Synthesis and structure activity relationship studies of novel Staphylococcus aureus Sortase A inhibitors

European Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2010, Pages 3752-3761

  Chenna, Bala Chandra ^a   King, Jason R ^a   Shinkre, Bidhan A ^a   Glover, Amanda L ^a   Lucius, Aaron L ^a   Velu, Sadanandan E ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

Antibacterial; Inhibitor; Sortase; Staphylococcus aureus; Structure activity relationship; Synthesis

Indexed keywords

3 (FURAN 2 YL) N (3 (HYDROXYMETHYL) 4 MORPHOLINOPHENYL)ACRYLAMIDE; 5 (3 (FURAN 2 YL) N METHYLACRYLAMIDO) 2 MORPHOLINOBENZOIC ACID; 5 (3 (FURAN 2 YL)ACRYLAMIDO) 2 (PIPERIDIN 1 YL)BENZOIC ACID; 5 (3 (FURAN 2 YL)ACRYLAMIDO) 2 MORPHOLINOBENZOIC ACID; 5 (3 (FURAN 2 YL)PROPANAMIDO) 2 MORPHOLINOBENZOIC ACID; 5 (3 (THIOPHEN 2 YL)ACRYLAMIDO) 2 (PIPERIDIN 1 YL)BENZOIC ACID; 5 (3 (THIOPHEN 2 YL)ACRYLAMIDO) 2 MORPHOLINOBENZAMIDE; 5 (3 (THIOPHEN 2 YL)ACRYLAMIDO) 2 MORPHOLINOBENZOIC ACID; 5 (3 (THIOPHEN 2 YL)ALLYLAMINO) 2 MORPHOLINOBENZOIC ACID; 5 (3 (THIOPHEN 2 YL)PROPANAMIDO) 2 MORPHOLINOBENZOIC ACID; 5 (3 (THIOPHEN 2 YL)PROPIOLAMIDO) 2 MORPHOLINOBENZOIC ACID; 5 (N METHYL 3 (THIOPHEN 2 YL)ACRYLAMIDO) 2 MORPHOLINOBENZOIC ACID; METHYL 5 (3 (FURAN 2 YL) N METHYLACRYLAMIDO) 2 MORPHOLINOBENZOATE; METHYL 5 (3 (FURAN 2 YL)ACRYLAMIDO) 2 (PIPERIDIN 1 YL)BENZOATE; METHYL 5 (3 (FURAN 2 YL)ACRYLAMIDO) 2 MORPHOLINOBENZOATE; METHYL 5 (3 (FURAN 2 YL)PROPANAMIDO) 2 MORPHOLINOBENZOATE; METHYL 5 (3 (THIOPHEN 2 YL)ACRYLAMIDO) 2 (PIPERIDIN 1 YL)BENZOATE; METHYL 5 (3 (THIOPHEN 2 YL)ACRYLAMIDO) 2 MORPHOLINOBENZOATE; METHYL 5 (3 (THIOPHEN 2 YL)ALLYLAMINO) 2 MORPHOLINOBENZOATE; METHYL 5 (3 (THIOPHEN 2 YL)PROPANAMIDO) 2 MORPHOLINOBENZOATE; METHYL 5 (3 (THIOPHEN 2 YL)PROPIOLAMIDO) 2 MORPHOLINOBENZOATE; METHYL 5 (N METHYL 3 (THIOPHEN 2 YL)ACRYLAMIDO) 2 MORPHOLINOBENZOATE; METHYL 5 AMINO 2 (PIPERIDIN 1 YL)BENZOATE; METHYL 5 AMINO 2 MORPHOLINOBENZOATE; METHYL 5 NITRO 2 (PIPERIDIN 1 YL)BENZOATE; N (3 (HYDROXYMETHYL) 4 MORPHOLINOPHENYL) 3 (THIOPHEN 2 YL)ACRYLAMIDE; N (3 FORMYL 4 MORPHOLINOPHENYL) 3 (FURAN 2 YL)ACRYLAMIDE; N (3 FORMYL 4 MORPHOLINOPHENYL) 3 (THIOPHEN 2 YL)ACRYLAMIDE; SORTASE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; FLUORESCENCE RESONANCE ENERGY TRANSFER; NONHUMAN; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

AMINOACYLTRANSFERASES; BACTERIAL PROTEINS; CYSTEINE ENDOPEPTIDASES; DRUG DISCOVERY; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MUTATION; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77955551005     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.05.024     Document Type: Article

References (34)

1. R.M. Klevens, M.A. Morrison, J. Nadle, S. Petit, K. Gershman, S. Ray, L.H. Harrison, R. Lynfield, G. Dumyati, J.M. Townes, A.S. Craig, E.R. Zell, G.E. Fosheim, L.K. McDougal, R.B. Carey, and S.K. Fridkin Invasive methicillin-resistant Staphylococcus aureus infections in the United States J. Am. Med. Assoc. 298 2007 1763 1771
2. S.V. Kazakova, J.C. Hageman, M. Matava, A. Srinivasan, L. Phelan, B. Garfinkel, T. Boo, S. McAllister, J. Anderson, B. Jensen, D. Dodson, D. Lonsway, L.K. McDougal, M. Arduino, V.J. Fraser, G. Killgore, F.C. Tenover, S. Cody, and D.B. Jernigan A clone of methicillin-resistant Staphylococcus aureus among professional football players N. Engl. J. Med. 352 2005 468 475
3. I.B. Gosbell, T. Barbagiannakos, S.A. Neville, J.L. Mercer, A.M. Vickery, F.G. O'Brien, G.W. Coombs, M.J. Malkowski, and J.C. Pearson Non-multiresistant methicillin-resistant Staphylococcus aureus bacteraemia in Sydney, Australia: emergence of EMRSA-15, Oceania, Queensland and Western Australian MRSA strains Pathology 38 2006 239 244
4. M. Gilbert, J. MacDonald, D. Gregson, J. Siushansian, K. Zhang, S. Elsayed, K. Laupland, T. Louie, K. Hope, M. Mulvey, J. Gillespie, D. Nielsen, V. Wheeler, M. Louie, A. Honish, G. Keays, and J. Conly Outbreak in Alberta of community-acquired (USA300) methicillin-resistant Staphylococcus aureus in people with a history of drug use, homelessness or incarceration Can. Med. Assoc. J. 175 2006 149 154
5. M.D. David, A.M. Kearns, S. Gossain, M. Ganner, and A. Holmes Community-associated meticillin-resistant Staphylococcus aureus: nosocomial transmission in a neonatal unit J. Hosp. Infect. 64 2006 244 250
6. H.C. Baggett, T.W. Hennessy, K. Rudolph, D. Bruden, A. Reasonover, A. Parkinson, R. Sparks, R.M. Donlan, P. Martinez, K. Mongkolrattanothai, and J.C. Butler Community-onset methicillin-resistant Staphylococcus aureus associated with antibiotic use and the cytotoxin Panton-Valentine leukocidin during a furunculosis outbreak in rural Alaska J. Infect. Dis. 189 2004 1565 1573
7. W. Zhu, N.C. Clark, L.K. McDougal, J. Hageman, L.C. McDonald, and J.B. Patel Vancomycin-resistant Staphylococcus aureus isolates associated with Inc18-like vanA plasmids in Michigan Antimicrob. Agents Chemother. 52 2008 452 457
8. S. Chang, D.M. Sievert, J.C. Hageman, M.L. Boulton, F.C. Tenover, F.P. Downes, S. Shah, J.T. Rudrik, G.R. Pupp, W.J. Brown, D. Cardo, and S.K. Fridkin Infection with vancomycin-resistant Staphylococcus aureus containing the vanA resistance gene N. Engl. J. Med. 348 2003 1342 1347
9. Anonymous Staphylococcus aureus resistant to vancomycin-United States MMWR 51 2002 565 566
10. Anonymous Vancomycin-resistant Staphylococcus aureus-New York MMWR 53 2004 322
11. W.W. Navarre, and O. Schneewind Surface proteins of gram-positive bacteria and mechanisms of their targeting to the cell wall envelope Microbiol. Mol. Biol. Rev. 63 1999 174 229
12. P. Cossart, and R. Jonquieres Sortase, a universal target for therapeutic agents against gram-positive bacteria? Proc. Natl. Acad. Sci. U S A. 97 2000 5013 5015
13. V.A. Fischetti, V. Pancholi, and O. Schneewind Conservation of a hexapeptide sequence in the anchor region of surface proteins from gram-positive cocci Mol. Microbiol. 4 1990 1603 1605
14. O. Schneewind, P. Model, and V. Fischetti Sorting of protein A to the staphylococcal cell wall Cell 70 1992 267 281
15. O. Schneewind, D. Mihaylova-Petkov, and P. Model Cell wall sorting signals in surface proteins of gram-positive bacteria EMBO J. 12 1993 4803 4811
16. W.W. Navarre, and O. Schneewind Proteolytic cleavage and cell wall anchoring at the LPXTG motif of surface proteins in gram-positive bacteria Mol. Microbiol. 14 1994 115 121
17. A.M. Perry, H. Ton-That, S.K. Mazmanian, and O. Schneewind Anchoring of surface proteins to the cell wall of Staphylococcus aureus. III. Lipid II is an in vivo peptidoglycan substrate for sortase-catalyzed surface protein anchoring J. Biol. Chem. 277 2002 16241 16248
18. I.M. Jonsson, S.K. Mazmanian, O. Schneewind, T. Bremell, and A. Tarkowski The role of Staphylococcus aureus sortase A and sortase B in murine arthritis Microb. Infect. 5 2003 775 780
19. S.K. Mazmanian, G. Liu, E.R. Jensen, E. Lenoy, and O. Schneewind Staphylococcus aureus sortase mutants defective in the display of surface proteins and in the pathogenesis of animal infections Proc. Natl. Acad. Sci. U S A. 97 2000 5510 5515
20. T.C. Barnett, and J.R. Scott Differential recognition of surface proteins in Streptococcus pyogenes by two sortase gene homologs J. Bacteriol. 184 2002 2181 2191
21. H. Bierne, S.K. Mazmanian, M. Trost, M.G. Pucciarelli, G. Liu, P. Dehoux, L. Jansch, F. Garcia-del Portillo, O. Schneewind, and P. Cossart Inactivation of the srtA gene in Listeria monocytogenes inhibits anchoring of surface proteins and affects virulence Mol. Microbiol. 43 2002 869 881
22. T.C. Bolken, C.A. Franke, K.F. Jones, G.O. Zeller, C.H. Jones, E.K. Dutton, and D.E. Hruby Inactivation of the srtA gene in Streptococcus gordonii inhibits cell wall anchoring of surface proteins and decreases in vitro and in vivo adhesion Infect. Immun. 69 2001 75 80
23. C. Garandeau, H. Reglier-Poupet, I. Dubail, J.L. Beretti, P. Berche, and A. Charbit The sortase SrtA of Listeria monocytogenes is involved in processing of internalin and in virulence Infect. Immun. 70 2002 1382 1390
24. I.M. Jonsson, S.K. Mazmanian, O. Schneewind, M. Verdrengh, T. Bremell, and A. Tarkowski On the role of Staphylococcus aureus sortase and sortase-catalyzed surface protein anchoring in murine septic arthritis J. Infect. Dis. 185 2002 1417 1424
25. S.S. Kang, J.G. Kim, T.H. Lee, and K.B. Oh Flavonols inhibit sortases and sortase-mediated Staphylococcus aureus clumping to fibrinogen Biol. Pharm. Bull. 29 2006 1751 1755
26. S.H. Kim, D.S. Shin, M.N. Oh, S.C. Chung, J.S. Lee, I.M. Chang, and K.B. Oh Inhibition of sortase, a bacterial surface protein anchoring transpeptidase, by beta-sitosterol-3-O-glucopyranoside from Fritillaria verticillata Biosci. Biotechnol. Biochem. 67 2003 2477 2479
27. S.W. Kim, I.M. Chang, and K.B. Oh Inhibition of the bacterial surface protein anchoring transpeptidase sortase by medicinal plants Biosci. Biotechnol. Biochem. 66 2002 2751 2754
28. C.J. Scott, A. McDowell, S.L. Martin, J.F. Lynas, K. Vandenbroeck, and B. Walker Irreversible inhibition of the bacterial cysteine protease- transpeptidase sortase (SrtA) by substrate-derived affinity labels Biochem. J. 366 2002 953 958
29. K.B. Oh, S.H. Kim, J. Lee, W.J. Cho, T. Lee, and S. Kim Discovery of diarylacrylonitriles as a novel series of small molecule sortase A inhibitors J. Med. Chem. 47 2004 2418 2421
30. B.C. Chenna, B.A. Shinkre, J.R. King, A.L. Lucius, S.V. Narayana, and S.E. Velu Identification of novel inhibitors of bacterial surface enzyme Staphylococcus aureus Sortase A Bioorg. Med. Chem. Lett. 18 2008 380 385
31. J.S. Skotnicki, R.M. Kearney, and A.L. Smith Synthesis of secorapamycin esters and amides Tetrahedron Lett. 35 1994 197 200
32. R.G. Kruger, P. Dostal, and D.G. McCafferty Development of a high-performance liquid chromatography assay and revision of kinetic parameters for the Staphylococcus aureus sortase transpeptidase SrtA Anal. Biochem. 326 2004 42 48
33. H. Ton-That, S.K. Mazmanian, K.F. Faull, and O. Schneewind Anchoring of surface proteins to the cell wall of Staphylococcus aureus. Sortase catalyzed in vitro transpeptidation reaction using LPXTG peptide and NH(2)-Gly(3) substrates J. Biol. Chem. 275 2000 9876 9881
34. D.H. Wadsworth, S.M. Geer, and M.R. Detty Preparation of arylpropiolate esters from trichlorocyclopropenium cation and elaboration of the esters to unsymmetrical 1,4-pentadiyn-3-ones and unsymmetrical tellurapyranones J. Org. Chem. 52 1987 3662 3668