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New Types of Antibacterial Biocides 2.0

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Molecular Pharmacology".

Deadline for manuscript submissions: 30 July 2024 | Viewed by 10529

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Guest Editor
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia
Interests: application of electrochemical methods in organic chemistry and synthesis; elaboration of selective synthetic methods in electroorganic and organic chemistry; domino and multicomponent reactions with C-H acids, carbonyls and olefins; development of synthetic approaches to new classes of antiseptics and disinfectants
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Special Issue Information

Dear Colleagues,

Today, the development of new highly effective antiseptics, disinfectants, and materials that bestow antimicrobial activity, environmental safety, and relatively low toxicity is of exceptional importance for significant areas of chemistry and materials science. The SARS-CoV-2 (COVID-19) pandemic, which began in 2020, has contributed to a sharp increase in the use of disinfectants, which multiply the risk of developing bacterial resistance and could lead to a sharp decrease in the effectiveness of biocidal in the future. A separate challenge for the scientific community is the ability of microorganisms to organize themselves into biofilms, i.e., a structured community in a self-produced polymeric matrix. The formation of biofilms is a global problem affecting various spheres of life. Thus, biofilms cause up to 80% of chronic human bacterial infections, and contribute to the development of microbial tolerance to traditional drugs and multidrug resistance. The ever-increasing number of resistant bacterial strains is of great concern, because if this problem is left unaddressed, by 2050, antimicrobial resistance (AMR) could claim more lives than cancer.

In general, there are two main strategies for combating biofilms: preventing their formation or destroying/removing already formed biofilm. Amino acids and antimicrobial peptides, metal chelators, quorum sensing inhibitors, surfactants, and other antibiofilm agents can be effectively used at different stages of biofilm formation.

The aim of the Special Issue is to review recent research on the synthesis and application of new antibacterial biocides. Full articles, short communications, and reviews are accepted for publication in the Special Issue. 

Prof. Dr. Anatoly N. Vereshchagin
Guest Editor

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Keywords

  • antimicrobial biocides
  • pathogens
  • bacterial resistance
  • microbial biofilms
  • quaternary ammonium compounds
  • antiseptics

Published Papers (6 papers)

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Research

20 pages, 9164 KiB  
Article
New Biocides Based on N4-Alkylcytidines: Effects on Microorganisms and Application for the Protection of Cultural Heritage Objects of Painting
by Liudmila A. Alexandrova, Ivan A. Oskolsky, Dmitry A. Makarov, Maxim V. Jasko, Inna L. Karpenko, Olga V. Efremenkova, Byazilya F. Vasilyeva, Darya A. Avdanina, Anna A. Ermolyuk, Elizaveta E. Benko, Stanislav G. Kalinin, Tat’yana V. Kolganova, Maria Ya. Berzina, Irina D. Konstantinova, Alexander O. Chizhov, Sergey N. Kochetkov and Alexander A. Zhgun
Int. J. Mol. Sci. 2024, 25(5), 3053; https://doi.org/10.3390/ijms25053053 - 6 Mar 2024
Viewed by 764
Abstract
The rapid increase in the antibiotic resistance of microorganisms, capable of causing diseases in humans as destroying cultural heritage sites, is a great challenge for modern science. In this regard, it is necessary to develop fundamentally novel and highly active compounds. In this [...] Read more.
The rapid increase in the antibiotic resistance of microorganisms, capable of causing diseases in humans as destroying cultural heritage sites, is a great challenge for modern science. In this regard, it is necessary to develop fundamentally novel and highly active compounds. In this study, a series of N4-alkylcytidines, including 5- and 6-methylcytidine derivatives, with extended alkyl substituents, were obtained in order to develop a new generation of antibacterial and antifungal biocides based on nucleoside derivatives. It has been shown that N4-alkyl 5- or 6-methylcytidines effectively inhibit the growth of molds, isolated from the paintings in the halls of the Ancient Russian Paintings of the State Tretyakov Gallery, Russia, Moscow. The novel compounds showed activity similar to antiseptics commonly used to protect works of art, such as benzalkonium chloride, to which a number of microorganisms have acquired resistance. It was also shown that the activity of N4-alkylcytidines is comparable to that of some antibiotics used in medicine to fight Gram-positive bacteria, including resistant strains of Staphylococcus aureus and Mycobacterium smegmatis. N4-dodecyl-5- and 6-methylcytidines turned out to be the best. This compound seems promising for expanding the palette of antiseptics used in painting, since quite often the destruction of painting materials is caused by joint fungi and bacteria infection. Full article
(This article belongs to the Special Issue New Types of Antibacterial Biocides 2.0)
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19 pages, 20324 KiB  
Article
Synthesis, Characterization, and Bioactivity of Mesoporous Bioactive Glass Codoped with Zinc and Silver
by Tsung-Ying Yang, Guann-In Chern, Wei-Hsun Wang and Chi-Jen Shih
Int. J. Mol. Sci. 2023, 24(18), 13679; https://doi.org/10.3390/ijms241813679 - 5 Sep 2023
Viewed by 1270
Abstract
Due to the overconsumption of antimicrobials, antibiotic-resistant bacteria have become a critical health issue worldwide, especially methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (VRE). Recently, many efforts have been made to load metals into bioactive glasses to enhance the multifunctionality of materials, [...] Read more.
Due to the overconsumption of antimicrobials, antibiotic-resistant bacteria have become a critical health issue worldwide, especially methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (VRE). Recently, many efforts have been made to load metals into bioactive glasses to enhance the multifunctionality of materials, such as antibacterial and osteoinductive functions. Zinc has been documented to stimulate the gene expression of various regulatory factors in bone cells. Meanwhile, previous studies have reported that silver and zinc could be a promising antibacterial combination with synergistic antimicrobial effects. Here, we sought to develop a biomaterial coreleasing zinc and silver, designated 80S-ZnAg, and to evaluate its antibacterial activity and biocompatibility. The textural analyses demonstrated different coreleasing patterns of zinc and silver for the materials. The chemical characterization revealed that the zinc in 80S-ZnAg could be the network modifier when its molar ratio was high, releasing more zinc; zinc could also be the network former when its molar ratio was low, showing an extremely low rate of release. However, the ICP results for 80S-Zn3Ag2 demonstrated up to 7.5 ppm of zinc and 67.6 ppm of silver. Among all the 80S-ZnAg materials, 80S-Zn3Ag2 demonstrated more marked antibacterial activity against MRSA and VRE than the others, with inhibition zones of 11.5 and 13.4 mm, respectively. The cytotoxicity assay exhibited nearly 90% cell viability at 20 mg/mL of 80-Zn3Ag2. Further clinical study is needed to develop an innovative biomaterial to address the issue of antibiotic resistance. Full article
(This article belongs to the Special Issue New Types of Antibacterial Biocides 2.0)
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17 pages, 2382 KiB  
Article
The Antimicrobial and Antibiofilm Potential of New Water-Soluble Tris-Quaternary Ammonium Compounds
by Nikita A. Frolov, Mary A. Seferyan, Anvar B. Valeev, Evgeniya A. Saverina, Elena V. Detusheva and Anatoly N. Vereshchagin
Int. J. Mol. Sci. 2023, 24(13), 10512; https://doi.org/10.3390/ijms241310512 - 22 Jun 2023
Cited by 3 | Viewed by 1576
Abstract
The invention and innovation of highly effective antimicrobials are always crucial tasks for medical and organic chemistry, especially at the current time, when there is a serious threat of shortages of effective antimicrobials following the pandemic. In the study presented in this article, [...] Read more.
The invention and innovation of highly effective antimicrobials are always crucial tasks for medical and organic chemistry, especially at the current time, when there is a serious threat of shortages of effective antimicrobials following the pandemic. In the study presented in this article, we established a new approach to synthesizing three novel series of bioactive water-soluble tris-quaternary ammonium compounds using an optimized one-pot method, and we assessed their antimicrobial and antibiofilm potential. Five pathogenic microorganisms of the ESKAPE group, including highly resistant clinical isolates, were used as the test samples. Moreover, we highlighted the dependence of antibacterial activity from the hydrophilic–hydrophobic balance of the QACs and noted the significant performance of the desired products on biofilms with MBEC as low as 16 mg/L against bacteria and 8 mg/L against fungi. Particularly notable was the high activity against Pseudomonas aeruginosa and Acinetobacter baumannii, which are among the most resilient bacteria known. The presented work will provide useful insights for future research on the topic. Full article
(This article belongs to the Special Issue New Types of Antibacterial Biocides 2.0)
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14 pages, 2916 KiB  
Article
The Conditions Matter: The Toxicity of Titanium Trisulfide Nanoribbons to Bacteria E. coli Changes Dramatically Depending on the Chemical Environment and the Storage Time
by Olga V. Zakharova, Valeria V. Belova, Peter A. Baranchikov, Anna A. Kostyakova, Dmitry S. Muratov, Gregory V. Grigoriev, Svetlana P. Chebotaryova, Denis V. Kuznetsov and Alexander A. Gusev
Int. J. Mol. Sci. 2023, 24(9), 8299; https://doi.org/10.3390/ijms24098299 - 5 May 2023
Viewed by 1610
Abstract
In this work, we present an analysis of the antibacterial activity of TiS3 nanostructures in water and 0.9% NaCl solution suspensions. TiS3 nanoribbons 1–10 µm long, 100–300 nm wide, and less than 100 nm thick were produced by the direct reaction [...] Read more.
In this work, we present an analysis of the antibacterial activity of TiS3 nanostructures in water and 0.9% NaCl solution suspensions. TiS3 nanoribbons 1–10 µm long, 100–300 nm wide, and less than 100 nm thick were produced by the direct reaction of pure titanium powder with elemental sulphur in a quartz tube sealed under vacuum. For the toxicity test of a bioluminescent strain of E. coli we used concentrations from 1 to 0.0001 g L−1 and also studied fresh suspensions and suspensions left for 24 h. The strongest toxic effect was observed in freshly prepared water solutions where the luminescence of bacteria decreased by more than 75%. When saline solution was substituted for water or when the solutions were stored for 24 h it resulted in a considerable decrease in the TiS3 antibacterial effect. The toxicity of TiS3 in water exceeded the toxicity of the reference TiO2 nanoparticles, though when saline solution was used instead of water the opposite results were observed. In addition, we did not find a relationship between the antibacterial activity of water suspensions of nanoribbons and the stability of their colloidal systems, which indicates an insignificant contribution to the toxicity of aggregation processes. In 0.9% NaCl solution suspensions, toxicity increased in proportion to the increase in the zeta potential. We suppose that the noted specificity of toxicity is associated with the emission of hydrogen sulphide molecules from the surface of nanoribbons, which, depending on the concentration, can either decrease or increase oxidative stress, which is considered the key mechanism of nanomaterial cytotoxicity. However, the exact underlying mechanisms need further investigation. Thus, we have shown an important role of the dispersion medium and the period of storage in the antibacterial activity of TiS3 nanoribbons. Our results could be used in nanotoxicological studies of other two-dimensional nanomaterials, and for the development of novel antibacterial substances and other biomedical applications of this two-dimensional material. Full article
(This article belongs to the Special Issue New Types of Antibacterial Biocides 2.0)
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41 pages, 9947 KiB  
Article
First X-ray Crystal Structure Characterization, Computational Studies, and Improved Synthetic Route to the Bioactive 5-Arylimino-1,3,4-thiadiazole Derivatives
by Ziad Moussa, Alejandro Perez Paz, Zaher M. A. Judeh, Ahmed Alzamly, Haythem A. Saadeh, Basim H. Asghar, Sara Alsaedi, Bayan Masoud, Salama Almeqbaali, Saeda Estwani, Amna Aljaberi, Munirah M. Al-Rooqi and Saleh A. Ahmed
Int. J. Mol. Sci. 2023, 24(4), 3759; https://doi.org/10.3390/ijms24043759 - 13 Feb 2023
Cited by 3 | Viewed by 2245
Abstract
N-arylcyanothioformamides are useful coupling components for building key chemical intermediates and biologically active molecules in an expedited and efficient manner. Similarly, substituted (Z)-2-oxo-N-phenylpropanehydrazonoyl chlorides have been utilized in numerous one-step heteroannulation reactions to assemble the structural core of [...] Read more.
N-arylcyanothioformamides are useful coupling components for building key chemical intermediates and biologically active molecules in an expedited and efficient manner. Similarly, substituted (Z)-2-oxo-N-phenylpropanehydrazonoyl chlorides have been utilized in numerous one-step heteroannulation reactions to assemble the structural core of several different types of heterocyclic compounds. Herein, we demonstrate the effectiveness of the reaction of N-arylcyanothioformamides with various substituted (Z)-2-oxo-N-phenylpropanehydrazonoyl chlorides to produce, stereoselectively and regioselectively, a range of 5-arylimino-1,3,4-thiadiazole derivatives decorated with a multitude of functional groups on both aromatic rings. The synthetic methodology features mild room-temperature conditions, large substrate scope, wide array of functional groups on both reactants, and good to high reaction yields. The products were isolated by gravity filtration in all cases and structures were confirmed by multinuclear NMR spectroscopy and high accuracy mass spectral analysis. Proof of molecular structure of the isolated 5-arylimino-1,3,4-thiadiazole regioisomer was obtained for the first time by single-crystal X-ray diffraction analysis. Crystal-structure determination was carried out on (Z)-1-(5-((3-fluorophenyl)imino)-4-(4-iodophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)ethan-1-one and (Z)-1-(4-phenyl-5-(p-tolylimino)-4,5-dihydro-1,3,4-thiadiazol-2-yl)ethan-1-one. Similarly, the tautomeric structures of the N-arylcyanothioformamides and (Z)-geometries of the 2-oxo-N-phenylpropanehydrazonoyl chloride coupling partners were proven by X-ray diffraction studies. As representative examples, crystal-structure determination was carried out on (4-ethoxyphenyl)carbamothioyl cyanide and (Z)-N-(2,3-difluorophenyl)-2-oxopropanehydrazonoyl chloride. Density functional theory calculations at the B3LYP-D4/def2-TZVP level were carried out to rationalize the observed experimental findings. Full article
(This article belongs to the Special Issue New Types of Antibacterial Biocides 2.0)
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16 pages, 2480 KiB  
Article
Antimicrobial and Virucidal Potential of Morpholinium-Based Ionic Liquids
by Jakub Michalski, Julia Sommer, Peter Rossmanith, Anna Syguda, Tomasz Clapa and Patrick Mester
Int. J. Mol. Sci. 2023, 24(2), 1686; https://doi.org/10.3390/ijms24021686 - 14 Jan 2023
Cited by 1 | Viewed by 2306
Abstract
Witnessed by the ongoing spread of antimicrobial resistant bacteria as well as the recent global pandemic of the SARS-CoV-2 virus, the development of new disinfection strategies is of great importance, and novel substance classes as effective antimicrobials and virucides are urgently needed. Ionic [...] Read more.
Witnessed by the ongoing spread of antimicrobial resistant bacteria as well as the recent global pandemic of the SARS-CoV-2 virus, the development of new disinfection strategies is of great importance, and novel substance classes as effective antimicrobials and virucides are urgently needed. Ionic liquids (ILs), low-melting salts, have been already recognized as efficient antimicrobial agents with prospects for antiviral potential. In this study, we examined the antiviral activity of 12 morpholinium based herbicidal ionic liquids with a tripartite test system, including enzyme inhibition tests, virucidal activity determination against five model viruses and activity against five bacterial species. The antimicrobial and enzymatic tests confirmed that the inhibiting activity of ILs corresponds with the number of long alkyl side chains and that [Dec2Mor]+ based ILs are promising candidates as novel antimicrobials. The virucidal tests showed that ILs antiviral activity depends on the type and structure of the virus, revealing enveloped Phi6 phage as highly susceptible to the ILs action, while the non-enveloped phages PRD1 and MS2 proved completely resistant to ionic liquids. Furthermore, a comparison of results obtained for P100 and P001 phages demonstrated for the first time that the susceptibility of viruses to ionic liquids can be dependent on differences in the phage tail structure. Full article
(This article belongs to the Special Issue New Types of Antibacterial Biocides 2.0)
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