Synthesis and antibacterial activity of new tetrakisquaternary ammonium compounds based on pentaerythritol and 3-hydroxypyridine

Vereshchagin, Anatoly N.; Minaeva, Alexandra P.; Egorov, Mikhail P.

doi:10.1007/s11172-021-3122-6

Cited by 9 publications

(8 citation statements)

References 19 publications

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“…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 wellknown pyridinium antiseptic CPC 5 several times. An overview of the antibacterial activity of multiple QACs, analyzed in the review, is shown in Table 6.…”

Section: Dicationic Ionic Liquidsmentioning

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

170

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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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Section: Dicationic Ionic Liquidsmentioning

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

170

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“…While similar red blood cell lysis was observed, superior activity against both Gram-negative bacteria and MRSA strains was reported [ 18 ]. Tetrakis quaternary ammonium compounds based on pentaerythritol having four cationic heads were synthesized by Vereshchagin et al, and evaluated against MRSA, Escherichia coli , and Pseudomonas aeruginosa [ 19 ]. The compound having a C8 chain was superior in its antibacterial activity to commercially available chlorhexidine, digluconate, and octenidine hydrochloride [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Anti Gram-Positive Bacteria Activity of Synthetic Quaternary Ammonium Lipid and Its Precursor Phosphonium Salt

Bacchetti,

Schito,

Milanese

et al. 2024

IJMS

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Organic ammonium and phosphonium salts exert excellent antimicrobial effects by interacting lethally with bacterial membranes. Particularly, quaternary ammonium lipids have demonstrated efficiency both as gene vectors and antibacterial agents. Here, aiming at finding new antibacterial devices belonging to both classes, we prepared a water-soluble quaternary ammonium lipid (6) and a phosphonium salt (1) by designing a synthetic path where 1 would be an intermediate to achieve 6. All synthesized compounds were characterized by Fourier-transform infrared spectroscopy and Nuclear Magnetic Resonance. Additionally, potentiometric titrations of NH3+ groups 1 and 6 were performed to further confirm their structure by determining their experimental molecular weight. The antibacterial activities of 1 and 6 were assessed first against a selection of multi-drug-resistant clinical isolates of both Gram-positive and Gram-negative species, observing remarkable antibacterial activity of both compounds against Gram-positive isolates of Enterococcus and Staphylococcus genus. Further investigations on a wider variety of strains of these species confirmed the remarkable antibacterial effects of 1 and 6 (MICs = 4–16 and 4–64 µg/mL, respectively), while 24 h-time-killing experiments carried out with 1 on different S. aureus isolates evidenced a bacteriostatic behavior. Moreover, both compounds 1 and 6, at the lower MIC concentration, did not show significant cytotoxic effects when exposed to HepG2 human hepatic cell lines, paving the way for their potential clinical application.

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“…Fortunately, many research groups have been developing alternative approaches to the synthesis of disinfectant amphiphiles over these same recent decades. This has resulted in a growing variety of compound architectures, including the number of cationic ammonium centers, [15][16][17][18] variation in nonpolar groups, [19][20][21] and even more recently a push towards nonnitrogenous amphiphilic disinfectant structures. [22,23] The inclusion of more than one cationic center has repeatedly been shown to engender superior antimicrobial activity, as well as diminished susceptibility to bacterial resistance.…”

Section: Introductionmentioning

confidence: 99%

Double BAC and Triple BAC: A Systematic Analysis of the Disinfectant Properties of Multicationic Derivatives of Benzalkonium Chloride (BAC)

Toles

Sanchez

et al. 2023

ChemMedChem

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Over the past decades, the shortcomings of established quaternary ammonium disinfectants have become increasingly clear. Although benzalkonium chloride (BAC) has enjoyed nearly a century of significantly protecting human health through surgical preparation, home use, and industrial applications, increasing levels of bacterial resistance have rendered it decreasingly effective. In light of more recent efforts that have informed us that multicationic amphiphilic disinfectants show both higher activity as well as diminished susceptibility to resistance, we embarked on the preparation of 27 multicationic QACs in an attempt to clearly document structure‐activity relationships of next‐generation BAC structures. Select biscationic BAC derivatives demonstrate single‐digit micromolar activity against all seven bacteria tested and MIC values of 2‐ to 32‐fold better than BAC. Particularly notable is the improvement against the more concerning bacteria like Acinetobacter baumannii and Pseudomonas aeruginosa, which pose a modern threat to legacy disinfectants like BAC. With simple synthetic paths, consistently high yields (averaging ∼80 %), and strong biological activity, potent structures with clear SAR trends and strong therapeutic indices have been established.

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Synthesis and antibacterial activity of new tetrakisquaternary ammonium compounds based on pentaerythritol and 3-hydroxypyridine

Cited by 9 publications

References 19 publications

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

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

Anti Gram-Positive Bacteria Activity of Synthetic Quaternary Ammonium Lipid and Its Precursor Phosphonium Salt

Double BAC and Triple BAC: A Systematic Analysis of the Disinfectant Properties of Multicationic Derivatives of Benzalkonium Chloride (BAC)

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