New synthetic derivatives of isoindoline-dione: synthesis, neuroprotection assay and impact on the expression level of oxidative stress-related genes in neuronal-like cell line

References

• Hou Y, Dan X, Babbar M, et al. Ageing as a risk factor for neurodegenerative disease. Nat Rev Neurol. 2019;15(10):565–581. doi:10.1038/s41582-019-0244-7.
   PubMed Web of Science ®Google Scholar
• Park SY, Choi MH, Park G, et al. Petasites japonicus bakkenolide B inhibits lipopolysaccharide-induced pro-inflammatory cytokines via AMPK/Nrf2 induction in microglia. Int J Mol Med. 2018;41(3):1683–1692. doi:10.3892/ijmm.2017.3350.
   PubMed Web of Science ®Google Scholar
• Douglas PM, Dillin A. Protein homeostasis and aging in neurodegeneration. J Cell Biol. 2010;190(5):719–729. doi:10.1083/jcb.201005144.
   PubMed Web of Science ®Google Scholar
• de Oliveira JS, Abdalla FH, Dornelles GL, et al. Neuroprotective effects of berberine on recognition memory impairment, oxidative stress, and damage to the purinergic system in rats submitted to intracerebroventricular injection of streptozotocin. Psychopharmacology. 2019;236(2):641–655. doi:10.1007/s00213-018-5090-6.
   PubMed Web of Science ®Google Scholar
• McMahon M, Itoh K, Yamamoto M, et al. The cap “n” collar basic leucine zipper transcription factor Nrf2 (NF-E2 p45-related factor 2) controls both constitutive and inducible expression of intestinal detoxification and glutathione biosynthetic enzymes. Cancer Res. 2001;61(8):3299–3307.
   PubMed Web of Science ®Google Scholar
• Tonelli C, Chio IIC, Tuveson DA. Transcriptional regulation by Nrf2. Antioxid Redox Signal. 2018;29(17):1727–1745. doi:10.1089/ars.2017.7342.
   PubMed Web of Science ®Google Scholar
• Lu SC. Regulation of glutathione synthesis. Mol Aspects Med. 2009;30(1-2):42–59. doi:10.1016/j.mam.2008.05.005.
   PubMed Web of Science ®Google Scholar
• Ma L, Liu JIA, Lin Q, et al. Eugenol protects cells against oxidative stress via Nrf2. 2021;21(2):107–115. doi: 10.3892/etm.2020.9539.
   Google Scholar
• McMahon M, Thomas N, Itoh K, et al. Dimerization of substrate adaptors can facilitate Cullin-mediated ubiquitylation of proteins by a “tethering” mechanism: a two-site interaction model for the Nrf2-Keap1 complex. J Biol Chem. 2006;281(34):24756–24768. doi:10.1074/jbc.M601119200.
   PubMed Web of Science ®Google Scholar
• Tong KI, Kobayashi A, Katsuoka F, et al. Two-site substrate recognition model for the Keap1-Nrf2 system: a hinge and latch mechanism. Biol Chem. 2006;387(10-11):1311–1320. doi:10.1515/BC.2006.164.
   PubMed Web of Science ®Google Scholar
• Bellezza I, Giambanco I, Minelli A, et al. Nrf2-Keap1 signaling in oxidative and reductive stress. Biochim Biophys Acta Mol Cell Res. 2018;1865(5):721–733. doi:10.1016/j.bbamcr.2018.02.010.
   PubMed Web of Science ®Google Scholar
• Hansen JM, Watson WH, Jones DP. Compartmentation of Nrf-2 redox control: regulation of cytoplasmic activation by glutathione and DNA binding by thioredoxin-1. Toxicol Sci. 2004;82(1):308–317. doi:10.1093/toxsci/kfh231.
   PubMed Web of Science ®Google Scholar
• Pohl F, Teixeira-Castro A, Costa MD, et al. Gst-4-dependent suppression of neurodegeneration in C. elegans models of Parkinson’s and Machado-Joseph disease by rapeseed pomace extract supplementation. Front Neurosci. 2019;13(OCT):1091. doi:10.3389/fnins.2019.01091.
   PubMedGoogle Scholar
• Rebai A, Chbili C, Ben Amor S, et al. Effects of glutathione S-transferase M1 and T1 deletions on Parkinson’s disease risk among a North African population. Rev Neurol. 2021;177(3):290–295. doi:10.1016/j.neurol.2020.03.013.
   PubMedGoogle Scholar
• Sui G, Li T, Zhang B, et al. Recent advances on synthesis and biological activities of aurones. Bioorg Med Chem. 2021;29(September 2020):115895. doi:10.1016/j.bmc.2020.115895.
   PubMedGoogle Scholar
• Hu X, Li C, Wang Q, et al. Dimethyl fumarate ameliorates doxorubicin-induced cardiotoxicity by activating the Nrf2 pathway. Front Pharmacol. 2022;13(April):872057. doi:10.3389/fphar.2022.872057.
   PubMedGoogle Scholar
• Szkatuła D, Krzyżak E, Stanowska P, et al. A new n-substituted 1h-isoindole-1,3(2h)-dione derivative – synthesis, structure and affinity for cyclooxygenase based on in vitro studies and molecular docking. Int J Mol Sci. 2021;22(14):1–21.
   Web of Science ®Google Scholar
• Moon EY, Oh JM, Kim YH, et al. Clitocybins, novel isoindolinone free radical scavengers, from mushroom Clitocybe aurantiaca inhibit apoptotic cell death and cellular senescence. Biol Pharm Bull. 2009;32(10):1689–1694. doi:10.1248/bpb.32.1689.
   PubMed Web of Science ®Google Scholar
• Unni S, Deshmukh P, Krishnappa G, et al. Structural insights into the multiple binding modes of dimethyl fumarate (DMF) and its analogs to the Kelch domain of Keap1. FEBS J. 2021;288(5):1599–1613. doi:10.1111/febs.15485.
   PubMed Web of Science ®Google Scholar
• Davood A, Shafaroodi H, Amini M, et al. Design, synthesis and protection against pentylenetetrazole-induced seizure of N-aryl derivatives of the phthalimide pharmacophore. Med Chem. 2012;8(5):953–963. doi:10.2174/157340612802084289.
   PubMed Web of Science ®Google Scholar
• Davood A, Iman M, Pouriaiee H, et al. Novel derivatives of phthalimide with potent anticonvulsant activity in PTZ and MES seizure models. Iran J Basic Med Sci. 2017;20(4):430–437.
   PubMed Web of Science ®Google Scholar
• Davood A, Amini M, Azimidoost L, et al. Docking, synthesis, and pharmacological evaluation of isoindoline derivatives as anticonvulsant agents. Med Chem Res. 2013;22(7):3177–3184. doi:10.1007/s00044-012-0256-y.
   Web of Science ®Google Scholar
• Dehghan E, Zhang Y, Saremi B, et al. Hydralazine induces stress resistance and extends C. elegans lifespan by activating the NRF2/SKN-1 signalling pathway. Nat Commun. 2017;8(1):2223. doi:10.1038/s41467-017-02394-3.
   PubMedGoogle Scholar
• Lopachin RM, Gavin T. Molecular mechanisms of aldehyde toxicity: a chemical perspective. Chem Res Toxicol. 2014;27(7):1081–1091. doi:10.1021/tx5001046.
   PubMed Web of Science ®Google Scholar
• Huang M-Z, Yang Y-J, Liu X-W, et al. Aspirin eugenol ester attenuates oxidative injury of vascular endothelial cells by regulating NOS and Nrf2 signalling pathways. Br J Pharmacol. 2019;176(7):906–918. doi:10.1111/bph.14592.
   PubMed Web of Science ®Google Scholar
• Park JS, Leem YH, Park JE, et al. Neuroprotective effect of β-lapachone in MPTP-induced Parkinson’s disease mouse model: involvement of astroglial p-AMPK/Nrf2/HO-1 signaling pathways. Biomol Ther. 2019;27(2):178–184. doi:10.4062/biomolther.2018.234.
   PubMed Web of Science ®Google Scholar