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Related Concept Videos

Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

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Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan...
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Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

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The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
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Gene Regulation in Microbial Communities: Quorum Sensing01:28

Gene Regulation in Microbial Communities: Quorum Sensing

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Quorum sensing is a mechanism of bacterial communication that enables coordinated gene expression in response to changes in population density. This facilitates collective behaviors that enhance survival, resource acquisition, and ecological adaptation. This process relies on small signaling molecules called autoinducers that accumulate as bacterial populations grow. When a critical threshold concentration of autoinducers is reached, bacterial cells collectively modify gene expression,...
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Antimicrobial Proteins01:23

Antimicrobial Proteins

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Antimicrobial proteins are important components of the immune system. They aid the body in combating pathogens by either killing them directly or hindering their replication processes. Four main types of antimicrobial substances are interferons, the complement system, iron-binding proteins, and antimicrobial proteins.
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Antibacterial peptidomimetics based on guanidine-functionalized di-tertiary amides.

Ghayah Bahatheg1,2, Rajesh Kuppusamy1,3, Lissy M Hartmann4

  • 1School of Chemistry, The University of New South Wales (UNSW) Sydney NSW 2052 Australia g.bahatheg@unsw.edu.au r.kuppusamy@unsw.edu.au n.kumar@unsw.edu.au.

RSC Medicinal Chemistry
|November 6, 2025
PubMed
Summary

Novel guanidinium tertiary amides, a type of peptoid, show potent antibacterial activity and biofilm disruption against key pathogens. These stable, cell-penetrating compounds offer a promising new class of antimicrobial agents with low toxicity.

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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

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Area of Science:

  • Medicinal Chemistry
  • Peptidomimetics
  • Antimicrobial Agents

Background:

  • Tertiary amides, like peptoids, are advanced peptidomimetics offering improved stability and activity over natural antimicrobial peptides.
  • Guanidino compounds are recognized for their cell-penetrating properties, making them attractive in drug development.
  • Combining peptoid backbone properties with guanidine's cell-penetrating ability and antimicrobial peptide (AMP)-like features is a novel strategy.

Purpose of the Study:

  • To investigate the impact of modifying guanidino groups on the antibacterial activity of tertiary amides.
  • To design and synthesize a library of guanidinium tertiary amides incorporating lipophilic, hydrophobic, and cationic features.
  • To evaluate the antibacterial efficacy, biofilm disruption capabilities, and safety profile of these novel compounds.

Main Methods:

  • Design and synthesis of a library of bromo-phenyl and dichloro-phenyl-based guanidinium tertiary amides.
  • Determination of minimum inhibitory concentrations (MICs) against *Staphylococcus aureus*, *Escherichia coli*, and *Pseudomonas aeruginosa*.
  • Assessment of biofilm disruption activity, membrane permeability, and cytotoxicity (HC50).

Main Results:

  • Compounds with guanidine bearing 3C and 6C alkylated cationic groups (19a, 20a, 19b, 20b) demonstrated the highest activity against all tested bacterial strains.
  • MIC values ranged from 1-2 μg mL-1 for *S. aureus*, 4-8 μg mL-1 for *E. coli*, and 16.5-35.6 μg mL-1 for *P. aeruginosa*.
  • Compound 19b effectively disrupted *S. aureus* biofilms (75%), and compound 19g disrupted *E. coli* biofilms (50%). Membrane studies indicated cell membrane depolarization and disruption. The most potent compounds showed no toxicity (HC50 > 50 μg mL-1).

Conclusions:

  • Modified guanidinium tertiary amides exhibit potent broad-spectrum antibacterial activity and significant biofilm disruption capabilities.
  • The incorporation of specific cationic group lengths (3C and 6C) is crucial for optimizing antimicrobial efficacy.
  • These peptoid-based compounds represent a promising, non-toxic class of novel antimicrobial agents with potential therapeutic applications.