Bis(indole) alkaloids as sortase A inhibitors from the sponge Spongosorites sp.

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 22, 2005, Pages 4927-4931

  Oh, Ki Bong ^a   Mar, Woongchon ^a   Kim, Sanghee ^a   Kim, Ji Yun ^a   Oh, Mi Na ^a   Kim, Jae Gyu ^a   Shin, Daehyun ^a   Sim, Chung J ^b   Shin, Jongheon ^a  

^a Seoul National University   (South Korea)

^b Hannam University   (South Korea)

Author keywords

Bis(indole) alkaloids; Sortase A inhibitory activity; Sponge

Indexed keywords

4,5 DIHYDRO 6'' DEOXYBROMOTOPSENTIN; 4,5 DIHYDROHAMACANTHIN A; BROMODEOXYTOPSENTIN; BROMOTOPSENTIN; CELL MEMBRANE PROTEIN; DEOXYTOPSENTIN; ENZYME INHIBITOR; FIBRONECTIN; HAMACANTHIN A; HAMACANTHIN DERIVATIVE; INDOLE ALKALOID; TOPSENTIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL VIRULENCE; DRUG ACTIVITY; ENZYME INHIBITION; NONHUMAN; SPONGE (PORIFERA); SPONGOSORITES; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; AMINOACYLTRANSFERASES; ANIMALS; BACTERIAL ADHESION; BACTERIAL PROTEINS; CYSTEINE ENDOPEPTIDASES; FIBRONECTINS; INDOLES; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PORIFERA; PROTEIN BINDING; STAPHYLOCOCCUS AUREUS;

SPONGOSORITES; STAPHYLOCOCCUS AUREUS;

EID: 25844457688     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.08.021     Document Type: Article

References (33)

1. L.E. Alksne, and S, J. Projan Curr. Opin. Biotechnol. 11 2000 625
2. O. Schneewind, P. Model, and V.A. Fischetti Cell 70 1992 267
3. S.K. Mazmanian, G. Liu, H. Ton-That, and O. Schneewind Science 285 1999 760
4. H. Ton-That, G. Liu, S.K. Mazmanian, K.F. Faull, and O. Schneewind Proc. Natl. Acad. Sci. U.S.A. 96 1999 12424
5. S.K. Mazmanian, G. Liu, E.R. Lenoy, and O. Schneewind Proc. Natl. Acad. Sci. U.S.A. 97 2000 5510
6. C.J. Scott, A. McDowell, S.L. Martin, J.F. Lynas, K. Vandenbroeck, and B. Walker Biochem. J. 366 2002 953
7. K.M. Connolly, B.T. Smith, R. Pilpa, U. Ilangovan, M.E. Jung, and R.T. Clubb J. Biol. Chem. 278 2003 34061
8. S.H. Kim, D.S. Shin, M.N. Oh, S.C. Chung, J.S. Lee, I.M. Chang, and K.B. Oh Biosci. Biotechnol. Biochem. 67 2003 2477
9. K.B. Oh, S.H. Kim, J. Lee, W.J. Cho, T. Lee, and S. Kim J. Med. Chem. 47 2004 2418
10. J.W. Blunt, B.R. Copp, M.H.G. Munro, P.T. Northcote, and M.R. Prinsep Nat. Prod. Rep. 21 2004 1 and earlier reports in the series.
11. K. Bartik, J.-C. Braekman, D. Daloze, C. Stoller, J. Huysecom, G. Vandevyver, and R. Ottinger Can. J. Chem. 65 1987 2118
12. S. Tsujii, K.L. Rinehart, S.P. Gunasekera, Y. Kashman, S.S. Cross, M.S. Lui, S.A. Pomponi, and M.C. Diaz J. Org. Chem. 53 1988 5446
13. S.A. Morris, and R.J. Andersen Tetrahedron 46 1990 715
14. S. Sakemi, and H.H. Sun J. Org. Chem. 56 1991 4304
15. A.E. Wright, S.A. Pomponi, S.S. Cross, and P. McCarthy J. Org. Chem. 57 1992 4772
16. S.P. Gunasekera, P.J. McCarthy, and M. Kelly-Borges J. Nat. Prod. 57 1994 1437
17. L.M. Murray, T.K. Lim, J.N.A. Hooper, and R.J. Capon Aust. J. Chem. 48 1995 2053
18. I. Mancini, G. Guella, C. Debitus, J. Waikedre, and F. Pietra Helv. Chim. Acta 79 1996 2075
19. J. Shin, Y. Seo, K.W. Cho, J.-R. Rho, and C.J. Sim J. Nat. Prod. 62 1999 647
20. A. Casapullo, G. Bifulco, I. Bruno, and R. Riccio J. Nat. Prod. 63 2000 447
21. D.W. Phife, R.A. Ramos, M. Feng, I. King, S.P. Gunasekera, A. Wright, M. Patel, J.A. Pachter, and S.J. Coval Bioorg. Med. Chem. Lett. 6 1996 2103
22. I. Kawasaki, M. Yamashita, and S. Ohta Chem. Pharm. Bull. 44 1996 1831
23. S. Achab Tetrahedron Lett. 31 1996 5503
24. C.-G. Yang, J. Wang, X.-X. Tang, and B. Jiang Tetrahedron: Asymmetry 13 2002 383
25. T. Kawasaki, T. Kouko, H. Totsuka, and K. Hiramatsu Tetrahedron Lett. 44 2003 8849
26. B. Bao, Q. Sun, X. Yao, J. Hong, C.-O. Lee, C.J. Sim, K.S. Im, and J.H. Jung J. Nat. Prod. 68 2005 711
27. Taxonomic identification: the sponge specimen was identified by C.J.S. on the basis of macro- and micro-morphological feature analysis. A voucher specimen (registry No. Spo. 45) is currently on deposit at the Natural History Museum, Hannam University, Korea, under the curatorship of C.J.S.
28. Δ24, 0.75 μg fluorescent peptide (Dabcyl-QALPETGEE- Edans), and prescribed concentration of test sample. Each of the test compound was dissolved in dimethylsulfoxide (DMSO), and diluted with sterilized distilled water before use (final 0.5% DMSO), which was found to have no effect on the enzyme activity when at a concentration of less than 1%. Appropriate blanks contained all of the above, with the exception of the test sample. Reactions were carried out for 1 h at 37°C and analyzed fluorometrically by 350 nm for excitation and 495 nm for recordings.
29. W.W. Navarre, and O. Schneewind Microbiol. Mol. Biol. Rev. 63 1999 174
30. I. Elgalai, and H.A. Foster J. Appl. Microbiol. 94 2003 413
31. 600 = 0.5). The culture was split into 5 ml aliquots, and test compound, or control treatment, was added as indicated. Every 30 min for 2.5 h following the addition of test compound, 0.65 ml cell suspension was removed and pelleted by centrifugation (10,000g for 10 min). After storing overnight at -20°C, pellets were resuspended in 0.65 ml phosphate-buffered saline (PBS) and distributed in 100 μl aliquots to individual wells of fibronectin-coated flat-bottomed 96-well microtiter plates. Following a 2-h incubation at 37°C, the cell suspension was removed and wells were washed with 0.15 ml PBS. Bound cells were then fixed by incubation for 30 min with 2% (v/v) glutaraldehyde. Following a second wash with PBS, cells were stained for 15 min with 0.1 ml crystal violet dye (12.5 g/L). Plates were washed again with PBS, covered with aluminum foil, and allowed to dry overnight (12-16 h). The absorbance at 560 nm was subsequently measured using a microtiter late reader.
32. B.A. Frankel, M. Bentley, R.G. Kruger, and D.G. McCafferty J. Am. Chem. Soc. 126 2004 3404
33. These strains were kindly provided by Prof. O. Schneewind (University of Chicago, Chicage, USA).