Antimicrobial activity and protease stability of peptides containing fluorinated amino acids

Journal of the American Chemical Society

Volumn 129, Issue 50, 2007, Pages 15615-15622

  Meng, He ^a   Kumar, Krishna ^a,b  

^a TUFTS UNIVERSITY   (United States)

^b TUFTS MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL; PROTEASE STABILITY;

AMINO ACIDS; BACTERIA; ENZYME ACTIVITY; FLUORINATION; HYDROPHOBICITY; THERMODYNAMIC STABILITY;

PEPTIDES;

AMINO ACID; BUFORIN II; FLUORINE; MAGAININ 2; MAGAININ DERIVATIVE; PROTEINASE; SYNTHETIC PEPTIDE; TRYPSIN; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CIRCULAR DICHROISM; ENZYME STABILITY; FLUORINATION; GRAM NEGATIVE SEPSIS; GRAM POSITIVE BACTERIUM; HEMOLYSIS; HYDROPHOBICITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR INTERACTION; NONHUMAN; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN DEGRADATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

AMINO ACID SEQUENCE; AMINO ACIDS; ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; CIRCULAR DICHROISM; ENDOPEPTIDASES; ERYTHROCYTES; ESCHERICHIA COLI; FLUORINE; HEMOLYSIS; HUMANS; HYDROPHOBICITY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PEPTIDES; ULTRACENTRIFUGATION;

EID: 37849047198     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075373f     Document Type: Article

References (54)

1. Coates, A.; Hu, Y. M.; Bax, R.; Page, C. Nat. Rev. Drug Discovery 2002, 1, (11), 895-910.
2. Zasloff, M. Nature 2002, 415, (6870), 389-395.
3. Hancock, R. E. W.; Sahl, H. G. Nat. Biotechnol. 2006, 24, (12), 1551-1557.
4. Tossi, A.; Sandri, L.; Giangaspero, A. Biopolymers 2000, 55, (1), 4-30.
5. Brogden, K. A. Nat. Rev. Microbiol. 2005, 3, (3), 238-250.
6. Ganz, T. Nat. Rev. Immunol. 2003, 3, (9), 710-720.
7. Matsuzaki, K. Biochim. Biophys. Acta 1999, 1462, (1-2), 1-10.
8. Shai, Y. Biochim. Biophys. Acta 1999, 1462, (1-2), 55-70.
9. Perron, G. G.; Zasloff, M.; Bell, G. Proc. R. Soc. London, Ser. B 2006, 273, (1583), 251-256.
10. Yeaman, M. R.; Yount, N. Y. Pharmacol. Rev. 2003, 55, (1), 27-55.
11. Zasloff, M. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, (15), 5449-5453.
12. Chen, H. C.; Brown, J. H.; Morell, J. L.; Huang, C. M. FEBS Lett. 1988, 236, (2), 462-466.
13. Porter, E. A.; Wang, X. F.; Lee, H. S.; Weisblum, B.; Gellman, S. H. Nature 2000, 404, (6778), 565-565.
14. Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, (25), 7324-7330.
15. Schmitt, M. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2004, 126, (22), 6848-6849.
16. Raguse, T. L.; Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, (43), 12774-12785.
17. Liu, D. H.; DeGrado, W. F. J. Am. Chem. Soc. 2001, 123, (31), 7553-7559.
18. Fernandez-Lopez, S.; Kim, H. S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G.; Weinberger, D. A.; Wilcoxen, K. M.; Ghadiri, M. R. Nature 2001, 412, (6845), 452-455.
19. Tew, G. N.; Liu, D. H.; Chen, B.; Doerksen, R. J.; Kaplan, J.; Carroll, P. J.; Klein, M. L.; DeGrado, W. F. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, (8), 5110-5114.
20. Liu, D. H.; Choi, S.; Chen, B.; Doerksen, R. J.; Clements, D. J.; Winkler, J. D.; Klein, M. L.; DeGrado, W. F. Angew. Chem., Int. Ed. 2004, 43, (9), 1158-1162.
21. Bilgiçer, B.; Fichera, A.; Kumar, K. J. Am. Chem. Soc. 2001, 123, (19), 4393-4399.
22. Bilgiçer, B.; Xing, X.; Kumar, K. J. Am. Chem. Soc. 2001, 123, (47), 11815-11816.
23. Tang, Y.; Ghirlanda, G.; Vaidehi, N.; Kua, J.; Mainz, D. T.; Goddard, W. A.; DeGrado, W. F.; Tirrell, D. A. Biochemistry 2001, 40, (9), 2790-2796.
24. Tang, Y.; Tirrell, D. A. J. Am. Chem. Soc. 2001, 123, (44), 11089-11090.
25. Lee, K. H.; Lee, H. Y.; Slutsky, M. M.; Anderson, J. T.; Marsh, E. N. G. Biochemistry 2004, 43, (51), 16277-16284.
26. Niemz, A.; Tirrell, D. A. J. Am. Chem. Soc. 2001, 123, (30), 7407-7413.
27. Bilgiçer, B.; Kumar, K. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, (43), 15324-15329.
28. Naarmann, N.; Bilgicer, B.; Meng, H.; Kumar, K.; Steinem, C. Angew. Chem., Int. Ed. 2006, 45, (16), 2588-2591.
29. Xing, X.; Fichera, A.; Kumar, K. Org. Lett. 2001, 3, (9), 1285-1286.
30. Schnolzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Pept. Protein Res. 1992, 40, (3-4), 180-193.
31. Chen, Y. H.; Yang, J. T.; Chau, K. H. Biochemistry 1974, 13, (16), 3350-3359.
32. Javadpour, M. M.; Barkley, M. D. Biochemistry 1997, 36, (31), 9540-9549.
33. Park, C. B.; Yi, K. S.; Matsuzaki, K.; Kim, M. S.; Kim, S. C. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, (15), 8245-8250.
34. Park, C. B.; Kim, H. S.; Kim, S. C. Biochem. Biophys. Res. Commun. 1998, 244, (1), 253-257.
35. Kobayashi, S.; Takeshima, K.; Park, C. B.; Kim, S. C.; Matsuzaki, K. Biochemistry 2000, 39, (29), 8648-8654.
36. Tachi, T.; Epand, R. F.; Epand, R. M.; Matsuzaki, K. Biochemistry 2002, 41, (34), 10723-10731.
37. Kobayashi, S.; Chikushi, A.; Tougu, S.; Imura, Y.; Nishida, M.; Yano, Y.; Matsuzaki, K. Biochemistry 2004, 43, (49), 15610-15616.
38. Yi, G. S.; Park, C. B.; Kim, S. C.; Cheong, C. FEBS Lett. 1996, 398, (1), 87-90.
39. Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, (32), 11516-11529.
40. Hilpert, K.; Volkmer-Engert, R.; Walter, T.; Hancock, R. E. W. Nat. Biotechnol. 2005, 23, (8), 1008-1012.
41. The peptide M2F5 was significantly more hemolytic than M2. The hydrophobicity of this peptide was significantly increased upon fluorination leading to both reduced antimicrobial activity and higher hemolytic activity.
42. Wieprecht, T.; Dathe, M.; Beyermann, M.; Krause, E.; Maloy, W. L.; MacDonald, D. L.; Bienert, M. Biochemistry 1997, 36, (20), 6124-6132.
43. Rozek, A.; Powers, J. P. S.; Friedrich, C. L.; Hancock, R. E. W. Biochemistry 2003, 42, (48), 14130-14138.
44. Latham, P. W. Nat. Biotechnol. 1999, 17, (8), 755-757.
45. Sato, A. K.; Viswanathan, M.; Kent, R. B.; Wood, C. R. Curr. Opin. Biotechnol. 2006, 17, (6), 638-642.
46. Schechte, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, (2), 157-162.
47. Zhang, C.; Ludin, C.; Eberle, M. K.; Stoeckli-Evans, H.; Keese, R. Helv. CHm. Acta 1998, 81, (1), 174-181.
48. Papo, N.; Shai, Y. J. Biol. Chem. 2005, 280, (11), 10378-10387.
49. Kuroda, K.; DeGrado, W. F. J. Am. Chem. Soc. 2005, 127, (12), 4128-4129.
50. Son, S.; Tanrikulu, I. C.; Tirrell, D. A. ChemBioChem 2006, 7, (8), 1251-1257.
51. Lee, H. Y.; Lee, K. H.; Al-Hashimi, H. M.; Marsh, E. N. G. J. Am. Chem. Soc. 2006, 128, (1), 337-343.
52. Vine, W. H.; Hsieh, K. H.; Marshall, G. R. J. Med. Chem. 1981, 24, (9), 1043-1047.
53. Hsieh, K. H.; Needleman, P.; Marshall, G. R. J. Med. Chem. 1987, 30, (6), 1097-1100.
54. The model structure was generated by automated homology modeling using SWISS-MODEL v3.5 (AACODE: P55897). Schwede, T.; Kopp, J.; Guex, N.; Peitsch, M. C. Nucleic Acids Res. 2003, 31, 3381-3385.