Binaphthyl-1,2,3-triazole peptidomimetics with activity against Clostridium difficile and other pathogenic bacteria

Wales, Steven M.; Hammer, Katherine A.; King, Amy McKarral; Tague, Andrew J.; Lyras, Dena; Riley, Thomas V.; Keller, P. A.; Pyne, Stephen G.

doi:10.1039/c5ob00576k

Cited by 31 publications

(37 citation statements)

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“…Regarding triazolyl amino acids, these residues have been broadly used in drug discovery due to the structural properties and the straightforward synthesis of the 1,2,3‐triazole ring . This nitrogen heterocycle has been described to be resistant to metabolic degradation and it is considered as a powerful pharmacophore .…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the formation of this heterocycle can be easily achieved through an alkyne‐azide cycloaddition under mild conditions that can be applied to derivatize peptide sequences. Various 1,2,3‐triazole‐containing peptides have been reported with a range of biological properties, including HIV‐1 cell entry inhibition, protease inhibition, or antimicrobial activity …”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection

et al. 2017

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The search for novel antimicrobial agents to be used for plant protection has prompted us to design analogues incorporating non-natural amino acids. Herein, we designed and synthesized cyclic peptidotriazoles derived from the lead antimicrobial cyclic peptide c(Lys-Lys-Leu -Lys-Lys -Phe-Lys-Lys-Leu-Gln) (BPC194). In particular, Leu and Lys were replaced by a triazolyl alanine, a triazolyl norleucine or a triazolyl lysine. These peptides were screened for their antibacterial activity against Xanthomonas axonopodis pv. vesicatoria, Erwinia amylovora, and Pseudomonas syringae pv. syringae, for their hemolysis and for their phytotoxicity. Results showed that the type of triazolyl amino acid and the substituent present at the triazole influenced the antibacterial and hemolytic activities. Moreover, the position of this residue was also crucial for the hemolysis. The lead compounds BPC548 and BPC550 exhibited high antibacterial activity (MIC of 3.1 to 25 μM), low hemolysis (19 and 26% at 375 μM, respectively) and low phytotoxicity. Therefore, these analogues could be used as new leads for the development of effective agents to control pathogenic bacteria responsible for plant diseases of economic importance.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection

et al. 2017

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“…133 The antibacterial activity of the compounds was evaluated, with a particular focus on the gastric anaerobe Clostridium difficile, where two dipeptides with a 1,5-and 1,4,5-substitution pattern were among the most active.…”

Section: Scheme 31 Comparison Of Thermal Versus Ruaac Synthesis Of Amentioning

confidence: 99%

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

et al. 2016

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The ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) affords 1,5-disubstituted 1,2,3-triazoles in one step and complements the more established copper-catalyzed reaction providing the 1,4-isomer. The RuAAC reaction has quickly found its way into the organic chemistry toolbox and found applications in many different areas, such as medicinal chemistry, polymer synthesis, organocatalysis, supramolecular chemistry and the construction of 2 electronic devices. This review discusses the mechanism, scope and applications of the RuAAC reaction, covering the literature during the last 10 years. CONTENTS

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“…The incorporation of a second bioisostere triazole in dicationic derivatives of biphenyl 82 gave an 8-fold increase in activity against E. coli compared to binaphthyl derivative 83 [105] (Figure 30).…”

Section: Development Of Peptidomimeticsmentioning

confidence: 99%

Short Cationic Peptidomimetic Antimicrobials

et al. 2019

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The rapid growth of antimicrobial resistance against several frontline antibiotics has encouraged scientists worldwide to develop new alternatives with unique mechanisms of action. Antimicrobial peptides (AMPs) have attracted considerable interest due to their rapid killing and broad-spectrum activity. Peptidomimetics overcome some of the obstacles of AMPs such as high cost of synthesis, short half-life in vivo due to their susceptibility to proteolytic degradation, and issues with toxicity. This review will examine the development of short cationic peptidomimetics as antimicrobials.

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Binaphthyl-1,2,3-triazole peptidomimetics with activity against Clostridium difficile and other pathogenic bacteria

Abstract: ) and vancomycin-resistant E. faecalis (MICs ≥4 µg mL -1

Cited by 31 publications

References 50 publications

Design, synthesis, and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection

Design, synthesis, and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

Short Cationic Peptidomimetic Antimicrobials

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