One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds

Shaaban, Saad; El‐Lateef, Hany M. Abd; Khalaf, Mai M.; Gouda, Mohamed; Youssef, Ibrahim

doi:10.3390/polym14112208

Cited by 12 publications

(22 citation statements)

References 92 publications

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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%

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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Section: Resultsmentioning

confidence: 99%

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

2022

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“…Organoselenium (OSe) hybrids have recently gained much attention as a result of their diverse applications, particularly in material and medicinal chemistry 16 , 17 . The selenium (Se) unprecedented characteristics and redox properties secured the potential biochemical and industrial applications of OSe agents 18 .…”

Section: Introductionmentioning

confidence: 99%

Corrosion mitigation characteristics of some novel organoselenium thiourea derivatives for acid pickling of C1018 steel via experimental and theoretical study

El‐Lateef

Khalaf

Gouda

et al. 2023

Sci Rep

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Two organoselenium thiourea derivatives, 1-(4-(methylselanyl)phenyl)-3-phenylthiourea (DS036) and 1-(4-(benzylselanyl)phenyl)-3-phenylthiourea (DS038) were produced and categorized using FTIR and NMR (1H and 13C). The effectiveness of the above two compounds as C-steel corrosion inhibitors in molar HCl was evaluated using the potentiodynamic polarization (PD) and electrochemical impedance spectroscopy (EIS) techniques. PD findings indicate that DS036 and DS038 have mixed-type features. EIS results show that growing their dose not only changes the polarization resistance of C-steel from 18.53 to 363.64 and 463.15 Ω cm2 but also alters the double layer capacitance from 710.9 to 49.7 and 20.5 μF cm−2 in the occurrence of 1.0 mM of DS036 and DS038, respectively. At a 1.0 mM dose, the organoselenium thiourea derivatives displayed the highest inhibition efficiency of 96.65% and 98.54%. The inhibitory molecule adsorption proceeded along the Langmuir isotherm on the steel substrate. The adsorption-free energy of the adsorption process was also intended and indicated a combined chemical and physical adsorption on the C-steel interface. FE-SEM studies support the adsorption and protective abilities of the OSe-based molecule inhibitor systems. In Silico calculations (DFT and MC simulations) explored the attraction between the studied organoselenium thiourea derivatives and corrosive solution anions on a Fe (110) surface. The obtained results show that these compounds can make a suitable preventing surface and control the corrosion rate.

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“…Selenium (Se), a non-metal trace element, belongs to the chalcogen family and has an essential role in the immune system protection and the growth suppression of different tumors [ 1 , 2 , 3 ]. Unsurprisingly, Se deficiency is implicated with the development of various diseases such as autoimmune disorders [ 4 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

“…The last decade has witnessed an increasing concern in the synthesis of OSe compounds due to their role in the modulation of oxidative stress related diseases [ 3 , 11 ]. Within this context, OSe compounds might act as antioxidants or pro-oxidants, depending on their environment [ 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

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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One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds

Cited by 12 publications

References 92 publications

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

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

Corrosion mitigation characteristics of some novel organoselenium thiourea derivatives for acid pickling of C1018 steel via experimental and theoretical study

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

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