Related Experiment Video
Updated: Jun 24, 2026

03:29
Synthesis and Assay of Vibrio Quorum Sensing Inhibitors
Published on: May 31, 2024
Quaternary ammonium N,N-dichloroamines as topical, antimicrobial agents
Charles Francavilla1, Eddy Low, Satheesh Nair
1NovaBay Pharmaceuticals Inc., Emeryville, CA 94608, United States.
Bioorganic & Medicinal Chemistry Letters
|April 14, 2009
Summary
Researchers synthesized new analogs of a topical antimicrobial agent. This led to the discovery of quaternary ammonium N,N-dichloroamines as a novel class of topical antimicrobials with promising activity.
Area of Science:
- Medicinal Chemistry
- Antimicrobial Agents
- Organic Synthesis
Background:
- Topical antimicrobial agents are crucial for combating infections.
- Development of novel antimicrobial classes is essential due to rising resistance.
- Previous work focused on a specific clinical candidate (iii).
Purpose of the Study:
- To synthesize backbone modified and sulfonic acid replacement analogs of clinical candidate (iii).
- To evaluate the antimicrobial activity and aqueous stability of these novel compounds.
- To identify new classes of topical antimicrobial agents.
Main Methods:
- Synthesis of modified analogs.
- Antimicrobial activity assays.
- Aqueous stability testing at pH 4 and pH 7.
Main Results:
- Successful synthesis of various analogs.
- Identification of quaternary ammonium N,N-dichloroamines.
- Demonstrated antimicrobial activities and stability profiles.
Conclusions:
- Quaternary ammonium N,N-dichloroamines represent a new class of topical antimicrobial agents.
- These compounds show potential for further development in treating topical infections.
Related Concept Videos
Hand hygiene
Asepsis is the practice of preventing or breaking the chain of infection. The nurse employs aseptic techniques to prevent the spread of microorganisms and reduce the risk of diseases. Hand hygiene is the cornerstone of aseptic techniques and is classified into medical and surgical asepsis. Medical asepsis includes hand hygiene and the use of gloves. Surgical asepsis, or the sterile technique, refers to practices that render and keep objects and areas free of microorganisms.
Hand washing...
Hand washing...
Chemical Agents for Microbial Control
Chemicals play important roles in controlling microbial growth by targeting microbial structures and functions as sanitizers, antiseptics, disinfectants, and sterilants.Alcohols are commonly used sanitizers, effectively disrupting lipid membranes, which compromises cell integrity. They are also used as antiseptics and disinfectants due to their rapid action and versatility.Phenols and their derivatives phenolics , known for denaturing proteins and disrupting cell membranes, are particularly...
Cholinergic Antagonists: Pharmacokinetics
Cholinergic antagonists—such as antimuscarinics—are available in oral, topical, ocular, parenteral, and inhalational formulations. Most antimuscarinics are oral formulations, while scopolamine is available as a topical patch, and ipratropium and tiotropium are available as inhalation aerosols or powders. Atropine, tropicamide, and cyclopentolate are topically instilled in the eye. Most antimuscarinics are lipid-soluble and readily absorbed from the gastrointestinal tract and the conjunctiva.
Antifungal Agents
Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to cholesterol contributes to...
Anthelminthic Agents
Anthelmintic drugs differ significantly from antiparasitic therapies targeting protozoa, primarily due to differences in parasite biology. Whereas most protozoal treatments act on proliferating cells, anthelmintics are typically directed against mature, nonproliferative helminths. The therapeutic approach considers the helminth's reliance on neuromuscular coordination, glucose metabolism, and microtubular integrity for survival, reproduction, and localization within the host. Most anthelmintics...
Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
