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Microbiocides Chemistry
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Microbiocides Chemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 43852

Special Issue Editor

Prof. Dr. Bogumil E. Brycki

E-Mail Website
Guest Editor
Department of Bioactive Compounds, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznan, Poland
Interests: organic synthesis; molecular interactions; surface chemistry; microbiocide chemistry; smart materials; corrosion inhibition; environmental chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Biocides are chemical substances for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products. Biocides are in the same class as herbicides, insecticides, rodenticides, molluscicides, and miticides. A special group of biocides are microbiocides, which are intended to reduce the population of microorganisms to a level that does not pose a threat, and includes antibacterials, antivirials, antifungals, as well as antiprotozoals and antialgae agents. Biocidal products usually consist of one or more active substances and some builders and conditioning agents, to regulate pH, viscosity, colour, etc. The products can be applied as water solutions, non-aqueous solutions, aerosols, or in a solid state. Microbiocides are used in medicine, pharmacy, the cosmetics industry, the veterinary, agricultural, and food industry, the paper industry, the textile industry, petrochemistry, the army, public places, consumer products, the protection of humanity’s heritage, and in many other instances.

The constantly increasing consumption of microbiocides poses risks to humans, animals, and the environment due to their toxic properties and associated use patterns.

Therefore, modern microbiocides should be characterized by biostatic and biocidal activity at the lowest possible concentrations against a wide variety of microorganisms. They should also have low toxicity and be safe to the ecosystem. Moreover, they should be able to be immobilized in natural polymers or inorganic carriers to form smart microbiocide materials that can be activated on demand only by physicochemical factors like pH, humidity, or temperature.

This Special Issue aims to review the latest synthetic or natural antimicrobial compounds that have been demonstrated to have good biocidal activity, low toxicity, efficient biodegradability, and the ability to prepare smart antimicrobial materials.

Prof. Bogumil E. Brycki
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Novel synthetic microbiocides, structural determination, in-silico/ab-initio antimicrobial discovery
  • Microbiocides from terrestrial and marine organisms, essential oils, bioactive phytochemicals
  • Safety, toxicological, and ecotoxicological profiles of novel microbiocides
  • Biodegradability of microbiocides
  • Biofilm control and eradication
  • Biocorrosion inhibitors
  • Antibiodeterioration microbiocides
  • Microbiocides in non-aqueous solutions
  • Antimicrobial anti-adhesive surfaces and coatings
  • Smart microbiocide materials
  • Antimicrobials in consumer products (textiles, paper towels, hygienic papers, working liquids)
  • Active packaging in the food industry
  • Bioinformatics, comparative genomics, and molecular docking for the identification of antimicrobial targets
  • Regulatory issues

Published Papers (7 papers)

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Research

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22 pages, 5067 KiB  
Article
Novel Bis-Ammonium Salts of Pyridoxine: Synthesis and Antimicrobial Properties
by Nikita V. Shtyrlin, Mikhail V. Pugachev, Sergey V. Sapozhnikov, Marsel R. Garipov, Rusalia M. Vafina, Denis Y. Grishaev, Roman S. Pavelyev, Renata R. Kazakova, Mariya N. Agafonova, Alfiya G. Iksanova, Svetlana A. Lisovskaya, Marina I. Zeldi, Elena S. Krylova, Elena V. Nikitina, Alina E. Sabirova, Airat R. Kayumov and Yurii G. Shtyrlin
Molecules 2020, 25(18), 4341; https://doi.org/10.3390/molecules25184341 - 22 Sep 2020
Cited by 15 | Viewed by 2922
Abstract
A series of 108 novel quaternary bis-ammonium pyridoxine derivatives carrying various substituents at the quaternary nitrogen’s and acetal carbon was synthesized. Thirteen compounds exhibited antibacterial and antifungal activity (minimum inhibitory concentration (MIC) 0.25–16 µg/mL) comparable or superior than miramistin, benzalkonium chloride, and chlorhexidine. [...] Read more.
A series of 108 novel quaternary bis-ammonium pyridoxine derivatives carrying various substituents at the quaternary nitrogen’s and acetal carbon was synthesized. Thirteen compounds exhibited antibacterial and antifungal activity (minimum inhibitory concentration (MIC) 0.25–16 µg/mL) comparable or superior than miramistin, benzalkonium chloride, and chlorhexidine. A strong correlation between the lipophilicity and antibacterial activity was found. The most active compounds had logP values in the range of 1–3, while compounds with logP > 6 and logP < 0 were almost inactive. All active compounds demonstrated cytotoxicity comparable with miramistin and chlorhexidine on HEK-293 cells and were three-fold less toxic when compared to benzalkonium chloride. The antibacterial activity of leading compound 5c12 on biofilm-embedded Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli or Pseudomonas aeruginosa was comparable or even higher than that of the benzalkonium chloride. In vivo 5c12 was considerably less toxic (LD50 1705 mg/kg) than benzalkonium chloride, miramistine, and chlorhexidine at oral administration on CD-1 mice. An aqueous solution of 5c12 (0.2%) was shown to be comparable to reference drugs efficiency on the rat’s skin model. The molecular target of 5c12 seems to be a cellular membrane as other quaternary ammonium salts. The obtained results make the described quaternary bis-ammonium pyridoxine derivatives promising and lead molecules in the development of the new antiseptics with a broad spectrum of antimicrobial activity. Full article
(This article belongs to the Special Issue Microbiocides Chemistry)
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14 pages, 2409 KiB  
Article
Antimicrobial Activity of Gemini Surfactants with Azapolymethylene Spacer
by Iwona Kowalczyk, Marta Pakiet, Adrianna Szulc and Anna Koziróg
Molecules 2020, 25(18), 4054; https://doi.org/10.3390/molecules25184054 - 04 Sep 2020
Cited by 11 | Viewed by 2501
Abstract
A series of 21 azapolymethylene gemini surfactants were obtained. The synthesis of the title surfactants in one- or two-step reaction proceeds with good yields. The structure and the purity of the synthesized compounds were determined by 1H and 13C NMR, ESI-MS [...] Read more.
A series of 21 azapolymethylene gemini surfactants were obtained. The synthesis of the title surfactants in one- or two-step reaction proceeds with good yields. The structure and the purity of the synthesized compounds were determined by 1H and 13C NMR, ESI-MS spectra, and elemental analysis. Moreover, 2D COSY, HMBC, and HSQC spectra were performed. The minimal inhibitory concentrations (MIC) of the synthesized compounds were determined against fungi: Candida albicans, Aspergillus niger, Penicillium chrysogenum and bacteria: Escherichia coli,Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis. Also, the critical micelle concentrations (CMC) were determined. The relationship between antimicrobial and surface activity and surfactant structure has been determined. Full article
(This article belongs to the Special Issue Microbiocides Chemistry)
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20 pages, 2462 KiB  
Article
The Synthesis, Self-Assembled Structures, and Microbicidal Activity of Cationic Gemini Surfactants with Branched Tridecyl Chains
by Martin Pisárčik, Matúš Pupák, Miloš Lukáč, Ferdinand Devínsky, Lukáš Hubčík, Marián Bukovský and Branislav Horváth
Molecules 2019, 24(23), 4380; https://doi.org/10.3390/molecules24234380 - 30 Nov 2019
Cited by 11 | Viewed by 3267
Abstract
Cationic gemini surfactants with polymethylene spacer and linear alkyl chains containing an even number of carbon atoms have been extensively studied in the recent past, with the emphasis put on the determination of their aggregation behaviour in aqueous solution and their biological properties. [...] Read more.
Cationic gemini surfactants with polymethylene spacer and linear alkyl chains containing an even number of carbon atoms have been extensively studied in the recent past, with the emphasis put on the determination of their aggregation behaviour in aqueous solution and their biological properties. However, the information on the aggregation of branched gemini surfactants with an odd number of carbon atoms in their alkyl chains is only sparsely reported in the literature. To help cover this gap in the research of cationic gemini surfactants, a series of branched bisammonium cationic gemini surfactants with an odd number of carbon atoms in alkyl chains (tridecane-2-yl chains) and a polymethylene spacer with a variable length ranging from 3 to 12 carbon atoms have been synthesized and investigated. Critical micelle concentration, which was determined by three methods, was found to be in the order 10−4 mol/L. A comparison of the obtained data of the novel series of tridecyl chain geminis with those of gemini surfactants with dodecyl chains and an identical spacer structure revealed that structural differences between both series of gemini surfactants result in different aggregation and surface properties for surfactants with 6 and 8 methylene groups in the spacer (N,N’-bis(tridecane-2-yl)-N,N,N’,N’-tetramethylhexane-1,6-diaminium dibromide and N,N’-bis(tridecane-2-yl)-N,N,N’,N’-tetramethyloctane-1,8-diaminium dibromide) with the cmc values 8.2 × 10−4 mol/L and 6.5 × 10−4 mol/L, respectively, as determined by surface tension measurements. Particle size analysis showed the formation of small stable spherical micelles in the interval between 2.8 and 5 nm and with zeta potential around +50 mV, which are independent of surfactant concentration and increase with the increasing spacer length. Microbicidal activity of 13-s-13 gemini surfactants was found to be efficient against Gram-positive, Gram-negative bacteria and yeast. Full article
(This article belongs to the Special Issue Microbiocides Chemistry)
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14 pages, 1542 KiB  
Article
Application of Biocides and Super-Absorbing Polymers to Enhance the Efficiency of Filtering Materials
by Katarzyna Majchrzycka, Małgorzata Okrasa, Anita Jachowicz, Justyna Szulc, Bogumił Brycki and Beata Gutarowska
Molecules 2019, 24(18), 3339; https://doi.org/10.3390/molecules24183339 - 13 Sep 2019
Cited by 7 | Viewed by 2966
Abstract
Studies on the functionalization of materials used for the construction of filtering facepiece respirators (FFRs) relate to endowing fibers with biocidal properties. There is also a real need for reducing moisture content accumulating in such materials during FFR use, as it would lead [...] Read more.
Studies on the functionalization of materials used for the construction of filtering facepiece respirators (FFRs) relate to endowing fibers with biocidal properties. There is also a real need for reducing moisture content accumulating in such materials during FFR use, as it would lead to decreased microorganism survival. Thus, in our study, we propose the use of superabsorbent polymers (SAPs), together with a biocidal agent (biohalloysite), as additives in the manufacturing of polypropylene/polyester (PP/PET) multifunctional filtering material (MFM). The aim of this study was to evaluate the MFM for stability of the modifier’s attachment to the polymer matrix, the degree of survival of microorganisms on the nonwoven, and its microorganism filtration efficiency. Scanning electron microscopy (SEM) and Fourier transform infrared (FTIR) spectroscopy were used to test the stability of the modifier’s attachment. The filtration efficiency was determined under conditions of dynamic aerosol flow of S. aureus bacteria. The survival rates (N%) of the following microorganisms were assessed: Escherichia coli and Staphylococcus aureus bacteria, Candida albicans yeast, and Aspergillus niger mold using the AATCC 100-2004 method. FTIR spectrum analysis confirmed the pre-established composition of MFM. The loss of the active substance from MFM in simulated conditions of use did not exceed 0.02%, which validated the stability of the modifier’s attachment to the PP/PET fiber structure. SEM image analysis verified the uniformity of the MFM structure. Lower microorganism survival rates were detected for S. aureus, C. albicans, and E. coli on the MFM nonwoven compared to control samples that did not contain the modifiers. However, the MFM did not inhibit A. niger growth. The MFM also showed high filtration efficiency (99.86%) against S. aureus bacteria. Full article
(This article belongs to the Special Issue Microbiocides Chemistry)
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11 pages, 791 KiB  
Article
Derivatization of Rosmarinic Acid Enhances its in vitro Antitumor, Antimicrobial and Antiprotozoal Properties
by Silvia Bittner Fialová, Martin Kello, Matúš Čoma, Lívia Slobodníková, Eva Drobná, Ivana Holková, Mária Garajová, Martin Mrva, Vlastimil Zachar and Miloš Lukáč
Molecules 2019, 24(6), 1078; https://doi.org/10.3390/molecules24061078 - 19 Mar 2019
Cited by 36 | Viewed by 4546
Abstract
On its own, rosmarinic acid possesses multiple biological activities such as anti-inflammatory, antimicrobial, cardioprotective and antitumor properties, and these are the consequence of its ROS scavenging and inhibitory effect on inflammation. In this study, two quaternary phosphonium salts of rosmarinic acid were prepared [...] Read more.
On its own, rosmarinic acid possesses multiple biological activities such as anti-inflammatory, antimicrobial, cardioprotective and antitumor properties, and these are the consequence of its ROS scavenging and inhibitory effect on inflammation. In this study, two quaternary phosphonium salts of rosmarinic acid were prepared for the purpose of increasing its penetration into biological systems with the aim of improving its antimicrobial, antifungal, antiprotozoal and antitumor activity. The synthetized molecules, the triphenylphosphonium and tricyclohexylphosphonium salts of rosmarinic acid, exhibited significantly stronger inhibitory effects on the growth of HCT116 cells with IC50 values of 7.28 or 8.13 μM in comparison to the initial substance, rosmarinic acid (>300 μM). For the synthesized derivatives, we detected a greater than three-fold increase of activity against Acanthamoeba quina, and a greater than eight-fold increase of activity against A. lugdunensis in comparison to rosmarinic acid. Furthermore, we recorded significantly higher antimicrobial activity of the synthetized derivatives when compared to rosmarinic acid itself. Both synthetized quaternary phosphonium salts of rosmarinic acid appear to be promising antitumor and antimicrobial agents, as well as impressive molecules for further research. Full article
(This article belongs to the Special Issue Microbiocides Chemistry)
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Review

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11 pages, 1021 KiB  
Review
Biocide Use in the Antimicrobial Era: A Review
by Imogen Anne Jones and Lovleen Tina Joshi
Molecules 2021, 26(8), 2276; https://doi.org/10.3390/molecules26082276 - 14 Apr 2021
Cited by 76 | Viewed by 9851
Abstract
Biocides are widely used in healthcare and industry to control infections and microbial contamination. Ineffectual disinfection of surfaces and inappropriate use of biocides can result in the survival of microorganisms such as bacteria and viruses on inanimate surfaces, often contributing to the transmission [...] Read more.
Biocides are widely used in healthcare and industry to control infections and microbial contamination. Ineffectual disinfection of surfaces and inappropriate use of biocides can result in the survival of microorganisms such as bacteria and viruses on inanimate surfaces, often contributing to the transmission of infectious agents. Biocidal disinfectants employ varying modes of action to kill microorganisms, ranging from oxidization to solubilizing lipids. This review considers the main biocides used within healthcare and industry environments and highlights their modes of action, efficacy and relevance to disinfection of pathogenic bacteria. This information is vital for rational use and development of biocides in an era where microorganisms are becoming resistant to chemical antimicrobial agents. Full article
(This article belongs to the Special Issue Microbiocides Chemistry)
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22 pages, 2340 KiB  
Review
Isothiazolinone Biocides: Chemistry, Biological, and Toxicity Profiles
by Vânia Silva, Cátia Silva, Pedro Soares, E. Manuela Garrido, Fernanda Borges and Jorge Garrido
Molecules 2020, 25(4), 991; https://doi.org/10.3390/molecules25040991 - 23 Feb 2020
Cited by 90 | Viewed by 16799
Abstract
The importance of isothiazole and of compounds containing the isothiazole nucleus has been growing over the last few years. Isothiazolinones are used in cosmetic and as chemical additives for occupational and industrial usage due to their bacteriostatic and fungiostatic activity. Despite their effectiveness [...] Read more.
The importance of isothiazole and of compounds containing the isothiazole nucleus has been growing over the last few years. Isothiazolinones are used in cosmetic and as chemical additives for occupational and industrial usage due to their bacteriostatic and fungiostatic activity. Despite their effectiveness as biocides, isothiazolinones are strong sensitizers, producing skin irritations and allergies and may pose ecotoxicological hazards. Therefore, their use is restricted by EU legislation. Considering the relevance and importance of isothiazolinone biocides, the present review describes the state-of-the-art knowledge regarding their synthesis, antibacterial components, toxicity (including structure–activity–toxicity relationships) outlines, and (photo)chemical stability. Due to the increasing prevalence and impact of isothiazolinones in consumer’s health, analytical methods for the identification and determination of this type of biocides were also discussed. Full article
(This article belongs to the Special Issue Microbiocides Chemistry)
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