Hydra amphiphiles: Using three heads and one tail to influence aggregate formation and to kill pathogenic bacteria

Gallagher, Tara; Marafino, John; Wimbish, Brenden K.; Volkers, Brandi; Fitzgerald, Gabriel; McKenna, Kristin; Floyd, Jason; Minahan, Nicholas T.; Walsh, Brenna J. C.; Thompson, Kirstie A.; Bruno, D. W.; Paneru, Monica; Djikeng, Sybelle; Masters, Stephanie; Haji, Suma; Seifert, Kyle; Caran, Kevin L.

doi:10.1016/j.colsurfb.2017.06.010

Cited by 2 publications

(3 citation statements)

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“…To this end, we set out to prepare a series of mono‐ and bisQACs based on diamine cores that varied in their geometric rigidity. Fortunately, the TMEDA series is well known to our group and others . We thus turned toward the quaternization of the nitrogen atoms on the inexpensive dimethylpiperazine, available at only ≈$0.50 per gram.…”

Section: Methodsmentioning

confidence: 99%

“…Fortunately, the TMEDA series is well known to our group [14a] and others. [17,18] We thus turned towards the quaternization of the nitrogen atoms on the inexpensive dimethylpiperazine, available at only ~$0.50 per gram. In analogy to another more complicated piperazine structure we had previously investigated, [13] we found alkylation to be readily achieved with exposure to 2.2 equivalents of a suitable alkyl bromide in DMF at 120 ° C for 6 hours, as outlined in Scheme 2.…”

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confidence: 99%

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An Investigation into Rigidity–Activity Relationships in BisQAC Amphiphilic Antiseptics

et al. 2018

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Twenty-one mono- and biscationic quaternary ammonium amphiphiles (monoQACs and bisQACs) were rapidly prepared in order to investigate the effects of rigidity of a diamine core structure on antiseptic activity. As anticipated, bioactivity against a panel of 6 bacteria including MRSA strains was strong for bisQAC structures, and clearly correlated to the length of non-polar side chains. Modest advantages were noted for amide-containing side chains, as compared to straight-chained alkyl substituents. Surprisingly, antiseptics with more rigidly disposed side chains, such as those in DABCO-12,12, showed the highest level of antimicrobial activity, with single-digit MIC values or better against the entire bacterial panel, including submicromolar activity against a MRSA strain.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

An Investigation into Rigidity–Activity Relationships in BisQAC Amphiphilic Antiseptics

et al. 2018

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“…However, analogs containing ethyl groups at the charged nitrogen instead of methyl groups were more active [107]. Gallagher and colleagues found that tris-QACs with two alkyl tails 99 were more effective against Gram-negative bacteria than tris-QACs with one alkyl tail [141,142]. Tris-pyridinium salts 100 [143] and tetrapyridinium salts 101 [144] also comprised an efficient group of biocides with a broad spectrum of action and surpassed the activity of the well-known pyridinium antiseptic CPC 5 several times.…”

Section: Multiple-charged Qacs (Multi-qacs)mentioning

confidence: 99%

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials

Vereshchagin

Frolov

Egorova

et al. 2021

IJMS

152

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Quaternary ammonium compounds (QACs) belong to a well-known class of cationic biocides with a broad spectrum of antimicrobial activity. They are used as essential components in surfactants, personal hygiene products, cosmetics, softeners, dyes, biological dyes, antiseptics, and disinfectants. Simple but varied in their structure, QACs are divided into several subclasses: Mono-, bis-, multi-, and poly-derivatives. Since the beginning of the 20th century, a significant amount of work has been dedicated to the advancement of this class of biocides. Thus, more than 700 articles on QACs were published only in 2020, according to the modern literature. The structural variability and diverse biological activity of ionic liquids (ILs) make them highly prospective for developing new types of biocides. QACs and ILs bear a common key element in the molecular structure–quaternary positively charged nitrogen atoms within a cyclic or acyclic structural framework. The state-of-the-art research level and paramount demand in modern society recall the rapid development of a new generation of tunable antimicrobials. This review focuses on the main QACs exhibiting antimicrobial and antifungal properties, commercial products based on QACs, and the latest discoveries in QACs and ILs connected with biocide development.

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Hydra amphiphiles: Using three heads and one tail to influence aggregate formation and to kill pathogenic bacteria

Cited by 2 publications

References 50 publications

An Investigation into Rigidity–Activity Relationships in BisQAC Amphiphilic Antiseptics

An Investigation into Rigidity–Activity Relationships in BisQAC Amphiphilic Antiseptics

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials

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