Crown ether host-rotaxanes as cytotoxic agents

ACS Medicinal Chemistry Letters

Volumn 4, Issue 1, 2013, Pages 27-31

  Smithrud, David B ^a   Wang, Xiaoyang ^a   Tarapore, Pheruza ^b   Ho, Shuk Mei ^b,c  

^a UNIVERSITY OF CINCINNATI   (United States)

^b UNIVERSITY OF CINCINNATI MEDICAL CENTER   (United States)

^c VETERANS AFFAIRS MEDICAL CENTER   (United States)

Author keywords

apoptosis; calcium; crown ethers; magnesium; rotaxanes

Indexed keywords

CALCIUM; CROWN ETHER HOST ROTAXANE; CYTOTOXIC AGENT; DIMETHYL SULFOXIDE; IONOPHORE; LIPOCORTIN 5; MAGNESIUM; ROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; CELL DEATH; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; DRUG STRUCTURE; FLOW CYTOMETRY; IC 50; PRIORITY JOURNAL; VETERINARY MEDICINE;

BACTERIA (MICROORGANISMS);

EID: 84872294078     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3003204     Document Type: Article

References (29)

1. Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Lamb, J. D.; Christensen, J. J. Thermodynamic and Kinetic Data for Cation Macrocycle Interaction Chem. Rev. 1985, 85, 271-339
2. Hendrixson, R.; Mack, M.; Palmer, R.; Ottolenghi, A.; Ghirardelli, R. Oral Toxicity of Cyclic Polyethers-12-Crown-4, 15-Crown-5, and 18-Crown-6-in Mice Toxicol. Appl. Pharmacol. 1978, 44, 263-268
3. Marjanovic, M.; Kralj, M.; Supek, F.; Frkanec, L.; Piantanida, I.; Smuc, T.; Tusek-Bozic, L. Antitumor potential of crown ethers: Structure-activity relationships, cell cycle disturbances, and cell death studies of a series of ionophores J. Med. Chem. 2007, 50, 1007-1018
4. Gupta, P. B.; Onder, T. T.; Jiang, G.; Tao, K.; Kuperwasser, C.; Weinberg, R. A.; Lander, E. S. Identification of Selective Inhibitors of Cancer Stem Cells by High-Throughput Screening Cell 2009, 138, 645-659
5. Fuchs, D.; Heinold, A.; Opelz, G.; Daniel, V.; Naujokat, C. Salinomycin induces apoptosis and overcomes apoptosis resistance in human cancer cells Biochem. Biophys. Res. Commun. 2009, 390, 743-749
6. Ketola, K.; Vainio, P.; Fey, V.; Kallioniemi, O.; Iljin, K. Monensin Is a Potent Inducer of Oxidative Stress and Inhibitor of Androgen Signaling Leading to Apoptosis in Prostate Cancer Cells Mol. Cancer Ther. 2010, 9, 3175-3185
7. Park, W.; Kim, E.; Kim, B.; Lee, Y. Monensin-mediated growth inhibition in NCI-H929 myeloma cells via cell cycle arrest and apoptosis Int. J. Oncol. 2003, 23, 197-204
8. Park, W.; Kim, E.; Jung, C.; Kim, B.; Lee, Y. Monensin-mediated growth inhibition of SNU-C1 colon cancer cells via cell cycle arrest and apoptosis Int. J. Oncol. 2003, 22, 377-382
9. Park, W.; Jung, C.; Park, J.; Kim, K.; Kim, W.; Im, Y.; Lee, M.; Kang, W.; Park, K. Monensin inhibits the growth of renal cell carcinoma cells via cell cycle arrest or apoptosis Int. J. Oncol. 2003, 22, 855-860
10. Basque, J.; Martel, M.; Leduc, R.; Cantin, A. M. Lysosomotropic drugs inhibit maturation of transforming growth factor-beta Can. J. Physiol. Pharmacol. 2008, 86, 606-612
11. Blobe, G.; Schiemann, W.; Lodish, H. Mechanisms of disease: Role of transforming growth factor beta in human disease N. Engl. J. Med. 2000, 342, 1350-1358
12. Wang, X.; Zhu, J.; Smithrud, D. B. Synthesis and Investigation of Host-[2]Rotaxanes That Bind Metal Cations J. Org. Chem. 2010, 75, 3358-3370
13. Sauvage, J.-P.; Dietrich-Buchecker, C. O. Molecular Catenanes, Rotaxanes and Knots: A Journey through the World of Molecular Topology; Wiley-VCH: Weinheim, Germany, 1999.
14. Smukste, I.; Smithrud, D. B. Structure-function relationship of amino acid-[2]rotaxanes J. Org. Chem. 2003, 68, 2547-2558
15. Wang, X.; Bao, X.; McFarland-Mancini, M.; Isaacsohn, I.; Drew, A. F.; Smithrud, D. B. Investigation of the intracellular delivery of fluoresceinated peptides by a host-[2]rotaxane J. Am. Chem. Soc. 2007, 129, 7284-7293
16. Zhu, J.; House, B. E.; Fleck, E.; Isaacsohn, I.; Drew, A. F.; Smithrud, D. B. A host-rotaxane derivatized with carboxylic acids efficiently delivers a highly cationic fluoresceinated peptide Bioorg. Med. Chem. Lett. 2007, 17, 5058-5062
17. Wang, X.; Smithrud, D. B. Pt-rotaxanes as cytotoxic agents Bioorg. Med. Chem. Lett. 2011, 21, 6880-6883
18. Arbabian, A.; Brouland, J.; Gelebart, P.; Kovacs, T.; Bobe, R.; Enouf, J.; Papp, B. Endoplasmic reticulum calcium pumps and cancer Biofactors 2011, 37, 139-149
19. Moffitt, K. L.; Martin, S. L.; Walker, B. From sentencing to execution-the processes of apoptosis J. Pharm. Pharmacol. 2010, 62, 547-562
20. Barros, L.; Castro, J.; Bittner, C. Ion movements in cell death: from protection to execution Biol. Res. 2002, 35, 209-214
21. Duke, R.; Witter, R.; Nash, P.; Young, J.; Ojcius, D. Cytolysis Mediated by Ionophores and Pore-Forming Agents-Role of Intracellular Calcium in Apoptosis FASEB J. 1994, 8, 237-246
22. Alexandrova, R. I.; Zhivkova, T.; Alexandrov, M.; Miloshev, G.; Georgieva, M.; Pantcheva, I. N.; Mitewa, M. I. Cytostatic and cytotoxic properties of monensic acid and its biometal(II) complexes against human tumor/non-tumor cell lines Cent. Eur. J. Chem 2012, 10, 1464-1474
23. Chirase, N.; Greene, L.; Schelling, G.; Byers, F. Effect of Magnesium and Potassium on Microbial Fermentation in a Continuous Culture Fermentation System with Different Levels of Monensin Or Lasalocid J. Anim. Sci. 1987, 65, 1633-1638
24. Mollenhauer, H.; Morre, D.; Rowe, L. Alteration of Intracellular Traffic by Monensin-Mechanism, Specificity and Relationship to Toxicity Biochim. Biophys. Acta 1990, 1031, 225-246
25. Mitani, M.; Yamanishi, T.; Miyazaki, Y. Salinomycin-New Monovalent Cation Ionophore Biochem. Biophys. Res. Commun. 1975, 66, 1231-1236
26. Wolf, F. I.; Cittadini, A. R. M.; Maier, J. A. M. Magnesium and tumors: Ally or foe? Cancer Treat. Rev. 2009, 35, 378-382
27. Anghileri, L. J. Magnesium, calcium and cancer Magnesium Res. 2009, 22, 247-255
28. La Piana, G.; Gorgoglione, V.; Laraspata, D.; Marzulli, D.; Lofrumento, N. E. Effect of magnesium ions on the activity of the cytosolic NADH/cytochrome c electron transport system FEBS J. 2008, 275, 6168-6179
29. 2+ dynamic changes and thapsigargin-induced apoptosis in human cancer MCF7 cells Mol. Cell. Biochem. 2002, 229, 163-171