Diselenoamino acid derivatives as GPx mimics and as substrates of TrxR: in vitro and in silico studies

文献信息

发布日期 2018-04-23

DOI 10.1039/C8OB00451J

影响因子 3.876

作者

Pablo Andrei Nogara, Rogério Aquino Saraiva, Caroline Wagner, Eduardo Eliezer Alberto, Antonio Luiz Braga, Roselei Fachinetto, Paulo Cesar Piquini, João Batista Teixeira Rocha

查看原文

摘要

Excessive production of reactive species in living cells usually has pathological effects. Consequently, the synthesis of compounds which can mimic the activity of antioxidant enzymes has inspired great interest. In this study, a variety of diselenoamino acid derivatives from phenylalanine and valine were tested to determine whether they could be functional mimics of glutathione peroxidase (GPx) and substrates for liver thioredoxin reductase (TrxR). Diselenides C and D showed the best GPx mimicking properties when compared with A and B. We suppose that the catalytic activity of diselenide GPx mimics depends on the steric effects, which can be influenced by the number of carbon atoms between the selenium atom and the amino acid residue and/or by the amino acid lateral residue. Compounds C and D stimulated NADPH oxidation in the presence of partially purified hepatic mammalian TrxR, indicating that they are substrates for TrxR. Our study indicates a possible dissociation between the two pathways for peroxide degradation (i.e., via a substrate for TrxR or via mimicry of GPx) for compounds tested in this study, except for PhSeSePh, and the antioxidant activity of diselenoamino acids can also be attributed to their capacity to mimic GPx and to be a substrate for mammalian TrxR.

期刊推荐

Organic Geochemistry

Bulletin of Materials Science

Bioorganic Chemistry

Tetrahedron Letters

Dyes and Pigments

Applied Clay Science

Dental Materials

Applied Surface Science

Journal of Natural Products

Tetrahedron

相关文献

A COVID-19 vaccine candidate composed of the SARS-CoV-2 RBD dimer and Neisseria meningitidis outer membrane vesicles‡

Darielys Santana-Mederos, Rocmira Perez-Nicado, Yanet Climent, Laura Rodriguez, Belinda Sanchez Ramirez, Sonia Perez-Rodriguez, Meybi Rodriguez, Claudia Labrada, Tays Hernandez, Marianniz Diaz, Ivette Orosa, Ubel Ramirez, Reynaldo Oliva, Raine Garrido, Felix Cardoso, Mario Landys, Roselyn Martinez, Humberto Gonzalez, Tamara Hernandez, Rolando Ochoa-Azze, Jose L. Perez, Juliet Enriquez, Nibaldo Gonzalez, Yenicet Infante, Luis A. Espinosa, Yassel Ramos, Luis Javier González, Carmen Valenzuela, Ana Victoria Casadesus, Briandy Fernandez, Gertrudis Rojas, Beatriz Pérez-Massón, Yaima Tundidor, Ernesto Bermudez, Claudia A. Plasencia, Tammy Boggiano, Eduardo Ojito, Sonsire Fernandez, Françoise Paquet, Cheng Fang, Guang-Wu Chen, Daniel G. Rivera, Yury Valdes-Balbin, Dagmar Garcia-Rivera, Vicente Verez Bencomo

2021-12-08 Paper

DOI: 10.1039/D1CB00200G

What's all the phos about? Insights into the phosphorylation state of the RNA polymerase II C-terminal domain via mass spectrometry

Blase M. LeBlanc, R. Yvette Moreno, Edwin E. Escobar, Mukesh Kumar Venkat Ramani, Jennifer S. Brodbelt

2021-06-03 Review Article

DOI: 10.1039/D1CB00083G

Biosynthesis of alkyne-containing natural products

Xinyang Li, Jian-Ming Lv, Dan Hu

2020-12-21 Review Article

DOI: 10.1039/D0CB00190B

Synthesis and preliminary evaluation of octreotate conjugates of bioactive synthetic amatoxins for targeting somatostatin receptor (sstr2) expressing cells

Alla Pryyma, Kaveh Matinkhoo, Yong Jia Bu, Helen Merkens, Zhengxing Zhang, Francois Bénard, David M. Perrin

2021-10-07 Paper

DOI: 10.1039/D1CB00036E

Targeting a conserved structural element from the SARS-CoV-2 genome using l-DNA aptamers

Jing Li, Jonathan T. Sczepanski

2021-10-20 Paper

DOI: 10.1039/D1CB00172H

Metathramycin, a new bioactive aureolic acid discovered by heterologous expression of a metagenome derived biosynthetic pathway

Liwei Liu

2021-02-02 Paper

DOI: 10.1039/D0CB00228C

Targeting the RNA demethylase FTO for cancer therapy

2021-07-26 Review Article

DOI: 10.1039/D1CB00075F

Optogenetic modulation of real-time nanoscale dynamics of HCN channels using photoactivated adenylyl cyclases

Meenakshi Tanwar, Suneel Kateriya, Deepak Nair, Mini Jose

2021-03-08 Paper

DOI: 10.1039/D0CB00124D

In vivo delivery of a fluorescent FPR2/ALX-targeted probe using focused ultrasound and microbubbles to image activated microglia

Sophie V. Morse, Tamara Boltersdorf, Felicity N. E. Gavins, James J. Choi, Nicholas J. Long

2020-09-23 Communication

DOI: 10.1039/D0CB00140F

Contents list

2021-12-02 Front/Back Matter

DOI: 10.1039/D1CB90034J

来源期刊

Organic & Biomolecular Chemistry

CiteScore: 3.4

自引率: 10.3%

年发文量: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Diselenoamino acid derivatives as GPx mimics and as substrates of TrxR: in vitro and in silico studies

文献信息

期刊推荐

相关文献

A COVID-19 vaccine candidate composed of the SARS-CoV-2 RBD dimer and Neisseria meningitidis outer membrane vesicles‡

What's all the phos about? Insights into the phosphorylation state of the RNA polymerase II C-terminal domain via mass spectrometry

Biosynthesis of alkyne-containing natural products

Synthesis and preliminary evaluation of octreotate conjugates of bioactive synthetic amatoxins for targeting somatostatin receptor (sstr2) expressing cells

Targeting a conserved structural element from the SARS-CoV-2 genome using l-DNA aptamers

Metathramycin, a new bioactive aureolic acid discovered by heterologous expression of a metagenome derived biosynthetic pathway

Targeting the RNA demethylase FTO for cancer therapy

Optogenetic modulation of real-time nanoscale dynamics of HCN channels using photoactivated adenylyl cyclases

In vivo delivery of a fluorescent FPR2/ALX-targeted probe using focused ultrasound and microbubbles to image activated microglia

Contents list

您可能还喜欢

4-[[6-（3-苯基苯基）-7H-嘌呤-2-基]氨基]苯磺酰胺(CAS号：2079895-42-2)适用哪些法规指南？

反式-度骨化醇(CAS号：74007-20-8)的物理化学性质是什么？

莲花掌苷(CAS号：59282-56-3)的市场或研究趋势如何？

2-溴-6-(吡咯烷-1-基)吡啶-4-硼酸频那醇酯(CAS号：1150271-64-9)应用于哪些行业？

什么是methyl 2-(4-bromophenyl)-3-methylbutanoate(CAS号：1061284-70-5)？

CJC1-295(CAS号：863288-34-0)的物理化学性质是什么？

三正丁基锍碘(CAS号：18146-62-8)的市场或研究趋势如何？

雌二醇-[13C3]同位素内标(CAS号：1261254-48-1)通常如何合成？

N1-(2-吡啶甲基)-N2-(2-甲基-1-萘基)草酰胺(CAS号：2611225-93-3)的物理化学性质是什么？

如何处理含有十五碳烯酸甲酯(顺-10)(C15:1)标准品(CAS号：90176-52-6)的废料？

来源期刊

Organic & Biomolecular Chemistry

推荐化合物

Potassium phosphate hydrate (3:1:1)

1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione

Cyclohexylmagnesium Bromide

Chloromethyl ethyl carbonate

Methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate

推荐供应商