Design, synthesis and biological evaluation of novel unsymmetrical azines as quorum sensing inhibitors

Chourasiya, Sumit S.; Kathuria, Deepika; Singh, Shaminder; Sonawane, Vijay Chintaman; Chakraborti, Asit K.; Bharatam, Prasad V.

doi:10.1039/c5ra12925g

Cited by 25 publications

(19 citation statements)

References 51 publications

(49 reference statements)

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“…As mentioned earlier, both of the assayed traits are under the control of QS. 20 , 21 Interestingly, we found that albendazole has anti-QS activities in sub-MICs in a dose-dependent manner. Therefore, it can inhibit violacein production in C. violaceum .…”

Section: Introductionmentioning

confidence: 74%

“…We have performed this assay as previously described in one of our work. 20 In test tubes, 10 mL of LB broth was inoculated with plasB-gfp ( ASV) strain and was kept in incubation (overnight (O/N), 37 °C). An O/N growth culture was diluted 1:40 (about 125 µL of O/N culture was added to 4.875 mL of LB broth).…”

Section: Methodsmentioning

confidence: 99%

“…About after 24 hours of incubation, the chambers were added with 10 µL of albendazole (1 mM) and then kept for incubation (for 24 hours). 20 The 3-day old mature biofilms stained with PI, washed twice with phosphate buffer saline (PBS) to remove the unattached cells and subsequently the stained biofilms were fixed using fixative. The biofilms on coverslips were visualized on Nikon Confocal microscope and analyzed using NIS-elements software.…”

Section: Methodsmentioning

confidence: 99%

“… 19 We are working in the area of QS and screening several secondary metabolites produced by microorganisms subsequent to their QSI activity. 20 , 21 We have standardized various bioassays by testing several known inhibitors of QS against violacein pigment production in Chromobacterium violaceum and also green fluorescence protein production in P. aeruginosa lasB-gfp strain. As mentioned earlier, both of the assayed traits are under the control of QS.…”

Section: Introductionmentioning

confidence: 99%

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In silico identification of albendazole as a quorum sensing inhibitor and its in vitro verification using CviR and LasB receptors based assay systems

Singh¹,

Bhatia²

2018

Bioimpacts

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Introduction:Quorum sensing inhibition (QSI) is one of the vital tools to overcome emerging virulence of pathogenic bacteria which aims at curbing bacterial resistance. Targeting QS (quorum sensing) as chemotherapy is less likely to generate resistance among pathogens as it targets only the adaptation and not the survival mechanism of the pathogen. Several QS inhibitors were developed in the recent past but none of them managed to have clinical application due to known toxic effects for human consumption. A rapid development of QS inhibitor drugs could be achieved by verification of the QSI activity of drugs which are already in clinical use with known pharmacology. Recently, a known FDA approved clinical drug niclosamide belonging to an anthelmintic class is found to exhibit QSI activity. Methods: We have focused our study on Albendazole, another FDA approved clinical drug belonging to the same class for its potential to act as QSI. The structure-based molecular docking is used for finding putative interactions made by this drug with the CviR and LasB receptor protein of Chromobacterium violaceum and Pseudomonas aeruginosa , respectively. Further, the in vitro activity of this drug has been evaluated by employing CviR and LasB receptor-based bioassay. The efficacy of this drug alone and in combination with antibiotic Tobramycin to inhibit P. aeruginosa based biofilms was also analyzed by developing the biofilms on chambered glass slides and performing anti-biofilm assay. Results: Further, this drug found to inhibit purple pigment violacein production in C. violaceum , which is under the control of C6-AHL-CviR mediated QS in this human pathogen. The in vivo bioassays results suggested that albendazole has great potential to act as a QS inhibitor as found inhibiting violacein production in C. violaceum and biofilm formation in P. aeruginosa , respectively. Conclusion: It is that structure-based molecular docking guided bioassay evaluation is an efficient tool for finding the new therapeutic use of old drugs which could have more chances to come easily in clinical application for their newly identified therapeutic uses.

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Section: Introductionmentioning

confidence: 74%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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In silico identification of albendazole as a quorum sensing inhibitor and its in vitro verification using CviR and LasB receptors based assay systems

Singh¹,

Bhatia²

2018

Bioimpacts

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“…Carbones with the general formula (NHC) → C ← (NHC) were theoretically designed, later generated and proven to carry interesting chemical bond characteristics . Compounds with the general formula (NHC) → E ← (NHC) (EBH, C, Si, Ge, and P ⊕ ), (I) and compounds with the general formula (NHC) → E–E ← (NHC) (E–EB 2 , Si 2 , Ge 2 , N 2 , P 2 , As 2 , N‐P), (II) were reported (Fig. ).…”

Section: Introductionmentioning

confidence: 99%

Donor→acceptor coordination interactions in 1,3‐bis(NHC)triazenyl Cations: An electronic structure analysis

Singh

Bharatam

2019

J Comput Chem

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Donor!acceptor coordination interactions (L ! N) between ligands and nitrogen center as in L ! N È L were reported in the recent past. This article describes the possibility of L ! N coordination interactions in triazenyl cation species L ! N 3 È L. A few 1,3-bis(NHC)triazenyl cation species were experimentally known, the electronic structure analysis reported in this work reveals the presence of L ! N (donor!acceptor) interactions in these species. Molecular orbital analysis, NBO charge analysis, energy decomposition analysis, and so forth, confirm the possibility of L ! N coordination bond character. Ten molecules with the general formula L ! N 3 È L have been designed carrying L ! N 3 È L interactions.

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Access to Fluorescent Azines from N‐Heterocyclic Carbene Precursors and N‐Tosylhydrazones

Wei

Chen

et al. 2017

Adv Synth Catal

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Design, synthesis and biological evaluation of novel unsymmetrical azines as quorum sensing inhibitors

Abstract: In this report, novel unsymmetrical azines have been designed and synthesised by using one pot approach. Further, they were evaluated as quorum sensing inhibitors.

Cited by 25 publications

References 51 publications

In silico identification of albendazole as a quorum sensing inhibitor and its in vitro verification using CviR and LasB receptors based assay systems

In silico identification of albendazole as a quorum sensing inhibitor and its in vitro verification using CviR and LasB receptors based assay systems

Donor→acceptor coordination interactions in 1,3‐bis(NHC)triazenyl Cations: An electronic structure analysis

Access to Fluorescent Azines from N‐Heterocyclic Carbene Precursors and N‐Tosylhydrazones

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