Discovery of Trp-His and His-Arg analogues as new structural classes of short antimicrobial peptides

Journal of Medicinal Chemistry

Volumn 52, Issue 23, 2009, Pages 7421-7431

  Sharma, Rohit K ^a   Reddy, Ravi P ^a   Tegge, Werner ^b   Jain, Rahul ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; POLYPEPTIDE ANTIBIOTIC AGENT;

AMINO ACID SEQUENCE; ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC BIOSYNTHESIS; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CELL ASSAY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; ESCHERICHIA COLI; IC 50; KLEBSIELLA PNEUMONIAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PARTICLE SIZE; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS EPIDERMIDIS;

ANTIMICROBIAL CATIONIC PEPTIDES; BACTERIA; DIPEPTIDES; DRUG DISCOVERY; FUNGI; MICROBIAL SENSITIVITY TESTS;

EID: 72249120792     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900622d     Document Type: Article

References (26)

1. Walsh, C. Where will the new antibiotics come from?. Nat. Rev. Microbiol. 2003, 1, 65-70.
2. Finch, R. Bacterial resistance;the clinical challenge. Clin. Microbiol. Infect. 2002, 8, 21-32.
3. Shain, C. S. Telithromycin: the first of the ketolides. Ann. Pharmacother. 2002, 36, 452-464.
4. Daptomycin (cubicin) for skin and soft tissue infections. Med. Lett. Drugs Ther. 2004, 46, 11-12.
5. Papagianni, M. Ribosomally synthesized peptides with antimicrobial properties: biosynthesis, structure, function, and applications. Biotechnol. Adv. 2003, 21, 465-499.
6. Hancock, R. E. W.; Scott, M. G. The role of antimicrobial peptides in animal defences. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 8856-8861.
7. Tossi, A.; Sandri, L.; Giangaspero, A. Amphipatic, alpha-helical antimicrobial peptides. Biopolymers 2000, 55, 4-30.
8. Huang, H. W. Action of antimicrobial peptides: two-state model. Biochemistry 2000, 39, 8347-8352.
9. Hancock, R. E. W.; Lehrer, R. I. Cationic peptides: a new source of antibiotics. Trends. Biotechnol. 1998, 16, 82-88.
10. Sengupta, D.; Leontiadou, H.; Mark, A. E.; Marrink, S. J. Toroidal pores formed by antimicrobial peptides show significant disorder. Biochim. Biophys. Acta 2008, 1778, 2308-2317.
11. Reddy, K. V. R.; Yedery, R. D.; Aranha, C. Antimicrobial peptides: premises and promises. Int. J. Antimicrob. Agents 2004, 24, 536-547.
12. Yeaman, M. R.; Yount, N. Y. Mechanisms of Antimicrobial Peptide Action and Resistance. Pharmacol. Rev. 2003, 55, 27-55.
13. Sundriyal, S.; Sharma, R. K.; Jain, R.; Bharatam, P. V. Minimum requirements of hydrophobic and hydrophilic features in cationic peptide antibiotics (CPAs): pharmacophore generation and validation with cationic steroid antibiotics (CSAs). J. Mol. Model. 2008, 14, 265-278.
14. Kurogi, Y.; Guner, O. F. Pharmacophore modeling and threedimensional database searching for drug design using catalyst. Curr. Med. Chem. 2001, 8, 1035-1055.
15. Stroem, M. B.; Haug, B. E.; Skar, M. L.; Stensen, W.; Stiberg, T.; Svendsen, J. S. The pharmacophore of short cationic antibacterial peptides. J. Med. Chem. 2003, 46, 1567-1570.
16. Haug, B. E.; M. L.; Stensen, W.; Stiberg, T.; Svendsen, J. S. Bulky nonproteinogenic amino acids permit the design of very small and effective cationic antibacterial peptides. J. Med. Chem. 2004, 47, 4159-4162.
17. Chan, D. I.; Prenner, E. J.; Vogel, H. J. Tryptophan- and argininerich antimicrobial peptides: structures and mechanisms of action. Biochim. Biophys. Acta 2006, 1758, 1184-1202.
18. Kacprzyk, L.; Rydenga° rd, V.; Morgelin, M.; Davoudi, M.; Pasupuleti, M.; Malmsten, M.; Schmidtchen, A. Antimicrobial activity of histidine-rich peptides is dependent on acidic conditions. Biochim. Biophys. Acta 2007, 1768, 2667-2680.
19. Jain, R.; Cohen, L. A. Regiospecific alkylation of histidine and histamine at C-2. Tetrahedron 1997, 53, 2365-2370.
20. Jain, R.; Cohen, L. A.; King, M. M. Synthesis of novel ringsubstituted histidines and histamines. Tetrahedron 1997, 53, 4539-4548.
21. Kaur, N.; Lu, X.; Gershengorn, G. C.; Jain, R. Thyrotropinreleasing hormone (TRH) analogues that exhibit selectivity to TRH receptor subtype 2. J. Med. Chem. 2005, 48, 6162-6165.
22. Minisci, F. Novel applications of free-radical reactions in preparative organic chemistry. Synthesis 1973, 1-24.
23. Minisci, F.; Vismara, E.; Fontana, F. Recent developments of freeradical substitutions of heteroaromatic bases. Heterocycles 1989, 28, 489-519.
24. Sharma, R. K.; Jain, R. Unprecedented 1,10-carbonyldiimidazole mediated amidation of unprotected R-amino acids in water. Synlett 2007, 603-606. (Pubitemid 46423722)
25. Saginur, R.; Melissa, S.; Ferris, W.; Aaron, S. D.; Chan, F.; Lee, C.; Ramotar, K. Multiple combination bactericidal testing of staphylococcal biofilms from implant-associated infections. Antimicrob. Agents Chemother. 2006, 50, 55-61.
26. Stepanovic, S.; Vukovic, D.; Dakic, I.; Savic, B.; Svabic-Vlahovic, M. A modified microtiter-plate test for quantification of staphylococcal biofilm formation. J. Microbiol. Methods 2000, 40, 175-179. (Pubitemid 30107900)