Cross-linking protein glutathionylation mediated by O2-arylated bis-diazeniumdiolate "double JS-K"

Chemical Research in Toxicology

Volumn 25, Issue 12, 2012, Pages 2670-2677

  Holland, Ryan J ^a   MacIag, Anna E ^b   Kumar, Varun ^c   Shi, Lei ^c   Saavedra, Joseph E ^b   Prud'Homme, Robert K ^c   Chakrapani, Harinath ^d   Keefer, Larry K ^a  

^a FREDERICK NATIONAL LABORATORY FOR CANCER RESEARCH   (United States)

^b SAIC FREDERICK INC   (United States)

^c Princeton University   (United States)

^d INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; BIZ DIAZENIUMDIOLATE; GLUTATHIONE; GLUTATHIONE ANTIBODY; NITRIC OXIDE DONOR; SULFUR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLUTATHIONYLATION; PROTEIN CROSS LINKING;

ACETYLCYSTEINE; ACTINS; ANIMALS; ANTINEOPLASTIC AGENTS; AZO COMPOUNDS; CELL LINE, TUMOR; DINITROFLUOROBENZENE; FEMALE; GLUTATHIONE; HUMANS; MICE; MICE, NUDE; NANOPARTICLES; NITRIC OXIDE; OXYGEN; PIPERAZINES;

EID: 84871249632     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx3003142     Document Type: Article

References (22)

1. Xiong, Y., Uys, J. D., Tew, K. D., and Townsend, D. M. (2011) S-Glutathionylation: From molecular mechanisms to health outcomes Antioxid. Redox Signaling 15, 233-270
2. Mieyal, J. J., Gallogly, M. M., Qanungo, S., Sabens, E. A., and Shelton, M. D. (2008) Molecular mechanisms and clinical implications of reversible protein S-glutathionylation Antioxid. Redox Signaling 10, 1941-1988
3. Shami, P. J., Saavedra, J. E., Wang, L. Y., Bonifant, C. L., Diwan, B. A., Singh, S. V., Gu, Y., Fox, S. D., Buzard, G. S., Citro, M. L., Waterhouse, D. J., Davies, K. M., Ji, X., and Keefer, L. K. (2003) JS-K, a glutathione/glutathione S-transferase-activated nitric oxide donor of the diazeniumdiolate class with potent antineoplastic activity Mol. Cancer Ther. 2, 409-417
4. 2-aryl diazeniumdiolates in vitro and in vivo J. Med. Chem. 49, 4356-4366 (Pubitemid 44036679)
5. Kiziltepe, T., Hideshima, T., Ishitsuka, K., Ocio, E. M., Raje, N., Catley, L., Li, C.-Q., Trudel, L. J., Yasui, H., Vallet, S., Kutok, J. L., Chauhan, D., Mitsiades, C. S., Saavedra, J. E., Wogan, G. N., Keefer, L. K., Shami, P. J., and Anderson, K. C. (2007) JS-K, a GST-activated nitric oxide generator, induces DNA double-strand breaks, activates DNA damage response pathways, and induces apoptosis in vitro and in vivo in human multiple myeloma cells Blood 110, 709-718 (Pubitemid 47105410)
6. Maciag, A. E., Chakrapani, H., Saavedra, J. E., Morris, N. L., Holland, R. J., Kosak, K. M., Shami, P. J., Anderson, L. M., and Keefer, L. K. (2011) The nitric oxide prodrug JS-K is effective against non-small-cell lung cancer cells in vitro and in vivo: involvement of reactive oxygen species J. Pharmacol. Exp. Ther. 336, 313-320
7. Weyerbrock, A., Osterberg, N., Psarras, N., Baumer, B., Kogias, E., Werres, A., Bette, S., Saavedra, J. E., Keefer, L. K., and Papazoglou, A. (2012) JS-K, a glutathione S-transferase-activated nitric oxide donor with antineoplastic activity in malignant gliomas Neurosurgery 70, 497-510
8. Townsend, D. M., Findlay, V. J., Fazilev, F., Ogle, M., Fraser, J., Saavedra, J. E., Ji, X., Keefer, L. K., and Tew, K. D. (2006) A glutathione S -transferase π-activated prodrug causes kinase activation concurrent with S -glutathionylation of proteins Mol. Pharmacol. 69, 501-508 (Pubitemid 43121947)
9. Andrei, D., Maciag, A. E., Chakrapani, H., Citro, M. L., Keefer, L. K., and Saavedra, J. E. (2008) Aryl bis(diazeniumdiolates): Potent inducers of S -glutathionylation of cellular proteins and their in vitro antiproliferative activities J. Med. Chem. 51, 7944-7952
10. NAr reactions J. Org. Chem. 66, 3090-3098 (Pubitemid 32879751)
11. Mancini, I., Guella, G., Chiasera, G., and Pietra, F. (1998) Glutathione S -transferase catalysed dehalogenation of haloaromatic compounds which lack nitro groups near the reaction centre Tetrahedron Lett. 39, 1611-1614 (Pubitemid 28101585)
12. Kumar, V., Hong, S. Y., Maciag, A. E., Saavedra, J. E., Adamson, D. H., Prud'homme, R. K., Keefer, L. K., and Chakrapani, H. (2010) Stabilization of the nitric oxide (NO) prodrugs and anti-cancer leads, PABA/NO and Double JS-K, through incorporation into PEG-protected nanoparticles Mol. Pharmaceutics 7, 291-298
13. Wang, J., Tekle, E., Oubrahim, H., Mieyal, J. J., Stadtman, E. R., and Chock, P. B. (2003) Stable and controllable RNA interference: investigating the physiological function of glutathionylated actin Proc. Natl. Acad. Sci. U.S.A. 100, 5103-5106 (Pubitemid 36542665)
14. Wang, J., Boja, E. S., Tan, W., Tekle, E., Fales, H. M., English, S., Mieyal, J. J., and Chock, P. B. (2001) Reversible glutathionylation regulates actin polymerization in A431 cells J. Biol. Chem. 276, 47763-47766
15. Szajewski, R. P. and Whitesides, G. M. (1980) Rate constants and equilibrium constants for thiol-disulfide interchange reactions involving oxidized glutathione J. Am. Chem. Soc. 102, 2011-2025
16. Srivastava, S. K., Ramana, K. V., and Bhatnagar, A. (2005) Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options Endocr. Rev. 26, 380-392 (Pubitemid 40691299)
17. Reynaert, N. L., van der Vliet, A., Guala, A. S., McGovern, T., Hristova, M., Pantano, C., Heintz, N. H., Heim, J., Ho, Y. S., Matthews, D. E., Wouters, E. F., and Janssen-Heininger, Y. M. (2006) Dynamic redox control of NF-κB through glutaredoxin-regulated S-glutathionylation of inhibitory κB kinase β Proc. Natl. Acad. Sci. U.S.A. 103, 13086-13091 (Pubitemid 44338920)
18. Lou, Y. W., Chen, Y. Y., Hsu, S. F., Chen, R. K., Lee, C. L., Khoo, K. H., Tonks, N. K., and Meng, T. C. (2008) Redox regulation of the protein tyrosine phosphatase PTP1B in cancer cells FEBS J. 275, 69-88 (Pubitemid 350294063)
19. Ghezzi, P. and Di Simplicio, P. (2008) Glutathionylation pathways in drug response Curr. Opin. Pharmacol. 7, 398-403 (Pubitemid 47289262)
20. Eastman, A. (1987) Cross-linking of glutathione to DNA by cancer chemotherapeutic platinum coordination complexes Chem.-Biol. Interact. 61, 241-248 (Pubitemid 17071620)
21. Peterson, L. A., Phillips, M. B., Lu, D., and Sullivan, M. M. (2011) Polyamines are traps for reactive intermediates in furan metabolism Chem. Res. Toxicol. 24, 1924-1936
22. Zhu, X., Gallogly, M. M., Mieyal, J. J., Anderson, V. E., and Sayre, L. M. (2009) Covalent cross-linking of glutathione and carnosine to proteins by 4-oxo-2-nonenal Chem. Res. Toxicol. 22, 1050-1059