Enediyne natural products: Biosynthesis and prospect towards engineering novel antitumor agents

Current Medicinal Chemistry

Volumn 10, Issue 21, 2003, Pages 2317-2325

  Shen, Ben ^a   Liu, Wen ^a   Nonaka, Koichi ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Biosynthesis; C 1027; Calicheamicin; Combinatorial biosynthesis; Enediyne; Polyketide synthase

Indexed keywords

ALKENYLDIALKYNE DERIVATIVE; ANTIBIOTIC C 1027; ANTINEOPLASTIC AGENT; ANTINEOPLASTIC ANTIBIOTIC; CALICHEAMICIN DERIVATIVE; DYNEMICIN A; ESPERAMICIN A1; ESPERAMICIN DERIVATIVE; GEMTUZUMAB OZOGAMICIN; HYDROLYASE; KEDARCIDIN; MADUROPEPTIN; MONOCLONAL ANTIBODY; N 1999A2; NAMENAMICIN; POLYKETIDE SYNTHASE; SHISHIJIMICIN; UNCLASSIFIED DRUG; ZINOSTATIN;

COMBINATORIAL CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG MECHANISM; DRUG SPECIFICITY; DRUG SYNTHESIS; GENE CLUSTER; GENETIC MANIPULATION; MOLECULAR CLONING; MOLECULAR DYNAMICS; NONHUMAN; PHARMACEUTICAL ENGINEERING; REVIEW;

ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; CLONING, MOLECULAR; COMBINATORIAL CHEMISTRY TECHNIQUES; GENETIC ENGINEERING; MOLECULAR PROBES; MULTIGENE FAMILY;

EID: 0141953946     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867033456701     Document Type: Review

References (76)

1. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot., 1965, 18, 68.
2. Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett., 1985, 26, 331.
3. Lee, M.D.; Dunne, T.S.; Siegel, M.M.; Chang, C.C.; Morton, G.O.; Borders, D. B. J. Am. Chem. Soc., 1987, 109, 3464.
4. Lee, M.D.; Dinne, T.S.; Chang, C.C.; Ellestad, G.A.; Siegel, M.M,; Morton, G.O.; McGahren, W.J.; Borders, D.B. J. Am. Chem. Soc., 1987, 109, 3466.
5. Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc., 1987, 109, 3461.
6. Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K., Doyle, T.W. J. Am. Chem. Soc., 1987, 109, 3462.
7. Nicolaou, K.C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl., 1991, 30, 1387.
8. Doyle, T.W.; Border, D.B. Enediyne Entibiotics as Antitumor Agents. Marcel-Dekker: New York, 1995.
9. Smith, A.L.; Nicolaou, K.C. J. Med. Chem., 1996, 39, 2103.
10. Maeda, H.; Edo, K.; Ishida, N. Eds. Neocarzinostatin: The Past, Present, and Future of an Anticancer Drug. Springer-Verlag:New York, 1997.
11. Xi, Z.; Goldberg, I.H. in Comprehensive Natural Products Chemistry, Barton, D.; Nakanish, K.; Meth-Cohn, O., Eds. Elesiver:New York, 1999, vol 7, p.553.
12. Thrson, J.S.; Sievers, E.L.; Ahlert, J.; Shepard, E.; Whitwam, R.E.; Onwueme, K.C.; Ruppen, M. Curr. Pharm. Design., 2000, 6, 1841.
13. Jones, G.B.; Fouad, F.S. Curr. Pharm. Des., 2002, 8, 2415.
14. Oku, N.; Matsunaga, S.; Fusetani, N. J. Am. Chem. Soc., 2003, 125, 2044.
15. Ando, T.; Ishii, M.; Kajiura, T.; Kameyama, T.; Miwa, K.; Sugiura, Y. Tetrahedron Lett., 1998, 39, 6495.
16. Leet, J.E.; Schroeder, D.R.; Hofstead, S.J,; Golik, J.; Colson, K.L.; Huang, S.; Klohr, S.E.; Doyle, T.W; Matson, J.A. J. Am. Chem. Soc., 1992, 114, 7946.
17. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T. Tetrahehron Lett., 1993, 34, 2633.
18. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahehron Lett., 1993, 34, 2637.
19. Iida, K.; Fukuda, S.; Tanaka, T.; Hirama, M.; Imajo, S.; Ishiguro, M.; Yoshida, K.; Otani, T. Tetrahedron Lett., 1996, 37, 4997.
20. Otani, T.; Yoshida, K.; Sasaki, T.; Minami, Y. J. Antibiot., 1999, 52, 415.
21. Schroeder, D.R.; Colson, K.L.; Klohr, S.E.; Zein, N.; Langley, D.R.; Lee, M.S.; Matson, J.A.; Dolye, T.W. J. Am. Chem. Soc., 1994, 116, 9351.
22. Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot., 1989, 42, 1449.
23. Myers, A.G.; Fraley, M.E.; Tom, N.J.; Cohen, S.B.; Madar, D.J. Chem. Biol., 1995, 2, 33.
24. McDonald, L.A.; Capson, T.L.; Krishnamurth, G.; Ding, W.-D.; Ellestad, G.A.; Bernan, V.S.; Maiese, W.M.; Lassota, P.; Discafani, C.; Kramer, R.A.; Ireland, C.M. J. Am. Chem. Soc., 1996, 118, 10898.
25. Stassinopoulos, A.; Ji, J.; Gao, X.; Goldberg, I.H. Science, 1996, 272, 1943.
26. Ikemoton, N.; Kumar, R.A,; Ling, T.T.; Elleastad, G.A. Proc. Natl. Acad. Sci. USA, 1995, 92, 10506.
27. Dedon, P.C.; Goldberg, I.H. Chem. Res. Toxicol., 1992, 5, 311.
28. SugiuraY.; Shiraki, T.; Konishi, M.; Oki, T. Proc. Natl. Acad. Sci. USA., 1990, 87, 3831.
29. Zein, N.; Closon, K.L.; Leet, J.E.; Schroeder, D.R.; Solomon, W.; Dolye, T.W.; Casazza, A.M. Proc. Natl. Acad. Sci. USA., 1993, 90, 2822.
30. Nicolaou, K.C.; Stabila, P.; Esmaeli-Azad, B.; Wrasidlo, W.; Hiatt, A. Proc. Natl. Acad. Sci. USA., 1993, 90, 3142.
31. Kappen, L.S.; Goldberg, I.H. Science, 1993, 261, 1319.
32. Yu, L.; Goldberg, I.H.; Dedon, P.C. J. Biol. Chem., 1994, 269, 4144.
33. Hensens, O.D.; Chin, D.H.; Stassinopoulos, A.; Zink, D.L.; Kappen, L.S.; Goldberg, I.H. Proc. Natl. Acad. Sci. USA., 1994, 91, 4534.
34. Ho, S.N.; Boyer, S.H.; Schreiber, S.L.; Danishefsky, S.J.; Crabtree, G.R. Proc. Natl. Acad. Sci. USA., 1994, 91, 9203.
35. Schor, N.F.; Tyuina, Y.Y.; Fabisiak, J.P.; Tyurin, V.A.; Lazo, J.S.; Kagan, V.E. Brain Res., 1999, 831, 125.
36. Dziegielewski, J.; Beerman, T.A. J. Biol. Chem., 2002, 277, 20549.
37. Sielvers, E.L.; Appelbaum, F.R.; Spielberger, R.T.; Forman, S.J.; Flowers, D.; Smith, F.O.; Shannon-Dorcy, K.; Berger, M.S.; Bernstein, I.D. Blood, 1999, 93, 3678.
38. Brukner, I. Curr. Opin. Oncol. Endocr. Met. Invest. Drugs., 2000, 2, 344.
39. Hopwood, D.A. Chem. Rev., 1997, 97, 2465.
40. Cane, D.E.; Walsh, C.T.; Khosla, C. Science, 1998, 6, 319.
41. Shen, B. Curr. Top. Chem., 2000, 209, 1.
42. Staunton, J.; Wessman, K.J. Nat. Prod. Rep., 2001, 18, 380.
43. Strohl, W.R. Met. Engineer., 2001, 3, 4.
44. Du, L.; Shen, B. Curr. Opinion Drug Discov. Dev., 2001, 4, 215.
45. Rodriguez, E.; McDaniel, R. Curr. Opinion Microbiol., 2001, 4, 526.
46. Walsh, C.T. ChemBioChem, 2002, 3, 124.
47. Thorson, J.S.; Shen, B.; Whitwam, R.E.; Liu, W.; Li, Y.; Ahlert, J. Bioorg. Chem., 1999, 27, 172.
48. Zazopoulos, E.; Huang K.; Staffa, A.; Liu, W.; Bachmann, B.O.; Nonaka, K.; Ahlert, J.; Thorson, J.S.; Shen, B.; Farnet, C.M. Nat. Biotechnol., 2003, 21, 187.
49. Bentley, S.D.; Chater, K.F.; Cerdeno-Tarraga, A.M.; Challis, G.L.; Thomson, N.R.; James, K.D.; Harris, D.E.; Quail, M.A.; Kieser, H.; Harper, D.; Bateman, A.; Brown, S.; Chandra, G.; Chen, C.W.; Collins, M.; Cronin, A.; Fraser, A.; Goble, A.; Hidalgo, J.; Hornsby, T.; Howarth, S.; Huang, C.H.; Kieser, T.; Larke, L.; Murphy, L.; Oliver, K.; O'Neil, S.; Rabbinowitsch, E.; Rajandream, M.A.; Rutherford, K.; Rutter, S.; Seeger, K.; Saunders, D.; Sharp, S.; Squares, R.; Squares, S.; Taylor, K.; Warren, T.; Wietzorrek, A.; Woodward, J.; Bartell, B.G.; Parkhill, J.; Hopwood, D.A. Nature, 2002, 417, 141.
50. Omura, S.; Ikeda, H.; Ishikawa, J.; Hanamoto, A.; Takahashi, C.; Shinose, M.; Takahashi, Y.; Horikawa, H.; Nakazawa, H.; Osonoe, T.; Kikuchi, H.; Shiba, T.; Sakaki, Y.; Hattori, M. Proc. Natl. Acad. Sci. USA, 2001, 98, 12215.
51. Ikeda, H.; Ishikawa, J.; Hanamoto, A.; Shinose, M.; Kikuchi, H.; Shiba, T.; Sakaki, Y.; Hattori, M.; Omura, S. Nat. Biotechnol., 2003, 21, in press.
52. Liu, W.; Shen, B. Antimicrob. Agents Chemother., 2000, 44, 382.
53. Liu, W.; Christenson, S. D.; Standage, S.; Shen, B. Science, 2002, 297, 1170.
54. Trefzer, A.; Salas, J.A.; Bechthold, A. Nat. Prod. Rep., 1999, 16, 283.
55. He, X.M.; Liu, H.-w. Annu. Rev. Biochem., 2002, 71, 701.
56. Decker, H.; Gaisser, S.; Pelzer, S.; Schneider, P.; Westrich, L.; Wohlleben, W.; Bechthold, A. FEMS Microbiol. Lett., 1996, 141, 195.
57. Sakata, N.; Ikeno, S.; Hori, M.; Hamada, M.; Otani, T. Biosci. Biotech. Biochem., 1992, 56, 1592.
58. Maeda, H.; Glaser, C.B.; Kuromizu, K.; Meienhofer, J. Arch. Biochem. Biophys., 1974, 164, 379.
59. Gibson, B.W.; Herlihy, W.C.; Samy, T.S.A.; Hahm, K.S., Maeda, H.,; Meienhofer, J.; Biemann, K. J. Biol. Chem., 1984, 259, 10801.
60. Whitwam, R. E.; Ahlert, J.; Holman, T.R.; Ruppen, M.; Thorson, J.S. J. Am. Chem. Soc., 2000, 122, 1556.
61. Ahlert, J.; Shepard, E.; Lomovskaya, N.; Zazopoulos, E.; Staffa A.; Bachmann, B. O.; Huang, K.; Fonstein L.; Czisny, A.; Whitwam, R.E.; Farnet, C.M.; Thorson, J.S. Science, 2002, 297, 1173.
62. Ruan, X.; Stassi, D.; Lax, S.A.; Katz, L. Gene, 1997, 203, 1.
63. Santi, D.V.; Siani, M.A.; Julien, B.; Kupfer, D.; Roe, B. Gene, 2000, 247, 97.
64. Shen. B. Curr. Opinion Chem. Biol., 2003, 7, 285.
65. Liu, W.; Ahlert, J.; Gao, Q.; Wendt-Pienkowski, E.; Shen, B. Thorson, J.S.; submitted.
66. Hensens, O.D.; Ginger, J.-L.; Goldberg, L.H. J. Am. Chem. Soc., 1989, 111, 3295.
67. Tokiwa, Y.; Miyoshi-Saitosh, M.; Kobayashi, H.; Sunaga, R.; Konishi, M.; Oki, T.; Iwasaki, S. J. Am. Chem. Soc., 1992, 114, 4107.
68. Lam, K.S.; Veitch, J.A.; Golik, J.; Krishnan, B. J. Am. Chem. Soc., 1993, 115, 12340.
69. Kieser, T.; Bibb, M.J.; Buttner, M.J.; Chater, K.F.; Hopwood, D.A. Practical Streptomyces Genetics. The John Innes Foundation: Norwich, U.K., 2000.
70. Gillespie, D.E.; Brady, S.F.; Bettermann, A.D.; Cianciotto, N.P.; Liles, M.R.; Rondon, M.R.; Clardy, J.; Goodman, R.M.; Handelsman, J. Appl. Environ. Microbiol., 2002, 68, 4301.
71. Brady, S.F.; Chao, C.J.; Clardy, J. J. Am. Chem. Soc., 2002, 124, 9968.
72. Zengler, K.; Toledo, G.; Rappe, M.; Elkins, J.; Mathur, E.J.; Short, J.M.; Keller, M. Proc. Natl. Acad. Sci., 2002, 99, 15681.
73. Miao, V.; Cöeffet-LeGal, M.-F.; Penn, J.; Whiting, A.; Parr, I.; Bouchard, M.; Silva, C.; Doekel, S.; Alexander, D.; Martin, S.; Gibson, T.; Brost, R.; Sinneman, S., Henton-Jones, D.; Chapple, J.P.; Daavies, J.E.; Baltz, R.H.; Brian, P. Abstract S123, Society for Industrial Microbiology Annual Meeting, August 11-15, 2002, Philadelphia, PA.
74. Sosio, M.; Giusino, F.; Cappellano, C.; Bossi, E.; Puglia, A.M.; Donadio, S. Nat. Biotechnol., 2000, 18, 343.
75. Sosio, M.; Bossi, E.; Donadio, S. Nucleic Acids Res., 2001, 37, e37.
76. Donadio, S., Monciardini, P.; Aldunia, R.; Mazza, P.; Chiocchini, C.; Cavaletti, L.; Sosio, M.; Puglia, A.M. J. Biotechnol., 2002, 99, 187.