Special Issue "Synthesis and Biological Activity of Antimicrobial Agents"

A special issue of Antibiotics (ISSN 2079-6382). This special issue belongs to the section "Novel Antimicrobial Agents".

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 14668

Special Issue Editor

Dr. Maria Fernanda N. N. Carvalho
E-Mail Website
Guest Editor
Instituto Superior Técnico, University of Lisbon, 1049-001 Lisbon, Portugal
Interests: synthesis of coordination and organic compounds; medicinal chemistry; drugs; bioactive compounds; redox properties
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The synthesis, characterization and evaluation of the antimicrobial properties of organic or coordination compounds is the first step in realizing new antimicrobial agents. Bioinformatic analysis and the study of redox properties and reaction mechanisms help in understanding, redesigning and optimizing the characteristics of potential active molecules for fighting microorganisms (bacteria, fungi, and viruses).

At the moment, infection by the virus SARS-CoV-2 is a threat clearly perceived all over the world. Less widespread and broadcasted is the concern regarding microorganisms such as bacteria and fungi, especially for those with depleted immune systems. According to the European Centre for Disease Control, 3.8 million people acquire healthcare-associated infections and ca. 90,000 people die from them per year (data from 2018) in the EU.

The aim of this Special Issue is to put together relevant research on molecules that have the potential to contribute to reducing the number of fatalities caused by bacteria or fungi, as well as controlling microorganisms on agricultural crops and food.

Prof. Dr. M. Fernanda N. N. Carvalho
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. Antibiotics is an international peer-reviewed open access monthly 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 2000 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

  • bacteria
  • fungi
  • organic compounds
  • coordination compounds
  • synthesis
  • bioinformatic analysis

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Published Papers (12 papers)

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Editorial

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Editorial
Synthesis and Biological Activity of Antimicrobial Agents
Antibiotics 2022, 11(3), 337; https://doi.org/10.3390/antibiotics11030337 - 04 Mar 2022
Viewed by 639
Abstract
New antimicrobial agents are urgent and necessary to overcome the acquired resistance of microorganisms to existing antibiotics and antifungals [...] Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)

Research

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Article
Synthesis of Alkyne-Substituted Dihydropyrrolones as Bacterial Quorum-Sensing Inhibitors of Pseudomonas aeruginosa
Antibiotics 2022, 11(2), 151; https://doi.org/10.3390/antibiotics11020151 - 25 Jan 2022
Cited by 2 | Viewed by 1074
Abstract
The Quorum-sensing system in Pseudomonas aeruginosa is responsible for the pathogenicity and the production of virulence factors and biofilm formation. Dihydropyrrolones were previously found to act as inhibitors of QS-dependent bacterial phenotypes. In this study, a range of dihydropyrrolone (DHP) analogues was synthesized [...] Read more.
The Quorum-sensing system in Pseudomonas aeruginosa is responsible for the pathogenicity and the production of virulence factors and biofilm formation. Dihydropyrrolones were previously found to act as inhibitors of QS-dependent bacterial phenotypes. In this study, a range of dihydropyrrolone (DHP) analogues was synthesized via the lactone-lactam conversion of lactone intermediates followed by the formation of novel acetylene analogues of dihydropyrrolones from brominated dihydropyrrolones via Sonogashira coupling reactions in moderate to high yields. Upon biological testing, the most potent compounds, 3940 and 44, showed higher bacterial quorum-sensing inhibitory (QSI) activity against P. aeruginosa reporter strain at 62.5 µM. Structure–activity relationship studies revealed that di-alkynyl substituent at the exocyclic position of DHPs possessed higher QSI activities than those of mono-alkynyl DHPs. Moreover, a hexyl-substituent at C3 of DHPs was beneficial to QSI activity while a phenyl substituent at C4 of DHPs was detrimental to QSI activity of analogues. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Bacillus-Mediated Silver Nanoparticle Synthesis and Its Antagonistic Activity against Bacterial and Fungal Pathogens
Antibiotics 2021, 10(11), 1334; https://doi.org/10.3390/antibiotics10111334 - 01 Nov 2021
Cited by 5 | Viewed by 894
Abstract
In this article, the supernatant of the soil-borne pathogen Bacillus mn14 was used as the catalyst for the synthesis of AgNPs. The antibacterial and antifungal activity of Bs-AgNPs was evaluated, in which S. viridans and R. solani showed susceptibility at 70 µL and [...] Read more.
In this article, the supernatant of the soil-borne pathogen Bacillus mn14 was used as the catalyst for the synthesis of AgNPs. The antibacterial and antifungal activity of Bs-AgNPs was evaluated, in which S. viridans and R. solani showed susceptibility at 70 µL and 100 µL concentrations. Enzyme properties of the isolates, according to minimal inhibitory action and a growth-enhancing hormone–indole acetic acid (IAA) study of the isolates, were expressed in TLC as a purple color with an Rf value of 0.7. UV/Vis spectroscopy revealed the presence of small-sized AgNPs, with a surface plasmon resonance (SPR) peak at 450 nm. The particle size analyzer identified the average diameter of the particles as 40.2 nm. The X-ray diffraction study confirmed the crystalline nature and face-centered cubic type of the silver nanoparticle. Scanning electron microscopy characterized the globular, small, round shape of the silver nanoparticle. AFM revealed the two-dimensional topology of the silver nanoparticle with a characteristic size ranging around 50 nm. Confocal microscopy showed the cell-wall disruption of S. viridans treated with Bs-AgNPs. High-content screening and compound microscopy revealed the destruction of mycelia of R. solani after exposure to Bs-AgNPs. Furthermore, the Bs-AgNPs cured sheath blight disease by reducing lesion length and enhancing root and shoot length in Oryza sativa seeds. This soil-borne pathogen Bacillus-mediated synthesis approach of AgNPs appears to be cost-efficient, ecofriendly, and farmer-friendly, representing an easy way of providing valuable nutritious edibles in the future. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Biosynthesis of Smaller-Sized Platinum Nanoparticles Using the Leaf Extract of Combretum erythrophyllum and Its Antibacterial Activities
Antibiotics 2021, 10(11), 1275; https://doi.org/10.3390/antibiotics10111275 - 20 Oct 2021
Cited by 6 | Viewed by 798
Abstract
Nanobiotechnology is a promising field in the development of safe antibiotics to combat the increasing trend of antibiotic resistance. Nature is a vast reservoir for green materials used in the synthesis of non-toxic and environmentally friendly nano-antibiotics. We present for the first time [...] Read more.
Nanobiotechnology is a promising field in the development of safe antibiotics to combat the increasing trend of antibiotic resistance. Nature is a vast reservoir for green materials used in the synthesis of non-toxic and environmentally friendly nano-antibiotics. We present for the first time a facile, green, cost-effective, plant-mediated synthesis of platinum nanoparticles (PtNPs) using the extract of Combretum erythrophyllum (CE) plant leaves. The extract of CE served as both a bio-reductant and a stabilizing agent. The as-synthesized PtNPs were characterized using ultraviolet-visible (UV–Vis) absorption spectroscopy, high-resolution transmission electron microscopy (HR-TEM), Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), and dynamic light scattering (DLS) techniques. The HR-TEM image confirmed that the PtNPs are ultrasmall, spherical, and well dispersed with an average particle diameter of 1.04 ± 0.26 nm. The PtNPs showed strong antibacterial activities against pathogenic Gram-positive Staphylococcus epidermidis (ATCC 14990) at a minimum inhibitory concentration (MIC) of 3.125 µg/mL and Gram-negative Klebsiella oxytoca (ATCC 8724) and Klebsiella aerogenes (ATCC 27853) at an MIC value of 1.56 µg/mL. The CE-stabilized PtNPs was mostly effective in Klebsiella species that are causative organisms in nosocomial infections. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa
Antibiotics 2021, 10(10), 1272; https://doi.org/10.3390/antibiotics10101272 - 19 Oct 2021
Cited by 2 | Viewed by 733
Abstract
Fourteen new camphorimine Au(I) complexes were synthesized and characterized by spectroscopic (NMR, FTIR) and elemental analysis. The structural arrangement of three selected examples were computed by Density Functional Theory (DFT) showing that the complexes essentially keep the {AuI-CN} unit. The Minimum [...] Read more.
Fourteen new camphorimine Au(I) complexes were synthesized and characterized by spectroscopic (NMR, FTIR) and elemental analysis. The structural arrangement of three selected examples were computed by Density Functional Theory (DFT) showing that the complexes essentially keep the {AuI-CN} unit. The Minimum Inhibition Concentrations (MIC) were assessed for all complexes showing that they are active towards the Gram-negative strains E. coli ATCC25922, P. aeruginosa 477, and B. contaminans IST408 and the Gram-positive strain S. aureus Newman. The complexes display very high activity towards P. aeruginosa 477 and B. contaminans IST408 with selectivity towards B. contaminans. An inverse correlation between the MIC values and the gold content was found for B. contaminans and P. aeruginosa. However, plots of MIC values and Au content for P. aeruginosa 477 and B. contaminans IST408 follow distinct trends. No clear relationship could be established between the MIC values and the redox potentials of the complexes measured by cyclic voltammetry. The MIC values are essentially independent of the redox potentials either cathodic or anodic. The complexes K3[{Au(CN)2}3(A4L)] (8, Y = m-OHC6H4) and K3[{Au(CN)2}3(B2L)]·3H2O (14, Z = p-C6H4) display the lower MIC values for the two strains. In normal fibroblast cells, the IC50 values for the complexes are ca. one order of magnitude lower than their MIC values, although higher than that of the precursor KAu(CN)2. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Cationic Polymer-Coated Magnetic Nanoparticles with Antibacterial Properties: Synthesis and In Vitro Characterization
Antibiotics 2021, 10(9), 1077; https://doi.org/10.3390/antibiotics10091077 - 06 Sep 2021
Cited by 4 | Viewed by 966
Abstract
Uniformly sized magnetite nanoparticles (Dn = 16 nm) were prepared by a thermal decomposition of Fe(III) oleate in octadec-1-ene and stabilized by oleic acid. The particles were coated with Sipomer PAM-200 containing both phosphate and methacrylic groups available for the attachment [...] Read more.
Uniformly sized magnetite nanoparticles (Dn = 16 nm) were prepared by a thermal decomposition of Fe(III) oleate in octadec-1-ene and stabilized by oleic acid. The particles were coated with Sipomer PAM-200 containing both phosphate and methacrylic groups available for the attachment to the iron oxide and at the same time enabling (co)polymerization of 2-(dimethylamino)ethyl methacrylate and/or 2-tert-butylaminoethyl methacrylate at two molar ratios. The poly[2-(dimethylamino)ethyl methacrylate] (PDMAEMA) and poly[2-(dimethylamino)ethyl methacrylate-co-2-tert-butylaminoethyl methacrylate] [P(DMAEMA-TBAEMA)] polymers and the particles were characterized by 1H NMR spectroscopy, size-exclusion chromatography, transmission electron microscopy, dynamic light scattering, thermogravimetric analysis, magnetometry, and ATR FTIR and atomic absorption spectroscopy. The antimicrobial effect of cationic polymer-coated magnetite nanoparticles tested on both Escherichia coli and Staphylococcus aureus bacteria was found to be time- and dose-responsive. The P(DMAEMA-TBAEMA)-coated magnetite particles possessed superior biocidal properties compared to those of P(DMAEMA)-coated one. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Dual Agents: Fungal Macrocidins and Synthetic Analogues with Herbicidal and Antibiofilm Activities
Antibiotics 2021, 10(8), 1022; https://doi.org/10.3390/antibiotics10081022 - 23 Aug 2021
Cited by 3 | Viewed by 1081
Abstract
Eight analogues of the bioherbicides macrocidin A (1) and Z (2) with structural variance in the size of the macrocycle, its para- or meta-cyclophane character, and its functional groups were synthesized on two modular routes and tested [...] Read more.
Eight analogues of the bioherbicides macrocidin A (1) and Z (2) with structural variance in the size of the macrocycle, its para- or meta-cyclophane character, and its functional groups were synthesized on two modular routes and tested for herbicidal, antibiotic, and antibiofilm activities. Apart from the lead compounds 1 and 2, the structurally simplified dihydromacrocidin Z (3) and normacrocidin Z (4) showed high herbicidal activity in either thistles, dandelions or in both. The derivatives 2, 3, and dibromide 9 also inhibited the growth of Staphylococcus aureus biofilms by ca 70% when applied at subtoxic concentrations as low as ca 20 µM, which are unlikely to induce bacterial resistance. They also led to the dispersion of preformed biofilms of S. aureus, exceeding a similar effect by microporenic acid A, a known biofilm inhibitor. Compounds 3 and 9 showed no noticeable cytotoxicity against human cancer and endothelial cells at concentrations below 50 µM, making them conceivable candidates for application as anti-biofilm agents in a medicinal context. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Facile Green, Room-Temperature Synthesis of Gold Nanoparticles Using Combretum erythrophyllum Leaf Extract: Antibacterial and Cell Viability Studies against Normal and Cancerous Cells
Antibiotics 2021, 10(8), 893; https://doi.org/10.3390/antibiotics10080893 - 22 Jul 2021
Cited by 10 | Viewed by 1119
Abstract
We herein report a facile, green, cost-effective, plant-mediated synthesis of gold nanoparticles (AuNPs) for the first time using Combretum erythrophyllum (CE) plant leaves. The synthesis was conducted at room temperature using CE leaf extract serving as a reducing and capping agent. The as-synthesized [...] Read more.
We herein report a facile, green, cost-effective, plant-mediated synthesis of gold nanoparticles (AuNPs) for the first time using Combretum erythrophyllum (CE) plant leaves. The synthesis was conducted at room temperature using CE leaf extract serving as a reducing and capping agent. The as-synthesized AuNPs were found to be crystalline, well dispersed, and spherical in shape with an average diameter of 13.20 nm and an excellent stability of over 60 days. The AuNPs showed broad-spectrum antibacterial activities against both pathogenic Gram-positive (Staphylococcus epidermidis (ATCC14990), Staphylococcus aureus (ATCC 25923), Mycobacterium smegmatis (MC 215)) and Gram-negative bacteria (Proteus mirabilis (ATCC 7002), Escherichia coli (ATCC 25922), Klebsiella pneumoniae (ATCC 13822), Klebsiella oxytoca (ATCC 8724)), with a minimum inhibition concentration of 62.5 µg/mL. In addition, the as-synthesized AuNPs were highly stable with exceptional cell viability towards normal cells (BHK- 21) and cancerous cancer cell lines (cervical and lung cancer). Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Bioactive Coatings with Ag-Camphorimine Complexes to Prevent Surface Colonization by the Pathogenic Yeast Candida albicans
Antibiotics 2021, 10(6), 638; https://doi.org/10.3390/antibiotics10060638 - 26 May 2021
Cited by 1 | Viewed by 1103
Abstract
Currently there is a gap between the rate of new antifungal development and the emergence of resistance among Candida clinical strains, particularly threatened by the extreme adhesiveness of C. albicans to indwelling medical devices. Two silver camphorimine complexes, [Ag(OH){OC10H14N(C [...] Read more.
Currently there is a gap between the rate of new antifungal development and the emergence of resistance among Candida clinical strains, particularly threatened by the extreme adhesiveness of C. albicans to indwelling medical devices. Two silver camphorimine complexes, [Ag(OH){OC10H14N(C6H4)2NC10H14O}] (compound P) and [{Ag(OC10H14NC6H4CH3-p)}2(μ-O)] (compound Q), are herein demonstrated as having high inhibiting activity towards the growth of Candida albicans and Candida glabrata clinical strains resistant to azoles, the frontline antifungals used in clinical practice. Compounds P and Q were also explored as bioactive coatings to prevent colonization by C. albicans and colonize the surface of indwelling medical devices, resulting in persistent infections. Functionalization of stainless steel with polycaprolactone (PCL) matrix embedded with compounds P or Q was reported for the first time to inhibit the colonization of C. albicans by 82% and 75%, respectively. The coating of PCL loaded with Q or P did not cause cytotoxic effects in mammalian cells, demonstrating the biocompatibility of the explored approach. The identification and further exploration of new approaches for surface engineering based on new molecules that can sensitize resistant strains, as herein demonstrated for complexes P and Q, is a significant step forward to improve the successful treatment of candidiasis. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Article
Effects of Antifungal Carriers Based on Chitosan-Coated Iron Oxide Nanoparticles on Microcosm Biofilms
Antibiotics 2021, 10(5), 588; https://doi.org/10.3390/antibiotics10050588 - 17 May 2021
Cited by 5 | Viewed by 1234
Abstract
Resistance of Candida species to conventional therapies has motivated the development of antifungal nanocarriers based on iron oxide nanoparticles (IONPs) coated with chitosan (CS). This study evaluates the effects of IONPs-CS as carriers of miconazole (MCZ) or fluconazole (FLZ) on microcosm biofilms. Pooled [...] Read more.
Resistance of Candida species to conventional therapies has motivated the development of antifungal nanocarriers based on iron oxide nanoparticles (IONPs) coated with chitosan (CS). This study evaluates the effects of IONPs-CS as carriers of miconazole (MCZ) or fluconazole (FLZ) on microcosm biofilms. Pooled saliva from two healthy volunteers supplemented with C. albicans and C. glabrata was the inoculum for biofilm formation. Biofilms were formed for 96 h on coverslips using the Amsterdam Active Attachment model, followed by 24 h treatment with nanocarriers containing different concentrations of each antifungal (78 and 156 µg/mL). MCZ or FLZ (156 µg/mL), and untreated biofilms were considered as controls. Anti-biofilm effects were evaluated by enumeration of colony-forming units (CFUs), composition of the extracellular matrix, lactic acid production, and structure and live/dead biofilm cells (confocal laser scanning microscopy-CLSM). Data were analyzed by one-way ANOVA and Fisher LSD’s test (α = 0.05). IONPs-CS carrying MCZ or FLZ were the most effective treatments in reducing CFUs compared to either an antifungal agent alone for C. albicans and MCZ for C. glabrata. Significant reductions in mutans streptococci and Lactobacillus spp. were shown, though mainly for the MCZ nanocarrier. Antifungals and their nanocarriers also showed significantly higher proportions of dead cells compared to untreated biofilm by CLSM (p < 0.001), and promoted significant reductions in lactic acid, while simultaneously showing increases in some components of the extracellular matrix. These findings reinforce the use of nanocarriers as effective alternatives to fight oral fungal infections. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Review

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Review
Synthesis of Antimicrobial Benzimidazole–Pyrazole Compounds and Their Biological Activities
Antibiotics 2021, 10(8), 1002; https://doi.org/10.3390/antibiotics10081002 - 19 Aug 2021
Cited by 16 | Viewed by 2063
Abstract
The synthesis of new compounds with antimicrobial and antiviral properties is a central objective today in the context of the COVID-19 pandemic. Benzimidazole and pyrazole compounds have remarkable biological properties, such as antimicrobial, antiviral, antitumor, analgesic, anti-inflammatory, anti-Alzheimer’s, antiulcer, antidiabetic. Moreover, recent literature [...] Read more.
The synthesis of new compounds with antimicrobial and antiviral properties is a central objective today in the context of the COVID-19 pandemic. Benzimidazole and pyrazole compounds have remarkable biological properties, such as antimicrobial, antiviral, antitumor, analgesic, anti-inflammatory, anti-Alzheimer’s, antiulcer, antidiabetic. Moreover, recent literature mentions the syntheses and antimicrobial properties of some benzimidazole–pyrazole hybrids, as well as other biological properties thereof. In this review, we aim to review the methods of synthesis of these hybrids, the antimicrobial activities of the compounds, their correlation with various groups present on the molecule, as well as their pharmaceutical properties. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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Review
Bactericidal and Virucidal Activities of Biogenic Metal-Based Nanoparticles: Advances and Perspectives
Antibiotics 2021, 10(7), 783; https://doi.org/10.3390/antibiotics10070783 - 28 Jun 2021
Cited by 16 | Viewed by 1859
Abstract
Much progress has been achieved in the preparation and application of engineered nanoparticles (NPs) in the field of medicine, mainly for antibacterial and antiviral applications. In the war against bacteria and viruses, besides traditional antibiotics and antiviral drugs, metal-based nanoparticles, such as silver [...] Read more.
Much progress has been achieved in the preparation and application of engineered nanoparticles (NPs) in the field of medicine, mainly for antibacterial and antiviral applications. In the war against bacteria and viruses, besides traditional antibiotics and antiviral drugs, metal-based nanoparticles, such as silver (AgNPs), copper (CuNPs), copper oxides (CuO-NPs), iron oxide (FeO-NPs), zinc oxide (ZnO-NPs), and titanium oxide (TiO2-NPs) have been used as potent antimicrobial agents. These nanoparticles can be synthesized by traditional methods, such as chemical and physical routes, or more recently by biogenic processes. A great variety of macro and microorganisms can be successfully used as reducing agents of metal salt precursors in the biogenic synthesis of metal-based NPs for antimicrobial activity. Depending on the nature of the biological agent, NPs with different sizes, aggregation states, morphology, surface coatings and charges can be obtained, leading to different antimicrobial effects. Considering the drug resistance to traditional therapies, the development of versatile nanomaterials with potent antimicrobial effects is under intensive investigation. In this sense, this review presents and discusses the recent progress in the preparation and application of metal-based nanoparticles biogenically synthesized for antibacterial and antivirus applications. The strength and limitations are critically discussed. Full article
(This article belongs to the Special Issue Synthesis and Biological Activity of Antimicrobial Agents)
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