Synthesis, Characterization and Physicochemical Analysis of some Mannofuranoside Derivatives with Potent Antimicrobial Activity

Hassan, Firoj; Nasibullah, Malik; Ahmad, Naseem; Kamal, Azhar; Rizvi, Syed Mohammad Danish; Khan, Mohd Sajid; Khan, Abdul Rahman

doi:10.13005/ojc/330606

Cited by 3 publications

(2 citation statements)

References 24 publications

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“…From the identified bioactive compounds, Pyrrolo[1,2-a]pyrazine-1,4-dione,hexahydro-3-(phenylmethyl)-Cyclo(D-phenylalanyl-L-prolyl) is well-known for its potent inhibitory effect on multidrug-resistant S. aureus and other pathogenic bacteria [ 73 ]. Mannofuranoside and its derivatives are also reported as strong antimicrobial agents, specifically against pathogenic fungi and several pathogenic Gram-positive and Gram-negative bacteria [ 74 ]. 1-Heneicosanol is known for its antibacterial and antifungal activities [ 75 ] as well as for its anti-tuberculosis activity [ 76 ].…”

Section: Discussionmentioning

confidence: 99%

Inhibition of Bacterial Adhesion and Antibiofilm Activities of a Glycolipid Biosurfactant from Lactobacillus rhamnosus with Its Physicochemical and Functional Properties

et al. 2021

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Biosurfactants derived from different microbes are an alternative to chemical surfactants, which have broad applications in food, oil, biodegradation, cosmetic, agriculture, pesticide and medicine/pharmaceutical industries. This is due to their environmentally friendly, biocompatible, biodegradable, effectiveness to work under various environmental conditions and non-toxic nature. Lactic acid bacteria (LAB)-derived glycolipid biosurfactants can play a major role in preventing bacterial attachment, biofilm eradication and related infections in various clinical settings and industries. Hence, it is important to explore and identify the novel molecule/method for the treatment of biofilms of pathogenic bacteria. In the present study, a probiotic Lactobacillus rhamnosus (L. rhamnosus) strain was isolated from human breast milk. Firstly, its ability to produce biosurfactants, and its physicochemical and functional properties (critical micelle concentration (CMC), reduction in surface tension, emulsification index (% EI24), etc.) were evaluated. Secondly, inhibition of bacterial adhesion and biofilm eradication by cell-bound biosurfactants from L. rhamnosus was performed against various biofilm-forming pathogens (B. subtilis, P. aeruginosa, S. aureus and E. coli). Finally, bacterial cell damage, viability of cells within the biofilm, exopolysaccharide (EPS) production and identification of the structural analogues of the crude biosurfactant via gas chromatography–mass spectrometry (GC–MS) analysis were also evaluated. As a result, L. rhamnosus was found to produce 4.32 ± 0.19 g/L biosurfactant that displayed a CMC of 3.0 g/L and reduced the surface tension from 71.12 ± 0.73 mN/m to 41.76 ± 0.60 mN/m. L. rhamnosus cell-bound crude biosurfactant was found to be effective against all the tested bacterial pathogens. It displayed potent anti-adhesion and antibiofilm ability by inhibiting the bacterial attachment to surfaces, leading to the disruption of biofilm formation by altering the integrity and viability of bacterial cells within biofilms. Our results also confirm the ability of the L. rhamnosus cell-bound-derived biosurfactant to damage the architecture of the biofilm matrix, as a result of the reduced total EPS content. Our findings may be further explored as a green alternative/approach to chemically synthesized toxic antibiofilm agents for controlling bacterial adhesion and biofilm eradication.

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Section: Discussionmentioning

confidence: 99%

Inhibition of Bacterial Adhesion and Antibiofilm Activities of a Glycolipid Biosurfactant from Lactobacillus rhamnosus with Its Physicochemical and Functional Properties

et al. 2021

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“…clavatus (MTCC 1323) and C . albicans (MTCC 227)] by modified microdilution method . Zone of inhibition of all derivatives was determined and compared with standard methotrexate and fluconazole, which were used as reference drug.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, Molecular Modeling, and Biological Evaluation of 1,2,4‐Triazole‐pyridine Hybrids as Potential Antimicrobial Agents

Ahirwar¹,

Ahirwar²,

Lanjhiyana³

et al. 2018

Journal of Heterocyclic Chem

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A novel 1,2,4‐triazole‐pyridine hybrid derivatives were synthesized by the reaction of nicotinohydrazide with carbon disulfide to yield potassium‐3‐pyridyl‐dithiocarbazate (I). This was further cyclized with ammonia solution to yield 5‐mercapto‐substituted 1,2,4‐triazole‐pyridine hybrid (II). This was finally reacted with different substituted benzyl derivatives to produce 1,2,4‐triazole‐pyridine hybrid derivatives (III). The purity of the derivatives was confirmed by thin‐layer chromatography and melting point. Structure of these derivatives was set up by determining its infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectroscopy. Further, the synthesized derivatives were evaluated for their in vitro antimicrobial activity against the three Gram‐negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Acinetbacter baumannii), three Gram‐positive bacteria (Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis), and two fungus (Aspergillus clavatus and Candida albicans). Minimal inhibitory concentration was also determined against same microorganism. Out of all synthesized derivatives, two derivatives, that is, 3‐(5‐(2‐bromobenzylthio)‐4H‐1,2,4‐triazol‐3‐yl)pyridine and 3‐(5‐(2,4‐dibromobenzylthio)‐4H‐1,2,4‐triazol‐3‐yl)pyridine showing more potent antibacterial activity. Docking studies were performed by using Argus lab, and all the derivatives exhibited good docking scores between −10.5369 and −11.8477 kcal/mol and were better as compared with standard drug methotrexate against a dihydrofolate reductase protein fragment from E. coli and Lactobacillus (4DFR). Among all compounds, 4h has shown the maximum docking score and found in agreement to in vitro antimicrobial studies.

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In-vitro and in-silico analysis of methanolic crude extracts of Mountain knotgrass Aerva lanta (L.) against two lepidopteran pests and non-target species

Kalvikkarasan,

Muthusamy,

Prabhakaran

et al. 2023

Toxin Reviews

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Synthesis, Characterization and Physicochemical Analysis of some Mannofuranoside Derivatives with Potent Antimicrobial Activity

Cited by 3 publications

References 24 publications

Inhibition of Bacterial Adhesion and Antibiofilm Activities of a Glycolipid Biosurfactant from Lactobacillus rhamnosus with Its Physicochemical and Functional Properties

Inhibition of Bacterial Adhesion and Antibiofilm Activities of a Glycolipid Biosurfactant from Lactobacillus rhamnosus with Its Physicochemical and Functional Properties

Synthesis, Characterization, Molecular Modeling, and Biological Evaluation of 1,2,4‐Triazole‐pyridine Hybrids as Potential Antimicrobial Agents

In-vitro and in-silico analysis of methanolic crude extracts of Mountain knotgrass Aerva lanta (L.) against two lepidopteran pests and non-target species

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