A novel bifunctional mitochondria-targeted anticancer agent with high selectivity for cancer cells

Scientific Reports

Volumn 5, Issue , 2015, Pages

  He, Huan ^a   Li, Dong Wei ^a   Yang, Li Yun ^a   Fu, Li ^a   Zhu, Xun Jin ^b   Wong, Wai Kwok ^b   Jiang, Feng Lei ^a   Liu, Yi ^a  

^a WUHAN UNIVERSITY   (China)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; 4-(2-(INDOL-3-YL)VINYL)-1-METHYLPYRIDINIUM; ANTINEOPLASTIC AGENT; BORON DERIVATIVE; CONTRAST MEDIUM; FLUORESCENT DYE; INDOLE DERIVATIVE; PYRIDINIUM DERIVATIVE;

ANIMAL; APOPTOSIS; CELL SURVIVAL; DRUG EFFECTS; FLUORESCENCE MICROSCOPY; HUMAN; MITOCHONDRION; MOUSE; NEOPLASMS, EXPERIMENTAL; PATHOLOGY; PROCEDURES; REPRODUCIBILITY; SENSITIVITY AND SPECIFICITY; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BORON COMPOUNDS; CELL LINE, TUMOR; CELL SURVIVAL; CONTRAST MEDIA; FLUORESCENT DYES; HUMANS; INDOLES; MICE; MICROSCOPY, FLUORESCENCE; MITOCHONDRIA; NEOPLASMS, EXPERIMENTAL; PYRIDINIUM COMPOUNDS; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY;

EID: 84940922735     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep13543     Document Type: Article

References (40)

1. Ralph, S. J., Low, P., Dong, L., Lawen, A. & Neuzil, J. Mitocans: mitochondrial targeted anti-cancer drugs as improved therapies and related patent documents. Recent Pat. Anti-Canc. 1(3), 327-346 (2006).
2. Frantz, M.-C. & Wipf, P. Mitochondria as a target in treatment. Environ. Mol. Mutagen. 51, 462-475 (2010).
3. Modica-Napolitano, J. S. & Aprille, J. R. Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells. Adv. Drug Deliver. Rev. 49, 63-70 (2001).
4. Kramer, P. A., Ravi, S., Chacko, B., Johnson, M. S. & Darley-Usmar, V. M. A review of the mitochondrial and glycolytic metabolism in human platelets and leukocytes: Implications for their use as bioenergetic biomarkers. Redox Biol. 2, 206-210 (2014).
5. Baracca, A., Sgarbi, G., Solaini, G. & Lenaz, G. Rhodamine 123 as a probe of mitochondrial membrane potential: evaluation of proton flux through F0 during ATP synthesis. BBA-Bioenergetics 1606, 137-146 (2003).
6. Rousaki, A. et al. Allosteric drugs: the interaction of anti-tumor compound MKT-077 with human Hsp70 chaperones. J. Mol. Biol. 411(3), 614-632 (2011).
7. Fantin, V. R., Berardi, M. J., Scorrano, L., Korsmeyer, S. J. & Leder, P. A novel mitochondriotoxic small molecule that selectively inhibits tumor cell growth. Cancer Cell 2, 29-42 (2002).
8. Fantin, V. R. & Leder, P. F16, a mitochondriotoxic compound, triggers apoptosis or necrosis depending on the genetic background of the target carcinoma cell. Cancer Res. 64, 329-336 (2004).
9. Murphy, M. P. & Smith, R. A. J. Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annu. Rev. Pharmacol. Toxicol. 47, 629-656 (2007).
10. Neuzil, J., Dong, L.-F., Rohlena, J., Truksa, J. & Ralph, S. J. Classification of mitocans, anti-cancer drugs acting on mitochondria. Mitochondrion 13, 199-208 (2013).
11. Biasutto, L., Dong, L.-F., Zoratti, M. & Neuzil, J. Mitochondrially targeted anti-cancer agents. Mitochondrion 10, 670-681 (2010).
12. Jara, J. A. et al. Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice. J. Med. Chem. 57, 2440-2454 (2014).
13. Dickinson, B. C., Lin, V. S. & Chang, C. J. Preparation and use of MitoPY1 for imaging hydrogen peroxide in mitochondria of live cells. Nat. Protoc. 8, 1249-1259 (2013).
14. Lim, S.-Y., Hong, K.-H., Kim, D. I., Kwon, H. & Kim, H.-J. Tunable heptamethine-azo dye conjugate as an NIR fluorescent probe for the selective detection of mitochondrial glutathione over cysteine and homocysteine. J. Am. Chem. Soc. 136, 7018-7025 (2014).
15. Zhou, W., Wang, X.-Y., Hu, M., Zhu, C.-C. & Guo, Z.-J. A mitochondrion-targeting copper complex exhibits potent cytotoxicity against cisplatin-resistant tumor cells through multiple mechanisms of action. Chem. Sci. 5, 2761-2770 (2014).
16. Lee, M. H. et al. Mitochondria-immobilized pH-sensitive off-on fluorescent probe. J. Am. Chem. Soc. 136, 14136-14142 (2014).
17. Chamberlain, G. R., Tulumello, D. V. & Kelley, S. O. Targeted delivery of doxorubicin to mitochondria. ACS Chem. Biol. 8, 1389-1395 (2013).
18. Lee, M. H. et al. Mitochondrial thioredoxin-responding off-on fluorescent probe. J. Am. Chem. Soc. 134, 17314-17319 (2012).
19. Masanta, G. et al. A mitochondrial-targeted two-photon probe for zinc ion. J. Am. Chem. Soc. 133, 5698-5700 (2011).
20. Oliveira, S. et al. Targeting tumors with nanobodies for cancer imaging and therapy. J. Control. Release 172, 607-617 (2013).
21. Willmann, J. K., Bruggen, N., Dinkelborg, L. M. & Gambhir, S. S. Molecular imaging in drug development. Nat. Rev. Drug Discov. 7, 591-607 (2008).
22. Jiang, F.-L. et al. Amphiphilic bisporphyrin and its Yb(III) complex: improved cellular uptake and development of a bifunctional photodynamic therapeutic and near-infrared tumor imaging agent. ChemBioChem 9, 1034-1039 (2008).
23. Qi, Z.-D. et al. Biocompatible CdSe quantum dot-based photosensitizer under two-photon excitation for photodynamic therapy. J. Mater. Chem. 21, 2455-2458 (2011).
24. Li, D.-W. et al. A novel pH-sensitive (±)-α -tocopherol-5-fluorouracil adduct with antioxidant and anticancer properties. Chem. Commun. 47, 10713-10715 (2011).
25. Fu, L. et al. A ratiometric "two-in-one" fluorescent chemodosimeter for fluoride and hydrogen sulfide. Sensor. Actuat. B-Chem. 193, 701-707 (2014).
26. Guo, X., Rao, H., Fu, H., Jiang, Y. & Zhao, Y. An inexpensive and efficient copper catalyst for N-arylation of amines, amides and nitrogen-containing heterocycles. Adv. Synth. Catal. 348, 2197-2202 (2006).
27. Fu, L., Jiang, F.-L., Fortin, D., Harvey, P. D. & Liu, Y. A reaction-based chromogenic and fluorescent chemodosimeter for fluoride anions. Chem. Commun. 47, 5503-5505 (2011).
28. Cetin, Y. & Bullerman, L. B. Evaluation of reduced toxicity of zearalenone by extrusion processing as measured by the MTT cell proliferation assay. J. Agric. Food Chem. 53, 6558-6563 (2005).
29. Liao, P. et al. A positive feedback loop between EBP2 and c-Myc regulates rDNA transcription, cell proliferation, and tumorigensis. Cell Death Dis. 5, e1032 (2014).
30. Riccardi, C. & Nicoletti, I. Analysis of apoptosis by propidium iodide staining and flow cytometry. Nat. Protoc. 1(3), 1458-1461 (2006).
31. Elmore, S. Apoptosis: a review of programmed cell death. Toxicol Pathol. 35(4), 495-516 (2007).
32. Wlodkowic, D., Telford, W., Skommer, J. & Darzynkiewicz, Z. Apoptosis and beyond: cytometry in studies of programmed cell death. Methods Cell Biol. 103, 55-98 (2011).
33. Domingo-Gil, E. & Esteban, M. Role of mitochondria in apoptosis induced by the 2-5A system and mechanisms involved. Apoptosis 11, 725-738 (2006).
34. Labios, M. et al. Effects of eprosartan on mitochondrial membrane potential and H2O2 levels in leucocytes in hypertension. J. Hum. Hypertens. 22, 493-500 (2008).
35. Don, A. S. et al. A peptide trivalent arsenical inhibits tumor angiogenesis by perturbing mitochondrial function in angiogenic endothelial cells. Cancer Cell 3, 497-509 (2003).
36. Serrander, L. et al. NOX4 activity is determined by mRNA levels and reveals a unique pattern of ROS generation. Biochem. J. 406, 105-114 (2007).
37. Neuzil, J. et al. Induction of cancer cell apoptosis by α -tocopheryl succinate: molecular pathways and structural requirements. FASEB J. 15(2), 403-415 (2001).
38. Chen, Z., Zhang, H., Lu, W. & Huang, P. Role of mitochondria-associated hexokinase II in cancer cell death induced by 3-bromopyruvate. Biochim. Biophys. Acta 1787(5), 553-560 (2008).
39. Ihrlund, L. S., Hernlund, E., Khan, O. & Shoshan, M. C. 3-Bromopyruvate as inhibitor of tumour cell energy metabolism and chemopotentiator of platinum drugs. Mol. Oncol. 2, 94-101 (2008).
40. Zhang, X.-F., Zhang, J. & Liu, L. Fluorescence properties of twenty fluorescein derivatives: lifetime, quantum yield, absorption and emission spectra. J. Fluoresc. 24, 819-826 (2014).