Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids

Sapozhnikov, Sergey V.; Sabirova, Alina E.; Shtyrlin, Nikita V.; Druk, Anastasia Y.; Agafonova, Maria N.; Chirkova, Milana N.; Казакова, Рената Р.; Grishaev, Denis Yu.; Никишова, Т. В.; Krylova, Elena S; Никитина, Е. В.; Kayumov, Airat R.; Shtyrlin, Yu. G.

doi:10.1016/j.ejmech.2020.113100

Cited by 35 publications

(29 citation statements)

References 34 publications

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“…Shtyrlin and his colleagues created a pyridoxine-based QAC library, including bisderivatives, which will be discussed in the corresponding part of the review (Figure 16) [65][66][67][68][69][70]. It was found that the position of the substituent did not significantly affect the biocidal effect of methylpicolinates, possibly due to the small size of the methyl substituent.…”

Section: Single-charged Qacs (Mono-qacs)mentioning

confidence: 99%

“…Shtyrlin and his colleagues created a pyridoxine-based QAC library, including bisderivatives, which will be discussed in the corresponding part of the review (Figure 16) [65][66][67][68][69][70]. Pyridoxin functional derivatives 31-36 exhibited a broad spectrum of antibacterial and antifungal activity; at that time, they were more active against Gram-positive bacteria than Gram-negative bacteria.…”

Section: Single-charged Qacs (Mono-qacs)mentioning

confidence: 99%

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

Vereshchagin

Frolov

Egorova

et al. 2021

IJMS

169

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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: Single-charged Qacs (Mono-qacs)mentioning

confidence: 99%

“…Shtyrlin and his colleagues created a pyridoxine-based QAC library, including bisderivatives, which will be discussed in the corresponding part of the review (Figure 16) [65][66][67][68][69][70]. Pyridoxin functional derivatives 31-36 exhibited a broad spectrum of antibacterial and antifungal activity; at that time, they were more active against Gram-positive bacteria than Gram-negative bacteria.…”

Section: Single-charged Qacs (Mono-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

169

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“…Both A. polyphaga and A. griffini clinical strains have presented similar IC 50 against the cyst stage ( Table 1 ). There are different reports whose demonstrate the efficacy of the Chlorhexidine against these two Acanthamoeba stages ( Martín-Navarro et al, 2008 , 2013 ) and despite it has been described as one of the most effective treatments against AK ( Lorenzo-Morales et al, 2015 ), we have to highlight that Chlorhexidine presents a high toxicity in corneal cells ( Sapozhnikov et al, 2020 ). Matrix Ocular® is an already commercialized ophthalmic solution with a lubrication effect as main purpose and it is medically prescribed to protect the cornea and the conjunctiva after surgeries or epithelial damage.…”

Section: Discussionmentioning

confidence: 94%

“…Arabinogalactan (5% w/w) has been reported as a novel mucoadhesive polysaccharide which can be used for the treatment of dry eyes and corneal wounds and to heal the dry spots on cornea ( Burgalassi et al, 2007 ). Moreover, as it has been commented previously, Matrix Ocular® does not present any preservatives, whose could present toxic effects in corneal cells, such as Propylene Glycol or BAK ( Sapozhnikov et al, 2020 ). Novel polymers, like arabinogalactan, have demonstrated the potential to safely deliver drugs at a controlled rate in different ophthalmic formulations ( Pahuja et al, 2012 ).…”

Section: Discussionmentioning

confidence: 97%

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In vitro amoebicidal effects of arabinogalactan-based ophthalmic solution

Reyes-Batllé

Rodríguez-Talavera

Sifaoui

et al. 2021

International Journal for Parasitology: Drugs and Drug Resistan

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The main corneal infections reported worldwide are caused by bacteria and viruses but, recently, the number of Acanthamoeba keratitis (AK) cases has increased. Acanthamoeba genus is an opportunistic free living protozoa widely distributed in environmental and clinical sources, with two life-cycle stages: the trophozoite and the cyst. AK presents as primary symptoms eye redness, epithelial defects, photophobia and intense pain. An early diagnosis and an effective treatment are crucial to avoid blindness or eye removal but, so far, there is no established treatment to this corneal infection. Diverse research studies have reported the efficacy of commercialized eye drops and ophthalmic solutions against the two life cycle stages of Acanthamoeba strains, that usually present preservatives such as Propylene Glycol of Benzalkonium chloride (BAK). These compounds present toxic effects in corneal cells, favouring the inflammatory response in the so sensitive eye tissue. In the present work we have evaluated the efficacy of nine proprietary ophthalmic solutions with and without preservatives (ASDA Dry Eyes Eyedrops, Miren®, ODM5®, Ectodol®, Systane® Complete, Ocudox®, Matrix Ocular®, Alins® and Coqun®) against the two life cycle stages of three Acanthamoeba strains. Our work has demonstrated the high anti- Acanthamoeba activity of Matrix Ocular®, which induces the programmed cell death mechanisms in Acanthamoeba spp. trophozoites. The high efficacy and the absence of ocular toxic effects of Matrix Ocular®, evidences the use of the Arabinogalactan derivatives as a new source of anti-AK compounds.

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Synthesis and Antimicrobial Evaluation of Bis‐morpholine Triazine Quaternary Ammonium Salts

Morandini

Leonetti²,

Riello

et al. 2021

ChemMedChem

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Efficient, environmentally and economically sustainable, and nontoxic antibacterial products are of global relevance in the fight against microorganism contamination. In this work, an easy and straightforward method for the synthesis of bis‐morpholino triazine quaternary ammonium salts (bis‐mTQAS) is reported, starting from 2,4,6‐trichloro‐1,3,5‐triazine or 2,4‐dichloro‐6‐methoxy‐1,3,5‐triazine and various N‐alkylmorpholines. Bis‐mTQAS were tested as antimicrobials against Gram‐negative and Gram‐positive bacterial strains. The best‐performing bis‐mTQAS were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 at 50 and 400 μg/mL, respectively. Distinctively, bis‐mTQAS with the highest antimicrobial efficiency had lowest cytotoxicity.

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Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids

Cited by 35 publications

References 34 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

In vitro amoebicidal effects of arabinogalactan-based ophthalmic solution

Synthesis and Antimicrobial Evaluation of Bis‐morpholine Triazine Quaternary Ammonium Salts

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