Actin depolymerizing effect of trisoxazole-containing macrolides

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 11, 2011, Pages 3198-3201

  Chung, Soon Chun ^a   Lee, So Hyoung ^a   Jang, Kyoung Hwa ^b   Park, Wanki ^a   Jeon, Ju Eun ^b   Oh, Hana ^b   Shin, Jongheon ^b   Oh, Ki Bong ^a  

^a Seoul National University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

Actin depolymerization; Antifungal activity; Chondrosia corticata; Halichondramides

Indexed keywords

AMPHOTERICIN B; F ACTIN; HALICHONDRAMIDE; HALISHIGAMIDE D; JASPISAMIDE A; MACROLIDE; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; BACILLUS SUBTILIS; CANDIDA ALBICANS; CHONDROSIA CORTICATA; DEPOLYMERIZATION; ESCHERICHIA COLI; FLUORESCENCE; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTEUS VULGARIS; SALMONELLA TYPHIMURIUM; SPONGE (PORIFERA); STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; TRICHOPHYTON MENTAGROPHYTES; TRICHOPHYTON RUBRUM;

ANIMALS; ANTIFUNGAL AGENTS; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; FLUORESCENCE; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MACROLIDES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; OXAZOLES; POLYMERIZATION; PORIFERA; STRUCTURE-ACTIVITY RELATIONSHIP;

CHONDROSIA CORTICATA;

EID: 79956062262     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.04.069     Document Type: Article

References (21)

1. C.A. Schoenenberger, N. Bischler, B. Fahrenkrog, and U. Aebi Fed. Eur. Biochem. Soc. Lett. 529 2002 27
2. D.N. Robinson, and J.A. Spudich Trends Cell Biol. 10 2000 228
3. K.S. Yeung, and I. Paterson Angew. Chem., Int. Ed. 41 2002 4632
4. V.A. Klenchin, J.S. Allingham, R. King, J. Tanaka, G. Marriott, and I. Rayment Nat. Struct. Biol. 10 2003 1058
5. J.S. Allingham, A. Zampella, M.V. D′Auria, and I. Rayment Proc. Natl. Acad. Sci. U.S.A. 102 2005 14527
6. D.J. Faulkner Nat. Prod. Rep. 19 2002 1 48 and earlier reports in the series.
7. J.A. Roesener, and P.J. Scheuer J. Am. Chem. Soc. 108 1986 846
8. S. Matsunaga, N. Fusetani, K. Hashimoto, K. Koseki, and M. Noma J. Am. Chem. Soc. 108 1986 847
9. M.R. Kernan, T.F. Molinski, and D.J. Faulkner J. Org. Chem. 53 1988 5014
10. S. Matsunaga, N. Fusetani, K. Hashimoto, K. Koseki, M. Noma, H. Noguchi, and U. Sankawa J. Org. Chem. 54 1989 1360
11. J. Kobayashi, M. Tsuda, H. Fuse, T. Sasaki, and Y. Mikami J. Nat. Prod. 60 1997 150
12. J. Kobayashi, O. Murata, H. Shigemori, and T. Sasaki J. Nat. Prod. 56 1993 787
13. N. Fusetani, K. Yasumuro, S. Matsunaga, and K. Hashimoto Tetrahedron Lett. 1989 2809
14. S. Matsunaga, T. Sugawara, and N. Fusetani J. Nat. Prod. 61 1998 1164
15. P. Phuwapraisirisan, S. Matsunaga, R.W.M. Van Soest, and N. Fusetani J. Nat. Prod. 65 2002 942
16. M.A. Rashid, K.R. Gustafson, J.H. Cardellina II, and M.R. Boyd J. Nat. Prod. 58 1995 1120
17. J. Shin, H.-S. Lee, J.-Y. Kim, H.J. Shin, J.-W. Ahn, and V.J. Paul J. Nat. Prod. 67 2004 1889
18. Actin depolymerization assay: the rate of actin depolymerization in the presence of fluorescent filamentous F-actin was monitored according to the methods outlined in the Actin Polymerization Biochem Kit from Cytoskeleton Inc. The pyrene G-actin was prepared to 24 μM by adding G-buffer. Subsequently, 10× actin polymerization buffer was added to final concentration at 0.25×, and incubated at room temperature for 1 h. This polymerized pyrene F-actin solution was diluted with G-buffer to prepare 5-fold dilutions. 100 μl pyrene F-actin solution (final concentration of pyrene F-actin, 4.8 μM) was used to actin depolymerization assay. Measurement of the fluorescence was performed in a spectrophotometer (Perkin-Elmer) with excitation/emission wavelength at 360 and 410 nm, respectively, for 1 h every 1 min.
19. 5 colony-forming units (cfu)/ml of test bacteria was added to each well of a 96-well microtiter plate. Culture plates were incubated for 24 h at 37 °C. The minimum inhibitory concentration (MIC) values were determined as the lowest concentration of test compounds that inhibited bacterial growth. Ampicillin was used as a reference compound.
20. 4 cells/ml of test fungi was added to each well of a 96-well microtiter plate. Culture plates were incubated for 48-72 h at 28 °C. The MIC values were determined as the lowest concentration of test compounds that inhibited fungal growth. Amphotericin B was used as a reference compound.
21. M. Hori, S.Y. Saito, Y.Z. Shin, H. Ozaki, N. Fusetani, and H. Karaki FEBS Lett. 322 1993 151