Synthesis, characterization, structures and GPx mimicking activity of pyridyl and pyrimidyl based organoselenium compounds

Hodage, Ananda S.; Prabhu, C.; Phadnis, Prasad P.; Wadawale, Amey; Priyadarsini, K. Indira; Jain, Vimal K.

doi:10.1016/j.jorganchem.2012.08.035

Cited by 41 publications

(21 citation statements)

References 50 publications

(43 reference statements)

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“…The compounds, 2-bromopyrimidine, 2-chloro-4,6-dimethylpyrimidine [26], [M(PPh 3 ) 4 ], (M ¼ Pd [27], Pt [28]), [MCl 2 (P X P)] [P X P ¼ dppm (bis(diphenylphosphino) methane), dppe (1,2-bis(diphenylphosphino)ethane), dppp (1,3-bis(diphenylphosphino)propane)] [29,30] and the ligands (SeC 4 H 3 N 2 ) 2 [31], {SeC 4 H(4,6-Me) 2 N 2 } 2 and {TeC 4 H(4,6-R) 2 N 2 } 2 were prepared by literature methods. All syntheses were carried out under a nitrogen atmosphere in dry solvents.…”

Section: Methodsmentioning

confidence: 99%

Reactivity of dipyrimidyldiselenides with [M(PPh3)4] and 2-pyrimidylchalcogenolates with [MCl2(diphosphine)] (M = Pd or Pt)

Chauhan

Sharma

Kedarnath

et al. 2012

Journal of Organometallic Chemistry

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Section: Methodsmentioning

confidence: 99%

Reactivity of dipyrimidyldiselenides with [M(PPh3)4] and 2-pyrimidylchalcogenolates with [MCl2(diphosphine)] (M = Pd or Pt)

Chauhan

Sharma

Kedarnath

et al. 2012

Journal of Organometallic Chemistry

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“…Hodage et al have clearly summarized the strategies for the design of efficient Se-based catalysts: i) organoselenium compounds containing -OH, -NH 2 and -COOH groups are active; ii) diselenides are more active than the corresponding monoselenides; iii) diselenides showing weak secondary intramolecular interactions (Se•••X with X=O or N) show good activity; iv) diselenides containing heterocyclic rings are better catalysts than compounds bearing simple aryl groups [161].…”

Section: Low Molecular Weight Gpx Mimics: Experi-mental Modelsmentioning

confidence: 99%

“…Wilson et al reported a spectrophotometrical method based on the quantification of NADPH, used as a cofactor by glutathione reductase to transform GSSG to GSH [154]. Another widely used method involves thiobenzene (PhSH) as substrate and H 2 O 2 as the oxidant [145,161] 1 . The reaction between the thiol and H 2 O 2 is easily followed using UV, HPLC and/or NMR, and several modifications to the experimental protocol, e.g.…”

Section: Testing the Gpx-like Activity Of Diselenides: Experimental Mmentioning

confidence: 99%

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Tiezza¹,

Ribaudo

Orian³

2019

COC

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Organodiselenides are an important class of compounds characterized by the presence of two adjacent covalently bonded selenium nuclei. Among them, diaryldiselenides and their parent compound diphenyl diselenide attract continuing interest in chemistry as well as in close disciplines like medicinal chemistry, pharmacology and biochemistry. A search in SCOPUS database has revealed that in the last three years 105 papers have been published on the archetypal diphenyl diselenide and its use in organic catalysis and drug tests. The reactivity of the Se-Se bond and the redox properties of selenium make diselenides efficient catalysts for numerous organic reactions, such as Bayer- Villiger oxidations of aldehydes/ketones, epoxidations of alkenes, oxidations of alcohols and nitrogen containing compounds. In addition, organodiselenides might find application as mimics of glutathione peroxidase (GPx), a family of enzymes, which, besides performing other functions, regulate the peroxide tone in the cells and control the oxidative stress level. In this review, the essential synthetic and reactivity aspects of organoselenides are collected and rationalized using the results of accurate computational studies, which have been carried out mainly in the last two decades. The results obtained in silico provide a clear explanation of the anti-oxidant activity of organodiselenides and more in general of their ability to reduce hydroperoxides. At the same time, they are useful to gain insight into some aspects of the enzymatic activity of the GPx, inspiring novel elements for rational catalyst and drug design.

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“…Pyridine is an important chemical form present in several of biological molecules like vitamin, nucleic acid, etc. Additionally, it has been shown that diselenides containing heterocyclic ring (e.g., pyridine) are better catalysts than the compounds containing simple aryl groups e.g., diphenyl diselenide (Ph2Se2) [5,6]. On similar lines, we have recently reported the synthesis, purification, structure and biological activities of dipyridine diselenide (Py2Se2) and its amide derivative dinioctinamide diselenide (Nic2Se2) [5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Paradoxical Behavior of Organodiselenides: Pro-Oxidant to Antioxidant

Kunwar

2020

The 1st International Electronic Conference on Catalysis Sciences

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Over the years, organodiselenides have emerged as the biologically relevant class of molecules. On one hand, such compounds are known for pro-oxidant effects leading to toxicity in biological systems. On the other hand, there are growing evidences about their bio-mimetic activities as catalysts such as glutathione peroxidase (GPx)-like activity. Our recent work has explored this paradoxical behavior of diselenides in developing antioxidants and/or anticancer agents. For this, a number of alkyl and aryldiselenides have been evaluated in different biological models. The results have shown that aryl diselenides specifically pyridinediselenides alter the ratio of the intracellular thiol redox pairs (GSH and GSSG) towards reduction (antioxidant) rather than oxidation(pro-oxidant) to protect normal cells against radiation damage as well asto induce cytotoxicity in tumor cells. Further, these studies have also postulated that intracellular redox state, level of thioredoxin reductase (TrxR) and reductive intermediates (like selenol and/or selone) might play a very important role in the manifestation of the toxicities of aryl diselenides in cells

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Synthesis, characterization, structures and GPx mimicking activity of pyridyl and pyrimidyl based organoselenium compounds

Cited by 41 publications

References 50 publications

Reactivity of dipyrimidyldiselenides with [M(PPh3)4] and 2-pyrimidylchalcogenolates with [MCl2(diphosphine)] (M = Pd or Pt)

Reactivity of dipyrimidyldiselenides with [M(PPh3)4] and 2-pyrimidylchalcogenolates with [MCl2(diphosphine)] (M = Pd or Pt)

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Paradoxical Behavior of Organodiselenides: Pro-Oxidant to Antioxidant

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