Repurposed organoselenium tethered amidic acids as apoptosis inducers in melanoma cancer via P53, BAX, caspases-3, 6, 8, 9, BCL-2, MMP2, and MMP9 modulations

RSC Advances, Journal Year: 2024, Volume and Issue: 14(26), P. 18576 - 18587

Published: Jan. 1, 2024

Repurposed organoselenium tethered amidic acids as apoptosis inducers in melanoma.

Language: Английский

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Innovative Multitarget Organoselenium Hybrids With Apoptotic and Anti‐Inflammatory Properties Acting as JAK1/STAT3 Suppressors

Drug Development Research, Journal Year: 2025, Volume and Issue: 86(2)

Published: March 18, 2025

ABSTRACT Herein, we report the design, synthesis, and characterization of novel organoselenium (OSe) hybrids ( 5 – 19 ) via modifications lead, N ‐(4‐selaneylphenyl)‐2‐selaneylacetamide. The OSe‐based thiazol 9 showed highest growth inhibition % (GI%) 64.72% relative to positive reference doxorubicin (DOX), with a GI% 79.5%. Furthermore, OSe derivatives low values compared normal cell lines employed, demonstrating their selectivity. tethered ‐chloroacetamide Schiff base cytotoxic effect an IC 50 (25.07 11.61 µM), respectively, against A549 tumor line (34.22 20.12 HELA cancer line. Enzyme‐linked immunosorbent assay study JAK1 STAT3 inhibitory potentials compounds in cells both promising activities 25.07 µM, respectively. Protein expression analysis on upregulation P53, BAX, Caspases 3, 6, 8, as apoptotic proteins. However, candidates expressed downregulation antiapoptotic proteins (BCL2, MMP2, MMP9). Moreover, described examined inflammatory proteins: COX2, IL‐6, IL‐1β. In addition, compound potential cycle arrest at G0, S, G2‐M layers, increase cellular levels. Finally, molecular docking studies most toward target receptors, binding scores interactions exceeding that cocrystallized inhibitor JAK1.

Language: Английский

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Multifunctional Bioactivity of the [Cu(en)(Im)2](ClO4)2 Complex: Antimicrobial, Antibiofilm, and Anticancer Effects

The Microbe, Journal Year: 2025, Volume and Issue: unknown, P. 100307 - 100307

Published: March 1, 2025

Language: Английский

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Synthesis, Characterization, DFT and Molecular Docking Analysis of N-phenyl-2-((4-(3-phenylthioureido)phenyl)selanyl)acetamide

Oriental Journal Of Chemistry, Journal Year: 2025, Volume and Issue: 41(2)

Published: April 28, 2025

In this study, we disclose the synthesis of a new organoselenium (OSe) candidate, N-phenyl-2-((4-(3-phenylthioureido)phenyl)selanyl)acetamide (5), achieved in three synthetic steps starting from commercially available chemical, aniline. The chemical structure target OSe compound 5 was characterised using NMR, IR, and mass spectrometry. DFT calculations were performed. results reveal that 1 demonstrates lowest HOMO energy (-5.03 eV) most significant gap (3.62 eV), indicating high stability low reactivity. contrast, 2 shows highest (-3.62 smallest (1.31 confirming its reactivity stability. HB168 3 demonstrate intermediate properties with moderate Dipole Moment analysis highlights strong polarity (6.47 Debye) weak S2 (0.27 Debye). Additionally, displays electronegativity (3.22 electrophilicity index (2.86 further supporting Conversely, exhibits (6.71 electrophilic character. prepared docked against bacterial strain protein targets: Escherichia coli (ID: 5L3J) as gram-negative bacteria, whereas Bacillus Subtilis 7S3L) Staphylococcus aureus 3BL6) chosen gram-positive bacteria. Also, molecular docking performed drugs reference drug Ampicillin wide spectrum antibiotic Ebselen, Diphenyl diselenide Selenium containing drugs.

Language: Английский

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Exploring ADMET properties and the anticancer potential mechanism of a new organoselenium compound using network pharmacology and in vitro study

Ciência e Natura, Journal Year: 2025, Volume and Issue: 47, P. e88474 - e88474

Published: April 11, 2025

Complex genetic mutations and malignant transformations in cancers have plagued the world. Modified variants of nucleoside analogs proven to be allies hope promising new treatments anticancer therapy. However, it sometimes faces difficulties related its low bioavailability resistance mechanisms. In this study, investigative initial silico vitro analyses were performed on a organoselenium compound, 5-Se-(phenyl)-3-(ferulic-amido)-thymidine (AFAT-Se). Different platforms used explore ADMET properties possible pharmacological toxicological effects AFAT-Se, potential was assessed by studies. AFAT-Se complied with Lipinski's rules, exhibiting favorable pharmacokinetic properties, interaction common drug metabolic enzymes, toxicities that require further cytotoxicity toward HT-29 tumor cell line, as evidence an antineoplastic agent. Therefore, critical molecular targets identified cancer-related pathways; thus, is candidate for studies pathology.

Language: Английский

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Anticancer, Antimicrobial, and Antioxidant Activities of Organodiselenide-Tethered Methyl Anthranilates

Biomolecules, Journal Year: 2022, Volume and Issue: 12(12), P. 1765 - 1765

Published: Nov. 27, 2022

Novel methyl anthranilate-based organodiselenide hybrids were synthesized, and their chemical structures confirmed by state-of-the-art spectroscopic techniques. Their antimicrobial properties assessed against Staphylococcus aureus, Escherichia coli, Candida albicans microbial strains. Moreover, the antitumor potential was estimated liver breast carcinomas, as well primary fibroblast cell lines. The aureus strains more sensitive than coli toward OSe compounds. Interestingly, 2-amino-5-(methylselanyl) benzoate (14) showed similar antifungal activity to standard drug clotrimazole (IA% = 100%) manifested promising antibacterial E. 91.3%) S. 90.5%). Furthermore, minimum inhibitory concentration experiments of 14, which in turn comparable ampicillin drugs. anticancer pronounced HepG2 cells. 14 most cytotoxic (IC50 3.57 ± 0.1 µM), even Adriamycin 4.50 0.2 with therapeutic index (TI) 17 proposing its selectivity safety. Additionally, compounds dimethyl 5,5′-diselanediylbis(2-aminobenzoate) (5) exhibited antioxidants 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) 2,2-diphenyl-1-picrylhydrazyl (DPPH) vitro assays 96%, 92%, 91%, 86% radical scavenging activities compared 95% vitamin C DPPH ABTS assays, respectively. These results point antimicrobial, anticancer, antioxidant 5 warrant further studies.

Language: Английский

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Design, Synthesis, and Biological Evaluation of Novel Hydroxamic Acid-Based Organoselenium Hybrids

Pharmaceuticals, Journal Year: 2023, Volume and Issue: 16(3), P. 367 - 367

Published: Feb. 28, 2023

We report the design and synthesis of novel hydroxamic acid-tethered organoselenium (OSe) hybrids. Their antimicrobial anticancer activities were assessed against different microbes (e.g., Candida albicans (C. albicans), Escherichia coli (E. coli), Staphylococcus aureus (S. aureus)), as well liver breast carcinomas. OSe hybrid 8 showed promising activity, with IC50 = 7.57 ± 0.5 µM HepG2 9.86 0.7 MCF-7 cells. Additionally, compounds 15 exhibited activities, particularly C. (IA% 91.7 83.3) S. 90.5 71.4). The minimum inhibitory concentration (MIC) assay confirmed potential activity compound 8. 16 displayed good antioxidant compared to vitamin C in 2,2-diphenyl-1-picrylhydrazyl (DPPH) 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assays. These results indicate that acid-based hybrids have biological such anticancer, antimicrobial, properties, especially 8, 13, 15, 16, which warrant further studies.

Language: Английский

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Glutathione Peroxidase-like Antioxidant Activity of 1,3-Benzoselenazoles: Synthesis and In Silico Molecular Docking Studies as Pancreatic Lipase Inhibitors

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 16934 - 16948

Published: Nov. 27, 2023

The synthesis of 1,3-benzoselenazoles was achieved by the reaction corresponding bis[3-amino-N-(p-tolyl)benzamide-2-yl] diselenide, bis[3-amino-N-(4-methoxyphenyl)benzamide-2-yl] and bis[3-amino-N-(4-(dimethylamino)phenyl) benzamide-2-yl] diselenide with aryl aldehydes. continued to exist as planar molecules due presence secondary Se···O interactions revealed single-crystal X-ray analysis. in confirmed using natural bond orbital (NBO) atoms (AIM) calculations. Nucleus-independent chemical shift (NICS) values suggested aromatic character a five-membered benzoselenazole heterocyclic ring. glutathione peroxidase (GPx)-like antioxidant activity all assessed thiophenol assay, exhibiting greater than Ph2Se2 used reference. most active catalyst carrying strong electron-donating group (–NMe2) at ortho-position ring further investigated different concentrations thiophenol, H2O2, for determining their catalytic parameters. Moreover, potential applications against pancreatic lipase (PL) have been identified silico between sites 1LPB protein evaluated molecular docking study.

Language: Английский

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Organoselenium compounds as antioxidants

ARKIVOC, Journal Year: 2022, Volume and Issue: 2023(5), P. 69 - 92

Published: Dec. 1, 2022

Reactive oxygen species (ROS) are responsible for many of civilization's diseases, including cancer, diabetes, and Alzheimer's disease, decomposition products in the food industry, deterioration physicochemical properties polymers nanomaterials.In recent years, several organoselenium compounds have been synthesized used as peroxide scavengers, which source antioxidant substances.This review aims to collect divide obtained last twelve years with activity, can prove helpful a) medicine supplements preventing diseases caused by oxidative stress, b) additives oxidation, or c) materials industry Se-containing nanoparticles polymers.In addition, most common methods determining GPx-like activity presented.

Language: Английский

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Organoselenocyanates Tethered Methyl Anthranilate Hybrids with Promising Anticancer, Antimicrobial, and Antioxidant Activities

Inorganics, Journal Year: 2022, Volume and Issue: 10(12), P. 246 - 246

Published: Dec. 7, 2022

Novel methyl anthranilate-based organoselenocyanate hybrids were developed, and their structures confirmed by the state-of-the-art spectroscopic techniques. Their antimicrobial potency was estimated against various microbial strains (e.g., Candida albicans, Escherichia coli, Staphylococcus aureus). The S. aureus C. albicans more sensitive than E. coli toward organoselenocyanates. Interestingly, azoic derivatives 4 9, ester 6, phenoxy acetamide 15 showed promising activity. Moreover, antitumor potential liver breast carcinomas, as well primary fibroblasts. anticancer properties pronounced in HepG2 cells. organoselenocyanates 4, 10, interesting anti-HepG2 cytotoxic patterns. Additionally, 3, 10 exhibited antioxidant activities 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid 2,2-diphenyl-1-picrylhydrazyl vitro assays compared to ascorbic acid. These data point antimicrobial, anticancer, of warrant further studies.

Language: Английский

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