20S proteasome as novel biological target for organochalcogenanes

Piovan, Leandro; Milani, Priscila; Silva, Márcio S.; Moraes, Patrícia G.; Demasi, Marilene; Andrade, Leandro H.

doi:10.1016/j.ejmech.2013.12.011

Cited by 24 publications

(23 citation statements)

References 40 publications

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“…Furthermore, compounds containing chalcogen atoms have demonstrated a wide scope of pharmacological activities . Thus, the use of chiral organochalcogen compounds represents a great opportunity for increasing the range of synthetic intermediates and bioactive compounds . Among the methods used to obtain chiral chalcogen containing secondary alcohols, biocatalytic methods have exhibited a high effectivity …”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16] Thus, the use of chiral organochalcogen compounds represents a great opportunity for increasing the range of synthetic intermediates 17 and bioactive compounds. 18 Among the methods used to obtain chiral chalcogen containing secondary alcohols, biocatalytic methods have exhibited a high effectivity. 19 Considering the importance of organochalcogen compounds and secondary alcohol derivatives, and due to the possibility of exploring 77 Se and 125 Te NMR spectroscopy to study chirality, we report a method for NMR chiral discrimination and NMR assignment of the absolute configuration of chalcogen containing secondary alcohols.…”

Section: Introductionmentioning

confidence: 99%

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NMR chiral discrimination of chalcogen containing secondary alcohols

et al. 2018

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Here, we report the general strategies by which NMR spectroscopy can be used to determine the enantiopurity and absolute configuration of chalcogen containing secondary alcohols, including the evaluation of the use of chiral solvating and chiral derivatizing agents. The BINOL/DMAP ternary complex demonstrated a simple and fast protocol for determining enantiopurity. The drug Naproxen afforded a stable, nonhygroscopic, and readily available chiral derivatizing agent (CDA) for NMR chiral discrimination of chalcogen containing secondary alcohols. The chiral recognition by CDA and chiral solvating agent (CSA) was assessed using 1H, 77Se‐{1H}, and 125Te‐{1H} NMR spectroscopy. A simple model for the assignment of the absolute configuration from NMR data is presented.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

NMR chiral discrimination of chalcogen containing secondary alcohols

et al. 2018

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“…Since the discovery of selenium as a component of glutathione peroxidase [1,2] and of the 21 st amino acid, selenocysteine [3,4], selenium compounds have been increasingly investigated as potential therapeutic agents against a range of diseases [5][6][7][8][9][10]. Due to the chemical similarities to tellurium, selenium's heavier congener, tellurium compounds have also attracted interest in the pharmaceutical context [11,12].…”

Section: Introductionmentioning

confidence: 99%

Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes

Caracelli

Maganhi

Cardoso

et al. 2017

Zeitschrift Für Kristallographie - Crystalline Materials

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Abstract. The molecular structures of the halotelluroxetanes pMeOC6H4Te(X)[C(=C(H)Xꞌ)C(CH2)nO], X = Xꞌ = Cl and n = 6 (1) and X = Cl, Xꞌ = Br and n = 5 (4), show similar binuclear aggregates sustained by { … Te-O}2 cores comprising covalent Te-O and secondary Te⋯O interactions. The resulting C2ClO2(lone-pair) sets define pseudo-octahedral geometries. In each structure, C-X⋯(arene) interactions lead to supramolecular layers. Literature studies have shown these and related compounds (i.e. 2: X = Xꞌ = Cl and n = 5; 3: X = Xꞌ = Br and n = 5) to inhibit Cathepsins B, K, L and S to varying extents. Molecular docking calculations have been conducted on ligands (i.e. cations derived by removal of the telluriumbound X atoms) 1ꞌ-3ꞌ (note 3ꞌ = 4ꞌ) enabling correlations between affinity for sub-sites and inhibition. The common feature of all docked complexes was the formation of a Te-S covalent bond with cysteine residues, the relative stability of the ligands with an E-configuration and the formation of a C-O … π interaction with the phenyl ring; for 1ꞌ the Te-S covalent bond was weak, a result correlating with its low inhibition profile. At the next level differences are apparent, especially with respect to the interactions formed by the organic-ligand-bound halides.

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“…So, complement stability assays for some representative compounds were also performed using 125 Te NMR as analytical tool. Initially, the thermal stability of LQ02 in [D 6 ]DMSO was investigated at temperatures ranging from 25 to 65 °C [9h,25a] . The results obtained by 125 Te NMR are described in Figure 10, in which no significant changes in chemical shifts were observed, demonstrating the thermal stability of the studied organotellurane.…”

Section: Resultsmentioning

confidence: 98%

Synthesis, Mechanism Elucidation and Biological Insights of Tellurium(IV)‐Containing Heterocycles

Souza

Menezes

Garcia

et al. 2021

Chemistry A European J

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Inspired by the synthetic and biological potential of organotellurium substances, a series of five-and six-membered ring organotelluranes containing a TeÀ O bond were synthesized and characterized. Theoretical calculations elucidated the mechanism for the oxidation-cyclization processes involved in the formation of the heterocycles, consistent with chlorine transfer to hydroxy telluride, followed by a cyclization step with simultaneous formation of the new TeÀ O bond and deprotonation of the OH group. Moreover, theoretical calculations also indicated anti-diastereoisomers to be major products for two chirality center-containing compounds. Antileishmanial assays against Leishmania amazonensis promastigotes disclosed 1,2λ 4 -oxatellurane LQ50 (IC 50 = 4.1 � 1.0; SI = 12), 1,2λ 4 -oxatellurolane LQ04 (IC 50 = 7.0 � 1.3; SI = 7) and 1,2λ 4 -benzoxatellurole LQ56 (IC 50 = 5.7 � 0.3; SI = 6) as more powerful and more selective compounds than the reference, being up to four times more active. A stability study supported by 125 Te NMR analyses showed that these heterocycles do not suffer structural modifications in aqueousorganic media or at temperatures up to 65 °C.

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20S proteasome as novel biological target for organochalcogenanes

Cited by 24 publications

References 40 publications

NMR chiral discrimination of chalcogen containing secondary alcohols

NMR chiral discrimination of chalcogen containing secondary alcohols

Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes

Synthesis, Mechanism Elucidation and Biological Insights of Tellurium(IV)‐Containing Heterocycles

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