1,721
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis and characterisation of a new benzamide-containing nitrobenzoxadiazole as a GSTP1-1 inhibitor endowed with high stability to metabolic hydrolysis

, , ORCID Icon, , , , , ORCID Icon, ORCID Icon & ORCID Icon show all
Pages 1131-1139 | Received 27 Mar 2019, Accepted 05 May 2019, Published online: 06 Jun 2019

References

  • Ricci G, De Maria F, Antonini G, et al. 7-Nitro-2,1,3-benzoxadiazole derivatives, a new class of suicide inhibitors for glutathione S-transferases. Mechanism of action of potential anticancer drugs. J Biol Chem 2005;280:26397–405.
  • Ruzza P, Rosato A, Rossi CR, et al. Glutathione transferases as targets for cancer therapy. Anticancer Agents Med Chem 2009;9:763–77.
  • Dalzoppo D, Di Paolo V, Calderan L, et al. Thiol-activated anticancer agents: the state of the art. Anticancer Agents Med Chem 2017;17:4–20.
  • Sau A, Pellizzari Tregno F, Valentino F, et al. Glutathione transferases and development of new principles to overcome drug resistance. Arch Biochem Biophys 2010;500:116–22.
  • Allocati N, Masulli M, Di Ilio C, Federici L. Glutathione transferases: substrates, inihibitors and pro-drugs in cancer and neurodegenerative diseases. Oncogenesis 2018;7:8.
  • Turella P, Cerella C, Filomeni G, et al. Proapoptotic activity of new glutathione S-transferase inhibitors. Cancer Res 2005;65:3751–61.
  • De Luca A, Federici L, De Canio M, et al. New insights into the mechanism of JNK1 inhibition by glutathione transferase P1-1. Biochemistry 2012;51:7304–12.
  • Sau A, Filomeni G, Pezzola S, et al. Targeting GSTP1-1 induces JNK activation and leads to apoptosis in cisplatin-sensitive and -resistant human osteosarcoma cell lines. Mol Biosyst 2012;8:994–1006.
  • De Luca A, Mei G, Rosato N, et al. The fine-tuning of TRAF2-GSTP1-1 interaction: effect of ligand binding and in situ detection of the complex. Cell Death Dis 2014;5:e1015.
  • Sha HH, Wang Z, Dong SC, et al. Promising new anticancer compound. Biosci Rep 2018;38:BSR20171440.
  • De Luca A, Rotili D, Carpanese D, et al. A novel orally active water-soluble inhibitor of human glutathione transferase exerts a potent and selective antitumor activity against human melanoma xenografts. Oncotarget 2015;6:4126–43.
  • Graziani G, Artuso S, De Luca A, et al. A new water soluble MAPK activator exerts antitumor activity in melanoma cells resistant to the BRAF inhibitor vemurafenib. Biochem Pharmacol 2015;95:16–27.
  • Keppler D. Export pumps for glutathione S-conjugates. Free Radic Biol Med 1999;27:985–91.
  • Kannan R, Kuhlenkamp JF, Jeandidier E, et al. Evidence for carrier-mediated transport of glutathione across the blood–brain barrier in the rat. J Clin Invest 1990;85:2009–13.
  • Cacciatore I, Baldassarre L, Fornasari E, et al. Recent advances in the treatment of neurodegenerative diseases based on GSH delivery systems. Oxid Med Cell Longev 2012;2012:1.
  • Cacciatore I, Cornacchia C, Baldassarre L, et al. GPE and GPE analogues as promising neuroprotective agents. Mini Rev Med Chem 2012;12:13–23.
  • Fulci C, Rotili D, De Luca A, et al. A new nitrobenzoxadiazole-based GSTP1-1 inhibitor with a previously unheard of mechanism of action and high stability. J Enzyme Inhib Med Chem 2017;32:240–7.
  • Parkinson A, Ogilvie BW. Biotransformation of xenobiotics. In: Klaassen CD, ed. Casarett and Doull's toxicology: the basic science of poisons. 7th ed. New York (NY):McGraw-Hill; 2008:161–304.
  • Simons PC, Vander Jagt DL. Purification of glutathione S-transferases from human liver by glutathione-affinity chromatography. Anal Biochem 1977;82:334–41.
  • Habig WH, Pabst MJ, Jakoby WB. Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J Biol Chem 1974;249:7130–9.
  • Ross MK, Borazjani A, Wang R, et al. Examination of the carboxylesterase phenotype in human liver. Arch Biochem Biophys 2012;522:44–56.
  • Stella L, van de Weert M. Fluorescence quenching and ligand binding: a critical discussion of a popular methodology. J Mol Struct 2011;998:144–50.
  • Skehan P, Storeng R, Scudiero D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107–12.
  • Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem 2010;31:455–61.
  • Parker LJ, Bocedi A, Ascher DB, et al. Glutathione transferase P1-1 as an arsenic drug-sequestering enzyme. Protein Sci 2017;26:317–26.
  • Federici L, Lo Sterzo C, Pezzola S, et al. Structural basis for the binding of the anticancer compound 6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol to human glutathione S-transferases. Cancer Res 2009;69:8025–34.
  • Pettersen EF, Goddard TD, Huang CC, et al. UCSF Chimera - a visualization system for exploratory research and analysis. J Comput Chem 2004;25:1605–12.
  • Ruzza P, Rosato A, Nassi A, et al. Synthesis and preliminary in vitro biological evaluation of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a 4-mercaptophenol derivative designed as a novel bifunctional antimelanoma agent. J Med Chem 2009;52:4973–6.
  • Laizure SC, Herring V, Hu Z, et al. The role of human carboxylesterases in drug metabolism: have we overlooked their importance? Pharmacotherapy 2013;33:210–22.
  • Wu Y, Fan Y, Xue B, et al. Human glutathione S-transferase P1-1 interacts with TRAF2 and regulates TRAF2-ASK1 signals. Oncogene 2006;25:5787–800.
  • Hardeland R, Coto-Montes A, Poeggeler B. Circadian rhythms, oxidative stress, and antioxidative defense mechanisms. Chronobiol Int 2003;20:921–62.
  • Pekovic-Vaughan V, Gibbs J, Yoshitane H, Yang N, et al. The circadian clock regulates rhythmic activation of the NRF2/glutathione-mediated antioxidant defense pathway to modulate pulmonary fibrosis. Genes Dev 2014;28:548–60.