Design, synthesis and biological evaluation of Rose Bengal analogues as SecA inhibitors

ChemMedChem

Volumn 8, Issue 8, 2013, Pages 1384-1393

  Cui, Jianmei ^a   Jin, Jinshan ^a   Hsieh, Ying Hsin ^a   Yang, Hsiuchin ^a   Ke, Bowen ^a   Damera, Krishna ^a   Tai, Phang C ^a   Wang, Binghe ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Antimicrobial agents; Drug discovery; Rose bengal analogues; SecA inhibitors; Structure activity relationships

Indexed keywords

ADENOSINE TRIPHOSPHATASE; ANTIINFECTIVE AGENT; CARBOXYL GROUP; FLUORESCEIN DERIVATIVE; NAPHTHALENE DERIVATIVE; PROTEIN SECA; ROSE BENGAL;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERICIDAL ACTIVITY; DEHYDRATION; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; GRIGNARD REACTION; HALOGENATION; METHYLATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; SECRETORY PATHWAY; STRUCTURE ACTIVITY RELATION; SUZUKI REACTION;

EID: 84880971294     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300216     Document Type: Article

References (58)

1. L. B. Rice, Curr. Opin. Microbiol. 2009, 12, 476-481.
2. M. J. Sibbald, A. K. Ziebandt, S. Engelmann, M. Hecker, A. deJong, H. J. Harmsen, G. C. Raangs, I. Stokroos, J. P. Arends, J. Y. Dubois, J. M. vanDijl, Microbiol. Mol. Biol. Rev. 2006, 70, 755-788.
3. T. Chitlaru, O. Gat, Y. Gozlan, N. Ariel, A. Shafferman, J. Bacteriol. 2006, 188, 3551-3571.
4. T. A. Rapoport, B. Jungnickel, U. Kutay, Annu. Rev. Biochem. 1996, 65, 271-303.
5. T. G. Knott, C. Robinson, J. Biol. Chem. 1994, 269, 7843-7846.
6. D. B. Oliver, R. J. Cabelli, K. M. Dolan, G. P. Jarosik, Proc. Natl. Acad. Sci. USA 1990, 87, 8227-8231.
7. Y. Sugie, S. Inagaki, Y. Kato, H. Nishida, C. H. Pang, T. Saito, S. Sakemi, F. Dib-Hajj, J. P. Mueller, J. Sutcliffe, Y. Kojima, J. Antibiot. 2002, 55, 25-29.
8. C. A. Parish, M. deLaCruz, S. K. Smith, D. Zink, J. Baxter, S. Tucker-Samaras, J. Collado, G. Platas, G. Bills, M. T. Diez, F. Vicente, F. Pelaez, K. Wilson, J. Nat. Prod. 2009, 72, 59-62.
9. M. Li, Y. J. Huang, P. C. Tai, B. Wang, Biochem. Biophys. Res. Commun. 2008, 368, 839-845.
10. W. Chen, Y. J. Huang, S. R. Gundala, H. Yang, M. Li, P. C. Tai, B. Wang, Bioorg. Med. Chem. 2010, 18, 1617-1625.
11. M. Y. Jang, S. DeJonghe, K. Segers, J. Anne, P. Herdewijn, Bioorg. Med. Chem. 2011, 19, 702-714.
12. K. Segers, H. Klaassen, A. Economou, P. Chaltin, J. Anne, Anal. Biochem. 2011, 413, 90-96.
13. K. Segers, J. Anne, Chem. Biol. 2011, 18, 685-698.
14. Y. J. Huang, H. Wang, F. B. Gao, M. Li, H. Yang, B. Wang, P. C. Tai, ChemMedChem 2012, 7, 571-577.
15. D. Khan-Lim, M. Berry, Curr. Eye Res. 2004, 29, 311-317.
16. E. Wachter, C. Dees, J. Harkins, W. G. Fisher, T. Scott, Proc. SPIE 2002, 4622, 112-118.
17. G. D. Delprat, Arch. Intern. Med. 1923, 32, 401-410.
18. M. Kanei, Nihon Saikingaku Zasshi. 1983, 38, 645-647.
19. V. Decraene, J. Pratten, M. Wilson, Curr. Microbiol. 2008, 57, 269-273.
20. S. K. Srivastava, M. J. Modak, Biochemistry 1982, 21, 4633-4639.
21. S. K. Srivastava, M. J. Modak, Biochemistry 1983, 22, 2283-2288.
22. B. M. Sutherland, M. Randesi, K. Wang, K. Conlon, G. A. Epling, Biochemistry 1993, 32, 1788-1794.
23. K. Ogita, K. Hirata, D. G. Bole, S. Yoshida, Y. Tamura, A. M. Leckenby, T. Ueda, J. Neurochem. 2001, 77, 34-42.
24. J. G. Banks, R. G. Board, J. Carter, A. D. Dodge, J. Appl. Bacteriol. 1985, 58, 391-400.
25. Y. F. Sasaki, S. Kawaguchi, A. Kamaya, M. Ohshita, K. Kabasawa, K. Iwama, K. Taniguchi, S. Tsuda, Mutat. Res. 2002, 519, 103-119.
26. R. D. Rossoni, J. C. Junqueira, E. L. Santos, A. C. Costa, A. O. Jorge, Lasers Med. Sci. 2010, 25, 581-586.
27. Y. Guo, S. Rogelj, P. Zhang, Nanotechnology 2010, 21, 065102.
28. J. P. Rolim, M. A. de-Melo, S. F. Guedes, F. B. Albuquerque-Filho, J. R. deSouza, N. A. Nogueira, I. C. Zanin, L. K. Rodrigues, J. Photochem. Photobiol. B 2012, 106, 40-46.
29. C. Chui, A. Aoki, Y. Takeuchi, Y. Sasaki, K. Hiratsuka, Y. Abiko, Y. Izumi, J. Periodontal Res. 2013, in press; DOI:.
30. A. Shrestha, M. R. Hamblin, A. Kishen, Antimicrob. Agents Chemother. 2012, 56, 4876-4884.
31. K. Ishiyama, K. Nakamura, H. Ikai, T. Kanno, M. Kohno, K. Sasaki, Y. Niwano, PLoS One 2012, 7, e37871.
32. S. Wood, D. Metcalf, D. Devine, C. Robinson, J. Antimicrob. Chemother. 2006, 57, 680-684.
33. M. F. Ali, Lasers Med. Sci. 2011, 26, 267-275.
34. E. Wachter, C. Dees, J. Harkins, T. Scott, M. Petersen, R. E. Rush, A. Cada, Lasers Surg. Med. 2003, 32, 101-110.
35. M. Jemli, Z. Alouini, S. Sabbahi, M. Gueddari, J. Environ. Monit. 2002, 4, 511-516.
36. H. Wang, L. Lu, S. Zhu, Y. Li, W. Cai, Curr. Microbiol. 2006, 52, 1-5.
37. J. F. Thompson, P. Hersey, E. Wachter, Melanoma Res. 2008, 18, 405-411.
38. Provectus Pharmaceuticals. www.pvct.com (accessed May 2013).
39. J. P. Martin, N. Logsdon, Arch. Biochem. Biophys. 1987, 256, 39-49.
40. J. P. Martin, N. Logsdon, Photobiology 1987, 46, 45-53.
41. K. Koch, M. S. Biggers, J. Org. Chem. 1994, 59, 1216-1218.
42. A. Scopton, T. R. Kelly, J. Org. Chem. 2005, 70, 10004-10012.
43. I. Shiinaa, Y. Sanoa, K. Nakataa, M. Suzukia, T. Yokoyamaa, A. Sasakia, T. Orikasaa, T. Miyamotoa, M. Ikekitab, Y. Nagaharab, Y. Hasomeb, Bioorg. Med. Chem. 2007, 15, 7599-7617.
44. S. Adimurthy, G. Ramachandraiah, P. K. Ghosh, A. V. Bedekar, Tetrahedron Lett. 2003, 44, 5099-5101.
45. T. R. Kelly, X. Cai, F. Damkaci, S. B. Panicker, B. Tu, S. M. Bushell, I. Cornella, M. J. Piggott, R. Salives, M. Cavero, Y. Zhao, S. Jasmin, J. Am. Chem. Soc. 2007, 129, 376-386.
46. J. P. Heiskanen, O. E. O. Hormi, Tetrahedron 2009, 65, 518-524.
47. N. Janjic, D. Schloeder, A. Tramontano, J. Am. Chem. Soc. 1989, 111, 6374-6377.
48. Y. H. Hsieh, H. Zhang, B. R. Lin, N. Cui, B. Na, H. Yang, C. Jiang, S. F. Sui, P. C. Tai, J. Biol. Chem. 2011, 286, 44702-44709.
49. B. R. Lin, L. M. Gierasch, C. Jiang, P. C. Tai, J. Membr. Biol. 2006, 214, 103-113.
50. B. R. Lin, Y. H. Hsieh, C. Jiang, P. C. Tai, J. Membr. Biol. 2012, 245, 747-757.
51. G. P. Tegos, M. R. Hamblin, Antimicrob. Agents Chemother. 2006, 50, 196-203.
52. J. J. Inbaraj, B. M. Kukielczak, C. F. Chignell, Photochem. Photobiol. 2005, 81, 81-88.
53. T. N. Demidova, M. R. Hamblin, Antimicrob. Agents Chemother. 2005, 49, 2329-2335.
54. J. Jin, J. Cui, Y. Hsieh, H. Yang, B. Wang, P.C. Tai, unpublished results.
55. N. Ruiz, B. Falcone, D. Kahne, T. J. Silhavy, Cell 2005, 121, 307-317.
56. X. Chen, H. Xu, P. C. Tai, J. Biol. Chem. 1996, 271, 29698-29706.
57. X. Chen, T. Brown, P. C. Tai, J. Bacteriol. 1998, 180, 527-537.
58. Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Susceptibility Testing: 21st Informational Supplement, M100-S21, CLSI, Wayne, PA, USA, 2011.