A strategic approach to the synthesis of ferrocene appended chalcone linked triazole allied organosilatranes: Antibacterial, antifungal, antiparasitic and antioxidant studies

Singh, Gurjaspreet; Arora, Aanchal; Kalra, Pooja; Maurya, Indresh Kumar; Espinosa, Cristóbal; Esteban, M. Ángeles; Sinha, Sanjib; Goyal, Kapil; Sehgal, Rakesh

doi:10.1016/j.bmc.2018.11.038

Cited by 53 publications

(28 citation statements)

References 42 publications

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“…However, these compounds can be synthesized in the laboratory using the Claisen-Schmidt condensation method (Karimi-Sales;Mohaddes;Alipour, 2017). Chalcones demonstrate many biological activities such as anti-inflammatory, anti-tumor (Khanapure et al, 2018), antioxidant (Singh et al, 2018b), antidiabetic (Cai et al, 2017), antibacterial (Singh et al, 2018a), antifungal Jain, 2015;Fu et al, 2016;Illicachi et al, 2017), antiprotozoal (Illicachi et al, 2017;Tajuddeen et al, 2018), and antiparasitic (Kotlyar et al, 2019), as well as activities against Alzheimer's disease (Zhang et al, 2018b) and cholinesterase inhibition (Shah et al, 2018) among others. Chalcones can be excellent photosensitizers for PDT.…”

Section: Introductionmentioning

confidence: 99%

2-Hydroxychalcone as a Potent Compound and Photosensitizer Against Dermatophyte Biofilms

Bila

Costa-Orlandi

Vaso

et al. 2021

Front. Cell. Infect. Microbiol.

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Dermatophytes, fungi that cause dermatophytosis, can invade keratinized tissues in humans and animals. The biofilm-forming ability of these fungi was described recently, and it may be correlated with the long treatment period and common recurrences of this mycosis. In this study, we evaluated the anti-dermatophytic and anti-biofilm activity of 2-hydroxychalcone (2-chalcone) in the dark and photodynamic therapy (PDT)-mediated and to determine its mechanism of action. Trichophyton rubrum and Trichophyton mentagrophytes strains were used in the study. The antifungal susceptibility test of planktonic cells, early-stage biofilms, and mature biofilms were performed using colorimetric methods. Topographies were visualized by scanning electron microscopy (SEM). Human skin keratinocyte (HaCat) monolayers were also used in the cytotoxicity assays. The mechanisms of action of 2-chalcone in the dark and under photoexcitation were investigated using confocal microscopy and the quantification of ergosterol, reactive oxygen species (ROS), and death induction by apoptosis/necrosis. All strains, in the planktonic form, were inhibited after treatment with 2-chalcone (minimum inhibitory concentration (MIC) = 7.8-15.6 mg/L), terbinafine (TRB) (MIC = 0.008–0.03 mg/L), and fluconazole (FLZ) (1–512 mg/L). Early-stage biofilm and mature biofilms were inhibited by 2-chalcone at concentrations of 15.6 mg/L and 31.2 mg/L in all tested strains. However, mature biofilms were resistant to all the antifungal drugs tested. When planktonic cells and biofilms (early-stage and mature) were treated with 2-chalcone-mediated PDT, the inhibitory concentrations were reduced by four times (2–7.8 mg/L). SEM images of biofilms treated with 2-chalcone showed cell wall collapse, resulting from a probable extravasation of cytoplasmic content. The toxicity of 2-chalcone in HaCat cells showed higher IC50 values in the dark than under photoexcitation. Further, 2-chalcone targets ergosterol in the cell and promotes the generation of ROS, resulting in cell death by apoptosis and necrosis. Overall, 2-chalcone-mediated PDT is a promising and safe drug candidate against dermatophytes, particularly in anti-biofilm treatment.

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Section: Introductionmentioning

confidence: 99%

2-Hydroxychalcone as a Potent Compound and Photosensitizer Against Dermatophyte Biofilms

Bila

Costa-Orlandi

Vaso

et al. 2021

Front. Cell. Infect. Microbiol.

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“…Based on the last 40 years of academic and pharmaceutical industry inventions, only bedaquiline was the first novel anti-TB drug permitted by the United States Food and Drug Administration (US FDA) authority in December 2012, for the treatment of MDR-TB, [6] while delamanid was the second anti-TB agent to be approved by the European Medicines Agency in late 2013 [7] and pretomanid was the third drug to be approved by the US FDA in August 2019 [8,9] (Figure 1). Triazole pharmacophore with various functional groups/substitutions has been reported for its promising anti-TB [10][11][12][13][14][15][16][17][18][19][20][21], antiviral [22], antibacterial [23,24], antifungal [25,26], antioxidant [27][28][29][30], and antiglycation properties [31]. In addition, it also serves as an opener of Ca( 2+ )-activated potassium (maxi-K) channels [32] and demonstrates molluscicidal [33], hypoglycemic [34], antihypertensive and blood platelet aggregation inhibition [35] activities.…”

Section: Introductionmentioning

confidence: 99%

“…Triazole pharmacophore with various functional groups/substitutions has been reported for its promising anti-TB [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ], antiviral [ 22 ], antibacterial [ 23 , 24 ], antifungal [ 25 , 26 ], antioxidant [ 27 , 28 , 29 , 30 ], and antiglycation properties [ 31 ]. In addition, it also serves as an opener of Ca( 2+ )-activated potassium (maxi-K) channels [ 32 ] and demonstrates molluscicidal [ 33 ], hypoglycemic [ 34 ], antihypertensive and blood platelet aggregation inhibition [ 35 ] activities.…”

Section: Introductionmentioning

confidence: 99%

Anti-Tubercular Properties of 4-Amino-5-(4-Fluoro-3- Phenoxyphenyl)-4H-1,2,4-Triazole-3-Thiol and Its Schiff Bases: Computational Input and Molecular Dynamics

et al. 2020

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In the present investigation, the parent compound 4-amino-5-(4-fluoro-3-phenoxyphenyl)-4H-1,2,4-triazole-3-thiol (1) and its Schiff bases 2, 3, and 4 were subjected to whole-cell anti-TB against H37Rv and multi-drug-resistant (MDR) strains of Mycobacterium tuberculosis (MTB) by resazurin microtiter assay (REMA) plate method. Test compound 1 exhibited promising anti-TB activity against H37Rv and MDR strains of MTB at 5.5 µg/mL and 11 µg/mL, respectively. An attempt to identify the suitable molecular target for compound 1 was performed using a set of triazole thiol cellular targets, including β-ketoacyl carrier protein synthase III (FABH), β-ketoacyl ACP synthase I (KasA), CYP121, dihydrofolate reductase, enoyl-acyl carrier protein reductase, and N-acetylglucosamine-1-phosphate uridyltransferase. MTB β-ketoacyl ACP synthase I (KasA) was identified as the cellular target for the promising anti-TB parent compound 1 via docking and molecular dynamics simulation. MM(GB/PB)SA binding free energy calculation revealed stronger binding of compound 1 compared with KasA standard inhibitor thiolactomycin (TLM). The inhibitory mechanism of test compound 1 involves the formation of hydrogen bonding with the catalytic histidine residues, and it also impedes access of fatty-acid substrates to the active site through interference with α5–α6 helix movement. Test compound 1-specific structural changes at the ALA274–ALA281 loop might be the contributing factor underlying the stronger anti-TB effect of compound 1 when compared with TLM, as it tends to adopt a closed conformation for the access of malonyl substrate to its binding site.

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“…As a bioactive molecule, it is well known that natural and synthetic chalcone derivatives exhibit wide spectrum of chemotherapeutic properties such as antimicrobial [10], antioxidant [11], Chalcone structures are easily prepared via Claisen-Schmidt condensation between acetophenone and benzaldehyde or their substituted derivatives [20]. In the same way, their polyaromatic (i.e., anthracene, phenathrene, pyrene) counterparts can be obtained via replacing one (or two) ring(s) by a polyaromatic group, generating the so-called polyaromatic chalcones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterisation of Polyaromatic Chalcones with Electron Donation

Atahan

2020

Sakarya University Journal of Science

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In this study, a series of chalcone derivatives was successfully synthesized via condensation of 1acetylpyrene with dimethylamine, diphenylamine or carbazole containing benzaldehyde derivatives at basic conditions. Spectral characterisations were acquired by 1 and 2 dimensional NMR techniques and FTIR. In addition, UV-vis and thermal analysis studies were performed to determine their absorption properties and thermal behaviours, respectively. Lastly, surface and film generation properties were investigated by the means of SEM images on ITO glass to determine usability potential in organic electronics.

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A strategic approach to the synthesis of ferrocene appended chalcone linked triazole allied organosilatranes: Antibacterial, antifungal, antiparasitic and antioxidant studies

Cited by 53 publications

References 42 publications

2-Hydroxychalcone as a Potent Compound and Photosensitizer Against Dermatophyte Biofilms

2-Hydroxychalcone as a Potent Compound and Photosensitizer Against Dermatophyte Biofilms

Anti-Tubercular Properties of 4-Amino-5-(4-Fluoro-3- Phenoxyphenyl)-4H-1,2,4-Triazole-3-Thiol and Its Schiff Bases: Computational Input and Molecular Dynamics

Synthesis and Characterisation of Polyaromatic Chalcones with Electron Donation

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