Identification of an Iridium(III)-Based Inhibitor of Tumor Necrosis Factor-α

Journal of Medicinal Chemistry

Volumn 59, Issue 8, 2016, Pages 4026-4031

  Kang, Tian Shu ^a   Mao, Zhifeng ^b   Ng, Chan Tat ^a   Wang, Modi ^b   Wang, Wanhe ^b   Wang, Chunming ^a   Lee, Simon Ming Yuen ^a   Wang, Yitao ^a   Leung, Chung Hang ^a   Ma, Dik Lung ^b  

^a University of Macau   (Macao)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; IRIDIUM COMPLEX; METAL COMPLEX; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA INHIBITOR; TUMOR NECROSIS FACTOR RECEPTOR; IRIDIUM; PROTEIN BINDING; TUMOR NECROSIS FACTOR;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; PROTEIN BINDING; PROTEIN PROTEIN INTERACTION; SIGNAL TRANSDUCTION; ANTAGONISTS AND INHIBITORS; HEP-G2 CELL LINE; METABOLISM;

HEP G2 CELLS; HUMANS; IRIDIUM; NF-KAPPA B; PROTEIN BINDING; RECEPTORS, TUMOR NECROSIS FACTOR; SIGNAL TRANSDUCTION; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84968752804     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.6b00112     Document Type: Article

References (46)

1. Gasser, G.; Metzler-Nolte, N. The potential of organometallic complexes in medicinal chemistry Curr. Opin. Chem. Biol. 2012, 16, 84-91 10.1016/j.cbpa.2012.01.013
2. Leung, C.-H.; Lin, S.; Zhong, H.-J.; Ma, D.-L. Metal complexes as potential modulators of inflammatory and autoimmune responses Chem. Sci. 2015, 6, 871-884 10.1039/C4SC03094J
3. Liu, L.-J.; Lu, L.; Zhong, H.-J.; He, B.; Kwong, D. W.; Ma, D.-L.; Leung, C.-H. An iridium (III) complex inhibits JMJD2 activities and acts as a potential epigenetic modulator J. Med. Chem. 2015, 58, 6697-6703 10.1021/acs.jmedchem.5b00375
4. Ma, D.-L.; Chan, D. S.-H.; Leung, C.-H. Group 9 organometallic compounds for therapeutic and bioanalytical applications Acc. Chem. Res. 2014, 47, 3614-3631 10.1021/ar500310z
5. Song, X.; Qian, Y.; Ben, R.; Lu, X.; Zhu, H.-L.; Chao, H.; Zhao, J. Activation of C-H Bonds in Nitrones Leads to Iridium Hydrides with Antitumor Activity J. Med. Chem. 2013, 56, 6531-6535 10.1021/jm4004973
6. He, L.; Liao, S. Y.; Tan, C. P.; Lu, Y. Y.; Xu, C. X.; Ji, L. N.; Mao, Z. W. Cyclometalated iridium(III)-beta-carboline complexes as potent autophagy-inducing agents Chem. Commun. 2014, 50, 5611-5614 10.1039/c4cc01461h
7. Lu, L.; Wang, M.; Liu, L.-J.; Leung, C.-H.; Ma, D.-L. Label-Free Luminescent Switch-On Probe for Ochratoxin A Detection Using a G-Quadruplex-Selective Iridium (III) Complex ACS Appl. Mater. Interfaces 2015, 7, 8313-8318 10.1021/acsami.5b01702
8. Ye, R. R.; Tan, C. P.; He, L.; Chen, M. H.; Ji, L. N.; Mao, Z. W. Cyclometalated Ir(III) complexes as targeted theranostic anticancer therapeutics: combining HDAC inhibition with photodynamic therapy Chem. Commun. 2014, 50, 10945-10948 10.1039/C4CC05215C
9. Ye, R. R.; Tan, C. P.; Lin, Y. N.; Ji, L. N.; Mao, Z. W. A phosphorescent rhenium(I) histone deacetylase inhibitor: mitochondrial targeting and paraptosis induction Chem. Commun. 2015, 51, 8353-8356 10.1039/C5CC02354H
10. Liu, J.; Sun, R. W. Y.; Leung, C.-H.; Lok, C.-N.; Che, C.-M. nhibition of TNF-α stimulated nuclear factor-kappa B (NF-κB) activation by cyclometalated platinum(II) complexes Chem. Commun. 2012, 48, 230-232 10.1039/C1CC15317J
11. Ma, D. L.; Chan, D. S. H.; Leung, C. H. Drug repositioning by structure-based virtual screening. Chem. Soc. Rev. 2013, 42, 2130-2141 10.1039/c2cs35357a
12. Ma, D. L.; Liu, L. J.; Leung, K. H.; Chen, Y. T.; Zhong, H. J.; Chan, D. S. H.; Wang, H. M. D.; Leung, C. H. Antagonizing STAT3 dimerization with a rhodium (III) complex Angew. Chem., Int. Ed. 2014, 53, 9178-9182 10.1002/anie.201404686
13. Zhong, H. J.; Yang, H.; Chan, D. S. H.; Leung, C. H.; Wang, H. M.; Ma, D. L. A metal-based inhibitor of NEDD8-activating enzyme PLoS One 2012, 7, e49574 10.1371/journal.pone.0049574
14. Lu, L.; Shiu-Hin Chan, D.; Kwong, D. W. J.; He, H. Z.; Leung, C. H.; Ma, D. L. Detection of nicking endonuclease activity using a G-quadruplex-selective luminescent switch-on probe Chem. Sci. 2014, 5, 4561-4568 10.1039/C4SC02032D
15. Mukhopadhyay, S.; Gupta, R. K.; Paitandi, R. P.; Rana, N. K.; Sharma, G.; Koch, B.; Rana, L. K.; Hundal, M. S.; Pandey, D. S. Synthesis, Structure, DNA/Protein Binding, and Anticancer Activity of Some Half-Sandwich Cyclometalated Rh(III) and Ir(III) Complexes Organometallics 2015, 34, 4491-4506 10.1021/acs.organomet.5b00475
16. Xie, P.; Streu, C.; Qin, J.; Bregman, H.; Pagano, N.; Meggers, E.; Marmorstein, R. The crystal structure of BRAF in complex with an organoruthenium inhibitor reveals a mechanism for inhibition of an active form of BRAF kinase Biochemistry 2009, 48, 5187-5198 10.1021/bi802067u
17. Anand, R.; Maksimoska, J.; Pagano, N.; Wong, E. Y.; Gimotty, P. A.; Diamond, S. L.; Meggers, E.; Marmorstein, R. Toward the development of a potent and selective organoruthenium mammalian sterile 20 kinase inhibitor J. Med. Chem. 2009, 52, 1602-1611 10.1021/jm8005806
18. Ember, S. W. J.; Zhu, J. Y.; Olesen, S. H.; Martin, M. P.; Becker, A.; Berndt, N.; Georg, G. I.; Schönbrunn, E. Acetyl-Lysine Binding Site of Bromodomain-Containing Protein 4 (BRD4) Interacts with Diverse Kinase Inhibitors ACS Chem. Biol. 2014, 9, 1160-1171 10.1021/cb500072z
19. Zhong, H.-J.; Lu, L.; Leung, K.-H.; Wong, C. C.; Peng, C.; Yan, S.-C.; Ma, D.-L.; Cai, Z.; Wang, H.-M. D.; Leung, C.-H. An iridium (III)-based irreversible protein-protein interaction inhibitor of BRD4 as a potent anticancer agent Chem. Sci. 2015, 6, 5400-5408 10.1039/C5SC02321A
20. Palladino, M. A.; Bahjat, F. R.; Theodorakis, E. A.; Moldawer, L. L. Anti-TNF-α therapies: the next generation Nat. Rev. Drug Discovery 2003, 2, 736-746 10.1038/nrd1175
21. Croft, M.; Benedict, C. A.; Ware, C. F. Clinical targeting of the TNF and TNFR superfamilies Nat. Rev. Drug Discovery 2013, 12, 147-168 10.1038/nrd3930
22. Lobito, A. A.; Gabriel, T. L.; Medema, J. P.; Kimberley, F. C. Disease causing mutations in the TNF and TNFR superfamilies: Focus on molecular mechanisms driving disease Trends Mol. Med. 2011, 17, 494-505 10.1016/j.molmed.2011.05.006
23. Kjeldsen, J.; Nielsen, J.; Larsen, M. D.; Qvist, N.; Nørgård, B. M. Postoperative use of anti-TNF-α agents in patients with Crohn's disease and risk of reoperation-a nationwide cohort study Am. J. Gastroenterol. 2015, 22, 599-606 10.1097/MIB.0000000000000647
24. Sánchez-Cano, D.; Callejas-Rubio, J. L.; Ruiz-Villaverde, R.; Ríos-Fernández, R.; Ortego-Centeno, N. Off-label uses of anti-TNF therapy in three frequent disorders: Behçet's disease, sarcoidosis, and noninfectious uveitis Mediators Inflammation 2013, 2013, 286857 10.1155/2013/286857
25. Miglets, A. W.; Viall, J. H.; Kataria, Y. P. Sarcoidosis of the head and neck Laryngoscope 1977, 87, 2038-2048 10.1288/00005537-197712000-00009
26. Ang, W. H.; Parker, L. J.; De Luca, A.; Juillerat-Jeanneret, L.; Morton, C. J.; Lo Bello, M.; Parker, M. W.; Dyson, P. J. Rational design of an organometallic glutathione transferase inhibitor Angew. Chem., Int. Ed. 2009, 48, 3854-3857 10.1002/anie.200900185
27. He, M. M.; Smith, A. S.; Oslob, J. D.; Flanagan, W. M.; Braisted, A. C.; Whitty, A.; Cancilla, M. T.; Wang, J.; Lugovskoy, A. A.; Yoburn, J. C. Small-molecule inhibition of TNF-α Science 2005, 310, 1022-1025 10.1126/science.1116304
28. Tully, S. E.; Rawat, M.; Hsieh-Wilson, L. C. Discovery of a TNF-α antagonist using chondroitin sulfate microarrays J. Am. Chem. Soc. 2006, 128, 7740-7741 10.1021/ja061906t
29. Spohn, G.; Guler, R.; Johansen, P.; Keller, I.; Jacobs, M.; Beck, M.; Rohner, F.; Bauer, M.; Dietmeier, K.; Kündig, T. M. A virus-like particle-based vaccine selectively targeting soluble TNF-α protects from arthritis without inducing reactivation of latent tuberculosis J. Immunol. 2007, 178, 7450-7457 10.4049/jimmunol.178.11.7450
30. Chan, D. S. H.; Lee, H. M.; Yang, F.; Che, C. M.; Wong, C. C.; Abagyan, R.; Leung, C. H.; Ma, D. L. Structure-Based Discovery of Natural-Product-like TNF-α Inhibitors Angew. Chem. 2010, 122, 2922-2926 10.1002/ange.200907360
31. Buller, F.; Zhang, Y.; Scheuermann, J.; Schäfer, J.; Bühlmann, P.; Neri, D. Discovery of TNF inhibitors from a DNA-encoded chemical library based on diels-alder cycloaddition Chem. Biol. 2009, 16, 1075-1086 10.1016/j.chembiol.2009.09.011
32. Leung, C. H.; Zhong, H. J.; Yang, H.; Cheng, Z.; Chan, D. S. H.; Ma, V. P. Y.; Abagyan, R.; Wong, C. Y.; Ma, D. L. A Metal-Based Inhibitor of Tumor Necrosis Factor-α Angew. Chem., Int. Ed. 2012, 51, 9010-9014 10.1002/anie.201202937
33. He, H. Z.; Chan, D. S.; Leung, C. H.; Ma, D. L. A highly selective G-quadruplex-based luminescent switch-on probe for the detection of gene deletion Chem. Commun. 2012, 48, 9462-9464 10.1039/c2cc32253f
34. He, L.; Liao, S.-Y.; Tan, C.-P.; Lu, Y.-Y.; Xu, C.-X.; Ji, L.-N.; Mao, Z.-W. Cyclometalated iridium (III)-β-carboline complexes as potent autophagy-inducing agents Chem. Commun. 2014, 50, 5611-5614 10.1039/c4cc01461h
35. Liu, L. J.; Leung, K. H.; Chan, D. S.; Wang, Y. T.; Ma, D. L.; Leung, C. H. Identification of a natural product-like STAT3 dimerization inhibitor by structure-based virtual screening Cell Death Dis. 2014, 5, e1293 10.1038/cddis.2014.250
36. 2+ ions using a luminescent iridium (III) complex PLoS One 2013, 8, e60114 10.1371/journal.pone.0060114
37. Lin, S.; He, B.; Yang, C.; Leung, C. H.; Mergny, J. L.; Ma, D. L. Luminescence switch-on assay of interferon-gamma using a G-quadruplex-selective iridium(III) complex Chem. Commun. 2015, 51, 16033-16036 10.1039/C5CC06655G
38. Liu, L. J.; Lu, L.; Zhong, H. J.; He, B.; Kwong, D. W.; Ma, D. L.; Leung, C. H. An Iridium(III) Complex Inhibits JMJD2 Activities and Acts as a Potential Epigenetic Modulator J. Med. Chem. 2015, 58, 6697-6703 10.1021/acs.jmedchem.5b00375
39. Ma, Y.; Xu, H.; Zeng, Y.; Ho, C.-L.; Chui, C.-H.; Zhao, Q.; Huang, W.; Wong, W.-Y. A charged iridophosphor for time-resolved luminescent CO 2 gas identification J. Mater. Chem. C 2015, 3, 66-72 10.1039/C4TC02014F
40. Wu, Y.; Jing, H.; Dong, Z.; Zhao, Q.; Wu, H.; Li, F. Ratiometric phosphorescence imaging of Hg (II) in living cells based on a neutral iridium (III) complex Inorg. Chem. 2011, 50, 7412-7420 10.1021/ic102082k
41. Woo, H.; Cho, S.; Han, Y.; Chae, W.-S.; Ahn, D.-R.; You, Y.; Nam, W. Synthetic control over photoinduced electron transfer in phosphorescence zinc sensors J. Am. Chem. Soc. 2013, 135, 4771-4787 10.1021/ja3123202
42. Lee, S.; You, Y.; Ohkubo, K.; Fukuzumi, S.; Nam, W. Highly efficient cycloreversion of photochromic dithienylethene compounds using visible light-driven photoredox catalysis Chem. Sci. 2014, 5, 1463-1474 10.1039/c3sc52900b
43. Lowry, M. S.; Hudson, W. R.; Pascal, R. A.; Bernhard, S. Accelerated luminophore discovery through combinatorial synthesis J. Am. Chem. Soc. 2004, 126, 14129-14135 10.1021/ja047156+
44. Tamayo, A. B.; Garon, S.; Sajoto, T.; Djurovich, P. I.; Tsyba, I. M.; Bau, R.; Thompson, M. E. Cationic bis-cyclometalated iridium (III) diimine complexes and their use in efficient blue, green, and red electroluminescent devices Inorg. Chem. 2005, 44, 8723-8732 10.1021/ic050970t
45. Helms, M.; Lin, Z.; Gong, L.; Harms, K.; Meggers, E. Method for the Preparation of Nonracemic Bis-Cyclometalated Iridium(III) Complexes Eur. J. Inorg. Chem. 2013, 2013, 4164-4172 10.1002/ejic.201300411
46. Chen, L.-A.; Xu, W.; Huang, B.; Ma, J.; Wang, L.; Xi, J.; Harms, K.; Gong, L.; Meggers, E. Asymmetric Catalysis with an Inert Chiral-at-Metal Iridium Complex J. Am. Chem. Soc. 2013, 135, 10598-10601 10.1021/ja403777k