An FAD-Dependent Pyridine Nucleotide-Disulfide Oxidoreductase Is Involved in Disulfide Bond Formation in FK228 Anticancer Depsipeptide

Chemistry and Biology

Volumn 16, Issue 6, 2009, Pages 585-593

  Wang, Cheng ^a   Wesener, Shane R ^a   Zhang, Hailong ^a   Cheng, Yi Qiang ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

CHEMBIO; PROTEINS

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DEPSIPEPTIDE; DISULFIDE; FLAVINE ADENINE NUCLEOTIDE; MUTANT PROTEIN; OXIDOREDUCTASE; ROMIDEPSIN;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; CHROMOBACTERIUM; CLASSIFICATION; ENZYMOLOGY; GENETICS; KINETICS; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY; NUCLEOTIDE SEQUENCE; PHYLOGENY;

ANTIBIOTICS, ANTINEOPLASTIC; CHROMOBACTERIUM; DEPSIPEPTIDES; DISULFIDES; FLAVIN-ADENINE DINUCLEOTIDE; KINETICS; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; MUTANT PROTEINS; NADH, NADPH OXIDOREDUCTASES; PHYLOGENY;

BACTERIA (MICROORGANISMS); CHROMOBACTERIUM VIOLACEUM;

EID: 67649522901     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2009.05.005     Document Type: Article

References (34)

1. Akif M., Suhre K., Verma C., and Mande S.C. Conformational flexibility of Mycobacterium tuberculosis thioredoxin reductase: crystal structure and normal-mode analysis. Acta Crystallogr. D Biol. Crystallogr. 61 (2005) 1603-1611
2. Argyrou A., and Blanchard J.S. Flavoprotein disulfide reductases: advances in chemistry and function. Prog. Nucleic Acid Res. Mol. Biol. 78 (2004) 89-142
3. Bardwell J.C., McGovern K., and Beckwith J. Identification of a protein required for disulfide bond formation in vivo. Cell 67 (1991) 581-589
4. Blencowe D.K., and Morby A.P. Zn(II) metabolism in prokaryotes. FEMS Microbiol. Rev. 27 (2003) 291-311
5. Bolden J.E., Peart M.J., and Johnstone R.W. Anticancer activities of histone deacetylase inhibitors. Nat Rev. Drug Discov. 5 (2006) 769-784
6. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
7. Bryk R., Lima C.D., Erdjument-Bromage H., Tempst P., and Nathan C. Metabolic enzymes of mycobacteria linked to antioxidant defense by a thioredoxin-like protein. Science 295 (2002) 1073-1077
8. Cheng Y.Q., Yang M., and Matter A.M. Characterization of a gene cluster responsible for the biosynthesis of anticancer agent FK228 in Chromobacterium violaceum No. 968. Appl. Environ. Microbiol. 73 (2007) 3460-3469
9. Chenna R., Sugawara H., Koike T., Lopez R., Gibson T.J., Higgins D.G., and Thompson J.D. Multiple sequence alignment with the Clustal series of programs. Nucleic Acids Res. 31 (2003) 3497-3500
10. Choi K.H., and Schweizer H.P. An improved method for rapid generation of unmarked Pseudomonas aeruginosa deletion mutants. BMC Microbiol. 5 (2005) 30
11. Dawson S., Malkinson J.P., Paumier D., and Searcey M. Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies. Nat. Prod. Rep. 24 (2007) 109-126
12. Giles N.M., Watts A.B., Giles G.I., Fry F.H., Littlechild J.A., and Jacob C. Metal and redox modulation of cysteine protein function. Chem. Biol. 10 (2003) 677-693
13. Hoang T.T., Karkhoff-Schweizer R.R., Kutchma A.J., and Schweizer H.P. A broad-host-range Flp-FRT recombination system for site-specific excision of chromosomally-located DNA sequences: application for isolation of unmarked Pseudomonas aeruginosa mutants. Gene 212 (1998) 77-86
14. Hwang K., Piekarz R.L., Bates S.E., Figg W.D., and Sparreboom A. Determination of the cyclic depsipeptide FK228, a histone deacetylase inhibitor, by liquid chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 809 (2004) 81-86
15. Jacob C. A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat. Prod. Rep. 23 (2006) 851-863
16. Kadokura H., Katzen F., and Beckwith J. Protein disulfide bond formation in prokaryotes. Annu. Rev. Biochem. 72 (2003) 111-135
17. Kim H.S., Schell M.A., Yu Y., Ulrich R.L., Sarria S.H., Nierman W.C., and DeShazer D. Bacterial genome adaptation to niches: divergence of the potential virulence genes in three Burkholderia species of different survival strategies. BMC Genomics 6 (2005) 174
18. Lennon B.W., Williams Jr. C.H., and Ludwig M.L. Crystal structure of reduced thioredoxin reductase from Escherichia coli: structural flexibility in the isoalloxazine ring of the flavin adenine dinucleotide cofactor. Protein Sci. 8 (1999) 2366-2379
19. Lombo F., Velasco A., Castro A., de la Calle F., Brana A.F., Sanchez-Puelles J.M., Mendez C., and Salas J.A. Deciphering the biosynthesis pathway of the antitumor thiocoraline from a marine actinomycete and its expression in two streptomyces species. ChemBioChem 7 (2006) 366-376
20. Martin J.L., Bardwell J.C., and Kuriyan J. Crystal structure of the DsbA protein required for disulphide bond formation in vivo. Nature 365 (1993) 464-468
21. Masakuni, O., Toshio, G., Takashi, F., Yasuhiro, H., and Hirotsugu, U. (1991). FR901375 substance and production thereof. JP3141296 (A).
22. Masuoka Y., Nagai A., Shin-ya K., Furihata K., Nagai K., Suzuki K., Hayakawa Y., and Seto H. Spiruchostatins A and B, novel gene expression-enhancing substances produced by Pseudomonas sp. Tetrahedron Lett. 42 (2001) 41-44
23. Mieyal J.J., Starke D.W., Gravina S.A., and Hocevar B.A. Thioltransferase in human red blood cells: kinetics and equilibrium. Biochemistry 30 (1991) 8883-8891
24. Nakajima H., Kim Y.B., Terano H., Yoshida M., and Horinouchi S. FR901228, a potent antitumor antibiotic, is a novel histone deacetylase inhibitor. Exp. Cell Res. 241 (1998) 126-133
25. Nakamoto H., and Bardwell J.C. Catalysis of disulfide bond formation and isomerization in the Escherichia coli periplasm. Biochim. Biophys. Acta 1694 (2004) 111-119
26. Nogle L.M., and Gerwick W.H. Somocystinamide A, a novel cytotoxic disulfide dimer from a Fijian marine cyanobacterial mixed assemblage. Org. Lett. 4 (2002) 1095-1098
27. Rautio J., Kumpulainen H., Heimbach T., Oliyai R., Oh D., Jarvinen T., and Savolainen J. Prodrugs: design and clinical applications. Nat. Rev. Drug Discov. 7 (2008) 255-270
28. Sambrook J., and Russell D.W. Molecular Cloning: A Laboratory Manual, Third Edition (2000), Cold Spring Harbor Laboratory, Cold Spring Harbor, NY
29. Shigematsu N., Ueda H., Takase S., Tanaka H., Yamamoto K., and Tada T. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. II. Structure determination. J. Antibiot. (Tokyo) 47 (1994) 311-314
30. Tang G.L., Cheng Y.Q., and Shen B. Leinamycin biosynthesis revealing unprecedented architectural complexity for a hybrid polyketide synthase and nonribosomal peptide synthetase. Chem. Biol. 11 (2004) 33-45
31. Ueda H., Manda T., Matsumoto S., Mukumoto S., Nishigaki F., Kawamura I., and Shimomura K. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. III. Antitumor activities on experimental tumors in mice. J. Antibiot. (Tokyo) 47 (1994) 315-323
32. Waksman G., Krishna T.S., Williams Jr. C.H., and Kuriyan J. Crystal structure of Escherichia coli thioredoxin reductase refined at 2 A resolution. Implications for a large conformational change during catalysis. J. Mol. Biol. 236 (1994) 800-816
33. Watanabe K., Hotta K., Praseuth A.P., Koketsu K., Migita A., Boddy C.N., Wang C.C., Oguri H., and Oikawa H. Total biosynthesis of antitumor nonribosomal peptides in Escherichia coli. Nat. Chem. Biol. 2 (2006) 423-428
34. Yoo C.B., and Jones P.A. Epigenetic therapy of cancer: past, present and future. Nat. Rev. Drug Discov. 5 (2006) 37-50