Antimicrobial peptides containing unnatural amino acid exhibit potent bactericidal activity against ESKAPE pathogens

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 1, 2013, Pages 205-214

  Hicks, R P ^a   Abercrombie, J J ^b   Wong, R K ^b   Leung, K P ^b  

^a EAST CAROLINA UNIVERSITY   (United States)

^b US ARMY INSTITUTE OF SURGICAL RESEARCH   (United States)

Author keywords

Antimicrobial peptides; Cellular toxicity; ESKAPE; MBC; MIC; Unusual amino acids

Indexed keywords

AMINO ACID DERIVATIVE; DIPEPTIDE; OCTAHYDROINDOLECARBOXYLIC ACID; POLYPEPTIDE ANTIBIOTIC AGENT; TETRAHYDROISOQUINOLINECARBOXYLIC ACID; UNCLASSIFIED DRUG;

ACINETOBACTER BAUMANNII; AMINO ACID SEQUENCE; ANTIBIOTIC SENSITIVITY; ARTICLE; BACTERIAL MEMBRANE; BACTERIAL STRAIN; BACTERICIDAL ACTIVITY; CHEMICAL COMPOSITION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENTEROBACTER; ENTEROCOCCUS FAECIUM; HUMAN; HUMAN CELL; IN VITRO STUDY; KLEBSIELLA PNEUMONIAE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHYSICAL CHEMISTRY; PSEUDOMONAS AERUGINOSA; SKIN FIBROBLAST; STAPHYLOCOCCUS AUREUS; WOUND INFECTION;

ACINETOBACTER BAUMANNII; AMINO ACID SEQUENCE; AMINO ACIDS; ANTI-INFECTIVE AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; BACTERIA; BACTERIAL INFECTIONS; CELL LINE; ENTEROBACTER; HUMANS; KLEBSIELLA PNEUMONIAE; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

ACINETOBACTER BAUMANNII; BACTERIA (MICROORGANISMS); ENTEROBACTER; ENTEROCOCCUS FAECIUM; KLEBSIELLA; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84870953774     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.10.039     Document Type: Article

References (83)

1. B. Cookson J. Appl. Microbiol. 99 2005 989
2. J. Davies Science 264 1994 375
3. G.E. Schutze, S.L. Kaplan, and R.F. Jacobs Infection 22 1994 233
4. B. Bechinger J. Pept. Sci. 17 2011 306
5. R.M. Epand, and R.F. Epand J. Pept. Sci. 17 2011 298
6. C.R. Bonapace, R.L. White, L.V. Friedrich, and J.A. Bosso Diagn. Microbiol. Infect. Dis. 38 2000 43
7. R. Chait, A. Craney, and R. Kishony Nature 446 2007 668
8. L. Drago, E. De Vecchi, L. Nicola, A. Colombo, A. Guerra, and M.R. Gismondo Chemotherapy 50 2004 202
9. K. Bush ASM News 70 2004 282
10. Hartl, G.; World Health, Organization, 2000.
11. D.M. Shlaes, S.J. Projan, and J.E. Edwards ASM News 70 2004 275
12. Y. Huang, J. Huang, and Y. Chen Protein Cell 1 2010 143
13. T. Godballe, L.L. Nilsson, P.D. Petersen, and H. Jenssen Chem. Biol. Drug Des. 77 2011 107
14. J. Song Int. J. Antimicrob. Agents 32 2008 S207
15. B. Findlay, G.G. Zhanel, and F. Schweizer Antimicrob. Agents Chemother. 54 2010 4049
16. K. Lohner Gen. Physiol. Biophys. 28 2009 105
17. M.A. Fox, J.E. Thwaite, D.O. Ulaeto, T.P. Atkins, and H.S. Atkins Peptides 33 2012 197
18. S.A. Jang, H. Kim, J.Y. Lee, J.R. Shin, D.J. Kim, J.H. Cho, and S.C. Kim Peptides 34 2012 283
19. W. Kamysz Nucl. Med. Rev. 8 2005 78
20. L. Zhang, S.C. Harris, and T.J. Falla Therapeutic Application of Innate Immunity Peptides 2005 Horizon Bioscience San Diego
21. O. Toke Biopolymers 80 2005 717
22. D.A. Phoenix, F. Harris, S. Dennison, L. Chatfield, Z. Sayed, and S.J.E.C. Hussain Qua L. 1 2003 44
23. S.R. Dennison, J. Wallace, F. Harris, and D.A. Phoenix Protein Pept. Lett. 12 2005 31
24. Y.M. Song, Y. Park, S.S. Lim, S.-T. Yang, E.-R. Woo, S. Park, J.S. Lee, J.I. Kim, K.-S. Hahm, Y. Kim, and S.Y. Shin Biochemistry 44 2005 12094
25. D.A. Devine, and R.E.W. Hancock Curr. Pharm. Des. 8 2002 703
26. R.E.W. Hancock Exp. Opin. Invest. Drugs 7 1998 167
27. M. Zasloff Nature 415 2002 389
28. G. Wang, X. Li, and Z. Wang Nucleic Acids Res. 37 2009 D933
29. H. Khandelia, J.H. Ipsen, and O.G. Mouritsen Biochim. Biophys. Acta 1778 2008 1528
30. J.-P.S. Powers, and R.E.W. Hancock Peptides 24 2003 1681
31. K.A. Brogden Nat. Rev. Microbiol. 3 2005 238
32. Y. Shai Biochem. Biophys. Acta 1462 1999 55
33. Y. Shai, and Z. Oren Peptides 22 2001 1629
34. N. Sitaram, and R. Nagaraj Biochem. Biophys. Acta 1462 1999 29
35. M.R. Yeaman, and N.Y. Yount Pharmacol. Rev. 55 2003 27
36. K. Matsuzaki Biochem. Biophys. Acta 1462 1999 1
37. N. Papo, and Y. Shai Biochemistry 42 2003 9346
38. H. Leontiadou, A.E. Mark, and S.J. Marrink J. Am. Chem. Soc. 128 2006 12156
39. Hancock, R. E. W.; Lehrer, R. Trends Biotechnol. 1998, 16, 82.
40. A. Giangaspero, L. Sandri, and A. Tossi Eur. J. Biochem. 268 2001 5589
41. N.R. Yeaman, and N.Y. Yount Pharmacol Rev. 55 2003 27
42. G.A. Grant Synthetic Peptides, A User's Guide 2002 Oxford University Press New York, NY
43. N.L. Benoiton Chemistry of Peptide Synthesis 2006 Taylor and Francis (CRC Press) Boca-Raton, FL
44. R.P. Hicks, J.B. Bhonsle, D. Venugopal, B.W. Koser, and A.J. Magill J. Med. Chem. 50 2007 3026
45. D. Venugopal, D. Klapper, A. Srouji, J.B. Bhonsle, R. Borschel, A. Mueller, A.L. Russell, B.C. Williams, and R.P. Hicks Bioorg. Med. Chem. 18 2010 5137
46. A.L. Russell, A.M. Kennedy, A. Spuches, D. Venugopal, J.B. Bhonsle, and R.P. Hicks Chem. Phys. Lipids 163 2010 488
47. S.P. Concannon J. Med. Microbiol. 52 2003 1083
48. J.M. Conlon, N. Al-Ghaferi, B. Abraham, and J. Leprince Methods 42 2007 349
49. J.S. Ma CHIMICA OGGI Chem. Today 2003 65
50. J.E. Oh, and K.H. Lee Bioorg. Med. Chem. 7 1999 2985
51. M. Goodman, and H. Shao Pure Appl. Chem. 66 1996 1303
52. T.L. Hendrickson, V. de Crecy-Lagard, and P. Schimmel Annu. Rev. Biochem. 73 2004 147
53. P.G. Vasudev, S. Chatterjee, N. Shamala, and P. Balaram Chem. Rev. 2010 10.1021/cr100100x published online
54. J.M. Sanderson Org. Biomol. Chem. 3 2005 201
55. B. Bechinger J. Membr. Biol. 156 1997 197
56. Hicks, R. P.; Russell, A. L. In Unnatural Amino Acids: Methods and Protocols, Methods in Molecular Biology, Pollegioni, L., Servi, S., Eds.; Springer Science, 2012; Vol. 794, p 135.
57. R.E.W. Hancock, and A. Rozek FEMS Microbiol. Lett. 206 2002 143
58. D.E. Karageorgopoulos, and M.E. Falagas Lancet. Infect. Dis 8 2008 751
59. M.N. Melo, R. Ferre, and M.A. Castanho Nat. Rev. 7 2009 245
60. M. Pohanka, and P. Skladal Folia Microbiol. 54 2009 263
61. F.J. Bikker, W.E. Kaman-van Zanten, A.M. de Vries-van de Ruit, I. Voskamp-Visser, P.A. van Hooft, R.H. Mars-Groenendijk, P.C. de Visser, and D. Noort Chem. Biol. Drug Des. 68 2006 148
62. J.B. Bhonsle, D. Venugopal, D.P. Huddler, A.J. Magill, and R.P. Hicks J. Med. Chem. 50 2007 6545
63. M.J.S. Fernández-Vidal, A.S. Ladokhin, and S.H. White J. Mol. Biol. 370 2007 459
64. R.E. Hancock, and A. Patrzykat Curr. Drug Targets Infect. Disord. 2 2002 79
65. A.L. Russell, A.M. Kennedy, A.M. Spuches, W.S. Gibson, D. Venugopal, D. Klapper, A.H. Srouji, J.B. Bhonsle, and R.P. Hicks Chem. Phys. Lipids 164 2011 740
66. A.L. Russell, B.C. Williams, A. Spuches, D. Klapper, A.H. Srouji, and R.P. Hicks Bioorg. Med. Chem. 20 2012 1723
67. T. Wieprecht, M. Beyermann, and J. Seelig Biochemistry 38 1999 10377
68. A.J. Mason, A. Marquette, and B. Bechinger Biophys. J. 93 2007 4289
69. A.L. Russell, A.M. Spuches, B. Williams, D. Venugopal, D. Klapper, A.H. Srouji, and R.P. Hicks Bioorg. Med. Chem. 19 2011 7008
70. F. Bringezu, S. Wen, S. Dante, T. Hauss, M. Majerowicz, and A. Waring Biochemistry 46 2007 5678
71. K. Lohner, and E.J. Prenner Biochim. Biophys. Acta 1462 1999 141
72. Y. Sakayori, M. Muramatsu, S. Hanada, Y. Kamagata, S. Kawamoto, and J. Shuma Microbiology 149 2003 2901
73. M. Tsai, R.L. Ohniwa, Y. Kato, S.L. Takeshita, T. Ohta, S. Saito, H. Hayashi, and K. Morikawa BMC Microbiol. 11 2011 13
74. Tossi, A.; Sandri, L.; Giangaspero, A. In Proceeding of the 27th European Peptide Symposium Sorrento; Benedetti, E., Pedone, C., Eds.; Edizioni Ziino: Napoli, Italy, 2002.
75. V. Teixeira, M.J. Feio, and M. Bastos Prog. Lipid Res. 51 2012 149
76. J. Andra, T. Goldmann, C.M. Ernst, A. Peschel, and T. Gutsmann J. Biol. Chem. 286 2011 18692
77. E. Kilelee, A. Pokorny, M.R. Yeaman, and A.S. Bayer Antimicrob. Agents Chemother. 54 2010 4476
78. C.C.L. Scott, S.R.A. Makula, and W.R.J. Finnerty Bacteriology 127 1976 469
79. H.U. Kim, T.Y. Kim, and S.Y. Lee Mol. BioSyst. 6 2010 339
80. Russell, A., L.; Klapper, D.; Srouji, A. H.; Bhonsle, J. B.; Borschel, R.; Mueller, A.; Hicks, R. P. In Antibacterial Agents/Book 2, Bobbarala, V., Ed.; InTech Publishing, 2012; Vol. ISBN 979-953-307-747-4.
81. S.Y. Shin, S.-T. Yang, E.J. Park, S.H. Eom, W.K. Song, and J.L. Kim J. Pept. Res. 58 2001 504
82. Z. Jiang, A.I. Vasil, J.D. Hale, R.E.W. Hancock, M.L. Vasil, and R.S. Hodges Pept. Sci. 90 2008 369
83. Y. Chen, M.T. Guarnieri, A.I. Vasil, M.L. Vasil, C.T. Mant, and R.S. Hdges Antimicrob. Agents Chemother. 51 2007 1398