Sulfur, selenium and tellurium containing amines act as effective carbonic anhydrase activators

Tanini, Damiano; Capperucci, Antonella; Supuran, Claudiu T.

doi:10.1016/j.bioorg.2019.03.062

Cited by 42 publications

(31 citation statements)

References 44 publications

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“…As stated above, a number of organotellurium compounds have been employed as glutathione−peroxidase (GPx) mimics, being often capable to efficiently reduce harmful hydrogen peroxide to water by using thiols as co‐substrate. In this context, the GPx‐like activity of O‐, N‐, and S‐containing dialkyl‐ and aryl−alkyl tellurides has been recently reported . However, the catalytic antioxidant activity of homologous functionalised ditellurides remained unexplored, mainly because of the lack of methodologies for their synthesis.…”

Section: Resultsmentioning

confidence: 99%

“…A tellurium-mediated S N 2X-type mechanism presumably accounts for this process. [28] This on water methodology was also amenable to Michael acceptors, thus providing a simple and direct access to novel functionalised tellurides ( Table 1, entries [13][14][15][16]. Indeed, tellurium-containing bis-ester 6 a, bis-nitrile 6 b, and bis-sulfone 6 c were smoothly achieved through a clean unprecedented telluro-Michael addition of Na 2 Te to electron-deficient alkenes, such as methyl acrylate, acrylonitrile, and phenyl vinyl sulfone.…”

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

“…In this context, the GPx-like activity of O-, N-, and Scontaining dialkyl-and arylÀ alkyl tellurides has been recently reported. [9b, 13,38] However, the catalytic antioxidant activity of homologous functionalised ditellurides remained unexplored, mainly because of the lack of methodologies for their synthesis. Therefore, having developed a route to access unreported substituted ditellurides, their thiolÀ peroxidase-like activity was next pursued in order to compare their catalytic properties with those of structurally related functionalised tellurides.…”

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

“…In addition, the promising catalytic and pharmacological properties of O‐ and N‐containing organochalcogenides have prompted researchers to design and synthesise novel functionalised organochalcogenides . Suitably substituted β‐hydroxy‐ and β‐amino‐ tellurides were demonstrated to be excellent mimics of GPx and also exhibited remarkable activity as carbonic anhydrase activators and inhibitors…”

Section: Introductionmentioning

confidence: 99%

“…In addition, the promising catalytic and pharmacological properties of O-and Ncontaining organochalcogenides have prompted researchers to design and synthesise novel functionalised organochalcogenides. [9,12] Suitably substituted βhydroxy-and β-amino-tellurides were demonstrated to be excellent mimics of GPx [9b,c,f] and also exhibited remarkable activity as carbonic anhydrase activators [13] and inhibitors. [14] However, while diaryl-ditellurides [15] and diaryl or arylÀ alkyl-tellurides [16] have been widely studied, dialkyl substituted analogues have been far less explored and the development of a general and convenient route towards functionalised organotellurides would be highly desirable.…”

Section: Introductionmentioning

confidence: 99%

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Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

2020

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The on water reaction of sodium telluride with electrophiles has been explored. Na2Te, generated in situ through the rongalite (sodium hydroxymethanesulfinate)‐promoted reduction of elemental tellurium, reacts with a wide variety of electrophiles, including strained heterocycles, haloalkanes, Michael acceptors, and aryl diazonium salts, providing simple and rapid access to a broad range of novel functionalised symmetrical tellurides. The methodology well tolerated the presence of versatile functional groups such as alchohols, amines, esters, nitriles, and sulfones and allowed the incorporation of tellurium atoms into biologically relevant natural‐derived products. Furthermore, in the case of the nucleophilic ring opening of epoxides and aziridines, a judicious tuning of the reaction conditions enabled the synthesis of unreported β‐hydroxy‐ and β‐amino‐ditellurides, which were further employed as precursors of new functionalised unsymmetrical dialkyl tellurides. The thiol−peroxidase catalytic activity of hydroxy‐ditellurides has also been investigated in order to compare their antioxidant properties with those of homologous tellurides.

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Section: Resultsmentioning

confidence: 99%

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

2020

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Synthesis and Applications of Organic Selenols

Tanini

Capperucci

2021

Adv Synth Catal

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The synthesis and the study of organoselenium compounds have received much attention over the past decades. Selenium-containing organic molecules are widely used in organic synthesis, materials science, and medicinal chemistry. Selenium -and more specifically the amino acid selenocysteine, bearing a selenol (SeH) moiety -is present in at least 25 human protein families, whose biological functions have not been completely identified. Amongst the variety of organoselenium compounds, selenols are a versatile class of molecules easily undergoing a broad array of useful transformations. Because of the unique properties of the SeH group, selenol chemistry has important applications in chemical sciences, spanning from organic synthesis to materials chemistry and biology. This review summarises currently available methodologies for the synthesis of selenols and highlights applications of selenols in chemical sciences and biology. Conclusions and Outlook 5.1. Safety Measures

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Unveiling tomorrow: Carbonic anhydrase activators and inhibitors pioneering new frontiers in Alzheimer's disease

Mishra,

Sethi

2024

Archiv der Pharmazie

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Alzheimer's disease (AD) is a neurodegenerative disorder and a principal basis of dementia in the elderly population globally. Recently, human carbonic anhydrases (hCAs, EC 4.2.1.1) were demonstrated as possible new targets for treating AD. hCAs are vital for maintaining pH balance and performing other physiological processes as they catalyze the reversible hydration of carbon dioxide to bicarbonate and a proton. Current research indicates that hCA plays a role in brain functions critical for transmitting neural signals. Activation of carbonic anhydrase (CA) has emerged as a promising avenue in addressing memory loss and cognitive issues. Conversely, the exploration of CA inhibition represents a novel frontier in this field. By enhancing glial fitness and cerebrovascular health and blocking amyloid‐β (Aβ)‐induced mitochondrial dysfunction pathways, cytochrome C (CytC) release, caspase 9 activation, and H2O2 generation in neurons, CA inhibitors improve cognition and lessen the pathology caused by Aβ. Recent research has pushed hCAs into the spotlight as critical players in AD pathogenesis and precise therapeutic targets. The captivating dilemma of choosing between hCA inhibitors and activators looms large, as inhibitors reduce Aβ aggregation and improve cerebral blood flow, while activators enhance cerebrovascular functions and restore pH balance. The current review sheds light on the clinical evidence for hCAs and the roles of inhibitors and activators in AD. Additionally, this review offers a fascinating outlook on the data that may aid medicinal chemists in designing and developing new leads that are more effective and selective for upcoming in vitro and in vivo studies, allowing for the discovery and introduction of novel drug candidates for the treatment of AD to the market and into the clinical pipeline.

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Sulfur, selenium and tellurium containing amines act as effective carbonic anhydrase activators

Cited by 42 publications

References 44 publications

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Synthesis and Applications of Organic Selenols

Unveiling tomorrow: Carbonic anhydrase activators and inhibitors pioneering new frontiers in Alzheimer's disease

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