Dissociation of antimicrobial and hemolytic activities of gramicidin S through N-methylation modification

ChemMedChem

Volumn 8, Issue 11, 2013, Pages 1865-1872

  Li, Yangmei ^a   Bionda, Nina ^a   Yongye, Austin ^a   Geer, Phaedra ^a   Stawikowski, Maciej ^a   Cudic, Predrag ^a   Martinez, Karina ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

Antimicrobial activity and selectivity; Conformation; Drug discovery; Molecular modeling; Peptide methylation

Indexed keywords

GRAMICIDIN DERIVATIVE; GRAMICIDIN S; LEUCINE; N METHYLALANINE; PROLINE; ALANINE; ANTIINFECTIVE AGENT; GRAMICIDIN; N-METHYLALANINE;

AMINO ACID SUBSTITUTION; ANTIMICROBIAL ACTIVITY; ARTICLE; BETA SHEET; BETA TURN; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DISSOCIATION; DRUG SYNTHESIS; ESCHERICHIA COLI; HEMOLYSIS; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; KLEBSIELLA PNEUMONIAE; METHYLATION; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SALMONELLA; STAPHYLOCOCCUS AUREUS; ANALOGS AND DERIVATIVES; BACTERIA; CHEMISTRY; DRUG EFFECTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

ALANINE; ANTI-INFECTIVE AGENTS; BACTERIA; GRAMICIDIN; HEMOLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN STRUCTURE, SECONDARY;

EID: 84890873931     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300232     Document Type: Article

References (30)

1. K. Kawano, T. Yoneya, T. Miyata, K. Yoshikawa, F. Tokunaga, Y. Terada, S. Iwanaga, J. Biol. Chem. 1990, 265, 15365-15367.
2. V. N. Kokryakov, S. S. Harwig, W. A. Panyutich, A. A. Shevchenko, G. M. Aleshina, O. V. Shamova, H. A. Korneva, R. I. Lehrer, FEBS Lett. 1993, 327, 231-236.
3. T. V. Ovchinnikova, G. M. Aleshina, S. V. Balandin, A. D. Krasnosdembskaya, M. L. Markelov, E. I. Frolova, Y. F. Lenova, A. A. Tagaev, E. G. Krasnodembsky, V. N. Kokryakov, FEBS Lett. 2004, 577, 209-214.
4. P. M. Hwang, N. Zhou, X. Shan, C. H. Arrowsmith, H. J. Vogel, Biochemistry 1998, 37, 4288-4298.
5. S. U. Patel, R. Osborn, S. Rees, J. M. Thornton, Biochemistry 1998, 37, 983-990.
6. P. I. Silva, Jr., S. Daffre, P. Bulet, J. Biol. Chem. 2000, 275, 33464-33470.
7. M. Trabi, H. J. Schirra, D. J. Craik, Biochemistry 2001, 40, 4211-4221.
8. a) T. Mogi, H. Ui, K. Shiomi, S. Omura, K. Kita, FEBS Lett. 2008, 582, 2299-2302
9. b) T. Mogi, Y. Murase, M. Mori, K. Shiomi, S. Omura, M. P. Paranagama, K. Kita, J. Biochem. 2009, 146, 491-499.
10. a) G. M. Grotenbreg, E. Spalburg, A. J. de Neeling, G. A. van der Marel, H. S. Overkleeft, J. H. van Boom, M. Overhand, Bioorg. Med. Chem. 2003, 11, 2835-2841
11. b) A. W. Tuin, D. K. Palachanis, A. Buizert, G. M. Grotenbreg, E. Spalburg, A. J. de Neeling, R. H. Mars-Groenendijk, D. Noort, G. A. van der Marel, H. S. Overkleeft, M. Overhand, Eur. J. Org. Chem. 2009, 4231-4241.
12. a) C. Solanas, B. G. de La Torre, M. Fernandez-Reyes, C. M. Santiveri, M. A. Jimanez, L. Rivas, A. I. Jimanez, D. Andreu, C. Cativiela, J. Med. Chem. 2009, 52, 664-674
13. b) C. Solanas, B. G. de La Torre, M. Fernandez-Reyes, C. M. Santiveri, M. A. Jimanez, L. Rivas, A. I. Jimanez, D. Andreu, C. Cativiela, J. Med. Chem. 2010, 53, 4119-4129.
14. E. J. Prenner, M. Kiricsi, M. Jelokhani-Niaraki, R. N. A. H. Lewis, R. S. Hodges, R. N. McElhaney, J. Biol. Chem. 2005, 280, 2002 -2011.
15. B. Laufer, J. Chatterjee, A. O. Frank, H. Kessler, J. Pept. Sci. 2009, 15, 141-146.
16. a) Y. Li, Y. Yu, M. Giulianotti, R. A. Houghten, J. Comb. Chem. 2008, 10, 613-616
17. b) J. A. Camarero, A. Adeva, T. W. Muir, Lett. Pept. Sci. 2000, 7, 17-21.
18. N. Bionda, M. Stawikowshi, R. Stawikowska, M. Cudic, F. Lopez-Vallejo, D. Treitl, J. Medina-Franco, P. Cudic, Chem Med Chem 2012, 7, 871-882.
19. a) T. Wieprecht, M. Dathe, M. Beyermann, E. Krause, W. L. Maloy, D. L. MacDonald, M. Bienert, Biochemistry 1997, 36, 6124-6132
20. b) Y. Chen, M. T. Guarnieri, A. I. Vasil, M. L. Vasil, C. T. Mant, R. S. Hodges, Antimicrob. Agents Chemother. 2007, 51, 1398-1406.
21. a) E. M. Krauss, S. I. Chan, J. Am. Chem. Soc. 1982, 104, 6953-6961
22. b) K. Yamada, S.-s. Shinoda, H. Oku, K. Komagoe, T. Katsu, R. Katakai, J. Med. Chem. 2006, 49, 7592-7595.
23. N. J. Baxter, M. P. Williamson, J. Biomol. NMR 1997, 9, 359-369.
24. a) M. Kawai, H. Yamamura, R. Tanaka, H. Umemoto, C. Ohmizo, S. Higuchi, T. Katsu, J. Pept. Res. 2005, 65, 98-104
25. b) K. Yamada, S.-s. Shinoda, H. Oku, K. Komagoe, T. Katsu, R. Katakai, J. Med. Chem. 2006, 49, 7592 -7595.
26. C. McInnes, L. H. Kondejewski, R. S. Hodges, B. D. Sykes, J. Biol. Chem. 2000, 275, 14287-14292.
27. R. A. Houghten, Proc. Natl. Acad. Sci. USA 1985, 82, 5131-5135.
28. A. B. Yongye, Y. Li, M. A. Giulianotti, Y. Yu, R. A. Houghten, K. Martinez-Mayorga, J. Comput.-Aided Mol. Des. 2009, 23, 677-689.
29. E. R. Turpin, J. D. Hirst, Chem. Phys. Lett. 2012, 543, 142-147.
30. J. C. Phillips, R. Braun, W. Wang, J. Gumbart, E. Tajkhorshid, E. Villa, C. Chipot, R. D. Skeel, L. Kala, K. Schulten, J. Comput. Chem. 2005, 26, 1781-1802.