17893-46-8Relevant academic research and scientific papers
Receptor-Ligand Interaction Measured by Inductively Coupled Plasma Mass Spectrometry and Selenium Labeling
Cheignon, Clémence,Cordeau, Emmanuelle,Prache, Nolween,Cantel, Sonia,Martinez, Jean,Subra, Gilles,Arnaudguilhem, Carine,Bouyssiere, Brice,Enjalbal, Christine
, p. 10173 - 10184 (2018)
In the search for an alternative strategy to the radioactivity measurement conventionally performed to probe receptor-ligand interactions in pharmacological assays, we demonstrated that selenium labeling of the studied ligand combined with elemental mass spectrometry was as efficient and robust as the reference method but devoid of its environmental and health hazards. The proof-of-concept was illustrated on two GPCR receptors, vasopressin (V1A) and cholecystokinin B (CCK-B), involving peptides as endogenous ligands. We proposed several methodologies to produce selenium-labeled ligands according to peptide sequences along with binding affinity constraints. A selection of selenopeptides that kept high affinities toward the targeted receptor were engaged in saturation and competitive binding experiments with subsequent sensitive RP-LC-ICP-MS measurements. Experimental values of affinity constant (Ki) were perfectly correlated to literature data, illustrating the general great potency of replacing radioactive iodine by selenium for ligand labeling to further undergo unaffected pharmacology experiments efficiently monitored by elemental mass spectrometry.
Zinc-mediated cleavage of diselenides: A novel synthesis of unsymmetrical diorganyl selenides in aqueous media
Movassagh, Barahman,Shamsipoor, Mojgan
, p. 121 - 122 (2005)
A convenient synthetic method has been developed for the preparation of unsymmetrical selenides through a one-pot zinc-mediated reaction of diselenides and active organic halides in aqueous media.
(Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity
Grollier, Kevin,De Zordo-Banliat, Arnaud,Bourdreux, Flavien,Pegot, Bruce,Dagousset, Guillaume,Magnier, Emmanuel,Billard, Thierry
supporting information, p. 6028 - 6033 (2021/03/15)
The synthesis of molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups is described via an efficient two-step strategy based on a metal-free photoredox catalyzed decarboxylative trifluoromethylselenolation with good yields up to 88 %, which raised to 98 % in flow chemistry conditions. The flow methods allowed also to scale up the reaction. The mechanism of this key reaction was studied. The physicochemical characterization of these emerging groups was performed by determining their Hansch–Leo lipophilicity parameters with high values up to 2.24. This reaction was also extended to perfluoroalkylselenolation with yields up to 95 %. Finally, this method was successfully applied to the functionalization of relevant bioactive molecules such as tocopherol or estrone derivatives.
Radical-mediated reactions of α-bromo aluminium thioacetals, α-bromothioesters, and xanthates for thiolactone synthesis
McCourt, Ruairí O.,Dénès, Fabrice,Scanlan, Eoin M.
, (2018/04/24)
Thiolactones have attracted considerable attention in recent years as bioactive natural products, lead compounds for drug discovery, molecular probes, and reagents for polymerisation. We have investigated radical-mediated C-C bond forming reactions as a s
Synthesis of functionalized organoselenium materials: Selenides and diselenides containing cholesterol
Frizon, Tiago E.,Rafique, Jamal,Saba, Sumbal,Bechtold, Ivan H.,Gallardo, Hugo,Braga, Antonio L.
supporting information, p. 3470 - 3476 (2015/06/08)
Abstract A simple and efficient procedure for the synthesis of three new series of chalcogen liquid crystals, based on selenides and diselenides, containing cholesterol in their structure, is described. Thermal and liquid crystalline properties were investigated by POM, DSC, TGA and XRD scattering. Six of the nine molecules synthesized showed liquid crystal properties, with smectic mesomorphism. All the compounds presented good thermal stability. The smectic mesomorphism was confirmed through XRD analysis. The morphology of the surface of the films was investigated by using atomic force microscopy (AFM). All prepared diselenides showed good glutathione peroxidase like activity and one of the diselenides was 3.3 times more active than the standard Ebselen.
Light-mediated total synthesis of 17-deoxyprovidencin
Toelle, Nina,Weinstabl, Harald,Gaich, Tanja,Mulzer, Johann
supporting information, p. 3859 - 3862 (2014/05/06)
An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring. Photochemistry is the key: An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photoinduced Z/E isomerization to a highly strained conformationally restricted ring system, and the stereoselective formation of two epoxides on the macrocycle.
One-pot synthesis of phenylseleno N-acetyl α-amino acids: Supra-molecular self-assembling in organoselenium compounds
Parashiva Prabhu,Phadnis, Prasad P.,Wadawale, Amey,Priyadarsini, K. Indira,Jain, Vimal K.
, p. 140 - 147 (2013/10/01)
A convenient one-pot synthesis of phenylseleno N-acetyl α-amino acids, PhSeCH2C(O)NHC(R)COOH (R = H (1), Me (2), PhCH2 (3), 4-HOC6H4CH2 (4) and CH2OH (5)) is reported. These compounds have been characterized by microanalyses, UV-Vis, IR and NMR (1H, 13C, 77Se) spectroscopy. The molecular structures of [PhSeCH2CONHCH2COOH] (1), [PhSeCH2CONHCH(CH2C6H4OH-4)COOH] (4) and [PhSeCH2CONHCH(CH2OH)COOH] (5) have been established by X-ray diffraction analyses. These compounds are associated in the solid state through hydrogen bonding to give supra-molecular self-assembled structures. Free radical scavenging activity of these compounds has also been evaluated by DPPH assay.
Diverging chemoselective reactions of separable amide rotational isomers
Li, Xiben,Curran, Dennis P.
supporting information; experimental part, p. 612 - 614 (2010/05/19)
[Chemical equation presented] Diverging chemoselective reactions of a pair of amide rotamers have been observed by separating the rotamers and then reacting them individually. Reduction of (Z)-N-allyl-2-(phenylselanyl)-W-(2,4,6- tri-iert-butylphenyl)aceta
Convenient preparation of benzylseleno- and phenylselenoalkanoic acids: Reagents for synthesis of organoselenium compounds
Bhalla, Aman,Sharma, Sitansh,Bhasin, Kuldip K.,Bari, Shamsher S.
, p. 783 - 793 (2007/10/03)
An efficient and operationally simple route to benzylseleno- and phenylselenoalkanoic acids from ethyl benzyl/phenylselenoalkanoates is described. This involves preparation of ethyl benzyl/phenylselenoalkanoates as substrates by reaction of dibenzyl/diphenyl diselenide and sodium borohydride with ethyl chloroalkanoates in ethanol followed by basic hydrolysis and subsequent acidification. Copyright Taylor & Francis Group, LLC.
Diastereoselective aldolization with N-phenylselanylacetyl derivatives
Franck, Xavier,Langlois, Emilie,Outurquin, Francis
, p. 719 - 724 (2008/01/04)
The asymmetric introduction of the phenylselanyl moiety using chiral N-phenyselanylacetyloxazolidin-2-thiones and -thiazolidin-2-thiones is reported. The diastereoselectivity is complete in favor of the syn isomer and the aldols so obtained are valuable intermediates for the synthesis of more functionalized molecules such as amino alcohols, after chemoselective activation of the selenium and substitution by nucleophilic nitrogen. Georg Thieme Verlag Stuttgart.
