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Microbiocides Chemistry II

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 2021) | Viewed by 27135

Special Issue Editor


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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
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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.

Because of the wide interest in the first edition of the Molecules Special Issue “Microbiocides Chemistry,” we announce the second edition of this Special Issue, “Microbiocides Chemistry II.” 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. Dr. Bogumil Brycki
Guest Editor

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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 (5 papers)

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Research

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19 pages, 3328 KiB  
Article
Anthelmintic Effect of Leucaena leucocephala Extract and Its Active Compound, Mimosine, on Vital Behavioral Activities in Caenorhabditis elegans
by Amal Widaad, Ihsan Nazurah Zulkipli and Mark I. R. Petalcorin
Molecules 2022, 27(6), 1875; https://doi.org/10.3390/molecules27061875 - 14 Mar 2022
Cited by 4 | Viewed by 4194
Abstract
Helminth infections continue to be a neglected global threat in tropical regions, and there have been growing cases of anthelmintic resistance reported towards the existing anthelmintic drugs. Thus, the search for a novel anthelmintic agent has been increasing, especially those derived from plants. [...] Read more.
Helminth infections continue to be a neglected global threat in tropical regions, and there have been growing cases of anthelmintic resistance reported towards the existing anthelmintic drugs. Thus, the search for a novel anthelmintic agent has been increasing, especially those derived from plants. Leucaena leucocephala (LL) is a leguminous plant that is known to have several pharmacological activities, including anthelmintic activity. It is widely known to contain a toxic compound called mimosine, which we believed could be a potential lead candidate that could exert a potent anthelmintic effect. Hence, this study aimed to validate the presence of mimosine in LL extract and to investigate the anthelmintic effect of LL extract and mimosine on head thrashing, egg-laying, and pharyngeal pumping activities using the animal model Caenorhabditis elegans (C. elegans). Mimosine content in LL extract was confirmed through an HPLC analysis of spiking LL extract with different mimosine concentrations, whereby an increasing trend in peak heights was observed at a retention time of 0.9 min. LL extract and mimosine caused a significant dose-dependent increase in the percentage of worm mortality, which produced LC50s of 73 mg/mL and 6.39 mg/mL, respectively. Exposure of C. elegans to different concentrations of LL extract and mimosine significantly decreased the head thrashing, egg-laying, and mean pump amplitude of pharyngeal pumping activity. We speculated that these behavioral changes are due to the inhibitory effect of LL extract and mimosine on an L-type calcium channel called EGL-19. Our findings provide evidential support for the potential of LL extract and its active compound, mimosine, as novel anthelmintic candidates. However, the underlying mechanism of the anthelmintic action has yet to be elucidated. Full article
(This article belongs to the Special Issue Microbiocides Chemistry II)
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13 pages, 2485 KiB  
Article
The Chemical Profiling, Docking Study, and Antimicrobial and Antibiofilm Activities of the Endophytic fungi Aspergillus sp. AP5
by Mohamed A. Abdelgawad, Ahmed A. Hamed, AbdElAziz A. Nayl, Mona Shaban E. M. Badawy, Mohammed M. Ghoneim, Ahmed M. Sayed, Hossam M. Hassan and Noha M. Gamaleldin
Molecules 2022, 27(5), 1704; https://doi.org/10.3390/molecules27051704 - 05 Mar 2022
Cited by 9 | Viewed by 2432
Abstract
Growing data suggest that Aspergillus niger, an endophytic fungus, is a rich source of natural compounds with a wide range of biological properties. This study aimed to examine the antimicrobial and antibiofilm capabilities of the Phragmites australis-derived endophyte against a set [...] Read more.
Growing data suggest that Aspergillus niger, an endophytic fungus, is a rich source of natural compounds with a wide range of biological properties. This study aimed to examine the antimicrobial and antibiofilm capabilities of the Phragmites australis-derived endophyte against a set of pathogenic bacteria and fungi. The endophytic fungus Aspergillus sp. AP5 was isolated from the leaves of P. australis. The chemical profile of the fungal crude extract was identified by spectroscopic analysis using LC-HRESIMS. The fungal-derived extract was evaluated for its antimicrobial activity towards a set of pathogenic bacterial and fungal strains including Staphylococcus aureus, Pseudomonas aeruginosa, Proteus vulgaris, Klebsiella sp., Candida albicans, and Aspergillus niger. Moreover, antibiofilm activity toward four resistant biofilm-forming bacteria was also evaluated. Additionally, a neural-networking pharmacophore-based visual screening predicted the most probable bioactive compounds in the obtained extract. The AP5-EtOAc extract was found to have potent antibacterial activities against S. aureus, E. coli, and Klebsiella sp., while it exhibited low antibacterial activity toward P. Vulgaris and P. aeruginosa and displayed anticandidal activity. The AP5-EtOAc extract had significant antibiofilm activity in S. aureus, followed by P. aeruginosa. The active metabolites’ antifungal and/or antibacterial activities may be due to targeting the fungal CYP 51 and/or the bacterial Gyr-B. Full article
(This article belongs to the Special Issue Microbiocides Chemistry II)
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15 pages, 1260 KiB  
Article
Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part
by Bogumil Eugene Brycki, Adrianna Szulc, Iwona Kowalczyk, Anna Koziróg and Ewelina Sobolewska
Molecules 2021, 26(19), 5759; https://doi.org/10.3390/molecules26195759 - 23 Sep 2021
Cited by 11 | Viewed by 2166
Abstract
Due to their large possibility of the structure modification, alkylammonium gemini surfactants are a rapidly growing class of compounds. They exhibit significant surface, aggregation and antimicrobial properties. Due to the fact that, in order to achieve the desired utility effect, the minimal concentration [...] Read more.
Due to their large possibility of the structure modification, alkylammonium gemini surfactants are a rapidly growing class of compounds. They exhibit significant surface, aggregation and antimicrobial properties. Due to the fact that, in order to achieve the desired utility effect, the minimal concentration of compounds are used, they are in line with the principle of greenolution (green evolution) in chemistry. In this study, we present innovative synthesis of the homologous series of gemini surfactants modified at the spacer by the ether group, i.e., 3-oxa-1,5-pentane-bis(N-alkyl-N,N-dimethylammonium bromides). The critical micelle concentrations were determined. The minimal inhibitory concentrations of the synthesized compounds were determined against bacteria Escherichia coli ATCC 10536 and Staphylococcus aureus ATCC 6538; yeast Candida albicans ATCC 10231; and molds Aspergillus niger ATCC 16401 and Penicillium chrysogenum ATCC 60739. We also investigated the relationship between antimicrobial activity and alkyl chain length or the nature of the spacer. The obtained results indicate that the synthesized compounds are effective microbicides with a broad spectrum of biocidal activity. Full article
(This article belongs to the Special Issue Microbiocides Chemistry II)
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16 pages, 1673 KiB  
Article
Engineering of Streptoalloteichus tenebrarius 2444 for Sustainable Production of Tobramycin
by Lena Mitousis, Hannes Maier, Luka Martinovic, Andreas Kulik, Sigrid Stockert, Wolfgang Wohlleben, Alfred Stiefel and Ewa M. Musiol-Kroll
Molecules 2021, 26(14), 4343; https://doi.org/10.3390/molecules26144343 - 18 Jul 2021
Cited by 3 | Viewed by 3148
Abstract
Tobramycin is a broad-spectrum aminoglycoside antibiotic agent. The compound is obtained from the base-catalyzed hydrolysis of carbamoyltobramycin (CTB), which is naturally produced by the actinomycete Streptoalloteichus tenebrarius. However, the strain uses the same precursors to synthesize several structurally related aminoglycosides. Consequently, the [...] Read more.
Tobramycin is a broad-spectrum aminoglycoside antibiotic agent. The compound is obtained from the base-catalyzed hydrolysis of carbamoyltobramycin (CTB), which is naturally produced by the actinomycete Streptoalloteichus tenebrarius. However, the strain uses the same precursors to synthesize several structurally related aminoglycosides. Consequently, the production yields of tobramycin are low, and the compound’s purification is very challenging, costly, and time-consuming. In this study, the production of the main undesired product, apramycin, in the industrial isolate Streptoalloteichus tenebrarius 2444 was decreased by applying the fermentation media M10 and M11, which contained high concentrations of starch and dextrin. Furthermore, the strain was genetically engineered by the inactivation of the aprK gene (∆aprK), resulting in the abolishment of apramycin biosynthesis. In the next step of strain development, an additional copy of the tobramycin biosynthetic gene cluster (BGC) was introduced into the ∆aprK mutant. Fermentation by the engineered strain (∆aprK_1-17L) in M11 medium resulted in a 3- to 4-fold higher production than fermentation by the precursor strain (∆aprK). The phenotypic stability of the mutant without selection pressure was validated. The use of the engineered S. tenebrarius 2444 facilitates a step-saving, efficient, and, thus, more sustainable production of the valuable compound tobramycin on an industrial scale. Full article
(This article belongs to the Special Issue Microbiocides Chemistry II)
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Review

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21 pages, 2294 KiB  
Review
Piper betle (L): Recent Review of Antibacterial and Antifungal Properties, Safety Profiles, and Commercial Applications
by Ni Made Dwi Mara Widyani Nayaka, Maria Malida Vernandes Sasadara, Dwi Arymbhi Sanjaya, Putu Era Sandhi Kusuma Yuda, Ni Luh Kade Arman Anita Dewi, Erna Cahyaningsih and Rika Hartati
Molecules 2021, 26(8), 2321; https://doi.org/10.3390/molecules26082321 - 16 Apr 2021
Cited by 51 | Viewed by 14275
Abstract
Piper betle (L) is a popular medicinal plant in Asia. Plant leaves have been used as a traditional medicine to treat various health conditions. It is highly abundant and inexpensive, therefore promoting further research and industrialization development, including in the food and pharmaceutical [...] Read more.
Piper betle (L) is a popular medicinal plant in Asia. Plant leaves have been used as a traditional medicine to treat various health conditions. It is highly abundant and inexpensive, therefore promoting further research and industrialization development, including in the food and pharmaceutical industries. Articles published from 2010 to 2020 were reviewed in detail to show recent updates on the antibacterial and antifungal properties of betel leaves. This current review showed that betel leaves extract, essential oil, preparations, and isolates could inhibit microbial growth and kill various Gram-negative and Gram-positive bacteria as well as fungal species, including those that are multidrug-resistant and cause serious infectious diseases. P. betle leaves displayed high efficiency on Gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa, Gram-positive bacteria such as Staphylococcus aureus, and Candida albicans. The ratio of MBC/MIC indicated bactericidal and bacteriostatic effects of P. betle leaves, while MFC/MIC values showed fungicidal and fungistatic effects. This review also provides a list of phytochemical compounds in betel leaves extracts and essential oils, safety profiles, and value-added products of betel leaves. Some studies also showed that the combination of betel leaves extract and essential oil with antibiotics (streptomycin, chloramphenicol and gentamicin) could provide potentiating antibacterial properties. Moreover, this review delivers a scientific resume for researchers in respected areas and manufacturers who want to develop betel leaves-based products. Full article
(This article belongs to the Special Issue Microbiocides Chemistry II)
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