O-Halogen-substituted arene linked selenium-N-heterocyclic carbene compounds induce significant cytotoxicity: Crystal structures and molecular docking studies

Hayat, Khizar; Shkeel, Mahwish; Iqbal, Muhammad Adnan; Quah, Ching Kheng; Wong, Qin Ai; Nazari, Mansoureh; Ahamed, Mohd. B. Khadeer; Hameed, Shahid

doi:10.1016/j.jorganchem.2022.122593

Cited by 9 publications

(5 citation statements)

References 67 publications

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“…Synthesis of the Se–NHC adduct was accomplished in three independent steps by following the procedure published recently . Very short-ranged peaks (3500–500 cm –1 ) are observed in the experimental FT-IR spectra, as demonstrated in Figure .…”

Section: Resultsmentioning

confidence: 99%

“…Stretching vibrations of C–C are observed between 1200 and 1750 cm –1 , and C–C bending vibration is found below 500 cm –1 . Bending vibrations of CH 3 and CH 2 are observed at 1131 and 1375 cm –1 , respectively …”

Section: Resultsmentioning

confidence: 99%

“…Bending vibrations of CH 3 and CH 2 are observed at 1131 and 1375 cm −1 , respectively. 26 A particular pattern in the FT-IR spectra was observed between 1460 and 1100 cm −1 that might be due to fundamental vibrational frequency of the carbon selenium (C�Se) bond. The similar behavior was confirmed by literature reflecting the vibrational frequency for the carbon selenium bond of imidiazolium adducts at 1222 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Characterization, and Evaluation of Antifungal Activity of 1-Butyl-3-hexyl-1H-imidazol-2(3H)-selenone by Surface-Enhanced Raman Spectroscopy

Huda,

Wasim,

Nawaz

et al. 2023

ACS Omega

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In the present research work, a selenium Nheterocyclic carbene (Se−NHC) complex/adduct was synthesized and characterized by using different analytical methods including FT-IR, 1 HNMR, and 13 CNMR. The antifungal activity of the Se−NHC complex against Aspergillus flavus (A. flavus) fungus was investigated with disc diffusion assay. Moreover, the biochemical changes occurring in this fungus due to exposure of different concentrations of the in-house synthesized compound are characterized by surfaceenhanced Raman spectroscopy (SERS) and are illustrated in the form of SERS spectral peaks. SERS analysis yields valuable information about the probable mechanisms responsible for the antifungal effects of the Se−NHC complex. As demonstrated by the SERS spectra, this Se−NHC complex caused denaturation and conformational changes in the proteins as well as decomposition of the fungal cell membrane. The SERS spectra were analyzed using two chemometric tools such as principal component analysis (PCA) and partial least-squares discriminant analysis (PLS-DA). The fungal samples' SERS spectra were differentiated using PCA, while various groups of spectra were discriminated with ultrahigh sensitivity (98%), high specificity (99.7%), accuracy (100%), and area under the receiver operating characteristic curve (87%) using PLS-DA.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis, Characterization, and Evaluation of Antifungal Activity of 1-Butyl-3-hexyl-1H-imidazol-2(3H)-selenone by Surface-Enhanced Raman Spectroscopy

Huda,

Wasim,

Nawaz

et al. 2023

ACS Omega

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“…Synthesis of imidazolium salt (1-isopentyl-3-pentyl-2,3-dihydro-1 H -imidazole, bromide salt) was completed in two separate phases according to the protocol of …”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of imidazolium salt (1-isopentyl-3-pentyl-2,3-dihydro-1H-imidazole, bromide salt) was completed in two separate phases according to the protocol of. 56 N-Alkylation of imidazole was initially accomplished via a simple reaction of alkyl imidazole in basic media. The following stage produces imidazolium salt by alkylating imidazole at its second nitrogen (N2) by reflux in 1,4-dioxane, as elaborated in Scheme 1.…”

Section: Methodsmentioning

confidence: 99%

Surface-Enhanced Raman Scattering (SERS) in Combination with PCA and PLS-DA for the Evaluation of Antibacterial Activity of 1-Isopentyl-3-pentyl-1H-imidazole-3-ium Bromide against Bacillus subtilis

Tahir,

Kamran,

Majeed

et al. 2024

ACS Omega

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In the current study, surface-enhanced Raman scattering (SERS) was performed to evaluate the antibacterial activity of lab-synthesized drug (1-isopentyl-3-pentyl-1H-imidazole-3-ium bromide salt) and commercial drug tinidazole againstBacillus subtilis. The changes in SERS spectral features were studied for unexposed bacillus and exposed one with various dosages of drug synthesized in the lab (1-isopentyl-3-pentyl-1H-imidazole-3-ium bromide salt), and SERS bands were assigned associated with the drug-induced biochemical alterations in bacteria. Multivariate data analysis tools including principal component analysis (PCA) and partial least-squares discriminant analysis (PLS-DA) have been utilized to analyze the antibacterial activity of the imidazole derivative (lab drug). PCA was employed in differentiating all the SERS spectral data sets associated with the various doses of the labsynthesized drug. There is clear discrimination among the spectral data sets of a bacterial strain treated with different concentrations of the drug, which are analyzed by PLS-DA with 86% area under the curve in receiver operating curve (ROC), 99% sensitivity, 100% accuracy, and 98% specificity. Various dominant spectral features are observed with a gradual increase in the different concentrations of the applied drug including 715, 850, 1002, 1132, 1237, 1396, 1416, and 1453 cm −1 , which indicate the possible biochemical changes caused in bacteria during the antibacterial activity of the lab-synthesized drug. Overall, the findings show that imidazole and imidazolium compounds generated from tinidazole with various alkyl lengths in the amide substitution can be effective antibacterial agents with low cytotoxicity in humans, and these results indicate the efficiency of SERS in pharmaceuticals and biomedical applications.

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Biological potential of vinyl/allyl substituted imidazole-based N-heterocyclic carbene adducts: synthesis, spectral and X-ray crystallographic structural characteristics

Kamal,

Ibrahim,

Al-Rawi

et al. 2023

Chem. Pap.

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O-Halogen-substituted arene linked selenium-N-heterocyclic carbene compounds induce significant cytotoxicity: Crystal structures and molecular docking studies

Cited by 9 publications

References 67 publications

Synthesis, Characterization, and Evaluation of Antifungal Activity of 1-Butyl-3-hexyl-1H-imidazol-2(3H)-selenone by Surface-Enhanced Raman Spectroscopy

Synthesis, Characterization, and Evaluation of Antifungal Activity of 1-Butyl-3-hexyl-1H-imidazol-2(3H)-selenone by Surface-Enhanced Raman Spectroscopy

Surface-Enhanced Raman Scattering (SERS) in Combination with PCA and PLS-DA for the Evaluation of Antibacterial Activity of 1-Isopentyl-3-pentyl-1H-imidazole-3-ium Bromide against Bacillus subtilis

Biological potential of vinyl/allyl substituted imidazole-based N-heterocyclic carbene adducts: synthesis, spectral and X-ray crystallographic structural characteristics

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