Day: September 16, 2022

Lamarche, J.;Bierla, K.;Ouerdane, L.;Szpunar, J.;Ronga, L.;Lobinski, R. published 《Mass spectrometry insights into interactions of selenoprotein P with auranofin and cisplatin》 in 2022. The article was appeared in 《Journal of Analytical Atomic Spectrometry》. They have made some progress in their research.Formula: C20H36AuO9PS The article mentions the following:

The reactivity of selenoprotein P (a serum selenoprotein containing 10 selenocysteine (SeCys), 17 cysteine (Cys) and 14 histidine (His) residues) with two metallodrugs (auranofin and cisplatin) was investigated. The selenoprotein was purified from human serum by sequential affinity chromatog. using immobilized metal (Co2+) affinity chromatog. (IMAC) and heparine affinity, followed by solid-phase extraction preconcentration The purified selenoprotein P was sequenced by nanoLC-MS/MS to reach a complete sequence coverage. It eluted from SEC as two major peaks likely to correspond to the glycosylated and non-glycosylated forms and a minor one, probably a truncated form. Size-exclusion chromatog. with the selective Se (78Se) and metal (197Au or 195Pt) detection by ICP MS showed the co-elution of selenoprotein P forms with Au and with Pt. SEC-ICP MS of the tryptic digest showed a considerable shift of the elution of selenium towards the lower mol. masses while preserving the co-elution of selenium and the metal at some elution times. NanoHPLC – electrospray MS/MS anal. of the post-reaction mixture demonstrated the formation of peptides with the privileged binding to Cys and His residues for cisplatin and SeCys and Cys residues for auranofin. 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.Formula: C20H36AuO9PS

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rimkus, Audrius;Sewald, Norbert published 《First Synthesis of a β²-Homoamino Acid by Enantioselective Catalysis》. The research results were published in《Organic Letters》 in 2003.Formula: C38H34NO2P The article conveys some information:

The enantioselective conjugate addition of diethylzinc to the activated nitroolefin Me 3-nitropropenoate is efficiently catalyzed by copper(I) complexes with BINOL-based enantiopure phosphoramidite ligands. The nitroolefin moiety acts as the predominant Michael acceptor, giving rise to the unambiguous formation of Me 2-ethyl-3-nitropropanoate. Moderate to excellent enantioselectivities and high chem. yields are obtained. The product can easily be transformed into a β²-homoamino acid, 2-[(tert-butoxycarbonyl)aminomethyl]butanoic acid. And (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) was used in the research process.

(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.Formula: C38H34NO2P

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Proetto, Maria T.;Alexander, Kelsey;Melaimi, Mohand;Bertrand, Guy;Gianneschi, Nathan C. published 《Cyclic (Alkyl)(Amino)Carbene (CAAC) Gold(I) Complexes as Chemotherapeutic Agents》 in 2021. The article was appeared in 《Chemistry – A European Journal》. 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:

Cyclic (Alkyl)(Amino)Carbenes (CAACs) have become forceful ligands for gold due to their ability to form very strong ligand-metal bonds. Inspired by the success of Auranofin and other gold complexes as antitumor agents, we have studied the cytotoxicity of bis- and mono-CAAC-gold complexes on different cancer cell lines: HeLa (cervical cancer), A549 (lung cancer), HT1080 (fibrosarcoma) and Caov-3 (ovarian cancer). Further investigations aimed at elucidating their mechanism of action are described. This includes quantification of affinities for TrxR, evaluation of their bioavailability and determination of associated cell death process. Moreover, Transmission Electron Microscopy (TEM) was used to study morphol. changes upon exposure. Noticeably, a significant reduction in non-specific binding to serum proteins was observed with CAAC complexes when compared to Auranofin. These results confirm the potential of CAAC-gold complexes in biol. environments, which may result in more specific drug-target interactions and decreased side effects. 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

Meng, Fanke;Haeffner, Fredrik;Hoveyda, Amir H. published 《Diastereo- and enantioselective reactions of bis(pinacolato)diboron, 1,3-enynes, and aldehydes catalyzed by an easily accessible bisphosphine-Cu complex》 in 2014. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.Reference of (R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl The article mentions the following:

Catalytic enantioselective multicomponent processes involving bis(pinacolato)diboron B₂(pin)₂, 1,3-enynes RCCCH:CH₂ (R = Ph, aryl, 3-thienyl, 1-cyclohexenyl, TIPSOCMe₂, Et₃Si), and aldehydes R¹CHO (R¹ = aryl, 3-benzo[b]thienyl, cinnamyl, cyclohexenyl, PhCH₂CH₂) resulting in chiral bis(homopropargyl) diols R¹CH(OH)CH(CH₂OH)CCR are disclosed; the resulting compounds contain a primary C-B(pin) bond, as well as alkyne- and hydroxyl-substituted tertiary carbon stereogenic centers. A critical feature is the initial enantioselective Cu-B(pin) addition to an alkyne-substituted terminal alkene. This and other key mechanistic issues have been investigated by DFT calculations Reactions are promoted by the Cu complex of a com. available enantiomerically pure bis-phosphine and are complete in 8 h at ambient temperature; products are generated in 66-94% yield (after oxidation or catalytic cross-coupling), 90:10 to >98:2 diastereomeric ratio, and 85:15-99:1 enantiomeric ratio. Aryl-, heteroaryl-, alkenyl-, and alkyl-substituted aldehydes and enynes can be used. Utility is illustrated through catalytic alkylation and arylation of the organoboron products as well as applications to synthesis of fragments of tylonolide and mycinolide IV.(R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl (cas: 1365531-84-5) were involved in the experimental procedure.

(R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl(cas: 1365531-84-5) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Reference of (R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Massai, Lara;Cirri, Damiano;Marzo, Tiziano;Messori, Luigi published 《Auranofin and its analogs as prospective agents for the treatment of colorectal cancer》. The research results were published in《Cancer Drug Resistance》 in 2022.Application of 34031-32-8 The article conveys some information:

A review. Today colorectal cancer (CRC) is one of the leading causes of cancer death worldwide. This disease is poorly chemo-sensitive toward the existing medical treatments so that new and more effective therapeutic agents are urgently needed and intensely sought. Platinum drugs, oxaliplatin in particular, were reported to produce some significant benefit in CRC treatment, triggering the general interest of medicinal chemists and oncologists for metal-based compounds as candidate anti-CRC drugs. Within this frame, gold compounds and, specifically, the established antiarthritic drug auranofin with its analogs, form a novel group of promising anticancer agents. Owing to its innovative mechanism of action and its favorable pharmacol. profile, auranofin together with its derivatives are proposed here as novel exptl. agents for CRC treatment, capable of overcoming resistance to platinum drugs. Some encouraging results in this direction have already been obtained. A few recent studies demonstrate that the action of auranofin may be further potentiated through the preparation of suitable pharmaceutical formulations capable of protecting the gold pharmacophore from unselective reactivity or through the design of highly synergic drug combinations. The perspectives of the research in this field are outlined. 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.Application of 34031-32-8

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Lloyd-Jones, Guy C.;Butts, Craig P. published 《Nickel(II) complexes bearing (phosphinoaryl)oxazoline ligands as pro-catalysts for Grignard cross-coupling》. The research results were published in《Tetrahedron》 in 1998.Synthetic Route of C25H26NOP The article conveys some information:

Ni(II) complexes bearing chiral (phosphinoaryl)oxazoline ligands, e.g., I, are pro-catalysts for cross-coupling of (Z)-styryl bromide with (1-phenylethyl)magnesium chloride. Under suitable conditions, there is a dynamic kinetic resolution resulting in moderate enantioselectivity. The nature of the substituent at the stereogenic center of the oxazoline ligand affects catalysis in two distinct ways: smaller substituents lead to improved rates and selectivities while polar substituents reverse the sense of asym. induction. The solid state structure of one [(phosphinoaryl)oxazoline]nickel(II) pro-catalyst was determined by single crystal x-ray diffraction. To complete the study, the researchers used (S)-2-(2-(Diphenylphosphanyl)phenyl)-4-isobutyl-4,5-dihydrooxazole (cas: 167693-62-1) .

(S)-2-(2-(Diphenylphosphanyl)phenyl)-4-isobutyl-4,5-dihydrooxazole(cas: 167693-62-1) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Synthetic Route of C25H26NOP

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Related Products of 34031-32-8In 2021, Wall, Stephanie B.;Li, Rui;Butler, Brittany;Burg, Ashley R.;Tse, Hubert M.;Larson-Casey, Jennifer L.;Carter, A. Brent;Wright, Clyde J.;Rogers, Lynette K.;Tipple, Trent E. published 《Auranofin-mediated NRF2 induction attenuates interleukin 1 beta expression in alveolar macrophages》. 《Antioxidants》published the findings. The article contains the following contents:

Background: Alveolar macrophages (AMs) are resident inflammatory cells in the lung that serve as early sentinels of infection or injury. We have identified thioredoxin reductase 1 inhibition by gold compounds increases activation of nuclear factor erythroid 2-related factor 2 (NRF2)-dependent pathways to attenuate inflammatory responses. The present studies utilized murine alveolar macrophages (MH-S) to test the hypothesis that the gold compound, auranofin (AFN), decreases interleukin (IL)-1β expression through NRF2-mediated interactions with nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) pathway genes and/or increases in glutathione synthesis. Methods: MH-S cells were treated with AFN and lipopolysaccharide (LPS) and analyzed at 6 and 24 h. The Il1b promoter was analyzed by chromatin immunoprecipitation for direct interaction with NRF2. Results: Expression of IL-1β, p-IκBα, p-p65 NF-kB, and NOD-, LRR-, and pyrin domain-containing protein 3 were elevated by LPS exposure, but only IL-1β expression was suppressed by AFN treatment. Both AFN and LPS treatments increased cellular glutathione levels, but attenuation of glutathione synthesis by buthionine sulfoximine (BSO) did not alter expression of Il-1β. Anal. revealed direct NRF2 binding to the Il1b promoter which was enhanced by AFN and inhibited the transcriptional activity of DNA polymerase II. Conclusions: Our data demonstrate that AFN-induced NRF2 activation directly suppresses IL-1β synthesis independent of NFκB and glutathione-mediated antioxidant mechanisms. NRF2 binding to the promoter region of IL1β directly inhibits transcription of the IL1β gene. Collectively, our research suggests that gold compounds elicit NRF2-dependent pulmonary protection by suppressing macrophage-mediated inflammation. 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 gold(I)-phosphine thiolate small molecule described to produce antiinflammatory and antiarthritic effects.Related Products of 34031-32-8

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rimkus, Audrius;Sewald, Norbert published 《Conjugate addition of organozinc compounds to nitroolefins》. The research results were published in《Synthesis》 in 2004.Recommanded Product: (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:

Sym. R¹₂Zn [R¹ = Et, NC(CH₂)₃, EtO₂C(CH₂)₃, etc.] or mixed diorganozinc compounds R¹ZnR² (R¹ = n-Bu, cyclohexyl, n-heptyl, etc.; R² = Me₃SiCH₂) smoothly react with a series of nitroolefins R³CH:CR⁴NO₂ [R³ = Ph, MeO₂C, (MeO)₂CH, R⁴ = H; R³ = EtO₂C, R⁴ = Me, Et] in the presence of catalytic amounts of copper(I) salts to provide synthetically versatile nitro compounds R¹R³CHCHR⁴NO₂ in moderate to good yields without racemization (when R¹ is chiral). Simple alkyl groups, functionalized residues, or mixed trimethylsilylmethyl (TMSM) organozinc compounds may be employed for conjugate addition, while the TMSM group is not being transferred. Ipso-Substitution is observed in absence of the copper(I) salt. Enantiomerically pure copper(I) complexes with BINOL based chiral phosphoramidite ligands efficiently catalyze the addition of dialkylzinc compounds to nitroalkenes. In nitro acrylates, the nitroolefin moiety acts as the more powerful Michael acceptor compared to the acrylate moiety. The products can easily be transformed into β²-homoamino acids, compounds of high relevance for different areas of preparative organic chem. And (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) was used in the research process.

(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.Recommanded Product: (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

Evans, Andris;Kavanagh, Kevin A. published 《Evaluation of metal-based antimicrobial compounds for the treatment of bacterial pathogens》 in 2021. The article was appeared in 《Journal of Medical Microbiology》. They have made some progress in their research.Name: ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold The article mentions the following:

A review. Antimicrobial resistance (AMR) is one of the greatest global health challenges of modern times and its prevalence is rising worldwide. AMR within bacteria reduces the efficacy of antibiotics and increases both the morbidity and the mortality associ- ated with bacterial infections. Despite this growing risk, few antibiotics with a novel mode of action are being produced, leading to a lack of antibiotics that can effectively treat bacterial infections with AMR. Metals have a history of antibacterial use but upon the discovery of antibiotics, often became overlooked as antibacterial agents. Meanwhile, metal-based complexes have been used as treatments for other diseases, such as the gold-containing drug auranofin, used to treat rheumatoid arthritis. Metal-based antibacterial compounds have novel modes of action that provide an advantage for the treatment of bacterial infections with resistance to conventional antibiotics. In this review, the antibacterial activity, mode of action, and potential for systemic use of a number of metal-based antibacterial complexes are discussed. The current limitations of these compounds are highlighted to determine if metal-based agents are a potential solution for the treatment of bacterial infections, especially those resistant to conventional antibiotics. 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 potent inhibitor of selenoenzyme thioredoxin reductase (TrxR), which is involved in defense against oxidative stress.Name: ((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

Formula: C20H36AuO9PS《Inhibition of thioredoxin reductase (TrxR) triggers oxidative stress-induced apoptosis in filarial nematode Setaria cervi channelized through ASK-1-p38 mediated caspase activation》 was published in 2021. The authors were Joardar, Nikhilesh;Sen, Animesh;Rath, Jnanendra;Babu, Santi P. Sinha, and the article was included in《Molecular & Biochemical Parasitology》. The author mentioned the following in the article:

Inhibition of an imperative antioxidant enzyme with subsequent death is a victorious and widely accepted strategy to combat various infectious diseases. Among different antioxidant enzymes, thioredoxin reductase (TrxR) is an exclusive one. Studies have revealed that direct inhibition of TrxR by different classes of chem. moieties promptly results in the death of an organism. Especially the structural as well as biochem. modifications of the enzyme upon inhibition project serious threat towards the subject organism. Herein, an attempt was made to inhibit TrxR of filarial species by administering Auranofin, 1 chloro 2,4 dinitrobenzene (CDNB), Curcumin, and a novel carbamo dithioperoxo(thioate) derivative (4a). Our study has revealed that inhibition of TrxR resulted in the induction of the classical CED pathway of apoptosis along with the intrinsic and extrinsic pathways of apoptosis (Caspase mediated) routed through the ASK-1/p38 axis. Druggability anal. of filarial TrxR for the selected compounds was performed in silico through mol. docking studies. Therefore, this study attempts to decipher the mechanism of apoptosis induction following TrxR inhibition. The safety of those four compounds in terms of dose and toxicity was taken under consideration. Thitherto, the mechanism of TrxR mediated initiation of cell death in filarial parasite has remained undercover, and therefore, it is a maiden report on the characterization of apoptosis induction upon TrxR inhibition which will eventually help in generating effective antifilarial drugs in the future. 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.Formula: C20H36AuO9PS

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis