Beware of N-Benzoyloxybenzamides
Abstract
:1. Introduction
2. Results and Discussion
3. Mechanism of Action
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- Macarron, R.; Banks, M.N.; Bojanic, D.; Burns, D.J.; Cirovic, D.A.; Garyantes, T.; Green, D.V.S.; Hertzberg, R.P.; Janzen, W.P.; Paslay, J.W.; et al. Impact of high-throughput screening in biomedical research. Nat. Rev. Drug Disc. 2011, 10, 188–195. [Google Scholar] [CrossRef] [PubMed]
- Aseeri, M.; Abad, J.L.; Delgado, A.; Fabriàs, G.; Triola, G.; Casas, J.J. High-throughput discovery of novel small-molecule inhibitors of acid Ceramidase. Enzyme. Inhib. Med. Chem. 2023, 38, 343–348. [Google Scholar] [CrossRef]
- Bedia, C.; Camacho, L.; Abad, J.L.; Fabriàs, G.; Levade, T.J. A simple fluorogenic method for determination of acid ceramidase activity and diagnosis of Farber disease. Lipid Res. 2010, 51, 3542–3547. [Google Scholar] [CrossRef] [PubMed]
- Azuma, N.; Obrien, J.S.; Moser, H.W.; Kishimoto, Y. Stimulation of Acid Ceramidase Activity by Saposin D. Arch. Biochem. Biophys. 1994, 311, 354–357. [Google Scholar] [CrossRef] [PubMed]
- Stowell, J.C.; Huot, R.I.; Van Voast, L.J. The Synthesis of N-Hydroxy-N′-phenyloctanediamide and Its Inhibitory Effect on Proliferation of AXC Rat Prostate Cancer Cells. Med. Chem. 1995, 38, 1411–1413. [Google Scholar] [CrossRef]
- Citarella, A.; Moi, D.; Pinzi, L.; Bonanni, D.; Rastelli, G. Hydroxamic Acid Derivatives: From Synthetic Strategies to Medicinal Chemistry Applications. ACS Omega 2021, 6, 21843–21849. [Google Scholar] [CrossRef]
- Izydore, R.A.; Debnath, M.L.; Woodard, T.; Wong, O.T.; Hall, I.H. Hypolipidemic activity of benzohydroxamic acids and dibenzohydroxamic acids in rodents. Res. Commun. Chem. Pathol. Pharmacol. 1990, 70, 307–321. [Google Scholar]
- Hall, I.H.; Barnes, B.J.; Ward, E.S.; Wheaton, J.R.; Izydore, R.A.J. Specific inhibition of Type II inosine monophosphate dehydrogenase activity of Tmolt4 T cell human leukaemia cells by 3-methoxy and di-benzohydroxamic acids, maleic hydrazide and malonic acids. Pharm. Pharmacol. 2001, 53, 749–755. [Google Scholar] [CrossRef]
- El Turk, F.; Fauvet, B.; Ouertatani-Sakouhi, H.; Lugari, A.; Betzi, S.; Roche, P.; Morelli, X.; Lashuel, H.A. An integrative in silico methodology for the identification of modulators of macrophage migration inhibitory factor (MIF) tautomerase activity. Bioorg. Med. Chem. 2010, 18, 5425–5440. [Google Scholar] [CrossRef]
- Hall, I.H.; Izydore, R.; Hall, E.S.; Miller, M.C., III; Daniels, D.L.; Debnath, M.L.; Woodard, T. The antineoplastic and cytotoxicity of benzohydroxamic acids and related derivatives in murine and human tumor cells. Anti-Cancer Drugs 1992, 3, 273–280. [Google Scholar] [CrossRef]
- Smith, G.F. Designing Drugs to Avoid Toxicity. In Progress in Medicinal Chemistry; Lawton, G., Witty, D.R., Eds.; Elsevier: Amsterdam, The Netherlands, 2011; Volume 50, pp. 1–47. [Google Scholar]
- Hutchison, A.J.; Yuan, J. Preparation of Diaryl Ureas as CB1 Antagonists. WO 2006049941, 11 May 2006. [Google Scholar]
- Okino, N.; He, X.; Gatt, S.; Sandhoff, K.; Ito, M.; Schuchman, E.H.J. The reverse activity of human acid ceramidase. Biol. Chem. 2003, 278, 29948–29953. [Google Scholar] [CrossRef] [PubMed]
- Realini, N.; Solorzano, C.; Pagliuca, C.; Pizzirani, D.; Armirotti, A.; Luciani, R.; Costi, M.P.; Bandiera, T.; Piomelli, D. Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity. Sci. Rep. 2013, 3, 1035. [Google Scholar] [CrossRef] [PubMed]
- Dementiev, A.; Joachimiak, A.; Nguyen, H.; Gorelik, A.; Illes, K.; Shabani, S.; Gelsomino, M.; Ahn, E.-Y.E.; Nagar, B.; Doan, N.J. Molecular Mechanism of Inhibition of Acid Ceramidase by Carmofur. Med. Chem. 2019, 62, 987–992. [Google Scholar] [CrossRef] [PubMed]
- Pizzirani, D.; Pagliuca, C.; Realini, N.; Branduardi, D.; Bottegoni, G.; Mor, M.; Bertozzi, F.; Scarpelli, R.; Piomelli, D.; Bandiera, T.J. Discovery of a New Class of Highly Potent Inhibitors of Acid Ceramidase: Synthesis and Structure–Activity Relationship (SAR). Med. Chem. 2013, 56, 3518–3530. [Google Scholar] [CrossRef]
- Pizzirani, D.; Bach, A.; Realini, N.; Armirotti, A.; Mengatto, L.; Bauer, I.; Girotto, S.; Pagliuca, C.; De Vivo, M.; Summa, M.; et al. Benzoxazolone Carboxamides: Potent and Systemically Active Inhibitors of Intracellular Acid Ceramidase. Angew. Chem. Int. 2015, 54, 485–489. [Google Scholar] [CrossRef]
- Bach, A.; Pizzirani, D.; Realini, N.; Vozella, V.; Russo, D.; Penna, I.; Melzig, L.; Scarpelli, R.; Piomelli, D.J. Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure–Activity Relationship (SAR) Studies. Med. Chem. 2015, 58, 9258–9272. [Google Scholar] [CrossRef]
- Di Martino, S.; Tardia, P.; Cilibrasi, V.; Caputo, S.; Mazzonna, M.; Russo, D.; Penna, I.; Realini, N.; Margaroli, N.; Migliore, M.; et al. Lead Optimization of Benzoxazolone Carboxamides as Orally Bioavailable and CNS Penetrant Acid Ceramidase Inhibitors. J. Med. Chem. 2020, 63, 3634–3664. [Google Scholar] [CrossRef]
- Caputo, S.; Di Martino, S.; Cilibrasi, V.; Tardia, P.; Mazzonna, M.; Russo, D.; Penna, I.; Summa, M.; Bertozzi, S.M.; Realini, N.; et al. Design, Synthesis, and Biological Evaluation of a Series of Oxazolone Carboxamides as a Novel Class of Acid Ceramidase Inhibitors. J. Med. Chem. 2020, 63, 15821–15851. [Google Scholar] [CrossRef]
- Diamanti, E.; Bottegoni, G.; Goldoni, L.; Realini, N.; Pagliuca, C.; Bertozzi, F.; Piomelli, D.; Pizzirani, D. Pyrazole-Based Acid Ceramidase Inhibitors: Design, Synthesis, and Structure–Activity Relationships. Synthesis 2016, 48, 2739–2756. [Google Scholar]
- Ortega, J.A.; Arencibia, J.M.; La Sala, G.; Borgogno, M.; Bauer, I.; Bono, L.; Braccia, C.; Armirotti, A.; Girotto, S.; Ganesan, A.; et al. Pharmacophore Identification and Scaffold Exploration to Discover Novel, Potent, and Chemically Stable Inhibitors of Acid Ceramidase in Melanoma Cells. Med. Chem. 2017, 60, 5800–5815. [Google Scholar] [CrossRef]
- Qi, T.; Fang, N.; Huang, W.; Chen, J.; Luo, Y.; Xia, Y. Iron(II)-Catalyzed Nitrene Transfer Reaction of Sulfoxides with N-Acyloxyamides. Org. Lett. 2022, 24, 5674–5678. [Google Scholar] [CrossRef] [PubMed]
- Floresta, G.; Patamia, V.; Mazzeo, P.P.; Lombardo, G.M.; Pistarà, V.; Bacchi, A.; Rescifina, A.; Punzo, F.J. Structural, morphological, and modeling studies of N-(benzoyloxy)benzamide as a specific inhibitor of Type II inosine monophosphate dehydrogenase. Mol. Struct. 2024, 1303, 137588. [Google Scholar] [CrossRef]
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Cubitt, J.; Davies, M.; Riseley, R.; Evans, G.; Gardiner, S.E.; Kariuki, B.M.; Ward, S.E.; Lloyd-Evans, E.; Waller-Evans, H.; Jones, D.H. Beware of N-Benzoyloxybenzamides. Molecules 2024, 29, 5143. https://doi.org/10.3390/molecules29215143
Cubitt J, Davies M, Riseley R, Evans G, Gardiner SE, Kariuki BM, Ward SE, Lloyd-Evans E, Waller-Evans H, Jones DH. Beware of N-Benzoyloxybenzamides. Molecules. 2024; 29(21):5143. https://doi.org/10.3390/molecules29215143
Chicago/Turabian StyleCubitt, Jonathan, Mari Davies, Ross Riseley, Gabrielle Evans, Sian E. Gardiner, Benson M. Kariuki, Simon E. Ward, Emyr Lloyd-Evans, Helen Waller-Evans, and D. Heulyn Jones. 2024. "Beware of N-Benzoyloxybenzamides" Molecules 29, no. 21: 5143. https://doi.org/10.3390/molecules29215143