Erratum: Correction to Design, Synthesis, and Antitumor Evaluation of Novel Histone Deacetylase Inhibitors Equipped with a Phenylsulfonylfuroxan Module as a Nitric Oxide Donor (Journal of Medicinal Chemistry (2015) 58 (4325-4338) DOI: 10.1021/acs.jmedchem.5b00317);Design, synthesis, and antitumor evaluation of novel histone deacetylase inhibitors equipped with a phenylsulfonylfuroxan module as a nitric oxide donor

Journal of Medicinal Chemistry

Volumn 58, Issue 10, 2015, Pages 4325-4338

  Duan, Wenwen ^a   Li, Jin ^a   Inks, Elizabeth S ^b   Chou, C James ^b   Jia, Yuping ^c   Chu, Xiaojing ^d   Li, Xiaoyang ^a   Xu, Wenfang ^a   Zhang, Yingjie ^a  

^a SHANDONG UNIVERSITY   (China)

^b MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^c Shandong Academy of Pharmaceutical Sciences   (China)

^d Bochuang International Biological Medicinal Institute   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2 CARBOXY 2 METHYLPROPOXY) 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 (3 CARBOXYPHENOXY) 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 (3 HYDROXY 2,2 DIMETHYLPROPOXY) 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 (4 CARBOXY 2 METHOXYPHENOXY) 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 (4 CARBOXYBUTOXY) 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE; 4 (4 CARBOXYPHENOXY) 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 (4 HYDROXYBUTOXY) 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [(2 CARBOXY 2 METHYLPENTYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [(3 CARBOXYALLYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE; 4 [(4 HYDROXYBUT 2 EN 1 YL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [(5 CARBOXYPENTYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE; 4 [(5 HYDROXYPENTYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [(6 CARBOXYHEXYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE; 4 [(7 CARBOXYHEPTYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [(7 HYDROXYHEPTYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [(8 HYDROXYOCTYL)OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [2 (2 HYDROXYETHOXY)ETHOXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [2 (CARBOXYMETHOXY)ETHOXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [2 [2 (2 HYDROXYETHOXY)ETHOXY]ETHOXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE; 4 [2 [2 (CARBOXYMETHOXY)ETHOXY]ETHOXY] 3 (PHENYLSULFONYL); 4 [4 (2 HYDROXYETHYL)PHENOXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [4 (CARBOXYMETHYL)PHENOXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [4 (HYDROXYMETHYL) 2 METHOXYPHENOXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [4 (HYDROXYMETHYL)PHENOXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [[2 (HYDROXYMETHYL) 2 METHYLPENTYL]OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE; 4 [[6 (HYDROXYAMINO) 6 OXOHEXYL]OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; 4 [[7 (HYDROXYAMINO) 7 OXOHEPTYL]OXY] 3 (PHENYLSULFONYL) 1,2,5 OXADIAZOLE 2 OXIDE; HISTONE DEACETYLASE INHIBITOR; NITRIC OXIDE DONOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTINEOPLASTIC AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CELL CYCLE ARREST; CELL CYCLE ASSAY; CELL CYCLE PROGRESSION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOSE RESPONSE; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ERYTHROLEUKEMIA CELL; FEMALE; G1 PHASE CELL CYCLE CHECKPOINT; GROWTH CURVE; HUMAN; HUMAN CELL; HUMAN TISSUE; IC50; IN VITRO STUDY; NEOPLASM; NONHUMAN; NUDE MOUSE; PHARMACOPHORE; TUMOR VOLUME; TUMOR XENOGRAFT; WESTERN BLOTTING; ANIMAL; BAGG ALBINO MOUSE; CELL CYCLE CHECKPOINT; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; HELA CELL LINE; MALE; ORAL DRUG ADMINISTRATION; SYNTHESIS; TUMOR CELL LINE;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHEMISTRY TECHNIQUES, SYNTHETIC; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HISTONE DEACETYLASE INHIBITORS; HUMANS; MALE; MICE, INBRED BALB C; NITRIC OXIDE DONORS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84930620274     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01075     Document Type: Erratum

References (34)

1. Muller, S.; H. Kramer, O. Inhibitors of HDACs-effective drugs against cancer Curr. Cancer Drug Targets 2010, 10, 210-228
2. Venugopal, B.; Evans, T. R. J. Developing histone deactylase inhibitors as anti-cancer therapeutics Curr. Med. Chem. 2011, 18, 1658-1671
3. Marielle, P.; Marina, P.; Monica, B.; Daniela, F. Histone deacetylase inhibitors: from bench to clinic J. Med. Chem. 2008, 51, 1505-1529
4. Bertrand, P. Inside HDAC with HDAC inhibitors Eur. J. Med. Chem. 2010, 45, 2095-2116
5. Li, Z.; Zhu, W.-G. Targeting histone deacetylases for cancer therapy: from molecular mechanisms to clinical implications Int. J. Biol. Sci. 2014, 7, 757-770
6. Marks, P. A. Discovery and development of SAHA as an anticancer agent Oncogene. 2007, 26, 1351-1356
7. Marks, P. A.; Breslow, R. Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug Nat. Biotechnol. 2007, 25, 84-90
8. Varasi, M.; Thaler, F.; Abate, A.; Bigogno, C.; Boggio, R.; Carenzi, G.; Cataudella, T.; Zuffo, R. D.; Fulco, M. C.; Rozio, M. G.; Mai, A.; Dondio, G.; Minucci, S.; Mercurio, C. Discovery, synthesis, and pharmacological evaluation of spiropiperidine hydroxamic acid based derivatives as structurally novel histone deacetylase (HDAC) inhibitors J. Med. Chem. 2011, 54, 3051-3064
9. Furchgott, R. F.; Zawadzki, J. V. The obligatory role of endothelial cells in the relaxation of arterial smooth muscle by acetylcholine Nature 1980, 288, 373-376
10. Scatena, R.; Bottoni, P.; Martorana, G. E. Nitric oxide donor drugs: an update on pathophysiology and threapreutically potential Expert Opin. Invest. Drugs 2005, 14, 835-846
11. Megson, I. L. Nitric oxide donor drugs Drugs Future 2000, 25, 701-705
12. Nathan, C. F.; Hibbs, J. B., Jr. Role of nitric oxide synthesis in macrophage antimicrobial activity Curr. Opin. Immunol. 1991, 3, 65-70
13. Stuehr, D. J.; Nathan, C. F. Nitric oxide. A macrophage product responsible for cytostasis and respiratory inhibition in tumor target cells J. Exp. Med. 1989, 169, 1543-1555
14. Bonfoco, E.; Krainc, D.; Ankarcrona, M. Apoptosis and necrosis: two distinct events induced, respectively, by mild and intense insults with N-methyl- d -aspartate or nitric oxide/superoxide in cortical cell cultures Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7162-7166
15. Konovalova, N. P.; Goncharova, S. A.; Volkova, L. M. Nitric oxide donor increase the efficiency of cytostatic therapy and retards the development of drug resistance Nitric Oxide 2003, 8, 59-64
16. Wang, P. G.; Xian, M.; Tang, X. P. Nitric oxide donors: chemical activities and biological applications Chem. Rev. 2002, 102, 1091-1134
17. Dhar, A.; Brindley, J. M.; Stark, C.; Citro, M. L.; Keefer, L. K.; Colburn, N. H. Nitric oxide does not mediate but inhibits transformation and tumor phenotype Mol. Cancer Ther. 2003, 2, 1285-1293
18. Maksimovic-Ivanic, D.; Mijatovic, S.; Harhaji, L.; Miljkovic, D.; Dabideen, D.; Fan Cheng, K.; Mangano, K.; Malaponte, G.; Al-Abed, Y.; Libra, M.; Garotta, G.; Nicoletti, F.; Stosic-Grujicic, S. Anticancer properties of the novel nitric oxide-donating compound (S, R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid-nitric oxide in vitro and in vivo Mol. Cancer Ther. 2008, 7, 510-520
19. Feelisch, M.; Schonafinger, K.; Noack, E. Thiol-mediated Generation of nitric oxide accounts for the vasodilator action of phenylsulfonylfuroxans Biochem. Pharmacol. 1992, 44, 1149-1157
20. Chen, L.; Zhang, Y.; Kong, X.; Lan, E.; Huang, Z.; Peng, S.; Kaufman, D. L.; Tian, J. Design, synthesis, and antihepatocellular carcinoma activity of nitric oxide releasing derivatives of oleanolic acid J. Med. Chem. 2008, 51, 4834-4838
21. Ling, Y.; Ye, X. L.; Ji, H.; Zhang, Y. H.; Lai, Y. Sh.; Peng, S. X.; Tian, J. D. Synthesis and evaluation of nitric oxide-releasing derivatives of farnesylthiosalicylic acid as anti-tumor agents Bioorg. Med. Chem. 2010, 18, 3448-3456
22. Moharram, S.; Zhou, A.; Wiebe, L. I.; Knaus, E. E. Design and synthesis of 3′- and 5′-O-(3-benzenesulfonylphenylsulfonylfuroxan-4-yl)-2′-deoxyuridines: biological evaluation as hybrid nitric oxide donor-nucleoside anticancer agents J. Med. Chem. 2004, 47, 1840-1846
23. Han, C.; Huang, Z. J.; Zheng, C.; Wan, L. D.; Zhang, L. W.; Peng, S. X.; Ding, K.; Ji, H. B.; Tian, J. D.; Zhang, Y. H. Novel hybrids of phenylsulfonylfuroxan and anilinopyrimidine as potent and selective epidermal growth factor receptor inhibitors for intervention of non-small-cell lung cancer J. Med. Chem. 2013, 56, 4738-4748
24. Illi, B.; Dello Russo, C.; Colussi, C.; Rosati, J.; Pallaoro, M.; Spallotta, F.; Rotili, D.; Valente, S.; Ragone, G.; Martelli, F.; Biglioli, P.; Steinkuhler, C.; Gallinari, P.; Mai, A.; Capogrossi, M. C.; Gaetano, C. Nitric oxide modulates chromatin folding in human endothelial cells via protein phosphatase 2A activation and class II histone deacetylases nuclear shuttling Circ. Res. 2008, 102, 51-58
25. Colussi, C.; Mozzetta, C.; Gurtner, A.; Illi, B.; Rosati, J.; Straino, S.; Ragone, G.; Pescatori, M.; Zaccagnini, G.; Antonini, A.; Minetti, G.; Martelli, F.; Piaggio, G.; Gallinari, P.; Steinkulher, C.; Clementi, E.; DellAversana, C.; Altucci, L.; Mai, A.; Capogrossi, M. C.; Puri, P. L.; Gaetano, C. HDAC2 blockade by nitric oxide and histone deacetylase inhibitors reveals a common target in duchenne muscular dystrophy treatment Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 19183-19187
26. Feng, J. H.; Jing, F. B.; Fang, H.; Gu, L. C.; Xu, W. F. Expression, purification, and S-nitrosylation of recombinant histone deacetylase 8 in Escherichia coli BioSci. Trends 2011, 5, 17-22
27. Nott, A.; Watson, P. M.; Robinson, J. D.; Crepaldi, L.; Riccio, A. S-Nitrosylation of histone deacetylase 2 induces chromatin remodeling in neurons Nature 2008, 455, 411-415
28. Spallotta, F.; Cencioni, C.; Straino, S.; Nanni, S.; Rosati, J.; Artuso, S.; Manni, I.; Colussi, C.; Piaggio, G.; Martelli, F.; Valente, S.; Mai, A.; Capogrossi, M. C.; Farsetti, A.; Gaetano, C. A nitric oxide-dependent cross-talk between class I and III histone deacetylases accelerates skin repair J. Biol. Chem. 2013, 288, 11004-11012
29. Kee, H. J.; Kook, H. Roles and targets of class I and IIa histone deacetylases in cardiac hypertrophy J. Biomed. Biotechnol. 2011, 928326
30. Isenberg, J. S.; Ridnour, L. A.; Espey, M. G.; Wink, D. A.; Roberts, D. D. Nitric oxide in wound-healing Microsurgery 2005, 25, 442-451
31. Soneja, A.; Drews, M.; Malinski, T. Role of nitric oxide, nitroxidative and oxidative stress in wound healing Pharmacol. Rep. 2005, 57, 108-119
32. Zhang, Y. J.; Fang, H.; Feng, J. H.; Jia, Y. P.; Wang, X. J.; Xu, W. F. Discovery of a tetrahydroisoquinoline-based hydroxamic acid derivative (ZYJ-34c) as histone deacetylase inhibitor with potent oral antitumor activities J. Med. Chem. 2011, 54, 5532-5539
33. Ling, Y.; Ye, X. L.; Zhang, Z.; Zhang, Y. H.; Lai, Y.; Ji, H.; Peng, S. X.; Tian, J. D. Novel nitric oxide-releasing derivatives of farnesylthiosalicylic acid: synthesis and evaluation of antihepatocellular carcinoma activity J. Med. Chem. 2011, 54, 3251-3259
34. Borretto, E.; Lazzarato, L.; Spallotta, F.; Cencioni, C.; DAlessandra, Y.; Gaetano, C.; Fruttero, R.; Gasco, A. Synthesis and biological evaluation of the first example of NO donor histone deacetylase inhibitor ACS Med. Chem. Lett. 2013, 4, 994-999