Evaluation of novel multifunctional organoselenium compounds as potential cholinesterase inhibitors against Alzheimer’s disease

Refaay, Dina A.; Ahmed, Dalia M.; Mowafy, Amr M.; Shaaban, Saad

doi:10.1007/s00044-022-02879-x

Cited by 16 publications

(20 citation statements)

References 61 publications

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“…Recently, OSe compounds gained much attention as possible drug candidates due to their various pharmacological properties [ 6 , 10 , 33 , 34 ]. Our group has reported several OSe candidates with potential anticancer, antimicrobial, and antioxidant activities [ 10 , 23 , 43 , 44 , 45 ]. Therefore, the anticancer attributes of the newly prepared OSe compounds were estimated using the MTT assay against MCF-7 and HepG2 and compared with their respective cytotoxicity in WI-38 primary cells.…”

Section: Resultsmentioning

confidence: 99%

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Novel Organoselenium Redox Modulators with Potential Anticancer, Antimicrobial, and Antioxidant Activities

2022

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Novel organic selenides were developed in good yields (up to 91%), and their chemical entities were confirmed by IR, MS, and 1H- and 13C-NMR spectroscopy. Their anticancer and antimicrobial properties were estimated against different human cancer (MCF-7 and HepG2) and healthy (WI-38) cell lines, as well as several microbial strains (Escherichia coli, Staphylococcus aureus, and Candida albicans). Furthermore, the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) bioassays were used for the estimation of the antioxidant activities. Generally, cytotoxicity results were more pronounced against the MCF-7 cells than HepG2 cells. Compound 2-((4-((1-hydroxynaphthalen-2-yl)diazenyl)phenyl)selanyl)-N-phenylacetamide (9) was the most cytotoxic, even more than doxorubicin, with IC50 of 3.27 ± 0.2 against 4.17 ± 0.2 µM and twelve-times more selective, respectively. Interestingly, compound 9 exhibited similar antimicrobial potential to reference antibacterial and antifungal drugs and comparable antioxidant activity to vitamin C. These results point to selective cytotoxicity against MCF-7 cells and interesting antimicrobial and antioxidant properties of some newly synthesized organic selenides, which in turn needs further in vitro studies.

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Section: Resultsmentioning

confidence: 99%

Section: Evaluation Of the Cytotoxicity Of Ose Compoundsmentioning

confidence: 99%

Novel Organoselenium Redox Modulators with Potential Anticancer, Antimicrobial, and Antioxidant Activities

2022

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“…Recently, OSe 2 compounds have drawn much attention in pharmaceutical chemistry owing to their broad medicinal applications (e.g., antioxidant, chemopreventive, and anticancer activities) [ 22 , 23 , 24 , 25 ]. Unluckily, the synthesis of OSe 2 compounds is limited by using toxic, expensive, and air-sensitive reagents (e.g., potassium selenocyanate) and commercially available selenium precursors.…”

Section: Resultsmentioning

confidence: 99%

“…OSe hybrids have recently gained much interest owing to their unprecedented cytoprotective and antioxidant activities [ 1 , 28 , 29 , 30 ]. We recently reported different OSe compounds with interesting antimicrobial, anticancer, and antioxidant activities [ 14 , 23 , 24 , 31 , 32 ]. We reported different tetrazole-based diselenides within this context with AChE inhibition and glutathione peroxidase-like activities [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

“…We recently reported different OSe compounds with interesting antimicrobial, anticancer, and antioxidant activities [ 14 , 23 , 24 , 31 , 32 ]. We reported different tetrazole-based diselenides within this context with AChE inhibition and glutathione peroxidase-like activities [ 23 ]. Furthermore, we also developed diselenide-based urea with promising anti-HepG2 and apoptosis-induction properties [ 14 ].…”

Section: Resultsmentioning

confidence: 99%

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

2022

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

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Telescoping Synthesis of 4‐Organyl‐5‐(organylselanyl)thiazol‐2‐amines Promoted by Ultrasound

Hellwig,

Bartz,

Santos

et al. 2024

ChemPlusChem

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In this work, we describe the synthesis of new 4‐organyl‐5‐(organylselanyl)thiazol‐2‐amine hybrids through a one‐pot two‐step protocol. The transition metal‐free method involves the use of ultrasound as an alternative energy source and Oxone® as oxidant. To obtain the products, a telescoping approach was used, in which 4‐organylthiazol‐2‐amines were firstly prepared under ultrasonic irradiation, followed by the addition of diorganyl diselenides and Oxone®. Thus, 16 compounds were prepared, with yields ranging from 61 % to 98 %, using 2‐bromoacetophenone derivatives and diorganyl diselenides as easily available starting materials.

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Evaluation of novel multifunctional organoselenium compounds as potential cholinesterase inhibitors against Alzheimer’s disease

Cited by 16 publications

References 61 publications

Novel Organoselenium Redox Modulators with Potential Anticancer, Antimicrobial, and Antioxidant Activities

Novel Organoselenium Redox Modulators with Potential Anticancer, Antimicrobial, and Antioxidant Activities

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

Telescoping Synthesis of 4‐Organyl‐5‐(organylselanyl)thiazol‐2‐amines Promoted by Ultrasound

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