Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

Medicinal Chemistry Research

Volumn 24, Issue 7, 2015, Pages 2838-2861

  Wright, Brian D ^a,b   Deblock, Michael C ^a,c   Wagers, Patrick O ^a   Duah, Ernest ^a   Robishaw, Nikki K ^a   Shelton, Kerri L ^a   Southerland, Marie R ^a   Debord, Michael A ^a   Kersten, Kortney M ^a   McDonald, Lucas J ^a   Stiel, Jason A ^a   Panzner, Matthew J ^a   Tessier, Claire A ^a   Paruchuri, Sailaja ^a   Youngs, Wiley J ^a  

^a UNIVERSITY OF AKRON   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c LERNER RESEARCH INSTITUTE   (United States)

Author keywords

Anti tumor; Anticancer; Apoptosis; Imidazolium cation; Imidazolium salt

Indexed keywords

1 (2 ETHYL 1 NAPHTHYL) 4,5 DICHLOROIMIDAZOLE; 1 BENZYL 4,5 DICHLORO 3 (NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 1 BUTYL 4,5 DICHLORO 3 (NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 1,3 BIS(NAPHTHALEN 2 YLMETHYL)BENZIMIDAZOLIUM BROMIDE; 1,3 BIS(NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 1,3 DIBENZYL 4,5 DICHLOROIMIDAZOLIUM BROMIDE; 1,3 DIMETHYL 7 (NAPHTHALEN 2 YLMETHYL)XANTHINE; 1,3,9 TRIMETHYL 7 (NAPHTHALEN 2 YLMETHYL)XANTHINIUM IODIDE; 3 BENZYL 4,5 DICHLORO 1 [2 (NAPHTHALEN 1 YL)ETHYL]IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 (NAPHTHALEN 2 YLMETHYL) 3 (QUINOLIN 2YLMETHYL)IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 DODECYL 3 (NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 ETHYL 3 (NAPHTHALEN 2 YLMETHYL) 1 PROPYL IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 ETHYL 3 (NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 HEPTYL 3 (NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 HEXYL 3 (NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 ISOPROPYL 3 (NAPHTHALEN 2 YLMETHYL)IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 [2 (NAPHTHALEN 1 YL)ETHYL] 3 (NAPHTHALEN 2 YLMETHYL) IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 [2 (NAPHTHALEN 2 YL)ETHYL] 3 (NAPHTHALEN 2 YLMETHYL) IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1 [2 (NAPHTHALEN 2 YL)ETHYL] IMIDAZOLE; 4,5 DICHLORO 1,3 BIS[2 (NAPHTHALEN 1 YL)ETHYL]IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 1,3 BIS[2 (NAPHTHALEN 2 YL)ETHYL] IMIDAZOLIUM BROMIDE; 4,5 DICHLORO 3 (NAPHTHALEN 2 YLMETHYL) 1 NONYLIMIDAZOLIUM BROMIDE; 4,5 DICHLORO 3 (NAPHTHALEN 2 YLMETHYL) 1 PENTYLIMIDAZOLIUM BROMIDE; ANTINEOPLASTIC AGENT; CASPASE 3; CISPLATIN; IMIDAZOLE DERIVATIVE; PROCASPASE 3; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL LYSATE; CELL VIABILITY; COMPARATIVE STUDY; CONTROLLED STUDY; CYTOLYSIS; DRUG SYNTHESIS; FLUORESCENCE; GEL ELECTROPHORESIS; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHILICITY; IMMUNOBLOTTING; IN VITRO STUDY; LIPOPHILICITY; LUNG CANCER CELL LINE; MASS SPECTROMETRY; MELTING POINT; MTT ASSAY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; WESTERN BLOTTING; X RAY DIFFRACTION;

EID: 84943355624     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-015-1330-z     Document Type: Article

References (36)

1. Bruker (1997) SMART (Version 5.625), SAINT (Version 6.22) and SHELXTL (Version 6.10)
2. Bruker (2007) APEX II. Bruker AXS Inc., Madison
3. Duah E, Adapala RK, Al-Azzam N, Kondeti V, Gombedza F, Thodeti CK, Paruchuri S (2013) Cysteinyl leukotrienes regulate endothelial cell inflammatory and proliferative signals through CysLT2 and CysLT1 receptors. Sci Rep 3:3274. doi:10.1038/srep03274
4. 6]-labelled 2-substituted naphthalenes. J Label Compd Radiopharm 53:801-803
5. Garrison JC, Youngs WJ (2005) Ag(I) N-heterocyclic carbene complexes: synthesis, structure, and application. Chem Rev 105:3978-4008
6. Garrison JC, Simons RS, Kofron WG, Tessier CA, Youngs WJ (2001a) Synthesis and structural characterization of a silver complex of a mixed-donor N-heterocyclic carbene linked cyclophane. Chem Commun 21:1780-1781
7. Garrison JC, Simons RS, Talley JM, Wesdemiotis C, Tessier CA, Youngs WJ (2001b) Synthesis and structural characterization of an imidazolium-linked cyclophane and the silver complex of an N-heterocyclic carbene-linked cyclophane. Organometallics 20:1276-1278
8. Gautier A, Cisnetti F (2012) Advances in metal-carbene complexes as potent anti-cancer agents. Metallomics 4:23-32
9. Hindi KM, Siciliano TJ, Durmus S, Panzner MJ, Medvetz DA, Reddy DV, Hogue LA, Hovis CE, Hilliard JK, Mallet RJ, Tessier CA, Cannon CL, Youngs WJ (2008) Synthesis, stability, and antimicrobial studies of electronically tuned silver acetate N-heterocyclic carbenes. J Med Chem 51:1577-1583
10. Hindi KM, Ditto AJ, Panzner MJ, Medvetz DA, Hovis CE, Han DS, Hilliard JK, Taylor JB, Yun YH, Cannon CL, Youngs WJ (2009a) The antimicrobial efficacy of sustained release silvercarbene complex-loaded L-tyrosine polyphosphate nanoparticles: characterization, in vitro and in vivo studies. Biomaterials 30:3771-3779
11. Hindi KM, Panzner MJ, Cannon CL, Youngs WJ (2009b) The medicinal applications of imidazolium carbene-metal complexes. Chem Rev 109:3859-3884
12. Kascatan-Nebioglu A, Melaiye A, Hindi KM, Durmus S, Panzner MJ, Hogue LA, Mallett RJ, Hovis CE, Coughenour M, Crosby SD, Milsted A, Ely DL, Tessier CA, Cannon CL, Youngs WJ (2006) Synthesis from caffeine of a mixed N-heterocyclic carbene-silver acetate complex active against resistant respiratory pathogens. J Med Chem 49:6811-6818
13. Katano K, Kondo A, Safaei R, Holzer A, Samimi G, Mishima M, Kuo YM, Rochdi M, Howell SB (2002) Acquisition of resistance to cisplatin is accompanied by changes in the cellular pharmacology of copper. Cancer Res 62:6559-6565
14. Kondeti V, Duah E, Al-Azzam N, Thodeti CK, Boyce JA, Paruchuri S (2013) Differential regulation of cysteinyl leukotriene receptor signaling by protein kinase C in human mast cells. PLoS One 158(8):e71536 PMID:23977066
15. Landsdown AB (2002) Silver I: its antibacterial properties and mechanism of action. J Wound Care 11:125-130
16. Landsdown AB (2004) A Review of the use of silver in wound care: facts and fallacies. Br J Nurs 13:S6-S19
17. Lansdown AB, Williams A (2004) How safe is silver in wound care. J Wound Care 13:131-136
18. Li Y, Hindi K, Watts KM, Taylor JB, Zhang K, Li Z, Hunstad DA, Cannon CL, Youngs WJ, Wooley KL (2010) Shell crosslinked nanoparticles carrying silver antimicrobials as therapeutics. Chem Commun 46:121-123
19. Lin JC, Huang RT, Lee CS, Bhattacharyya A, Hwang WS, Lin IJ (2009) Coinage metal - N-heterocyclic carbene complexes. Chem Rev 109:3561-3598
20. Malhotra SV, Kumar V (2010) A profile of the in vitro anti-tumor activity of imidazolium-based ionic liquids. Bioorg Med Chem Lett 20:581-585
21. Markova AA, Plyavnik NV, Tatarskii VV Jr, Shtil AA, Serebrennikova GA (2010) Novel alkyl cationic glycerolipids with a heterocyclic polar domain induce disturbances of the cell cycle and the death of human leukemia cells. Russ J Bioorg Chem 36(4):532-534
22. Medvetz DA, Hindi KM, Panzner MJ, Ditto AJ, Yun YH, Youngs WJ (2008) Anti-cancer activity of Ag(I) N-heterocyclic carbene complexes derived from 4,5-dichloro-1 H-imidazole. Metal Based Drugs 2008:384010
23. Oehinger L, Rubbiani R, Ott I (2013) N-heterocyclic carbene metal complexes in medicinal chemistry. Dalton Trans 42:3269-3284
24. Ornelas-Megiatto C, Shah PN, Wich PR, Cohen JL, Tagaev JA, Smolen JA, Wright BD, Panzner MJ, Youngs WJ, Frechet JMJ, Cannon CL (2012) Aerosolized antimicrobial agents based on degradable dextran nanoparticles loaded with silver carbene complexes. Mol Pharm 9(11):3012-3022
25. Panzner MJ, Deeraksa A, Smith A, Wright BD, Hindi KM, Kascatan-Nebioglu A, Torres AG, Judy BM, Hovis CE, Hilliard JK, Mallett RJ, Cope E, Estes DM, Cannon CL, Leid JG, Youngs WJ (2009) Synthesis and in vitro efficacy studies of silver carbene complexes on biosafety level 3 bacteria. Eur J Inorg Chem 13:1739-1745
26. Riduan SN, Zhang Y (2013) Imidazolium salts and their polymeric materials for biological applications. Chem Soc Rev 42:9055-9070
27. Russel AD, Path FR, Hugo WB (1994) Antimicrobial activity and action of silver. Prog Med Chem 31:351-370
28. Sheldrick GM (2008) A short history of SHELX. Acta Cryst A64:112
29. Siegel R, Naishadham D, Jemal A (2012) Cancer statistic. CA Cancer J Clin 54:8-29
30. Tolcher W, Mita A, Lewis LD, Garrett CR, Till E, Daud AI, Patnaik A, Papadopoulos K, Takimoto C, Bartels P, Keating A, Antonia S (2008) Phase I and pharmacokinetic study of YM155, a smallmolecule inhibitor of survivin. J Clin Oncol 26:5198-5203
31. Van Engeland M, Nieland L, Ramaekers F, Schutte B, Reutelingsperger C (1998) Annexin V affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry 31:1-9
32. Wright BD, Shah PN, McDonald LJ, Shaeffer ML, Wagers PO, Panzner MJ, Smolen J, Tagaev J, Tessier CA, Cannon CL, Youngs WJ (2012) Synthesis, characterization, and antimicrobial activity of silver carbene complexes derived from 4,5,6,7-tetrachlorobenzimidazole against antibiotic resistant bacteria. Dalton Trans 41:6500-6506
33. Yao X, Panichpisal K, Kurtzman N, Nugent K (2007) Cisplatin nephrotoxicity: a review. Am J Med Sci 334(2):115-124
34. Youngs WJ, Hindi K, Medvetz D (2012a) Metal complexes incorporated within biodegradable nanoparticles and their use in treating cancer. US Patent 8,282,944, filed May 28, 2009, issued October 9, 2012
35. Youngs WJ, Knapp AR, Wagers PO, Tessier CA (2012b) Nanoparticle encapsulated silver carbene complexes and their antimicrobial and anti-cancer properties: a perspective. Dalton Trans 41:327-336
36. Youngs W, Panzner M, Deblock M, Tessier C, Wright B, Wagers P, Robishaw N (2012c) Preparation of azolium and purinium salts as anti-cancer and antimicrobial agents. PCT Int Appl, WO2012149523A1 20121101