]35,36,[44][45][46][47]. The derivatization of γ-AApeptides is virtually unlimited due to the freedom of using readily available carboxylic acids.…”

Section: Synthesis Of γ-Aapeptidesmentioning

confidence: 99%

“…The results show that they can mimic HDPS and exhibit broad-spectrum activ- A helical scaffold of γ9 is also shown, in which red dots represent hydrophobic groups, and blue dots represent hydrophilic groups. Data taken from [37][38][39][40][41][42][43].…”

Section: γ-Aapeptides As Antimicrobial Agentsmentioning

confidence: 99%

“…To test the hypothesis, a series of lipidated cyclic γ-AApeptides including different numbers of amphiphilic γ-AApeptide building blocks were designed, synthesized and then measured for their activity against a range of multidrugresistant bacterial pathogens (Figure 4 & Table 1) [40]. Particularly, γ7, with a small amphipathic ring and a C 16 lipid tail outside, shows very potent activity against all tested drug-resistant stains.…”

Section: Lipo-cyclic Antimicrobial γ-Aapeptidesmentioning

confidence: 99%

“…For instance, they display inhibitory activity toward p53/MDM2 protein-protein interaction [31,32]. In addition, they also harness immune response and inhibit lipopolysaccharide (LPS)-activated Toll-like receptor 4 (TLR4) signaling [36]. In addition, γ-AApeptides have shown promise as potential antimicrobial agents [37][38][39][40][41][42][43].…”

mentioning

confidence: 99%

“…In addition, they also harness immune response and inhibit lipopolysaccharide (LPS)-activated Toll-like receptor 4 (TLR4) signaling [36]. In addition, γ-AApeptides have shown promise as potential antimicrobial agents [37][38][39][40][41][42][43]. Recently, γ-AApeptides exhibit comparable or enhanced performance compared with ciprofloxacin in the prevention of biofilm formation of both Gram-positive and Gram-negative bacteria [44].…”

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The Development of Antimicrobial γ-Aapeptides

et al. 2016

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Host-defense peptides (HDPs) are promising next generation of antibiotic agents, as they have the potential to circumvent emerging drug resistance, due to their mechanism of bacterial killing through disruption of their membranes. Nonetheless, HDPs have intrinsic drawbacks such as low-to-moderate activity, susceptibility to enzymatic degradation. In the past few years, we developed a new class of peptidomimetics named ‘γ-AApeptides’, which have superior resistance to proteolysis and a variety of diversification via straightforward synthesis. Our recent studies suggested that γ-AApeptides can mimic the bactericidal mechanism of HDPs and show potent and broad-spectrum activity against both Gram-positive and Gram-negative multidrug-resistant bacteria. In this review, we summarize our current studies of antimicrobial γ-AApeptides and discuss their potential future development as antimicrobial peptidomimetics.

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Section: Synthesis Of γ-Aapeptidesmentioning

confidence: 99%

Section: γ-Aapeptides As Antimicrobial Agentsmentioning

confidence: 99%

Section: Lipo-cyclic Antimicrobial γ-Aapeptidesmentioning

confidence: 99%

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The Development of Antimicrobial γ-Aapeptides

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Peptidomimetics as Antimicrobial Agents

Teng

Cai

2014

Novel Antimicrobial Agents and Strategies

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Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

Karaman

Zainel

Kapkac

et al. 2018

Archiv der Pharmazie

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1,3-Oxazolidine-2-one is an important heterocyclic ring participating in the chemical structure of many drugs. In this research, 22 new amide/sulfonamide/thiourea derivatives (1-22) were obtained by the reaction of (S)-4-(4-aminobenzyl)-2(1H)-1,3-oxazolidinone with 4-substituted benzoyl chlorides, 4-substituted benzene sulfonyl chlorides, and 4-substituted phenyl isothiocyanates. The structures of all synthesized compounds were clarified by FT-IR, NMR, and mass spectroscopic and elemental analysis techniques. The synthesized compounds were screened for their antimicrobial activity. Antimicrobial susceptibility and cellular physiology were evaluated using the microbroth dilution assay and the flow cytometry method. As a result, it was determined that compound 16 displayed better antimicrobial activity than chloramphenicol against Gram-positive bacteria, especially Staphylococcus aureus. In order to understand the mechanism of effect of the compounds on the cell membrane, fluorescence microscopy was used. Cell membrane damage of the Gram positive bacteria treated with compound 16 was observed as a result of intense staining with propidium iodide. In addition, genotoxicity, cytotoxicity, and absorption, distribution, metabolism, and excretion (ADME) parameters of compound 16 were examined and it was found as non-mutagenic and non-cytotoxic at the concentration at which it showed antimicrobial activity. According to the calculated ADME parameters and drug likeness scores, the compounds can be good drug candidates, especially compound 16.

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Lipidated Cyclic γ-AApeptides Display Both Antimicrobial and Anti-inflammatory Activity

Cited by 63 publications

References 40 publications

The Development of Antimicrobial γ-Aapeptides

The Development of Antimicrobial γ-Aapeptides

Peptidomimetics as Antimicrobial Agents

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

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