Sungsanpin, a lasso peptide from a deep-sea streptomycete

Journal of Natural Products

Volumn 76, Issue 5, 2013, Pages 873-879

  Um, Soohyun ^a   Kim, Young Joo ^b   Kwon, Hyuknam ^a   Wen, He ^a   Kim, Seong Hwan ^a   Kwon, Hak Cheol ^b   Park, Sunghyouk ^a   Shin, Jongheon ^a   Oh, Dong Chan ^a  

^a Seoul National University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; GELATINASE A; GELATINASE B; MESSENGER RNA; PEPTIDE DERIVATIVE; SUNGSANPIN; TISSUE INHIBITOR OF METALLOPROTEINASE 1; TISSUE INHIBITOR OF METALLOPROTEINASE 2; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CELL INVASION; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; EXTRACELLULAR MATRIX; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; LUNG NON SMALL CELL CANCER; MASS SPECTROMETRY; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; SEQUENCE ALIGNMENT; STREPTOMYCES; ULTRAVIOLET SPECTROSCOPY;

AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LUNG NEOPLASMS; MARINE BIOLOGY; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OCEANS AND SEAS; PEPTIDES; REPUBLIC OF KOREA; STREPTOMYCES;

EID: 84878239915     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np300902g     Document Type: Article

References (41)

1. Hill, R. T.; Fenical, W. Curr. Opin. Biotechnol. 2010, 21, 777-779
2. Molinski, T. F.; Dalisay, D. S.; Lievens, S. L.; Saludes, J. P. Nat. Rev. Drug Discovery 2009, 8, 69-85
3. Skropeta, D. Nat. Prod. Rep. 2008, 25, 1131-1166
4. Fenical, W.; Jensen, P. R. Nat. Chem. Biol. 2006, 2, 666-673
5. Pettit, R. K. Mar. Biotechnol. 2011, 13, 1-11
6. Li, D.; Wang, F.; Xiao, X.; Zeng, X.; Gu, Q.; Zhu, W. Arch. Pharm. Res. 2007, 30, 552-555
7. Gustafson, K.; Roman, M.; Fenical, W. J. Am. Chem. Soc. 1989, 111, 7519-7524
8. Schumacher, R. W.; Davidson, B. S.; Montenegro, D. A.; Berman, V. S. J. Nat. Prod. 1995, 58, 613-617
9. Oh, D.-C.; Williams, P. G.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Org. Lett. 2006, 8, 1021-1024
10. Hughes, C. C.; Prieto-Davo, A.; Jensen, P. R.; Fenical, W. Org. Lett. 2008, 10, 629-631
11. Hughes, C. C.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. J. Org. Chem. 2010, 75, 3240-3250
12. Oh, D.-C.; Poulsen, M.; Currie, C. R.; Clardy, J. Nat. Chem. Biol. 2009, 5, 391-393
13. Fujii, K.; Ikai, Y.; Oka, H.; Suzuki, M.; Harada, K. Anal. Chem. 1997, 69, 5146-5151
14. Hess, S.; Gustafson, K. R.; Milanowski, D. J.; Alvira, E.; Lipton, M. A.; Pannell, L. K. J. Chromatogr. A 2004, 1035, 211-219
15. Knappe, T. A.; Manzenrieder, F.; Mas-Moruno, C.; Linne, U.; Sasse, F.; Kessler, H.; Xie, X.; Marahiel, M. A. Angew. Chem., Int. Ed. 2011, 50, 8714-8717
16. Bayro, M. J.; Mukhopadhyay, J.; Swapna, G. V. T.; Huang, J. Y.; Ma, L.-C.; Sineva, E.; Dawson, P. E.; Montelione, G. T.; Ebright, R. H. J. Am. Chem. Soc. 2003, 125, 12382-12383
17. Rosengren, K. J.; Clark, R. J.; Daly, N. L.; Göransson, U.; Jones, A.; Craik, D. J. Am. Chem. Soc. 2003, 125, 12464-12474
18. Wilson, K.-A.; Kalkum, M.; Ottesen, J.; Yuzenkova, J.; Chait, B. T.; Landick, R.; Muir, T.; Severinov, K.; Darst, S. A. J. Am. Chem. Soc. 2003, 125, 12475-12483
19. Wyss, D. F.; Lahm, H. W.; Manneberg, M.; Labhardt, A. M. J. Antibiot. 1991, 44, 172-180
20. Knappe, T. A.; Linne, U.; Zirah, S.; Rebuffat, S.; Xie, X.; Marahiel, M. A. J. Am. Chem. Soc. 2008, 130, 11446-11454
21. Iwatsuki, M.; Tomoda, H.; Uchida, R.; Gouda, H.; Hirono, S.; Omura, S. J. Am. Chem. Soc. 2006, 128, 7486-7491
22. Esumi, Y.; Suzuki, Y.; Itoh, Y.; Uramoto, M.; Kimura, K.-I.; Goto, M.; Yoshihama, M.; Ichikawa, T. J. Antibiot. 2002, 55, 296-300
23. Katahira, R.; Shibata, K.; Yamasaki, M.; Matsuda, Y.; Yoshida, M. Bioorg. Med. Chem. 1995, 3, 1273-1280
24. Potterat, O.; Stephan, H.; Metzger, J. W.; Gnau, V.; Zähner, H.; Jung, G. Liebigs Ann. Chem. 1994, 7, 741-743
25. Detlefsen, D. J.; Hill, S. E.; Volk, K. J.; Klohr, S. E.; Tsunakawa, M.; Furumai, T.; Lin, P. F.; Nishio, M.; Kawano, K.; Oki, T.; Lee, M. S. J. Antibiot. 1995, 48, 1515-1517
26. Knappe, T. A.; Linne, U.; Xie, X.; Marahiel, M. A. FEBS Lett. 2010, 584, 785-789
27. Hegemann, J. D.; Zimmermann, M.; Xie, X.; Marahiel, M. A. J. Am. Chem. Soc. 2012, 135, 210-222
28. Maksimov, M. O.; Pelczer, I.; Link, A. J. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 15223-15228
29. Vincent, P. A.; Bellomio, A.; De Arcuri, B. F.; Farías, R. N.; Morero, R. D. Biochem. Biophys. Res. Commun. 2005, 331, 549-551
30. Fréchet, D.; Guitton, J. D.; Herman, F.; Faucher, D.; Helynck, G.; Monegier du Sorbier, B.; Ridoux, J. P.; James-Surcouf, E.; Vuilhorgne, M. J. Antibiot. 1994, 13, 888-889
31. Constantine, K. L.; Friedrichs, M. S.; Detlefsen, D.; Nishio, M.; Tsunakawa, M.; Furumai, T.; Ohkuma, H.; Oki, T.; Hill, S. J.; Bruccoleri, R. E.; Lin, P.-F.; Mueller, L. Biomol. NMR 1995, 5, 271-286
32. Yano, K.; Toki, S.; Nakanishi, S.; Ochiai, K.; Ando, K.; Yoshida, M.; Matsuda, Y.; Yamasaki, M. Bioorg. Med. Chem. 1996, 4, 115-120
33. Kimura, K.-I.; Kanou, F.; Takahashi, H.; Esumi, Y.; Uramoto, M.; Yoshihama, M. J. Antibiot. 1997, 50, 373-378
34. Kuznedelov, K.; Semenova, E.; Knappe, T. A.; Mukhamedyarov, D.; Srivastava, A.; Chatterjee, S.; Ebright, R. H.; Marahiel, M. A.; Severinov, K. J. Mol. Biol. 2011, 412, 842-848
35. Weber, W.; Fischli, W.; Hochuli, E.; Kupfer, E.; Weibel, E. K. J. Antibiot. 1991, 44, 164-171
36. Tanaka, T.; Tsukuda, E.; Nozawa, M.; Nonaka, H.; Ohno, T.; Kase, H.; Yamada, K.; Matsuda, Y. Mol. Pharmacol. 1994, 45, 724-730
37. Carney, D. N.; Hansen, H. H. N. Engl. J. Med. 2000, 343, 1261-1262
38. Ho, M. Y.; Leu, S. J.; Sun, G.-H.; Tao, M.-H.; Tang, S.-J.; Sun, K.-H. J. Immunol. 2009, 183, 6217-6226
39. Weiss, L. Adv. Cancer Res. 1990, 54, 159-211
40. Stetler-Stevenson, W. G.; Aznavoorian, S.; Liotta, L. A. Annu. Rev. Cell Biol. 1993, 9, 541-573
41. Westermarck, J.; Kähäri, V. M. FASEB J. 1999, 13, 781-792