Day: September 15, 2022

Chiappetta, Giovanni;Gamberi, Tania;Faienza, Fiorella;Limaj, Xhesika;Rizza, Salvatore;Messori, Luigi;Filomeni, Giuseppe;Modesti, Alessandra;Vinh, Joelle published 《Redox proteome analysis of auranofin exposed ovarian cancer cells (A2780)》 in 2022. The article was appeared in 《Redox Biology》. They have made some progress in their research.Recommanded Product: 34031-32-8 The article mentions the following:

The effects of Auranofin (AF) on protein expression and protein oxidation in A2780 cancer cells were investigated through a strategy based on simultaneous expression proteomics and redox proteomics determinations Bioinformatics anal. of the proteomics data supports the view that the most critical cellular changes elicited by AF treatment consist of thioredoxin reductase inhibition, alteration of the cell redox state, impairment of the mitochondrial functions, metabolic changes associated with conversion to a glycolytic phenotype, induction of ER stress. The occurrence of the above cellular changes was extensively validated by performing direct biochem. assays. Our data are consistent with the concept that AF produces its effects through a multitarget mechanism that mainly affects the redox metabolism and the mitochondrial functions and results into severe ER stress. Results are discussed in the context of the current mechanistic knowledge existing on AF.((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) were involved in the experimental procedure.

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.Recommanded Product: 34031-32-8

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Chen, Haoran;Yang, Ning;Yu, Liang;Li, Jiajia;Zhang, Hui;Zheng, Yahong;Xu, Mengran;Liu, Yanyan;Yang, Yi;Li, Jiabin published 《Synergistic Microbicidal Effect of AUR and PEITC Against Staphylococcus aureus Skin Infection.》 in 2022. The article was appeared in 《Frontiers in cellular and infection microbiology》. They have made some progress in their research.Safety of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold The article mentions the following:

Given the increasing prevalence of Staphylococcus aureus antibiotic resistance, there is an urgent need to repurpose approved drugs with known pharmacology and toxicology as an alternative therapeutic strategy. We have reported that the sustained monotherapy of auranofin (AUR) inevitably resulted in reduced susceptibility or even the emergence of resistance to AUR in S. aureus. However, whether drug combination could increase antibacterial activity while preventing AUR resistance is still unknown. Here, we focused on the important role of AUR combined with phenethyl isothiocyanate (PEITC) in skin infection and determined the synergistic antimicrobial effect on S. aureus by using checkerboard assays and time-kill kinetics analysis. This synergistic antimicrobial activity correlated with increased reactive oxygen species (ROS) generation, disruption of bacterial cell structure, and inhibition of biofilm formation. We also showed that AUR synergized with PEITC effectively restored the susceptibility to AUR via regulating thioredoxin reductase (TrxR) and rescued mice from subcutaneous abscesses through eliminating S. aureus pathogens, including methicillin-resistant S. aureus (MRSA). Collectively, our study indicated that the AUR and PEITC combination had a synergistic antimicrobial impact on S. aureus in vitro and in vivo. These results suggest that AUR and PEITC treatment may be a promising option for S. aureus infection. To complete the study, the researchers used ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) .

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.Safety of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Freire Boullosa, Laurie;Van Loenhout, Jinthe;Flieswasser, Tal;De Waele, Jorrit;Hermans, Christophe;Lambrechts, Hilde;Cuypers, Bart;Laukens, Kris;Bartholomeus, Esther;Siozopoulou, Vasiliki;De Vos, Winnok H.;Peeters, Marc;Smits, Evelien L. J.;Deben, Christophe published 《Auranofin reveals therapeutic anticancer potential by triggering distinct molecular cell death mechanisms and innate immunity in mutant p53 non-small cell lung cancer》 in 2021. The article was appeared in 《Redox Biology》. They have made some progress in their research.Synthetic Route of C20H36AuO9PS The article mentions the following:

To shed light on the mode of action, this study provides an in-depth anal. on the mol. mechanisms and immunogenicity of AF-mediated cytotoxicity in the non-small cell lung cancer (NSCLC) cell line NCI-H1299 (p53 Null) and its two isogenic derivates with mutant p53 R175H or R273H accumulation. TrxR is highly expressed in a panel of 72 NSCLC patients, making it a valid druggable target in NSCLC for AF. The presence of mutant p53 overexpression was identified as an important sensitizer for AF in (isogenic) NSCLC cells as it was correlated with reduced thioredoxin (Trx) levels in vitro. Transcriptome anal. revealed dysregulation of genes involved in oxidative stress response, DNA damage, granzyme A (GZMA) signaling and ferroptosis. Although functionally AF appeared a potent inhibitor of GPX4 in all NCI-H1299 cell lines, the induction of lipid peroxidation and consequently ferroptosis was limited to the p53 R273H expressing cells. In the p53 R175H cells, AF mainly induced large-scale DNA damage and replication stress, leading to the induction of apoptotic cell death rather than ferroptosis. Importantly, all cell death types were immunogenic since the release of danger signals (ecto-calreticulin, ATP and HMGB1) and dendritic cell maturation occurred irresp. of (mutant) p53 expression. Finally, we show that AF sensitized cancer cells to caspase-independent natural killer cell-mediated killing by downregulation of several key targets of GZMA.((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) were involved in the experimental procedure.

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a potent inhibitor of selenoenzyme thioredoxin reductase (TrxR), which is involved in defense against oxidative stress.Synthetic Route of C20H36AuO9PS

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Le Gal, Yann;Filatre-Furcate, Agathe;Lorcy, Dominique;Jeannin, Olivier;Roisnel, Thierry;Dorcet, Vincent;Fontinha, Diana;Francisco, Denise;Prudencio, Miguel;Martins, Marta;Soeiro, Catarina;Sousa, Silvia A.;Leitao, Jorge H.;Morais, Tania S.;Bartolo, Ines;Taveira, Nuno;Guerreiro, Joana F.;Marques, Fernanda published 《Broad Spectrum Functional Activity of Structurally Related Monoanionic Au(III) Bis(Dithiolene) Complexes》 in 2022. The article was appeared in 《International Journal of Molecular Sciences》. They have made some progress in their research.Electric Literature of C20H36AuO9PS The article mentions the following:

The biol. properties of sixteen structurally related monoanionic gold (III) bis(dithiolene/diselenolene) complexes were evaluated. The complexes differ in the nature of the heteroatom connected to the gold atom (AuS for dithiolene, AuSe for diselenolene), the substituent on the nitrogen atom of the thiazoline ring (Me, Et, Pr, iPr and Bu), the nature of the exocyclic atom or group of atoms (O, S, Se, C(CN)2) and the counter-ion (Ph4P+ or Et4N+). The anticancer and antimicrobial activities of all the complexes were investigated, while the anti-HIV activity was evaluated only for selected complexes. Most complexes showed relevant anticancer activities against Cisplatin-sensitive and Cisplatin-resistant ovarian cancer cells A2780 and OVCAR8, resp. After 48 h of incubation, the IC50 values ranged from 0.1-8 μM (A2780) and 0.8-29 μM (OVCAR8). The complexes with the Ph4P+ ([P]) counter-ion are in general more active than their Et4N+ ([N]) analogs, presenting IC50 values in the same order of magnitude or even lower than Auranofin. Studies in the zebrafish embryo model further showed that, despite their marked anticancer effect, the complexes with [P] counter-ion exhibited low in vivo toxicity. In general, the exocyclic exchange of sulfur by oxygen or ylidenemalononitrile (C(CN)2) enhanced the compounds toxicity. Most complexes containing the [P] counter ion exhibited exceptional antiplasmodial activity against the Plasmodium berghei parasite liver stages, with submicromolar IC50 values ranging from 400-700 nM. In contrast, antibacterial/fungi activities were highest for most complexes with the [N] counter-ion. Auranofin and two selected complexes [P][AuSBu(=S)] and [P][AuSEt(=S)] did not present anti-HIV activity in TZM-bl cells. Mechanistic studies for selected complexes support the idea that thioredoxin reductase, but not DNA, is a possible target for some of these complexes. The complexes [P] [AuSBu(=S)], [P] [AuSEt(=S)], [P] [AuSEt(=Se)] and [P] [AuSeiPr(=S)] displayed a strong quenching of the fluorescence intensity of human serum albumin (HSA), which indicates a strong interaction with this protein. Overall, the results highlight the promising biol. activities of these complexes, warranting their further evaluation as future drug candidates with clin. applicability. And ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) was used in the research process.

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a potent inhibitor of selenoenzyme thioredoxin reductase (TrxR), which is involved in defense against oxidative stress.Electric Literature of C20H36AuO9PS

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Howell, Gareth P.;Minnaard, Adriaan J.;Feringa, Ben L. published 《Asymmetric allylation of aryl aldehydes: studies on the scope and mechanism of the palladium catalyzed diethylzinc mediated umpolung using phosphoramidite ligands》. The research results were published in《Organic & Biomolecular Chemistry》 in 2006.Safety of (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine The article conveys some information:

Using modular, monodentate phosphoramidite ligands, enantioselective palladium catalyzed diethylzinc mediated allylation of aldehydes was achieved. The scope of the asym. C-C bond formation was investigated with respect to nucleophilic and electrophilic components and an alternative reaction mechanism is proposed based on our findings. To complete the study, the researchers used (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Safety of (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Wilsily, Ashraf;Fillion, Eric published 《Asymmetric Synthesis of Carboxylic Acid Derivatives Having an All-Carbon α-Quaternary Center through Cu-Catalyzed 1,4-Addition of Dialkylzinc Reagents to 2-Aryl Acetate Derivatives》. The research results were published in《Organic Letters》 in 2008.Name: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine The article conveys some information:

The asym. synthesis of carboxylic acid derivatives having an all-carbon α-quaternary center, e.g. I, has been achieved via copper-catalyzed 1,4-addition of dialkylzinc reagents to aryl acetate derivatives, e.g. II, in the presence of phosphoramidite ligand. High isolated yields and enantioselectivities were obtained. It was demonstrated that the Meldrum’s acid and ester moieties present on the all-carbon quaternary center allow for a wide variety of subsequent transformations, leading to the expedient preparation of succinimides, e.g. III, succinate esters and succinic acids, γ-butyrolactones, and β-amino acid derivatives(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) were involved in the experimental procedure.

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Name: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Quality Control of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold《ANCHOR-tagged equine herpesvirus 1: A new tool for monitoring viral infection and discovering new antiviral compounds》 was published in 2021. The authors were Quentin-Froignant, Charlotte;Kappler-Gratias, Sandrine;Top, Sokunthea;Bertagnoli, Stephane;Gallardo, Franck, and the article was included in《Journal of Virological Methods》. The author mentioned the following in the article:

Equine herpesvirus 1 (EHV-1) is a causative agent of respiratory disorders, abortion and myeloencephalopathy in horses and has an important impact on equine health and economy. Several bacterial artificial chromosomes have already been developed and enabled identification and functional characterization of EHV-1 genes. Unfortunately, little is known about its replication. Here, the ANCHOR system was inserted by targeted homologous recombination into the equine herpesvirus genome. This insertion led to the conversion of EHV-1 DNA to auto-fluorescent spots easily detectable by fluorescence microscopy, and enabled production of an auto-fluorescent EHV-1 ANCHORGFP with tropism and replication kinetic like the parental strain. High resolution imaging allowed first visualization of EHV-1 replication from apparition of first viral genome to large replicative centers, in single cells or inside syncytia. Combined with high content microscopy, EHV-1 ANCHORGFP leads to identification of auranofin and azacytidine-5 as new potential antivirals to treat EHV-1 infection.((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) were involved in the experimental procedure.

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a gold(I)-phosphine thiolate small molecule described to produce antiinflammatory and antiarthritic effects.Quality Control of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Lescure, Robin;Privat, Malorie;Pliquett, Jacques;Massot, Aurelie;Baffroy, Oceane;Busser, Benoit;Bellaye, Pierre-Simon;Collin, Bertrand;Denat, Franck;Bettaieb, Ali;Sancey, Lucie;Paul, Catherine;Goze, Christine;Bodio, Ewen published 《Near-infrared emitting fluorescent homobimetallic gold(I) complexes displaying promising in vitro and in vivo therapeutic properties》 in 2021. The article was appeared in 《European Journal of Medicinal Chemistry》. They have made some progress in their research.Electric Literature of C20H36AuO9PS The article mentions the following:

Three near-IR (NIR-I) optical theranostic systems were synthesized, characterized and studied in vitro and in vivo. These original homo-bimetallic gold(I)-based aza-BODIPY complexes proved to be trackable through near-IR optical imaging in cells and in mice. They display anti-proliferative properties in micromolar range against human and murine cancer cell lines (4T1, MDA-MB-231, CT26, and SW480). Moreover, the injection of the most promising theranostic agent in CT26 tumor-bearing BALB/c mice induced a significant anti-cancer activity. The experimental procedure involved many compounds, such as ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) .

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a gold(I)-phosphine thiolate small molecule described to produce antiinflammatory and antiarthritic effects.Electric Literature of C20H36AuO9PS

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Application In Synthesis of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold《Repurposing auranofin for treatment of Experimental Cerebral Toxoplasmosis》 was published in 2021. The authors were Abou-El-Naga, Iman Fathy;Mogahed, Nermine Mogahed Fawzy Hussein, and the article was included in《Acta Parasitologica》. The author mentioned the following in the article:

Abstract: Purposes: Evaluate the effect of auranofin on the early and late stages of chronic infection with Toxoplasma gondii avirulent ME49 strain. Methods: Swiss albino mice were orally inoculated with 10 cysts of Toxoplasma gondii, and orally treated with auranofin or septazole in daily doses of 20 mg/kg or 100 mg /kg, resp., for 30 days. Treatment began either on the same day of infection and mice were sacrificed at the 60th day postinfection or the treatment started after 60 days of infection and mice were sacrificed at the 90th day postinfection. Results: Auranofin significantly reduced the brain cyst burden and inflammatory reaction at both stages of infection compared to the infected non-treated control. More remarkably, auranofin significant reduced the brain cyst burden in the late stage, while septazole failed. Hydrogen peroxide level was significantly increased in the brain homogenate of mice treated with auranofin only at the early stage of infection. Ultrastructral studies revealed that the anti-Toxoplasma effect of auranofin is achieved by changing the membrane permeability and inducing apoptosis. Conclusions: Thus, auranofin could be an alternative for the standard treatment regimen of toxoplasmosis and these results are considered another achievement for the drug against parasitic infection. Being a FDA-approved drug, it can be rapidly evaluated in clin. trials. The experimental procedure involved many compounds, such as ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) .

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.Application In Synthesis of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Alexakis, Alexandre;Trevitt, Graham P.;Bernardinelli, Gerald published 《Tandem enantioselective conjugate addition: Electophile trapping reactions. Application in the formation of syn or anti aldols》 in 2001. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.SDS of cas: 201732-49-2 The article mentions the following:

2-Cyclohexen-1-one and 2-cyclohept-en-1-one underwent cupric triflate/phosphoramidate ligand catalyzed enantioselective addition of Et₂Zn to give homochiral zinc enolate intermediates which were trapped by cleavage reactions with acetals and orthoesters to give alkoxy substituted and protected 1,3-dicarbonyl products, resp. Thus, reaction of 2-cyclohexen-1-one in CH₂Cl₂ containing cupric triflate and the phosphoramidate ligand I with Et₂Zn at -30° for 30 min and then with Me₂C(OMe)₂ or HC(OMe)₃ in the presence of F₃B.OEt₂ gave the trans-ethylcyclohexanones II and III, resp. Application of chiral acetals, e.g. diphenyldioxolanes IV (R = Ph, 1-propenyl), to this reaction enabled three contiguous stereocenters and two carbon-carbon bonds to be generated in a tandem, one-pot reaction to give aldol products, e.g. V (R = Ph, allyl). The experimental procedure involved many compounds, such as (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.SDS of cas: 201732-49-2

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis