Caspase-3-Dependent Apoptosis of Citreamicin ε-Induced HeLa Cells Is Associated with Reactive Oxygen Species Generation

Chemical Research in Toxicology

Volumn 26, Issue 7, 2013, Pages 1055-1063

  Liu, Ling Li ^a   He, Li Sheng ^a   Xu, Ying ^a   Han, Zhuang ^a   Li, Yong Xin ^a   Zhong, Jia Liang ^b   Guo, Xian Rong ^c   Zhang, Xi Xiang ^c   Ko, Kam Ming ^a   Qian, Pei Yuan ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b Shanghai Institute of Pharmaceutical Industry   (China)

^c KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE 3; CITREAMICIN EPSILON A; CITREAMICIN EPSILON B; DNA NUCLEOTIDYLEXOTRANSFERASE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE; ANTINEOPLASTIC AGENT; CITREAMICIN ETA; OXAZOLE DERIVATIVE;

APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CELL STRAIN HEPG2; CONCENTRATION (PARAMETERS); CRYSTAL STRUCTURE; CRYSTALLIZATION; DIASTEREOISOMER; DRUG CYTOTOXICITY; ENZYME ACTIVATION; HELA CELL; IC 50; LIVER CELL CARCINOMA; NICK END LABELING; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; UTERINE CERVIX CANCER; WESTERN BLOTTING; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; HELA CELL LINE; HEPG2 CELL LINE; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; TUMOR CELL CULTURE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CASPASE 3; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HEP G2 CELLS; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXAZOLES; REACTIVE OXYGEN SPECIES; STEREOISOMERISM; STREPTOMYCES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84880312682     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx4000304     Document Type: Article

References (44)

1. Carter, G. T., Nietsche, J. A., Williams, D. R., and Borders, D. B. (1990) Citreamicins, novel antibiotics from Micromonospora citrea: Isolation, characterization, and structure determination J. Antibiot. 43, 504-512
2. Carter, G. T., Borders, D. B., Goodman, J. J., Ashcroft, J., Greenstein, M., Maiese, W. M., and Pearce, C. J. (1991) Biosynthetic origins of the polycyclic xanthone antibiotic, citreamicin J. Chem. Soc., Perkin Trans. 1 9, 2215-2219
3. Reich, M. F., Lee, V. J., Ashcroft, J., and Morton, G. O. (1993) An unusual cyclization product from the reaction of citreamicin η with sulfene J. Org. Chem. 58, 5288-5290
4. Peoples, A. J., Zhang, Q., Millett, W. P., Rothfeder, M. T., Pescatore, B. C., Madden, A. A., Ling, L. L., and Moore, C. M. (2009) Neocitreamicins I and II, Novel Antibiotics with Activity against Methicillin-Resistant Staphylococcus aureus and Vancomycin-Resistant Enterococci J. Antibiot. 61, 457-463
5. Hopp, D. C., Milanowski, D. J., Rhea, J., Jacobsen, D., Rabenstein, J., Smith, C., Romari, K., Clarke, M., Francis, L., Irigoyen, M., Luche, M., Carr, G. J., and Mocek, U. (2008) Citreamicins with Potent Gram-Positive Activity J Nat. Prod. 71, 2032-2035
6. Vaux, D. L. and Korsmeyer, S. J. (1999) Cell death in development Cell 96, 245-254
7. Sun, X. M., MacFarlane, M., Zhuang, J., Wolf, B. B., Green, D. R., and Cohen, G. M. (1999) Distinct caspase cascades are initiated in receptor-mediated and chemical-induced apoptosis J. Biol. Chem. 274, 5053-5060
8. Desagher, S. and Martinou, J. C. (2000) Mitochondria as the central control point of apoptosis Trends Cell Biol. 10, 369-377
9. McConkey, D. J. (1998) Biochemical determinants of apoptosis and necrosis Toxicol. Lett. 99, 157-168
10. Elmore, S. (2007) Apoptosis: A Review of Programmed Cell Death Toxicol. Pathol. 35, 495-516
11. Kamradt, M. C., Chen, F., and Cryns, V. L. (2001) The Small Heat Shock Protein αB-Crystallin Negatively Regulates Cytochrome c and Caspase-8-dependent Activation of Caspase-3 by Inhibiting Its Autoproteolytic Maturation J. Biol. Chem. 276, 16059-16063
12. Circu, M. L. and Aw, T. Y. (2010) Reactive oxygen species, cellular redox systems, and apoptosis Free Radical Biol. Med. 48, 749-762
13. Jones, D. C., Gunasekar, P. G., Borowitz, J. L., and Isom, G. E. (2000) Dopamine-Induced Apoptosis Is Mediated by Oxidative Stress and Is Enhanced by Cyanide in Differentiated PC12 Cells J. Neurochem. 74, 2296-2304
14. Circu, M. L., Moyer, M. P., Harrison, L., and Aw, T. Y. (2009) Contribution of glutathione status to oxidant-induced mitochondrial DNA damage in colonic epithelial cells Free Radical Biol. Med. 47, 1190-1198
15. Rachek, L. I., Yuzefovych, L. V., Ledoux, S. P., Julie, N. L., and Wilson, G. L. (2009) Troglitazone, but not rosiglitazone, damages mitochondrial DNA and induces mitochondrial dysfunction and cell death in human hepatocytes Toxicol. Appl. Pharmacol. 240, 348-354
16. Li, P. F., Dietz, R., and Vonharsdorf, R. (1997) Differential effect of hydrogen peroxide and superoxide anion on apoptosis and proliferation of vascular smooth muscle cells Circulation 96, 3602-3609
17. Rauen, U. and Degroot, H. (1998) Cold-induced release of reactive oxygen species as a decisive mediator of hypothermia injury to cultured liver cells Free Radical Biol. Med. 24, 1316-1323
18. Inayat-Hussain, S. H. and Ross, D. (2005) Intrinsic Pathway of Hydroquinone Induced Apoptosis Occurs via Both Caspase-Dependent and Caspase-Independent Mechanisms Chem. Res. Toxicol. 18, 420-427
19. Marshall, K. M. and Barrows, L. R. (2004) Biological activities of pyridoacridines Nat. Prod. Rep. 21, 731-751
20. Puentes, F., Fernandez, C., Gravalos, G., Baz, P., Millan, R., and Vazquez, E. (2003) New use of citreamicins., EP1292299.
21. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) Molecular Cloning. A Laboratory Manual, 2nd ed., pp 914-923, Cold Spring Harbor Laboratory Press, Plainview, NY.
22. Altschul, S. F., Madden, T. L., Schäffer, A. A., Zhang, J., Zhang, Z., Miller, W., and Lipman, D. J. (1997) Gapped BLAST and PSI-BLAST: A new generation of protein database search programs Nucleic Acids Res. 25, 3389-3402
23. Crystallographic data for citreamicin ε A (1) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre with deposition number 890247. Copies of the data can be obtained free of charge on application to the Director CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K. [fax, +44-(0) 1223-336033; or e-mail, deposit@ccdc.cam.ac.uk ].
24. Wang, H. and Joseph, J. A. (1999) Quantifying cellular oxidative stress by dichlorofluorescein assay using microplate reader Free Radical Biol. Med. 27, 612-616
25. Lebel, C. P., Ischiropoulos, H., and Bondy, S. C. (1992) Evaluation of the probe 2′,7′-dichlorofluorescein as an indicator of reactive oxygen species formation and oxidative stress Chem. Res. Toxicol. 5, 227-231
26. Angle, S. R., Rainier, J. D., and Woytowicz, C. (1997) Synthesis and Chemistry of Quinone Methide Models for the Anthracycline Antitumor Antibiotics J. Org. Chem. 62, 5884-5892
27. Darzynkiewicz, Z., Galkowski, D., and Zhao, H. (2008) Analysis of apoptosis by cytometry using TUNEL assay Methods 44, 250-254
28. Rohwer, F. and Azam, F. (2000) Detection of DNA damage in prokaryotes by terminal deoxyribonucleotide transferase-mediated dUTP nick end labeling Appl. Environ. Microbiol. 66, 1001-1006
29. Bolton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G., and Monks, T. J. (2000) Role of quinones in toxicology Chem. Res. Toxicol. 13, 135-160
30. Valderrama, J. A., Colonelli, P., Vasquez, D., Gonzalez, M. F., Rodriguez, J. A., and Theoduloz, C. (2008) Studies on quinones. Part 44: Novel angucyclinone N-heterocyclic analogues endowed with antitumoral activity Bioorg. Med. Chem. 16, 10172-10181
31. Liu, L.-L., Xu, Y., Han, Z., Li, Y.-X., Lu, L., Lai, P.-Y., Zhong, J.-L., Guo, X.-R., Zhang, X.-X., and Qian, P.-Y. (2012) Four New Antibacterial Xanthones from the Marine-Derived Actinomycetes Streptomyces caelestis Mar. Drugs 10, 2571-2583
32. White, P. F., Ham, J., Way, W. L., and Trevor, A. (1980) Pharmacology of ketamine isomers in surgical patients Anesthesiology 52, 231-239
33. Roos, W. P. and Kaina, B. (2006) DNA damage-induced cell death by apoptosis Trends Mol. Med. 12, 440-450
34. Han, J., Goldstein, L. A., Gastman, B. R., Rabinovitz, A., and Rabinowich, H. (2005) Disruption of Mcl-1 Bim Complex in Granzyme B-mediated Mitochondrial Apoptosis J. Biol. Chem. 280, 16383-16392
35. Monks, T. J., Hanzlik, R. P., Cohen, G. M., Ross, D., and Graham, D. G. (1992) Quinone chemistry and toxicity Toxicol. Appl. Pharmacol. 112, 2-16
36. O'Brien, P. J. (1991) Molecular mechanisms of quinone cytotoxicity Chem.-Biol. Interact. 80, 1-41
37. Ryter, S. W., Kim, H. P., Hoetzel, A., Park, J. W., Nakahira, K., Wang, X., and Choi, A. M. (2007) Mechanisms of cell death in oxidative stress Antioxid. Redox Signaling 9, 49-89
38. Zhang, A. Y., Yi, F., Zhang, G., Gulbins, E., and Li, P.-L. (2006) Lipid Raft Clustering and Redox Signaling Platform Formation in Coronary Arterial Endothelial Cells Hypertension 47, 74-80
39. Zhang, A. Y., Yi, F., Jin, S., Xia, M., Chen, Q. Z., Gulbins, E., and Li, P. L. (2007) Acid sphingomyelinase and its redox amplification in formation of lipid raft redox signaling platforms in endothelial cells Antioxid. Redox Signaling 9, 817-828
40. Schafer, F. Q. and Buettner, G. R. (2001) Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple Free Radical Biol. Med. 30, 1191-1212
41. Hirakawa, K., Oikawa, S., Hiraku, Y., Hirosawa, I., and Kawanishi, S. (2002) Catechol and Hydroquinone Have Different Redox Properties Responsible for Their Differential DNA-damaging Ability Chem. Res. Toxicol. 15, 76-82
42. Nutter, L. M., Wu, Y. Y., Ngo, E. O., Sierra, E. E., Gutierrez, P. L., and Abul-Hajj, Y. J. (1994) An o-quinone form of estrogen produces free radicals in human breast cancer cells: Correlation with DNA damage Chem. Res. Toxicol. 7, 23-28
43. 32P-postlabeling Carcinogenesis 12, 1181-1186
44. Shinabarger, D. (1999) Mechanism of action of the oxazolidinone antibacterial agents Expert Opin. Invest. Drugs 8, 1195-1202 Association