Synthetic analogs of indole-containing natural products as inhibitors of sortase A and isocitrate lyase

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 23, 2010, Pages 6882-6885

  Lee, Yeon Ju ^a   Han, Yu Ri ^a   Park, Wanki ^b   Nam, Seo Hee ^b   Oh, Ki Bong ^b   Lee, Hyi Seung ^a  

^a Korea Research Institute of Ships and Ocean Engineering   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

Carboline; Chemical library; Indole; Isocitrate lyase; Sortase A

Indexed keywords

BETA CARBOLINE; INDOLE DERIVATIVE; ISOCITRATE LYASE; NATURAL PRODUCT; SORTASE; SORTASE A; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS;

AMINOACYLTRANSFERASES; ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; BIOLOGICAL PRODUCTS; CANDIDA ALBICANS; CYSTEINE ENDOPEPTIDASES; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; INDOLES; ISOCITRATE LYASE; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

CANDIDA ALBICANS; STAPHYLOCOCCUS AUREUS;

EID: 78149282878     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.10.029     Document Type: Article

References (35)

1. J.W.H. Li, and J.C. Vederas Science 324 2009 161
2. A.L. Harvey Drug Discov. Today 13 2008 894
3. D.J. Newman, and G.M. Cragg J. Nat. Prod. 70 2007 461
4. K.S. Lam Trends Microbiol. 15 2007 279 and references cited therein
5. J.E. John Drug Discov. Today 15 2010 409
6. T.S. Bugni, B. Richard, L. Bhoite, D. Cimbora, M.K. Harper, and C.M. Ireland J. Nat. Prod. 71 2008 1095
7. R. Messer, C.A. Fuhrer, and R. Häner Curr. Opin. Chem. Biol. 9 2005 259
8. A.M. Boldi Curr. Opin. Chem. Biol. 8 2004 281
9. H.-S. Lee, K.-M. Yoon, Y.-R. Han, K.-J. Lee, S.-C. Chung, T.-I. Kim, S.-H. Lee, J. Shin, and K.-B. Oh Bioorg. Med. Chem. Lett. 19 2009 1051
10. H.-S. Lee, T.-H. Lee, S.H. Yang, H.J. Shin, J. Shin, and K.-B. Oh Bioorg. Med. Chem. Lett. 17 2007 2483
11. H. Ton-That, and O. Schneewind J. Biol. Chem. 274 1999 24316
12. S.K. Mazmanian, G. Liu, H. Ton-That, and O. Schneewind Science 285 1999 760
13. E.J. Muñoz-Elías, and J.D. McKinney Nat. Med. 11 2005 638
14. M.C. Lorez, and G.R. Fink Nature 412 2001 83
15. B.A. Frankel, M. Bentley, R.G. Kruger, and D.G. McCafferty J. Am. Chem. Soc. 126 2004 3404
16. K. Kudryavtsev, M.L. Bentley, and D.G. McCafferty Bioorg. Med. Chem. 17 2009 2886
17. N. Suree, S.W. Yi, W. Thieu, M. Marohn, R. Damoiseaux, A. Chan, M.E. Jung, and R.T. Clubb Bioorg. Med. Chem. 17 2009 7174
18. S.-H. Kim, D.-S. Shin, M.-N. Oh, S.-C. Chung, C.-S. Lee, and K.-B. Oh Biosci. Biotechnol. Biochem. 68 2004 421
19. B.-S. Park, J.-G. Kim, M.-R. Kim, S.-E. Lee, G.R. Takeoka, K.-B. Oh, and J.-H. Kim J. Agric. Food Chem. 53 2005 9005
20. K.H. Jang, S.-C. Chung, J. Shin, S.-H. Lee, T.-I. Kim, H.-S. Lee, and K.-B. Oh Bioorg. Med. Chem. Lett. 17 2007 5366
21. H.-S. Lee, T.-H. Lee, J.-H. Lee, C.-S. Chae, S.-C. Chung, D.-S. Shin, J. Shin, and K.-B. Oh J. Agric. Food Chem. 55 2007 6923
22. H.-C. Yang, J. Yu, K.-B. Oh, D.-S. Shin, W.-J. Cho, J. Shin, and S. Kim Arch. Pharm. Res. 30 2007 955
23. For the cloning, expression and purification of ICL from the genomic DNA of C. albicans (ATCC 10231) and the procedure for the evaluation of inhibitory activities of compounds against ICL, see: D.-S. Shin, S. Kim, H.-C. Yang, and K.-B. Oh J. Microbiol. Biotechnol. 15 2005 652
24. R. Hautzel, H. Anke, and W.S. Sheldric J. Antibiot. 43 1990 1240
25. For the procedure for the evaluation of inhibitory activities of compounds against SrtA, see Ref. 7d.
26. Natural products 1 and 7 show zero violations of Lipinski's rule of five and Veber rules. The physicochemical properties such as log P, polar surface are, number of hydrogen bond donors and acceptors, and number of rotational bonds were predicted using Molinspirations (Molinspiration Cheminformatics, Nova ulica 61, SK-900 26 Slovensky Grob, Slovak Republic. Available online at: http://www.molinspiration.com/cgi-bin/properties ). For Lipinski's rule of five, see: C.A. Lipinski, F. Lombardo, and B.W. Dominy Adv. Drug Deliv. Rev. 23 1997 3
27. For Veber rules, see; D.F. Veber, S.R. Johnson, H.Y. Cheng, B.R. Smith, K.W. Ward, and K.D. Kopple J. Med. Chem. 45 2002 2615
28. M.J. Thompson, V. Borsenberger, J.C. Louth, K.E. Judd, and B. Chen J. Med. Chem. 52 2009 7503
29. R. Gitto, D.L. Luca, S. Ferro, R. Citraro, G.D. Sarro, L. Costa, L. Ciranna, and A. Chimirri Bioorg. Med. Chem. 17 2009 1640
30. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797
31. J.I. Trujillo, M.J. Meyers, D.R. Anderson, S. Hegde, M.W. Mahoney, W.F. Vernier, I.P. Buchler, K.W. Wu, S. Yang, S.J. Hartman, and D.B. Reitz Bioorg. Med. Chem. Lett. 17 2007 4657
32. Y. Kawashima, A. Horiguchi, M. Taguchi, Y. Tuyuki, Y. Karasawa, H. Araki, and K. Hatayama Chem. Pharm. Bull. 43 1995 783
33. Y.-C. Shen, C.-Y. Chen, P.W. Hsieh, C.-Y. Duh, Y.-M. Lin, and C.-L. Ko Chem. Pharm. Bull. 53 2005 32
34. I.M. Jonsson, S.K. Mazmanian, O. Schneewind, T. Bremell, and A. Tarkowski Microbes Infect. 5 2003 775
35. S.K. Mazmanian, G. Liu, E.R. Lenoy, and O. Schneewind Proc. Natl. Acad. Sci. U.S.A. 97 2000 5510