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An efficient copper catalyzed fluoroalkyl‐selenization reaction of olefins has been developed, providing 1,2‐difluoroarylselenides in moderate to excellent yields. The readily available ethyl bromodifluoroacetate and diphenyl diselenide (Ph2Se2) have been employed as efficient radical precursor and selenization reagents to react with olefins. The reaction features a broad substrate scope, including substituted alkenes with various functional groups. [ABSTRACT FROM AUTHOR]

This article, published in the journal Synlett, discusses a study on the development of a rhodium-catalyzed direct vinylene annulation reaction. The researchers focused on using vinyl selenones as vinylene-transfer reagents and successfully demonstrated a three-component reaction to construct isoquinolone scaffolds. The article includes a table showing the optimization of reaction conditions. The study also explored the scope and limitations of the reaction system, proposing a mechanism for the coupling reaction and concluding that further optimization is needed. [Extracted from the article]

Ammonium persulfate is a mild oxidant capable of oxidizing the selenium-selenium bond through thermal activation or under drastic acid catalysis. In this paper we highlight that this reaction can be activated photochemically, starting from diphenyl diselenide in the absence of any organic or and/or metallic photocatalyst or additive. The protocol was applied to a well-known panel of selenoalkoxylation reactions and the obtained results clearly indicate the involvement of an electrophilic selenium reagent. [ABSTRACT FROM AUTHOR]

ABSTRACT The aim of this study was to evaluate the effects of diphenyl diselenide (PhSe) supplementation during the transition period on the metabolism, immunity, oxidative status, and milk production of postpartum dairy cows. Twenty-seven Holstein females were divided into groups: (PhSe) (DDG), which received 3 μmol/kg of (PhSe)2 in 4 mL of dimethyl sulfoxide (DMSO) subcutaneously, DMSO (DMSOG), and NaCl (NACLG) which received 4 mL of DMSO and 0.9% NaCl. Evaluation of body condition score (BCS), weighing and administrations were performed at 42, 28, and 14 days prepartum, and on the day of calving (0). On days 0, 7, 14, 21, and 35 postpartum, BCS was evaluated, and blood were collected. Colostrum was obtained from the first postpartum milking. Production was measured, and milk was collected on days 7, 14, 21, and 35 postpartum. DDG showed higher values of total protein (TP) and globulins (GLOB) 7 days postpartum and increase from day 0 to days 21 and 35. DDG immunoglobulin G (IgG) was higher on days 21 and 35, and increased between days 7 and 21. In postpartum TP, GLOB and IgG are physiologically reduced, therefore, the results indicate that supplementation of transition females with (PhSe) stimulated postpartum humoral immunity.

Neurotoxicity associated with chemotherapy is a debilitating side effect of cancer management in humans which reportedly involves inflammatory and oxidative stress responses. Diphenyl diselenide (DPDS) is an organoselenium compound which exhibits its anti-tumoral, anti-oxidant, anti-inflammatory and anti-mutagenic effects. Nevertheless, its possible effect on chemotherapy-induced neurotoxicity is not known. Using rat model, we probed the behavioral and biochemical effects accompanying administration of antineoplastic agent doxorubicin (7.5 mg/kg) and DPDS (5 and 10 mg/kg). Anxiogenic-like behavior, motor and locomotor insufficiencies associated with doxorubicin were considerably abated by both DPDS doses with concomitant enhancement in exploratory behavior as demonstrated by reduced heat maps intensity and enhanced track plot densities. Moreover, with exception of cerebral glutathione (GSH) level, superoxide dismutase (SOD) and glutathione peroxidase (GPx) activities, biochemical data demonstrated reversal of doxorubicin-mediated decline in cerebral and cerebellar antioxidant status indices and the increase in acetylcholinesterase (AChE) activity by both doses of DPDS. Also, cerebellar and cerebral lipid peroxidation, hydrogen peroxide as well as reactive oxygen and nitrogen species levels were considerably diminished in rats administered doxorubicin and DPDS. In addition, DPDS administration abated myeloperoxidase activity, tumour necrosis factor alpha and nitric oxide levels along with caspase-3 activity in doxorubicin-administered rats. Chemoprotection of doxorubicin-associated neurotoxicity by DPDS was further validated by histomorphometry and histochemical staining. Taken together, DPDS through offsetting of oxido-inflammatory stress and caspase-3 activation elicited neuroprotection in doxorubicin-treated rats. [ABSTRACT FROM AUTHOR]

A Sonogashira coupling of meta-iodocalix[4]arene with various terminal acetylenes confirmed that the meta position of calixarene is well addressable, and that both thermal and microwave protocols led to good yields of alkynylcalixarenes. Alkynes thus obtained were subjected to the ferric chloride and diphenyl diselenide-promoted electrophilic closure. It turns out that the calix[4]arenes give completely different bridging products than those described for the non-macrocyclic starting compounds. This can be demonstrated not only by the isolation of products with a six-membered ring (6-exo-dig), but mainly by the smooth formation of the 5-endo-dig cyclization, which has never been observed in the aliphatic series. An attempt at electrocyclization led to a high yield of the 1,2-diketone (oxidation of the starting alkyne), again in contrast to the reaction described for the acyclic derivatives. The structures of the unexpected products were unequivocally established by X-ray analysis and clearly demonstrate how the preorganized macrocyclic skeleton favors a completely different regioselectivity of cyclization reactions compared to common aliphatic compounds. [ABSTRACT FROM AUTHOR]

A low pKa (5.2), high polarizable volume (3.8 Å), and proneness to oxidation under ambient conditions make selenocysteine (Sec, U) a unique, natural reactive handle present in most organisms across all domains of life. Sec modification still has untapped potential for site‐selective protein modification and probing. Herein we demonstrate the use of a cyclometalated gold(III) compound, [Au(bnpy)Cl2], in the arylation of diselenides of biological significance, with a scope covering small molecule models, peptides, and proteins using a combination of multinuclear NMR (including 77Se NMR), and LC–MS. Diphenyl diselenide (Ph−Se)2 and selenocystine, (Sec)2, were used for reaction optimization. This approach allowed us to demonstrate that an excess of diselenide (Au/Se−Se) and an increasing water percentage in the reaction media enhance both the conversion and kinetics of the C−Se coupling reaction, a combination that makes the reaction biocompatible. The C−Se coupling reaction was also shown to happen for the diselenide analogue of the cyclic peptide vasopressin ((Se−Se)‐AVP), and the Bos taurus glutathione peroxidase (GPx1) enzyme in ammonium acetate (2 mM, pH=7.0). The reaction mechanism, studied by DFT revealed a redox‐based mechanism where the C−Se coupling is enabled by the reductive elimination of the cyclometalated Au(III) species into Au(I). [ABSTRACT FROM AUTHOR]

In the present study, synthesis of bis‐naphthol based organoselenium compounds has been described. The synthetic strategy involves electrophilic aromatic addition of alkyl/aryl selenium species at the electron rich center of 2,7‐dihydroxynaphthalene. The reaction with electrophilic selenylating reagents in situ generated by potassium persulphate and diselenides produced desired selenides. Synthesized compounds were studied for their glutathione peroxidase (GPx)‐like antioxidant activities using thiophenol assay. It was observed that all compounds exhibited greater GPx‐like antioxidant activity than diphenyl diselenide used as reference. Further, these GPx mimics were introduced for their antibacterial properties against biofilm formation by Bacillus subtilis and Pseudomonas aeruginosa. To support experimental details, molecular docking studies were also performed to elucidate in silico interactions between the active sites of proteins TsaA and LasR found in Bacillus subtilis and Pseudomonas aeruginosa, respectively. The minimum inhibitory concentration assay was performed for all the antioxidants against Bacillus subtilis and Pseudomonas aeruginosa. Additionally, hemolytic assay has also been carried out to check the impact on red blood cells. Cytotoxicity assessments of antioxidants have also been carried using MTT assay. [ABSTRACT FROM AUTHOR]

In this work, we have prepared some common diphenyl diselenide compounds and evaluated the solvent effect on the 77Se NMR chemical shift. Thus, 77Se NMR spectra of diphenyl diselenides containing electron-withdrawing or electron-donating groups were recorded in eight different deuterated solvents with distinct polarities. The effects of temperature and concentration were also assessed and were found to play a minor role in the precise values of 77Se chemical shift. Finally, a computational study was performed to rationalize the 77Se NMR chemical shift behavior and to highlight the limits of standard approaches. [ABSTRACT FROM AUTHOR]

Hypoxia plays a significant role in the development of various cerebral diseases, many of which are associated with the potential risk of recurrence due to mitochondrial damage. Conventional drug treatments are not always effective for hypoxia-related brain diseases, necessitating the exploration of alternative compounds. In this study, we investigated the potential of diphenyl diselenide [(PhSe)2] to ameliorate locomotor impairments and mitigate brain mitochondrial dysfunction in zebrafish subjected to hypoxia. Additionally, we explored whether these improvements could confer resistance to recurrent hypoxia. Through a screening process, an appropriate dose of (PhSe)2 was determined, and animals exposed to hypoxia received a single intraperitoneal injection of 100 mg/kg of the compound or vehicle. After 1 h from the injection, evaluations were conducted on locomotor deficits, (PhSe)2 content, mitochondrial electron transport system, and mitochondrial viability in the brain. The animals were subsequently exposed to recurrent hypoxia to assess the latency time to hypoxia symptoms. The findings revealed that (PhSe)2 effectively crossed the blood–brain barrier, attenuated locomotor deficits induced by hypoxia, and improved brain mitochondrial respiration by modulating complex III. Furthermore, it enhanced mitochondrial viability in the telencephalon, contributing to greater resistance to recurrent hypoxia. These results demonstrate the beneficial effects of (PhSe)2 on both hypoxia and recurrent hypoxia, with cerebral mitochondria being a critical target of its action. Considering the involvement of brain hypoxia in numerous pathologies, (PhSe)2 should be further tested to determine its effectiveness as a potential treatment for hypoxia-related brain diseases. [ABSTRACT FROM AUTHOR]

Simple Summary: The rearing of calves is a challenging phase in the production of dairy cattle. These animals face challenges from birth, as they require ingestion of colostral immunoglobulins for transfer of passive immunity, given that their immune systems are still immature. If there is a failure in the transfer of passive immunity, they become vulnerable to disease. This vulnerability, combined with stressors such as weaning, can predispose them to cellular oxidative stress. Similarly, to the immune system, the antioxidant defense system is also in the developmental stage, therefore, providing antioxidant substances during this phase could be a valuable option. Considering this, our team proposed to assess the impact of prepartum maternal selenium supplementation on the offspring, given its established benefits and its transfer through the placenta, colostrum, and milk. Diphenyl diselenide, an organic analog, was selected because of its anti-inflammatory and antioxidant properties. It can be administered safely subcutaneously, ensuring the correct dosage and facilitating its use at strategic times without any risk of toxicity. Maternal supplementation with diphenyl diselenide has been found to significantly increase passive immunity transfer rates in calves, as well as help establish and improve humoral immunity. This provides new insight into the immunomodulatory capabilities of this molecule. This study aimed to assess the impact of prepartum maternal diphenyl diselenide (PhSe)2 supplementation on the development, biochemical, immune, and antioxidant parameters of calves. Eighteen Holstein breed calves were used, born to females who were or were not subjected to supplementation, at 42, 28, and 14 days prior to calving. The (PhSe)2 group (DDG) was administered 3 μmol/kg of (PhSe)2 in 4 mL of dimethyl sulfoxide (DMSO), while the DMSO and NaCl groups were administered 4 mL of DMSO and 0.9% NaCl, subcutaneously. The calves were evaluated based on their weight, withers height, body condition score 24 h post-birth (0), as well on days 14, 28, 42, 56, 70. Blood samples were also taken to determine serum variables. Calves on the DDG showed higher average levels of total protein, albumin, and globulins on day 0, and the immunoglobulin G level was significantly higher than the other groups on days 0, 14, 56, 70. Maternal supplementation showed immunomodulatory effect on calves, evidenced by the exceptional rates of passive immunity transfer, as well as the enhancement of humoral immunity. Our research offers fresh insights into the immunomodulatory potential of (PhSe)2, making it a viable alternative in facing this challenging phase, rearing dairy calves. [ABSTRACT FROM AUTHOR]

Melasma is an acquired chronic condition characterized by hyperchromic patches in photo-exposed areas. The search for new compounds for the treatment of melasma without side effects is constant. In this context, the aim of this study was to investigate the in vitro cytotoxic and antimelanogenic effects of the trace elements Zinc (Zn) and Selenium (Se). In this study, we evaluated the effects of 30 µM hydroquinone, this concentration did not alter mitochondrial function (MTT assay), but increased the percentage of necrotic cells and levels of reactive species. Furthermore, it showed no influence on tyrosinase activity and melanin content. Unlike hydroquinone, exposure for 48 h to 100 µM Zn and 1 and 5 µM Se had no significant influence on the analysis of reactive species, as well as on the percentage of necrotic cells. Still, specifically in relation to 100 µM Zn, it decreased the melanin content. Given the above, the trace elements Zn and Se did not show toxicity at the concentrations tested and Zn showed a promising effect, however, the mechanism needs to be better explored in order to contribute to new and updated research in the fight against melasma with a perspective of therapeutic use. [ABSTRACT FROM AUTHOR]

The conjugation of active biomolecules provides insight into their bioreactivity, leading to many applications in biotechnology and materials science. Herein, we report L-selenocystine (SeC) bioconjugates of lipoic acid (universal antioxidant) and biotin (Vitamin-H). The SeC-bioconjugates, SeC-Biotin (1) and SeC-Lipoic acid (2) were synthesized using solid phase peptide synthesis (SPPS) method and were characterized by multinuclear 1D (1H, 13C, 77Se) and 2D (1H-1H COSY and 1H-13C TOCSY) NMR spectroscopy, ESI–MS spectrometry, and RP-HPLC. The GPx-like enzyme mimicking activity of the SeC-bioconjugates 1 and 2 has been investigated through the coupled reductase assay method for the catalytic reductions of hydrogen peroxide into water. A significant enhancement in GPx-like enzymatic activity was observed for both novel bioconjugates SeC-Biotin (1) and SeC-Lipoic acid (2) as compared to diphenyl diselenide (Ph2Se2), L-selenocystine (SeC), biotin, lipoic acid, and ebselen. [ABSTRACT FROM AUTHOR]

We report thermochromism in crystals of diphenyl diselenide (dpdSe) and diphenyl ditelluride (dpdTe), which is at variance with the commonly known mechanisms of thermochromism in molecular crystals. Variable temperature neutron diffraction studies indicated no conformational change, tautomerization or phase transition between 100 K and 295 K. High‐pressure crystallography studies indicated no associated piezochromism in dpdSe and dpdTe crystals. The evolution of the crystal structures and their electronic band structure with pressure and temperature reveal the contributions of intramolecular and intermolecular factors towards the origin of thermochromism—especially the intermolecular Se⋅⋅⋅Se and Te⋅⋅⋅Te chalcogen bonds and torsional modes of vibrations around the dynamic Se−Se and Te−Te bonds. Further, a co‐crystal of dpdSe with iodine (dpdSe‐I2) and an alloy crystal of dpdSe and dpdTe implied a predominantly intramolecular origin of the observed thermochromism associated with vibronic coupling. [ABSTRACT FROM AUTHOR]

Keywords: visible light; 3-methylindole; tryptamine; diphenyl diselenide; diphenyl phosphate EN visible light 3-methylindole tryptamine diphenyl diselenide diphenyl phosphate 3685 3692 8 10/19/23 20231102 NES 231102 Graph The incorporation of selenium into organic scaffolds is not only pivotal for understanding redox processes of biological system, [1] but also plays an important role in pharmaceuticals [5] wherein selenium-containing molecules serve as synthetic intermediates [6] and catalysts for the preparation of various bioactive compounds. When an additive diphenyl phosphate (DPP) was added, formation of desired C-2 Cbz-tryptamine selenide adduct was observed in good yield (entry 2). Transition-metal-catalyzed C2/C3-H activation of indole core (tryptamines) offers robust synthetic strategies to deliver functionalized cores. SP 1 sp H NMR (500 MHz, CDCl SB 3 sb ): = 8.56-8.46 (m, 1 H), 7.69 (d, I J i = 7.9 Hz, 1 H), 7.62 (d, I J i = 7.0 Hz, 1 H), 7.34 (d, I J i = 8.3 Hz, 1 H), 7.27 (s, 1 H), 7.23-7.18 (m, 5 H), 7.16 (s, 1 H), 4.76 (s, 1 H), 4.59 (dt, I J i = 11.6, 6.4 Hz, 2 H), 3.99 (q, I J i = 5.1, 3.1 Hz, 2 H), 3.86 (d, I J i = 4.0 Hz, 2 H), 3.24 (t, I J i = 7.1 Hz, 2 H), 2.32 (d, I J i = 3.6 Hz, 2 H), 2.22 (d, I J i = 4.7 Hz, 2 H), 1.96-1.91 (m, 3 H), 1.82-1.74 (m, 6 H), 1.68-1.66 (m, 2 H), 1.55-1.51 (m, 5 H), 1.30-1.24 (m, 4 H), 1.07 (dd, I J i = 14.4, 3.2 Hz, 2 H), 0.92 (s, 3 H), 0.67 (s, 3 H). [Extracted from the article]

m-Ditrifluoromethyl-diphenyl diselenide [DFDD (m-CF3-C6H4Se)2] is a disubstituted diaryl analog of diphenyl diselenide [DPDS (C6H5Se)2] in which a hydrogen atom on each aromatic ring is replaced by trifluoromethyl group (-CF3). Herein, we investigated the effect of the -CF3 group introduction on the GPx mimetic and antioxidant properties of DPDS. Animals were euthanized, brains were removed, and used for lipid peroxidation, cerebral sodium pump activity and thiols assays in vitro. Results showed that DFDD utilizes exogenous thiols [dithiol treitol (DTT), cysteine (Cys) and glutathione (GSH)] to reduce hydroperoxides. Furthermore, DFDD only protected against deoxyribose degradation in the presence of DTT. DFDD also exerted marked (p< 0.05) inhibitory effect on Fe2+or H2O2 or fenton reaction-induced lipid peroxidation in rat cerebral tissue homogenate. In addition, DFDD simultaneously (p< 0.05) inhibited pump activity and lipid peroxidation in cerebral tissue homogenate assaulted with prooxidants with proportionate depletion of thiol in the reaction system. This assay was repeated in the presence of DTT or Cys-or GSH and results revealed that enzyme's activity was not inhibited indicating that DFDD switched from enzymes's thiols to the oxidation of medium's thiols. It is rational to conclude that the introduction of -CF3 group to the aromatic rings of DFDD does not abolish its GPx mimetic and antioxidant properties and these still rely on thiols of cerebral electrogenic sodium pump. DFDD could be a suitable candidate for relative pharmacological effect and weak toxicity consequent to its possession of high electron withdrawing group. However, further research is needed in this regard.

[24] Subsequently, the groups of Cui, Xu, and Zhu developed visible-light-induced cascade (spiro)cyclizations of biaryl or indolyl ynones, alkyne-tethered cyclohexadienones, and 1,6-enynes, respectively, with diaryl diselenides under photocatalyst-free conditions. Photochemical reaction, visible light, cascade reaction, spirocyclization, spiroindolequinoline selenides, diselenides The reaction was found to be compatible with various substituted diphenyl diselenides B 2b b - B l b , but with a lower efficiency than with diphenyl diselenide ( B 2a b ), giving the corresponding products B 3ab b - B al b in moderate yields of 41-54% under the standard conditions. Keywords: photochemical reaction; visible light; cascade reaction; spirocyclization; spiroindolequinoline selenides; diselenides EN photochemical reaction visible light cascade reaction spirocyclization spiroindolequinoline selenides diselenides 2042 2046 5 10/09/23 20231024 NES 231024 Graph Organoselenides, especially selenylated annulated compounds, are highly valuable chemicals that have attracted considerable attention in medicinal chemistry, [1][2][3][4][5] materials science, [6] and organic synthesis [9] due to their unique biological activities and versatile synthetic applications. [Extracted from the article]

Luminescent diimine-Pt(IV) complexes [Pt(N^N)(Me)2(PhSe)2], (N^N = 2,2′-bipyridine (bpy, 1b), 1,10-phenanthroline (phen, 2b), and 4,4′-dimethyl-2,2′-bipyridine (Me2bpy, 3b), PhSe− = phenyl selenide were prepared and identified using multinuclear (1H, 13C{1H} and 77Se{1H}) NMR spectroscopy. The PhSe− ligands were introduced through oxidative addition of diphenyl diselenide to the non-luminescent Pt(II) precursors [Pt(N^N)(Me)2], N^N = (bpy, 1a), (phen, 2a), (Me2bpy, 3a), to give the luminescent Pt(IV) complexes 1b–3b. The UV-vis absorption spectra of 1b–3b are characterised by intense bands in the range 240–330 nm. We assigned them to transitions of essentially π−π* character with small metal and PhSe− ligand contributions with the help of TD-DFT (time-dependent density functional theory) calculations. The weak long-wavelength bands in the range 350–475 nm are of mixed ligand-to-metal charge transfer (L'MCT) (n(Se)→d(Pt)/intra-ligand charge transfer (IL'CT) (n(Se)→π*(Ph) or π(Ph)→π*(Ph))/ligand-to-ligand' charge transfer (LL'CT) (L = N^N, L' = PhSe−, M = Pt and n = lone pair) character. The Pt(IV) complexes showed broad emission bands in the solid state at 298 and 77 K, peaking at 560–595 nm with a blue shift upon cooling. Structured emission bands were obtained in the range 450–600 nm, with the maxima depending on the N^N ligands and the solvent polarity (CH2Cl2 vs. dimethyl sulfoxide (DMSO) and aqueous tris(hydroxymethyl)aminomethane hydrochloride (tris-HCl) buffer). The emissions originate from essentially ligand-centred triplet states (3LC) with mixed IL'CT/L'MCT contributions as concluded from the DFT calculation. Such dominating PhSe contributions to the emissive states are unprecedented in the world of luminescent diimine-Pt(IV) complexes. [ABSTRACT FROM AUTHOR]

A Sonogashira coupling of meta-iodocalix[4]arene with various terminal acetylenes confirmed that the meta position of calixarene is well addressable, and that both thermal and microwave protocols led to good yields of alkynylcalixarenes. Alkynes thus obtained were subjected to the ferric chloride and diphenyl diselenide-promoted electrophilic closure. It turns out that the calix[4]arenes give completely different bridging products than those described for the non-macrocyclic starting compounds. This can be demonstrated not only by the isolation of products with a six-membered ring (6-exo-dig), but mainly by the smooth formation of the 5-endo-dig cyclization, which has never been observed in the aliphatic series. An attempt at electrocyclization led to a high yield of the 1,2-diketone (oxidation of the starting alkyne), again in contrast to the reaction described for the acyclic derivatives. The structures of the unexpected products were unequivocally established by X-ray analysis and clearly demonstrate how the preorganized macrocyclic skeleton favors a completely different regioselectivity of cyclization reactions compared to common aliphatic compounds.

The novel severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) was the causative agent of the COVID-19 pandemic, a global public health problem. Despite the numerous studies for drug repurposing, there are only two FDA-approved antiviral agents (Remdesivir and Nirmatrelvir) for non-hospitalized patients with mild-to-moderate COVID-19 symptoms. Consequently, it is pivotal to search for new molecules with anti-SARS-CoV-2 activity and to study their effects in the human immune system. Ebselen (Eb) is an organoselenium compound that is safe for humans and has antioxidant, anti-inflammatory, and antimicrobial properties. Diphenyl diselenide ((PhSe)2) shares several pharmacological properties with Eb and is of low toxicity to mammals. Herein, we investigated Eb and (PhSe)2 anti-SARS-CoV-2 activity in a human pneumocytes cell model (Calu-3) and analyzed their toxic effects on human peripheral blood mononuclear cells (PBMCs). Both compounds significantly inhibited the SARS-CoV-2 replication in Calu-3 cells. The EC50 values for Eb and (PhSe)2 after 24 h post-infection (hpi) were 3.8 µM and 3.9 µM, respectively, and after 48 hpi were 2.6 µM and 3.4 µM. These concentrations are safe for non-infected cells, since the CC50 values found for Eb and (PhSe)2 on Calu-3 were greater than 200 µM. Importantly, the concentration rates tested on viral replication were not toxic to human PBMCs. Therefore, our findings reinforce the efficacy of Eb and demonstrate (PhSe)2 as a new candidate to be tested in future trials against SARS-CoV-2 infection/inflammation conditions. [ABSTRACT FROM AUTHOR]

The selenium element is essential to some life forms and its biological-chemistry function is mainly performed by the selenol/selenolate moiety (–SeH/–Se–) in a few selenoproteins. Many synthetic organoselenium compounds (OSeCs) have demonstrated important therapeutic applications, with the Ebselen and diphenyl diselenide being the most studied OSeCs. They could act as "hidden selenol" molecules, where the –SeH/–Se– are responsible for the reduction of dangerous peroxides and the protection against the neurotoxic methylmercury. However, their actual mechanisms of action at atomic/molecular level are still elusive. The main conundrum about OSeCs is how they can have quite different structures and similar in vivo action and at the same time modulate quite distinct physiological functions? The question is a hard one because we know little about the metabolism of OSeCs, the in vivo studies are always typically phenomenological, OSeCs have low selectivity and non-specific interactions with thiol-containing proteins. The use of in silico and in vitro models, followed by new analytical methodologies, will give important answers about the metabolism, reactivity, and specificity of OSeCs with specific biological targets, and a real advancement in the subfield of "pharmacological applications" of OSeCs. [ABSTRACT FROM AUTHOR]

Solubilization of diphenyl diselenide (DPDS) was studied in CTAB, OPE-10 and SDS surfactant solutions at 298 K. Solubility of DPDS increases with increase in the surfactant concentration due to its solubilization in micelles. UV-Vis, H1 NMR and FT-IR spectroscopy was used to study the interaction, location of diphenyl diselenide in the micelle. The change in free energy for solubilization of DPDS in micellar media confirmed the favorable solubilizations in SDS, OPE-10 and CTAB solutions. The DPDS solubility was higher in OPE-10 and CTAB compared to SDS surfactant aqueous solutions. [ABSTRACT FROM AUTHOR]

Selenium-promoted oxidations enable a broad range of valuable oxidative functional group interconversions. Anilines are oxidized with hydrogen peroxide in water in the presence of selenium catalysts. The selenium catalyst determines the nature of the oxidation product; whereas nitroarenes are obtained employing diphenyl diselenide or benzeneseleninic acid, azoxyarenes are formed using selenium dioxide or sodium seleninate. The reaction mechanism relies on the reactivity of Se(IV) active oxidants, while Se(VI) species have been demonstrated not to be involved in. [ABSTRACT FROM AUTHOR]

Triple-negative breast cancer (TNBC) is an aggressive, fast-growing tumor that is more likely to spread to distant organs. Among women diagnosed with breast cancer, the prevalence of TNBC is 20%, and treatment is currently limited to chemotherapy. Selenium (Se), an essential micronutrient, has been explored as an antiproliferative agent. Therefore, this study aimed to evaluate the effects of exposure to organic (selenomethionine, ebselen, and diphenyl diselenide) and inorganic (sodium selenate and sodium selenite) Se molecules in different breast cell lines. The compounds were tested at 1, 10, 50, and 100 μM for 48 h in the non-tumor breast cell line (MCF-10A) and TNBC derivatives cell lines (BT-549 and MDA-MB-231). The effects of Se on cell viability, apoptotic and necrotic processes, colony formation, and cell migration were analyzed. Exposure to selenomethionine and selenate did not alter the evaluated parameters. However, selenomethionine had the highest selectivity index (SI). The exposure to the highest doses of selenite, ebselen, and diphenyl diselenide resulted in antiproliferative and antimetastatic effects. Selenite had a high SI to the BT cell line; however, the SI of ebselen and diphenyl diselenide was low in both tumoral cell lines. In conclusion, the Se compounds had different effects on the breast cell lines, and additional tests are needed to reveal the antiproliferative effects of Se compounds. [ABSTRACT FROM AUTHOR]

A white light/iodosuccinimide (NIS)‐promoted three component reaction of alkenes, N‐sulfonylhydrazones, and diorganyl diselenides for synthesis of organylselenylethyl sulfonylhydrazones under air is disclosed. This intermolecular aminoselenylation of alkenes using N‐tosylhydrazones as nitrogen source was performed under mild conditions and well tolerated for common groups. In addition, heteroaryl and aliphatic diselenides also gave the target compounds. Gram‐scale reaction also carried out smoothly. This protocol has a wide range of substrates and affords moderate to high yields and excellent regioselectivities. The photoactive intermediates from the interaction between NIS and diphenyl diselenide was detected by UV‐visible absorption spectra, which matches the wavelength of the applied white LED. A reasonable mechanism was proposed based on UV‐visible light experiments and control experiments. [ABSTRACT FROM AUTHOR]

Considerable efforts have been devoted to Li-S batteries, typically the soluble polysulfides shuttling effect. As a typical transition metal sulfide, MoS2 is a magic bullet for addressing the issues of Li-S batteries, drawing increasing attention. In this study, we introduce amorphous MoS3 as analogous sulfur cathode material and elucidate the dynamic phase evolution in the electrochemical reaction. The metallic 1T phase incorporated 2H phase MoS2 with sulfur vacancies (SVs-1T/2H-MoS2) decomposed from amorphous MoS3 achieves refined mixing with the “newborn” sulfur at the molecular level and supplies continuous conduction pathways and controllable physical confinement. Meanwhile, the in situ-generated SVs-1T/2H-MoS2 allows lithium intercalation in advance at high discharge voltage (≥1.8 V) and enables fast electron transfer. Moreover, aiming at the unbonded sulfur, diphenyl diselenide (PDSe), as a model redox mediator is applied, which can covalently bond sulfur atoms to form conversion-type organoselenosulfides, changing the original redox pathway of “newborn” sulfur in MoS3, and suppressing the polysulfides shuttling effect. It also significantly lowers the activation energy and thus accelerates the sulfur reduction kinetics. Thus, the in situ-formed intercalation–conversion hybrid electrode of SVs-1T/2H-MoS2 and organoselenosulfides realizes enhanced rate capability and superior cycling stability. This work provides a novel concept for designing high-energy–density electrode materials. [ABSTRACT FROM AUTHOR]

This study aimed to assess the impact of prepartum maternal diphenyl diselenide (PhSe)2 supplementation on the development, biochemical, immune, and antioxidant parameters of calves. Eighteen Holstein breed calves were used, born to females who were or were not subjected to supplementation, at 42, 28, and 14 days prior to calving. The (PhSe)2 group (DDG) was administered 3 μmol/kg of (PhSe)2 in 4 mL of dimethyl sulfoxide (DMSO), while the DMSO and NaCl groups were administered 4 mL of DMSO and 0.9% NaCl, subcutaneously. The calves were evaluated based on their weight, withers height, body condition score 24 h post-birth (0), as well on days 14, 28, 42, 56, 70. Blood samples were also taken to determine serum variables. Calves on the DDG showed higher average levels of total protein, albumin, and globulins on day 0, and the immunoglobulin G level was significantly higher than the other groups on days 0, 14, 56, 70. Maternal supplementation showed immunomodulatory effect on calves, evidenced by the exceptional rates of passive immunity transfer, as well as the enhancement of humoral immunity. Our research offers fresh insights into the immunomodulatory potential of (PhSe)2, making it a viable alternative in facing this challenging phase, rearing dairy calves.

Background: Here we report a new selenium-based heterogeneous catalyst, which was prepared from the immobilization of diphenyl diselenide on amine-functionalized Santa Barbara Amorphous-15 (SBA-15). The catalyst characterization study has been confirmed by different analysis methods including Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction patterns (XRD), field-emission scanning electron microscopy (FE-SEM), and Brunauer–Emmett–Teller (BET) surface area analysis. Results: The newly designed catalyst was successfully applied in the green dehydration reaction of oximes to corresponding nitriles in the presence of hydrogen peroxide/air. To demonstrate the role of the catalyst in this study, the model reaction was also carried out in the absence of the catalyst and a trace yield of the relevant product was achieved. Conclusion: In this way, a series of nitrile derivatives were obtained with 72–96% yields, also, the catalyst could be separated easily and recycled for four consecutive runs with no obvious drop in catalytic activity. [ABSTRACT FROM AUTHOR]

[Display omitted] • Aromatic diselenides catalytic formation of multiple disulfide bonds in peptides. • Multiple disulfide bonds was correctly constructed by the catalytic reactions. • Good yield was achieved in various aqueous solutions. Multiple disulfide bonds (MBDs) play a critical role in maintaining the three-dimensional structure of peptides and proteins affording their pharmaceutical and biological activities. The efficient synthesis of correct MBDs in peptides and proteins remains a challenging task in chemical synthesis these compounds. In this work, aromatic diselenides including diphenyl diselenide (DPDS), bis(2-carboxyphenyl)diselenide (BCPDS), and 2,2′-dipyridyl diselenide (DPDDS) played as catalysts and were successfully used for the synthesis of correct MBDs in peptides. Good yields were achieved by use of the catalytic reactions under mild conditions, and the reaction time decreased with the trend of DPDDS < BCPDS < DPDS. A reaction mechanism was proposed, in which the formation of a selenenylsulfide intermediate played a critical role in the formation of correct MBDs in peptides. On the other hand, phenylselenenyl chloride (PSC) can oxidize fully reduced peptides to their correct MDBs forms. [ABSTRACT FROM AUTHOR]

Trichomoniasis is the most common nonviral sexually transmitted infection in the world, but its available therapies present low efficacy and high toxicity. Diphenyl diselenide (PhSe2) is a pharmacologically active organic selenium compound; however, its clinical use is hindered by its lipophilicity and toxicity. Nanocarriers are an interesting approach to overcome the limitations associated with this compound. This study designed and evaluated a vaginal hydrogel containing PhSe2-loaded Eudragit® RS100 and coconut oil nanocapsules for the treatment of trichomoniasis. Nanocapsules presented particle sizes in the nanometric range, positive zeta potential, a compound content close to the theoretical value, and high encapsulation efficiency. The nanoencapsulation maintained the anti-Trichomonas vaginalis action of the compound while improving the scavenger action in a DPPH assay. The hydrogels were prepared by thickening nanocapsule suspensions with locust bean gum (3%). The semisolids maintained the nanometric size of the particles and the PhSe2 content at around the initial concentration (1.0 mg/g). They also displayed non-Newtonian pseudo-plastic behavior and a highly mucoadhesive property. The chorioallantoic membrane method indicated the absence of hemorrhage, coagulation, or lysis. The compound, from both non-encapsulated and nano-based hydrogel delivery systems, remained on the surface of the bovine vaginal mucosa. Therefore, the formulations displayed the intended properties and could be a promising alternative for the treatment of trichomoniasis. [ABSTRACT FROM AUTHOR]

Hyperglycemia, oxidative stress, and inflammation play key roles in the onset and development of diabetic complications such as diabetic nephropathy (DN). Diphenyl diselenide (DPDS) is a stable and simple organic selenium compound with anti-hyperglycemic, anti-inflammatory, and anti-oxidative activities. Nevertheless, in vitro, the role and molecular mechanism of DPDS on DN remains unknown. Therefore, we investigated the effects of DPDS on tert-butyl hydrogen peroxide (t-BHP)-induced oxidative stress and lipopolysaccharide (LPS)-induced inflammation in rat glomerular mesangial (HBZY-1) cells and explored the underlying mechanisms. DPDS attenuated t-BHP-induced cytotoxicity, concurrent with decreased intracellular ROS and MDA contents and increased SOD activity and GSH content. Moreover, DPDS augmented the protein and mRNA expression of Nrf2, HO-1, NQO1, and GCLC in t-BHP-stimulated HBZY-1 cells. In addition, DPDS suppressed LPS-induced elevations of intracellular content and mRNA expression of interleukin (IL)-6, IL-1β and TNF-α. Furthermore, LPS-induced NFκB activation and high phosphorylation of JNK and ERK1/2 were markedly suppressed by DPDS in HBZY-1 cells. In summary, these data demonstrated that DPDS improves t-BHP-induced oxidative stress by activating the Nrf2/Keap1 pathway, and also improves LPS-induced inflammation via inhibition of the NFκB/MAPK pathways in HBZY-1 cells, suggesting that DPDS has the potential to be developed as a candidate for the prevention and treatment of DN. [ABSTRACT FROM AUTHOR]

[Display omitted] The organoselenium compounds belong to a class of synthetic molecules that displays a remarkable spectrum of promising pharmacological properties. Despite the huge amount of preclinical data that supports a bright outlook for organoselenium compounds, some toxicity issues and physicochemical limitations delay the development of more advanced studies. Currently, several scientific reports demonstrated that the association of nanotechnology has emerged as an alternative to improve solubility and safety issues of these molecules as well as enhance pharmacological properties. Therefore, our main objective was to address studies that reported the development and biological evaluations of nano-based formulations to synthetic organoselenium compounds incorporation by constructing an integrative literature review. The data survey was performed using the Science Direct, PubMed, Web of Science, and SCOPUS online databases, covering studies that were published from January 2011 up to October 2021. In the last decade, there has been an exponential growth in research regarding the incorporation of synthetic organoselenium compounds into distinct nanocarrier systems such as nanocapsules, nanoemulsions, micelles, and others, reinforcing that the association of such molecules and nanotechnology is a promising alliance. The reports investigated many nanosystems containing selenium organic molecules intending oral, intravenous, and cutaneous applications. Besides that, these systems were evaluated in a variety of in vitro techniques and in vivo models, concerning their pharmacological potential, biodistribution profile, and safety. In summary, the findings indicate that the production of nano-based formulations containing organoselenium compounds either improved physicochemical and biological properties or minimize toxicological issues of compounds. [ABSTRACT FROM AUTHOR]

Benzeneseleninic acid was used under visible light irradiation (white LEDs) to promote the oxidative cyclization of N‐propargyl amides to the respective 2‐substituted oxazole‐5‐carbaldehydes. A total of twelve 2‐aryl oxazole‐5‐carbaldehydes, six of them so far unprecedented, were prepared in 30–90 % yield in just 1 hour of reaction at room temperature. No metal catalysts, nor strong oxidants or heating were necessary, making this a mild method to access a valuable class of compounds. The only co‐products are water and diphenyl diselenide, that can be recovered and converted to new benzeneseleninic acid for a new reaction. [ABSTRACT FROM AUTHOR]

Background: Candida auris is an emergent fungal pathogen and a global concern, mostly due to its resistance to many currently available antifungal drugs. Objective: Thus, in response to this challenge, we evaluated the in vitro activity of potential new drugs, diphenyl diselenide (PhSe)2 and nikkomycin Z (nikZ), alone and in association with currently available antifungals (azoles, echinocandins, and polyenes) against Candida auris. Methods: Clinical isolates of C. auris were tested in vitro. (PhSe)2 and nikZ activities were tested alone and in combination with amphotericin B, fluconazole, or the echinocandins, micafungin and caspofungin. Results: (PhSe)2 alone was unable to inhibit C. auris, and antagonism or indifferent effects were observed in the combination of this compound with the antifungals tested. NikZ appeared not active alone either, but frequently acted cooperatively with conventional antifungals. Conclusion: Our data show that (PhSe)2 appears to not have a good potential to be a candidate in the development of new drugs to treat C. auris, but that nikZ is worthy of further study. [ABSTRACT FROM AUTHOR]

This short note elaborates a concise protocol for the synthesis of 2-[difluoro(phenylselenyl)methyl]benzo-1,3-thiazole in two steps from the commercially available reagent 2-aminobenzenethiol. The structures of the synthesized compounds are confirmed by 1H-NMR, 13C-NMR and 19F-NMR spectroscopy, infrared (IR) spectra, and high-resolution mass spectrometry.

The novel severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) was the causative agent of the COVID-19 pandemic, a global public health problem. Despite the numerous studies for drug repurposing, there are only two FDA-approved antiviral agents (Remdesivir and Nirmatrelvir) for non-hospitalized patients with mild-to-moderate COVID-19 symptoms. Consequently, it is pivotal to search for new molecules with anti-SARS-CoV-2 activity and to study their effects in the human immune system. Ebselen (Eb) is an organoselenium compound that is safe for humans and has antioxidant, anti-inflammatory, and antimicrobial properties. Diphenyl diselenide ((PhSe)2) shares several pharmacological properties with Eb and is of low toxicity to mammals. Herein, we investigated Eb and (PhSe)2 anti-SARS-CoV-2 activity in a human pneumocytes cell model (Calu-3) and analyzed their toxic effects on human peripheral blood mononuclear cells (PBMCs). Both compounds significantly inhibited the SARS-CoV-2 replication in Calu-3 cells. The EC50 values for Eb and (PhSe)2 after 24 h post-infection (hpi) were 3.8 µM and 3.9 µM, respectively, and after 48 hpi were 2.6 µM and 3.4 µM. These concentrations are safe for non-infected cells, since the CC50 values found for Eb and (PhSe)2 on Calu-3 were greater than 200 µM. Importantly, the concentration rates tested on viral replication were not toxic to human PBMCs. Therefore, our findings reinforce the efficacy of Eb and demonstrate (PhSe)2 as a new candidate to be tested in future trials against SARS-CoV-2 infection/inflammation conditions.

Background: Dermatophytoses are one of the most prevalent infectious diseases in the world for which the pace of developing new drugs has not kept pace with the observed therapeutic problems. Thus, searching for new antifungals with an alternative and novel mechanism of action is necessary. Objective: This study aimed to evaluate the antifungal activity of ebselen and diphenyl diselenide against Trichophyton mentagrophytes clinical isolates. Methods: In vitro antifungal susceptibility was assessed for organoselenium compounds used alone or in combination with allylamines and azoles according to the 3rd edition of the CLSI M38 protocol. Results: Ebselen demonstrated high antifungal activity with MICGM equal to 0.442 μg/mL and 0.518 μg/mL in the case of human and animal origin strains, respectively. The values of MICGM of diphenyl diselenide were higher: 17.36 μg/mL and 13.45 μg/mL for the human and animal isolates, respectively. Synergistic or additive effects between terbinafine and ebselen or diphenyl diselenide were observed in the case of 12% and 20% strains, respectively. In turn, the combination of itraconazole with diphenyl diselenide showed a synergistic effect only in the case of 6% of the tested strains, whereas no synergism was shown in the combination with ebselen. Conclusions: The results highlight the promising activity of organoselenium compounds against Trichophyton mentagrophytes. However, their use in combinational therapy with antifungal drugs seems to be unjustified due to the weak synergistic effect observed. [ABSTRACT FROM AUTHOR]

Candida krusei is a candidiasis etiological agent of relevance in the clinical setting because of its intrinsic resistance to fluconazole. Also, it has opened up new paths in the area of alternative therapeutic techniques. This project demonstrated the effects of diphenyl diselenide (PhSe)2 and p-cloro diphenyl diselenide (pCl-PhSe)2, two organochalcogen compounds, on relevant virulence factors for the early stage of the C. krusei host interaction and infection process. Both compounds inhibited adherence of C. krusei to both polystyrene surfaces and cervical epithelial cells and biofilm formation; the structure of the biofilm was also changed in a dose-dependent manner. In addition, both compounds inhibited C. krusei growth, but (PhSe)2 significantly increased the time duration of the lag phase and delayed the start of the exponential phase in growth kinetics. (PhSe)2 has more potential antifungal activity than (pCl-PhSe)2 in inhibiting the adherence to epithelial cells, biofilm formation, and growth of C. krusei. [ABSTRACT FROM AUTHOR]

Copper (Cu2+) is a biologically essential element that participates in numerous physiological processes. However, elevated concentrations of copper have been associated with cellular oxidative stress and neurodegenerative diseases. Organo‑selenium compounds such as diphenyl diselenide (DPDS) have in vitro and in vivo antioxidant properties. Hence, we hypothesized that DPDS may modulate the toxicity of Cu2+ in Drosophila melanogaster. The acute effects (4 days of exposure) caused by a high concentration of Cu2+ (3 mM) were studied using endpoints of toxicity such as survival and behavior in D. melanogaster. The potential protective effect of low concentration of DPDS (20 μM) against Cu2+ was also investigated. Adult flies aged 1–5 days post-eclosion (both sexes) were divided into four groups: Control, DPDS (20 μM), CuSO 4 (3 mM), and the combined exposure of DPDS (20 μM) and CuSO 4 (3 mM). Survival, biochemical, and behavioral parameters were determined. Co-exposure of DPDS and CuSO 4 increased acetylcholinesterase (AChE) activity and the generation of reactive oxygen species (ROS as determined by DFCH oxidation). Contrary to our expectation, the co-exposure reduced survival, body weight, locomotion, catalase activity, and cell viability in relation to control group. Taken together, DPDS potentiated the Cu2+ toxicity. [Display omitted] • First study to report the effects of co-exposure of DPDS and Cu2+ on D. melanogaster • Cu2+ and DPDS co-exposure alter the biochemical parameters of D. melanogaster. • Co-exposure of Cu2+ and DPDS decreases the survival and mobility of D. melanogaster. • The complex of DPDS and Cu2+ is toxic to D. melanogaster. [ABSTRACT FROM AUTHOR]

Oxidative stress is a key factor in the disruption of cartilage homeostasis during the development of osteoarthritis (OA). Organic selenium (Se)-containing compounds such as diselenides have excellent antioxidant activity and may prevent related diseases. We aimed to examine the benefits of the synthetic small molecule diphenyl diselenide (DPDSe) in OA models in vitro and in vivo. Our findings showed that DPDSe could maintain extracellular matrix (ECM) homeostasis and inhibit reactive oxygen species (ROS) production in IL-1β-treated chondrocytes. In a destabilization of the medial meniscus (DMM)-induced OA mouse model, intra-articular administration of DPDSe alleviated joint degeneration, as evidenced by a decrease in the OARSI score and the restoration of collagen II (COL2) and MMP-13 expression in cartilage tissues. We confirmed that DDS activated the nuclear factor erythroid 2-related factor 2 (Nrf2) pathway in IL-1β-treated chondrocytes, and its chondroprotective effects were significantly counteracted when Nrf2 signaling was blocked by the inhibitor ML385 or by siRNA-mediated Nrf2 knockdown. The relatively strong performance of DPDSe makes it an ideal candidate for further trials as a disease-modifying OA drug (DMOAD). • Diphenyl diselenide alleviates oxidative stress and degeneration in chondrocytes. • Diphenyl diselenide attenuates osteoarthritis (OA) development in mice. • Nrf2 activation mediates the chondroprotective effects of diphenyl diselenide. • Diselenides show potential as disease-modifying OA drugs (DMOADs). [ABSTRACT FROM AUTHOR]

[Display omitted] A simple yet efficient approach towards the synthesis of β -hydroxy selanylated ketones was developed from easily accessible chalcones and diphenyl diselenide through an electrochemical pathway. In this technique, diphenyl diselenide and water are the source of PhSe. and hydroxyl (–OH) groups that can be inserted at the α and β positions respectively producing β -hydroxy selanylated ketones in moderate to good yields. The reaction features difunctionalization of ketones, catalyst free, mild reaction conditions, stereo and regioselectivity in an undivided electrochemical cell at room temperature. For this transformation, a plausible radical mechanism has been put out. [ABSTRACT FROM AUTHOR]

A simple tert‐butyl hydroperoxide (TBHP)‐mediated method has been developed to construct selenated oxazolines/thiazolines under microwave irradiation. The selenocyclization of N‐allylbenzamides/benzthioamides could be achieved owing to the addition of an active electrophilic selenium species, generated in situ from diphenyl diselenide on reacting with TBHP, at their olefinic site. The reaction mechanism was confirmed by intercepting and characterizing all the proposed intermediates by ESI‐QTOF‐MS and NMR study. This method offers several advantages including simpler reaction conditions, shorter reaction time, catalyst‐free, thus rendering a competent alternative to the synthesis of selenated oxazolines/thiazolines in yields of upto 95 %. [ABSTRACT FROM AUTHOR]

Methylmercury (MeHg) is a ubiquitous environmental neurotoxicant whose mechanisms of action involve oxidation of endogenous nucleophilic groups (mainly thiols and selenols), depletion of antioxidant defenses, and disruption of neurotransmitter homeostasis. Diphenyl diselenide—(PhSe)2—a model diaryl diselenide, has been reported to display significant protective effects against MeHg-induced neurotoxicity under both in vitro and in vivo experimental conditions. In this study, we compared the protective effects of (PhSe)2 with those of RC513 (4,4′-diselanediylbis(2,6-di-tert-butylphenol), a novel diselenide-probucol-analog) against MeHg-induced toxicity in the neuronal (hippocampal) cell line HT22. Although both (PhSe)2 and RC513 significantly mitigated MeHg- and tert-butylhydroperoxide (t-BuOOH)-cytotoxicity, the probucol analog exhibited superior protective effects, which were observed earlier and at lower concentrations compared to (PhSe)2. RC513 treatment (at either 0.5 µM or 2 µM) significantly increased glutathione peroxidase (GPx) activity, which has been reported to counteract MeHg-toxicity. (PhSe)2 was also able to increase GPx activity, but only at 2 µM. Although both compounds increased the Gpx1 transcripts at 6 h after treatments, only RC513 was able to increase mRNA levels of Prx2, Prx3, Prx5, and Txn2, which are also involved in peroxide detoxification. RC513 (at 2 µM) significantly increased GPx-1 protein expression in HT22 cells, although (PhSe)2 displayed a minor (nonsignificant) effect in this parameter. In agreement, RC513 induced a faster and superior capability to cope with exogenously-added peroxide (t-BuOOH). In summary, when compared to the prototypical organic diaryl diselenide [(PhSe)2], RC513 displayed superior protective properties against MeHg-toxicity in vitro; this was paralleled by a more pronounced upregulation of defenses related to detoxification of peroxides, which are well-known MeHg-derived intermediate oxidant species. [ABSTRACT FROM AUTHOR]

This short note elaborates a concise protocol for the synthesis of 2-[difluoro(phenylselenyl)methyl]benzo-1,3-thiazole in two steps from the commercially available reagent 2-aminobenzenethiol. The structures of the synthesized compounds are confirmed by 1H-NMR, 13C-NMR and 19F-NMR spectroscopy, infrared (IR) spectra, and high-resolution mass spectrometry. [ABSTRACT FROM AUTHOR]

Selenium-catalysed oxidations are highly sought after in organic synthesis and biology. Herein, we report our studies on the on water selenium mediated oxidation of anilines. In the presence of diphenyl diselenide or benzeneseleninic acid, anilines react with hydrogen peroxide, providing direct and selective access to nitroarenes. On the other hand, the use of selenium dioxide or sodium selenite leads to azoxyarenes. Careful mechanistic analysis and 77Se NMR studies revealed that only Se(IV) species, such as benzeneperoxyseleninic acid, are the active oxidants involved in the catalytic cycle operating in water and leading to nitroarenes. While other selenium-catalysed oxidations occurring in organic solvents have been recently demonstrated to proceed through Se(VI) key intermediates, the on water oxidation of anilines to nitroarenes does not. These findings shed new light on the multifaceted nature of organoselenium-catalysed transformations and open new directions to exploit selenium-based catalysis. [ABSTRACT FROM AUTHOR]

We evaluated the in vitro activity of nikkomycin Z (NikZ) in combination with diphenyl diselenide (PhSe)2, two compounds previously shown to have anti-Sporothrix spp. activity. Eighteen isolates of Sporothrix spp. were tested in checkerboard assays. Synergism for inhibition and killing Sporothrix spp. occurred in 100% and 89% of the isolates, respectively. The anti-Sporothrix spp. activity of this combination provides a rationale for in vivo studies to evaluate the application of both compounds in sporotrichosis treatment. [ABSTRACT FROM AUTHOR]

Hyperglycemia, oxidative stress, and inflammation play key roles in the onset and development of diabetic complications such as diabetic nephropathy (DN). Diphenyl diselenide (DPDS) is a stable and simple organic selenium compound with anti-hyperglycemic, anti-inflammatory, and anti-oxidative activities. Nevertheless, in vitro, the role and molecular mechanism of DPDS on DN remains unknown. Therefore, we investigated the effects of DPDS on tert-butyl hydrogen peroxide (t-BHP)-induced oxidative stress and lipopolysaccharide (LPS)-induced inflammation in rat glomerular mesangial (HBZY-1) cells and explored the underlying mechanisms. DPDS attenuated t-BHP-induced cytotoxicity, concurrent with decreased intracellular ROS and MDA contents and increased SOD activity and GSH content. Moreover, DPDS augmented the protein and mRNA expression of Nrf2, HO-1, NQO1, and GCLC in t-BHP-stimulated HBZY-1 cells. In addition, DPDS suppressed LPS-induced elevations of intracellular content and mRNA expression of interleukin (IL)-6, IL-1β and TNF-α. Furthermore, LPS-induced NFκB activation and high phosphorylation of JNK and ERK1/2 were markedly suppressed by DPDS in HBZY-1 cells. In summary, these data demonstrated that DPDS improves t-BHP-induced oxidative stress by activating the Nrf2/Keap1 pathway, and also improves LPS-induced inflammation via inhibition of the NFκB/MAPK pathways in HBZY-1 cells, suggesting that DPDS has the potential to be developed as a candidate for the prevention and treatment of DN.

Bimetallic Rh–Co nanoparticles supported on nitrogen-doped porous carbon (Rh–Co/NPC) were synthesized from metal precursors and urea through a simple thermal decomposition/reduction under a nitrogen flow. The Rh–Co/NPC nanocatalyst which contains highly dispersed alloy nanoparticles (∼6 nm) showed high catalytic performance as well as good recyclability for the C–Se coupling reaction of diphenyl diselenide and aryl boronic acid and p-nitrophenol reduction. [ABSTRACT FROM AUTHOR]

Fungal infections are one of the most prevalent diseases in the world and there is a lack of new antifungal drug development for these diseases. We conducted a systematic review of the literature regarding the in vitro antifungal activity of the organoselenium compounds ebselen (Eb) and diphenyl diselenide [(PhSe)2]. A systematic review was carried out based on the search for articles with data concerning Minimal Inhibitory Concentration (MIC) values, indexed in international databases and published until August 2020. A total of 2337 articles were found, and, according to the inclusion and exclusion criteria used, 22 articles were included in the study. Inhibitory activity against 96% (200/208) and 95% (312/328) of the pathogenic fungi tested was described for Eb and [(PhSe)2], respectively. Including in these 536 fungal isolates tested, organoselenium activity was highlighted against Candida spp. Cryptococcus ssp. Trichosporon spp. Aspergillus spp. Fusarium spp. Pythium spp. and Sporothrix spp. with MIC values lower than 64 μg/mL. In conclusion, Eb and [(PhSe)2] have a broad spectrum of in vitro inhibitory antifungal activity. These data added with other pharmacological properties of these organoselenium compounds suggest that both compounds are potential future antifungal drugs. Whether MICs toward the upper end of the ranges described here are compatible with efficacious therapy, and whether they may achieve such end as a result of the favorable non-antimicrobial effects of selenium on the host, requires more in vivo testing. [ABSTRACT FROM AUTHOR]