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1.
Martina Durcik Prof. Päivi Tammela Michaela Barančoková Assist. Prof. Tihomir Tomašič Assoc. Prof. Janez Ilaš Prof. Danijel Kikelj Nace Zidar 《ChemMedChem》2018,13(2):186-198
ATP‐competitive inhibitors of DNA gyrase and topoisomerase IV are among the most interesting classes of antibacterial drugs that are unrepresented in the antibacterial pipeline. We developed 32 new N‐phenylpyrrolamides and evaluated them against DNA gyrase and topoisomerase IV from E. coli and Staphylococcus aureus. Antibacterial activities were studied against Gram‐positive and Gram‐negative bacterial strains. The most potent compound displayed an IC50 of 47 nm against E. coli DNA gyrase, and a minimum inhibitory concentration (MIC) of 12.5 μm against the Gram‐positive Enterococcus faecalis. Some compounds displayed good antibacterial activities against an efflux‐pump‐deficient E. coli strain (MIC=6.25 μm ) and against wild‐type E. coli in the presence of efflux pump inhibitor PAβN (MIC=3.13 μm ). Here we describe new findings regarding the structure–activity relationships of N‐phenylpyrrolamide DNA gyrase B inhibitors and investigate the factors that are important for the antibacterial activity of this class of compounds. 相似文献
2.
Madurga S Sánchez-Céspedes J Belda I Vila J Giralt E 《Chembiochem : a European journal of chemical biology》2008,9(13):2081-2086
We have studied the bacterial resistance to fluoroquinolones that arises as a result of mutations in the DNA gyrase target protein. Although it is known that DNA gyrase is a target of quinolone antibacterial agents, the molecular details of the quinolone-gyrase interaction remain unclear. The mode of binding of ciprofloxacin, levofloxacin, and moxifloxacin to DNA gyrase was analyzed by means of docking calculations over the surface of the QRDR of GyrA. The analysis of these binding models allows study of the resistance mechanism associated with gyrA mutations more commonly found in E. coli fluoroquinolone-resistant strains at the atomic level. Asp87 was found to be critical in the binding of these fluoroquinolones because it interacts with the positively charged nitrogens in these bactericidal drugs. The role of the other most common mutations at amino acid codon Ser83 can be explained through the contacts that the side chain of this residue establishes with fluoroquinolone molecules. Finally, our results strongly suggest that, although Arg121 has never been found to be associated with fluoroquinolone resistance, this residue makes a pivotal contribution to the binding of the antibiotic to GyrA and to defining its position in the QRDR of the enzyme. 相似文献
3.
Dr. Stephen J. Milner Christopher T. Carrick Prof. Kevin G. Kerr Dr. Anna M. Snelling Dr. Gavin H. Thomas Dr. Anne‐Kathrin Duhme‐Klair Dr. Anne Routledge 《Chembiochem : a European journal of chemical biology》2014,15(3):466-471
Mono‐ and disaccharide‐functionalised conjugates of the fluoroquinolone antibiotic ciprofloxacin have been synthesised and used as chemical probes of the bacterial uptake of glycosylated ciprofloxacin. Their antimicrobial activities against a panel of clinically relevant bacteria were determined: the ability of these conjugates to inhibit their target DNA gyrase and to be transported into the bacteria was assessed by using in vivo and in vitro assays. The data suggest a lack of active uptake through sugar transporters and that although the addition of monosaccharides is compatible with the inhibition of DNA gyrase, the addition of a disaccharide results in a significant decrease in antimicrobial activity. 相似文献
4.
David J. Sanabria-Ríos Christian Morales-Guzmán Joseph Mooney Solymar Medina Tomás Pereles-De-León Ashley Rivera-Román Carlimar Ocasio-Malavé Damarith Díaz Nataliya Chorna Néstor M. Carballeira 《Lipids》2020,55(2):101-116
In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C-3, C-6, C-8, C-9, C-10, and C-12 were carried out in four steps and with an overall yield of 34–78%. In addition, HDA analogs containing a sulfur atom at either C-4 or C-5 were also prepared in 69–77% overall yields, respectively. Results from this study revealed that the triple bond at C-2 is pivotal for the antibacterial activity displayed by 2-HDA, while the farther the position of the triple bond from the carbonyl group, the lower its bactericidal activity against gram-positive bacteria, including clinical isolates of methicillin-resistant Staphylococcus aureus (CIMRSA) strains. The potential of 2-HDA as an antibacterial agent was also assessed in five CIMRSA strains that were resistant to Ciprofloxacin (Cipro) demonstrating that 2-HDA was the most effective treatment in inhibiting their growth when compared with either Cipro alone or equimolar combinations of Cipro and 2-HDA. Moreover, it was proved that the inhibition of S. aureus DNA gyrase can be linked to the antibacterial activity displayed by 2-HDA. Finally, it was determined that the ability of HDA analogs to form micelles can be linked to their decreased activity against gram-positive bacteria, since critical micellar concentrations (CMC) between 50 and 300 μg/mL were obtained. 相似文献
5.
Dr. Variam U. Jeankumar Dr. Shalini Saxena Dr. Rahul Vats Rudraraju Srilakshmi Reshma Renuka Janupally Dr. Pushkar Kulkarni Prof. Perumal Yogeeswari Prof. Dharmarajan Sriram 《ChemMedChem》2016,11(5):539-548
In this study we explored the pharmaceutically underexploited ATPase domain of DNA gyrase (GyrB) as a potential platform for developing novel agents that target Mycobacterium tuberculosis. In this effort a combination of ligand‐ and structure‐based pharmacophore modeling was used to identify structurally diverse small‐molecule inhibitors of the mycobacterial GyrB domain based on the crystal structure of the enzyme with a pyrrolamide inhibitor (PDB ID: 4BAE ). Pharmacophore modeling and subsequent in vitro screening resulted in an initial hit compound 5 [(E)‐5‐(5‐(2‐(1H‐benzo[d]imidazol‐2‐yl)‐2‐cyanovinyl)furan‐2‐yl)isophthalic acid; IC50=4.6±0.1 μm ], which was subsequently tailored through a combination of molecular modeling and synthetic chemistry to yield the optimized lead compound 24 [(E)‐3‐(5‐(2‐cyano‐2‐(5‐methyl‐1H‐benzo[d]imidazol‐2‐yl)vinyl)thiophen‐2‐yl)benzoic acid; IC50=0.3±0.2 μm ], which was found to display considerable in vitro efficacy against the purified GyrB enzyme and potency against the H37Rv strain of M. tuberculosis. Structural handles were also identified that will provide a suitable foundation for further optimization of these potent analogues. 相似文献
6.
Gyrase ATPase Domain as an Antitubercular Drug Discovery Platform: Structure‐Based Design and Lead Optimization of Nitrothiazolyl Carboxamide Analogues
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Variam Ullas Jeankumar Janupally Renuka Sonali Kotagiri Shalini Saxena Shruti Singh Kakan Jonnalagadda Padma Sridevi Swapna Yellanki Pushkar Kulkarni Prof. Perumal Yogeeswari Prof. Dharmarajan Sriram 《ChemMedChem》2014,9(8):1850-1859
In this study, we explored the pharmaceutically underexploited mycobacterial gyrase ATPase (GyrB) domain as a template for a structure‐based virtual screening of our in‐house (BITS Pilani) compound collection to discover new inhibitors targeting Mycobacterium tuberculosis (M.tb.) The hit identified was further customized by using a combination of molecular docking and medicinal chemistry strategies to obtain an optimized analogue displaying considerable in vitro enzyme efficacy and bactericidal properties against the M.tb. H37Rv strain. The binding affinity of the ligand toward the GyrB domain was reascertained by differential scanning fluorimetry experiments. Further evaluation of the hERG toxicity (a major limitation among the previously reported N‐linked aminopiperidine analogues) indicated these molecules to be completely devoid of cardiotoxicity, a significant achievement within this class. 相似文献
7.
Synthesis of Albicidin Derivatives: Assessing the Role of N‐terminal Acylation on the Antibacterial Activity
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Dennis Kerwat Stefan Grätz Dr. Julian Kretz Maria Seidel Maria Kunert Dr. John B. Weston Prof. Dr. Roderich D. Süssmuth 《ChemMedChem》2016,11(17):1899-1903
The peptide antibiotic albicidin, which is synthesized by the plant pathogenic bacterium, Xanthomonas albilineans, represents the most prominent member of a new class of antibacterial gyrase inhibitors. It shows remarkable antibacterial activities against Gram‐positive and Gram‐negative microorganisms. Its unique structure potentially represents a new lead structure for the development of an antibacterial drug. Here we report the synthesis of 14 albicidin derivatives with structural variations at the N‐terminus, primarily investigating the effects of variation of cinnamoyl, phenylpropanoyl, and benzoyl residues. Gyrase inhibition in vitro and determination of minimal inhibitory concentrations were assessed in parallel. Activities in a nanomolar range and the importance of N‐acylation were demonstrated. 相似文献
8.
9.
Maolan Zhang Yuanliang Wang Guoming Zeng Shuang Yang Xiaoling Liao Da Sun 《应用聚合物科学杂志》2021,138(20):50451
Piperazine polymers poly(ethylenediaminetetraacetic dianhydride-co-piperazine) (PE) and MGF-Ct24E-modified poly(ethylenediaminetetraacetic dianhydride-co-piperazine) (PEM) showed good antibacterial activity. Considering their different applications, the effects of time, pH, and inoculation concentration of these antibacterials against Escherichia coli (E. coli) in unique environments were evaluated in this study. The results indicated that the MIC and MBC values of the polymers increased after the introduction of MGF-Ct24E into PE, but the two types of polymers still exhibited good antibacterial activity in a short time period under acidic conditions. In addition, we investigated the effect of the piperazine polymers on bacterial cell structure. It was clear that PE and PEM could destroy the bacterial cell wall, cell membrane and DNA, and their specific mechanism may be different. For PE, its carboxyl group could react with peptidoglycans on the E.coli cell wall to form holes on the bacterial surface, allowing PE to penetrate into the bacterial cell to damage DNA. For PEM, the alkaline MGF-Ct24E could adsorb E.coli and make it shrink, meanwhile, the PE component created small holes on the bacterial walls and membranes, and inserted into the bacteria to result in bactericidal effect. These findings reveal the potential usefulness of PE and PEM in biomedical applications. 相似文献
10.
Sangeeta Verma Dr. Sukhbir Lal Dr. Rakesh Narang Dr. Kalvatala Sudhakar 《ChemMedChem》2023,18(5):e202200571
Antibiotics are becoming gradually ineffective due to drug resistance, leading to greater difficulty in the treatment of infectious diseases. Therefore, the development of new chemical entities with different mechanisms of action is essential in the fight against resistant microorganisms. Various studies have shown that quinoline hydrazide/hydrazone derivatives possess several biological activities, such as antimalarial, antitubercular, anticancer, anti-inflammatory, and antimicrobial. Among these activities, the antibacterial activity of quinoline hydrazide/hydrazone derivatives is noteworthy. The synthetic flexibility of the quinoline ring has led to the development of a wide range of structurally diverse quinoline hydrazide/hydrazone derivatives, which can act at various bacterial targets such as DNA gyrase, glucosamine-6-phosphate synthase, enoyl ACP reductase, and 3-ketoacyl ACP reductase. This review emphasizes the antibacterial potential of various reported quinoline hydrazide/hydrazone derivatives based on substitution in the quinoline ring. The antibacterial activity of various metal-quinoline hydrazide/hydrazone complexes is also discussed. The aim of this review is to assemble and scrutinize the latest reports in this promising area of drug development. 相似文献
11.
Amr Sonousi Jonathan C. K. Quirke Dr. Prabuddha Waduge Tanja Janusic Marina Gysin Klara Haldimann Dr. Shan Xu Dr. Sven N. Hobbie Prof. Dr. Su-Hua Sha Prof. Dr. Jochen Schacht Prof. Dr. Christine S. Chow Prof. Dr. Andrea Vasella Prof. Dr. Erik C. Böttger Prof. Dr. David Crich 《ChemMedChem》2021,16(2):335-339
We describe the convergent synthesis of a 5-O-β-D-ribofuranosyl-based apramycin derivative (apralog) that displays significantly improved antibacterial activity over the parent apramycin against wild-type ESKAPE pathogens. In addition, the new apralog retains excellent antibacterial activity in the presence of the only aminoglycoside modifying enzyme (AAC(3)-IV) acting on the parent, without incurring susceptibility to the APH(3’) mechanism that disables other 5-O-β-D-ribofuranosyl 2-deoxystreptamine type aminoglycosides by phosphorylation at the ribose 5-position. Consistent with this antibacterial activity, the new apralog has excellent 30 nM activity (IC50) for the inhibition of protein synthesis by the bacterial ribosome in a cell-free translation assay, while retaining the excellent across-the-board selectivity of the parent for inhibition of bacterial over eukaryotic ribosomes. Overall, these characteristics translate into excellent in vivo efficacy against E. coli in a mouse thigh infection model and reduced ototoxicity vis à vis the parent in mouse cochlear explants. 相似文献
12.
Oussama Moussaoui Dr. Rajendra Bhadane Dr. Riham Sghyar Prof. Janez Ilaš Prof. El Mestafa El Hadrami Prof. Said Chakroune Dr. Outi M. H. Salo-Ahen 《ChemMedChem》2022,17(5):e202100714
Due to the ever-increasing antimicrobial resistance there is an urgent need to continuously design and develop novel antimicrobial agents. Inspired by the broad antibacterial activities of various heterocyclic compounds such as 2-quinolone derivatives, we designed and synthesized new methyl-(2-oxo-1,2-dihydroquinolin-4-yl)-L-alaninate-1,2,3-triazole derivatives via 1,3-dipolar cycloaddition reaction of 1-propargyl-2-quinolone-L-alaninate with appropriate azide groups. The synthesized compounds were obtained in good yield ranging from 75 to 80 %. The chemical structures of these novel hybrid molecules were determined by spectroscopic methods and the antimicrobial activity of the compounds was investigated against both bacterial and fungal strains. The tested compounds showed significant antimicrobial activity and weak to moderate antifungal activity. Despite the evident similarity of the quinolone moiety of our compounds with fluoroquinolones, our compounds do not function by inhibiting DNA gyrase. Computational characterization of the compounds shows that they have attractive physicochemical and pharmacokinetic properties and could serve as templates for developing potential antimicrobial agents for clinical use. 相似文献
13.
Chao Peng Tian Zhang Deliris N Ortiz‐Ortiz Apoorva Vishwakarma Hazel A Barton Abraham Joy 《Polymer International》2019,68(7):1255-1262
Each year, thousands of patients die from antimicrobial‐resistant bacterial infections that fail to respond to conventional antibiotic treatment. Antimicrobial polymers are a promising new method of combating antibiotic‐resistant bacterial infections. We have previously reported the synthesis of a series of narrow‐spectrum peptidomimetic antimicrobial polyurethanes that are effective against Gram‐negative bacteria, such as Escherichia coli; however, these polymers are not effective against Gram‐positive bacteria, such as Staphylococcus aureus. With the aim of understanding the correlation between chemical structure and antibacterial activity, we have subsequently developed three structural variants of these antimicrobial polyurethanes using post‐polymerization modification with decanoic acid and oleic acid. Our results show that such modifications converted the narrow‐spectrum antibacterial activity of these polymers into broad‐spectrum activity against Gram‐positive species such as S. aureus, however, also increasing their toxicity to mammalian cells. Mechanistic studies of bacterial membrane disruption illustrate the differences in antibacterial action between the various polymers. The results demonstrate the challenge of balancing antimicrobial activity and mammalian cell compatibility in the design of antimicrobial polymer compositions. © 2019 Society of Chemical Industry 相似文献
14.
Adsorption and antibacterial effect of copper-exchanged montmorillonite on Escherichia coli K88 总被引:1,自引:0,他引:1
Calcium montmorillonite (Ca-MMT), sodium montmorillonite (Na-MMT) and acid-activated montmorillonite (AAM), and their Cu2+-exchanged montmorillonites (Cu-MMT), Cu*Ca-MMT, Cu*Na-MMT and Cu*AAM, were used to study the antibacterial activity on Escherichia coli K88. AAM, Na-MMT and Ca-MMT showed some ability to reduce bacterial plate counts by 37.4%, 13.4% and 14.2%, respectively. Exchanging the montmorillonite with Cu2+ enhanced the antibacterial activity. The Cu*AAM, Cu*Na-MMT and Cu*Ca-MMT reduced the bacterial plate counts by 98.6%, 97.5% and 95.6%. Attempts were made to study the desorption of Cu2+ by washing with sterile physiological saline solution for 24 h. The washing solutions did not show a significant reduction of the bacterial counts, while the washed Cu-MMT retained their full antibacterial activity. Results from time-depending studies showed that the reduction of the bacterial counts by Cu-MMT increased during 24 h. The ranking of antibacterial activity of the three Cu-MMT was as Cu*AAM > Cu*Na-MMT > Cu*Ca-MMT. E. coli thrived optimally in a pH range from 5 to 7. Beyond this range, the bacterial counts decreased as the pH reduced the viability of the bacteria. The ranking of antibacterial activity of Cu-MMT was not affected by pH. The mechanism by which bacterial counts are reduced may involve the enhanced affinity of Cu-MMT for E. coli K88 and the antibacterial activity of Cu2+. 相似文献
15.
Mateusz Schabikowski Magdalena Laskowska Pawe Kowalczyk Andrii Fedorchuk Emma Szri-Doroghzi Zoltn Nmeth Dominika Ku
ma Barbara Gawdzik Aleksandra Wypych Karol Kramkowski ukasz Laskowski 《International journal of molecular sciences》2022,23(15)
In this article, we describe the antimicrobial properties of a new composite based on anodic aluminium oxide (AAO) membranes containing propyl-copper-phosphonate units arranged at a predetermined density inside the AAO channels. The samples were prepared with four concentrations of copper ions and tested as antimicrobial drug on four different strains of Escherichia coli (K12, R2, R3 and R4). For comparison, the same strains were tested with three types of antibiotics using the minimal inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) tests. Moreover, DNA was isolated from the analysed bacteria which was additionally digested with formamidopyrimidine-DNA glycosylase (Fpg) protein from the group of repair glycosases. These enzymes are markers of modified oxidised bases in nucleic acids produced during oxidative stress in cells. Preliminary cellular studies, MIC and MBC tests and digestion with Fpg protein after modification of bacterial DNA suggest that these compounds may have greater potential as antibacterial agents than antibiotics such as ciprofloxacin, bleomycin and cloxacillin. The described composites are highly specific for the analysed model Escherichia coli strains and may be used in the future as new substitutes for commonly used antibiotics in clinical and nosocomial infections in the progressing pandemic era. The results show much stronger antibacterial properties of the functionalised membranes on the action of bacterial membranes in comparison to the antibiotics in the Fpg digestion experiment. This is most likely due to the strong induction of oxidative stress in the cell through the breakdown of the analysed bacterial DNA. We have also observed that the intermolecular distances between the functional units play an important role for the antimicrobial properties of the used material. Hence, we utilised the idea of the 2D solvent to tailor them. 相似文献
16.
Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug‐Resistant Pseudomonas aeruginosa DNA
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Ya‐Nan Wang Dr. Rammohan R. Yadav Bheemanaboina Dr. Wei‐Wei Gao Jie Kang Dr. Gui‐Xin Cai Prof. Cheng‐He Zhou 《ChemMedChem》2018,13(10):1004-1017
A series of benzimidazole–quinolone hybrids as new potential antimicrobial agents were designed and synthesized. Bioactive assays indicated that some of the prepared compounds exhibited potent antibacterial and antifungal activities. Notably, 2‐fluorobenzyl derivative 5 b (ethyl 7‐chloro‐6‐fluoro‐1‐[[1‐[(2‐fluorophenyl)methyl]benzimidazol‐2‐yl]methyl]‐4‐oxo‐quinoline‐3‐carboxylate) showed remarkable antimicrobial activity against resistant Pseudomonas aeruginosa and Candida tropicalis isolated from infected patients. Active molecule 5 b could not only rapidly kill the tested strains, but also exhibit low toxicity toward Hep‐2 cells. It was more difficult to trigger the development of bacterial resistance of P. aeruginosa against 5 b than that against norfloxacin. Molecular docking demonstrated that 5 b could effectively bind with topoisomerase IV–DNA complexes, and quantum chemical studies theoretically elucidated the good antimicrobial activity of compound 5 b . Preliminary experimental reaction mechanism exploration suggested that derivative 5 b could not intercalate into DNA isolated from drug‐resistant P. aeruginosa, but was able to cleave DNA effectively, which might further block DNA replication to exert powerful bioactivities. In addition, compound 5 b is a promising antibacterial agent with membrane disruption abilities. 相似文献
17.
Rolf Büssing Bianka Karge Petra Lippmann Prof. Dr. Peter G. Jones Prof. Dr. Mark Brönstrup Prof. Dr. Ingo Ott 《ChemMedChem》2021,16(22):3402-3409
A series of (NHC)Au(I)Cl monocarbene complexes and their gold(III) analogues (NHC)Au(III)Cl3 were prepared and investigated as antibacterial agents and inhibitors of bacterial TrxR. The complexes showed stronger antibacterial effects against the Gram-positive MRSA and E. faecium strains than against several Gram-negative bacteria. All complexes were efficient inhibitors of bacterial thioredoxin reductase, indicating that inhibition of this enzyme might be involved in their mechanism of action. The efficacy of gold(I) and gold(III) analogues was comparable in most of the assays. The cytotoxicity of the gold NHC compounds against cancer and human cells was overall weaker than the activity against the Gram-positive bacteria, suggesting that their optimization as antibacterials warrants further investigation. 相似文献
18.
P. Araichimani G. Suresh Kumar K. M. Prabu Gopalu Karunakaran N. Van Minh Evgeny Kolesnikov Mikhail V. Gorshenkov 《International Journal of Applied Ceramic Technology》2021,18(3):583-589
Amorphous silica nanoparticles are a promising platform for constructing drug delivery vehicles owing to their high biocompatibility and favorable surface chemistry. In the current study, we report the preparation of amorphous silica nanoparticles using rice husk biowaste via easy and rapid microwave-assisted combustion. The obtained results from various characterizations indicate that the prepared sample is an amorphous form of silica nanoparticles having sizes 50–80 nm with high purity. Ciprofloxacin was used as the model drug and it was released from silica nanocarrier in a controlled and prolonged manner. The ciprofloxacin release kinetics was investigated using the Higuchi model and Ritger-Peppas model which corroborate that different process like desorption, diffusion, and surface erosion may be involved in the release of ciprofloxacin from the prepared silica nanocarrier. The antibacterial susceptibility test revealed that the ciprofloxacin loaded silica nanocarrier exhibit a bacterial inhibition zone about 32 ± 4 and 44 ± 3 mm against Escherichia coli and Staphylococcus aureus, respectively. This study can be useful to develop a versatile nanocarrier with controlled delivery of ciprofloxacin to treat different types of bacterial infections. 相似文献
19.
Bishweshwar Pant Mira Park Gunendra Prasad Ojha Dae-Up Kim Soo-Jin Park 《国际聚合物材料杂志》2018,67(12):739-744
Salicylic acid (SA)/polyurethane (PU) composite nanofiber mats were fabricated by introducing SA in PU solution during the electrospinning process. Cell viability assays showed that the as-prepared composite nanofibers had a good biocompatibility. Further, the composite mats showed good antibacterial performance against Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus bacteria. Easy fabrication, good mechanical properties, good biocompatibility as well as the antibacterial activity of PU nanofibers containing SA indicated their significant promise for a variety of potential medical applications such as tissue engineering, wound healing, and drug delivery system. 相似文献
20.
In this study, an innovative in situ green strategy was applied to prepare bacterial cellulose/silver nanocomposites using green tea as a substrate for the fermentation of Acetobacter xylinum bacteria and a reducing agent for the in situ synthesis of silver nanoparticles. The samples were analyzed by different characterization tests including field emission scanning electron microscopy (FESEM), X-ray diffraction analysis (XRD), UV–vis spectroscopy, atomic absorption spectroscopy, and ATR. The results indicated the excellent antibacterial activities with 100% bacterial reduction percentage and inhibition zones of 2.6 and 2.8 cm against S. aureus and E. coli, respectively. Moreover, water absorption percentage and vertical wicking measurements supported the hydrogel properties of the prepared bio-cellulose/silver nanocomposites. Finding of this research suggested the potential of the proposed green route for preparing antibacterial BC which can be regarded as a candidate for future wound healing applications. 相似文献