Discovery of novel histidine-derived lipo-amino acids: Applied in the synthesis of ultra-short antimicrobial peptidomimetics having potent antimicrobial activity, salt resistance and protease stability

European Journal of Medicinal Chemistry

Volumn 68, Issue , 2013, Pages 10-18

  Ahn, Mija ^a   Murugan, Ravichandran N ^a   Jacob, Binu ^c   Hyun, Jae Kyung ^a   Cheong, Chaejoon ^a   Hwang, Eunha ^a   Park, Hyo Nam ^a   Seo, Ji Hyung ^a   Srinivasrao, G ^a   Lee, Kyung S ^b   Shin, Song Yub ^c   Bang, Jeong Kyu ^a  

^a Korea Basic Science Institute (KBSI)   (South Korea)

^b NATIONAL CANCER INSTITUTE   (United States)

^c Chosun University   (South Korea)

Author keywords

Anti MRSA activity; Antimicrobial peptidomimetics; Histidine derived amino acid; Protease stability; Salt resistance

Indexed keywords

AMINO ACID DERIVATIVE; CATHELICIDIN ANTIMICROBIAL PEPTIDE LL 37; MELITTIN; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N (DECYL) LEVO HISTIDINE; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N (DECYL) LEVO HISTIDINE METHYL ESTER; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N (TRANS DEC 2 EN 1 YL) LEVO HISTIDINE METHYL ESTER; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N (TRIPHENYLMETHYL) LEVO HISTIDINE METHYL ESTER; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N BIS(DECYL) LEVO HISTIDINE METHYL ESTER; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N BIS(HEPTYL) LEVO HISTIDINE METHYL ESTER; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N,N BIS(DECYL) LEVO HISTIDINE METHYL ESTER; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N,N BIS(HEPTYL) LEVO HISTIDINE METHYL ESTER; N(ALPHA) [(9H FLUOREN 9 YLMETHOXY)CARBONYL] N,N BIS(TETRADECYL) LEVO HISTIDINE METHYL ESTER; POLYPEPTIDE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROL; DRUG DETERMINATION; DRUG EFFICACY; DRUG POTENCY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HEMOLYSIS; NONHUMAN; PSEUDOMONAS AERUGINOSA; SALMONELLA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

ANTI-MRSA ACTIVITY; ANTIMICROBIAL PEPTIDOMIMETICS; HISTIDINE-DERIVED AMINO ACID; PROTEASE STABILITY; SALT RESISTANCE;

ANTI-INFECTIVE AGENTS; BACTERIA; DRUG DISCOVERY; DRUG STABILITY; HISTIDINE; LIPOPROTEINS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PEPTIDE HYDROLASES; PEPTIDOMIMETICS; SALTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84881146636     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.07.008     Document Type: Article

References (24)

1. B. Findlay, G.G. Zhanel, and F. Schweizer Cationic amphiphiles, a new generation of antimicrobials inspired by the natural antimicrobial peptide scaffold Antimicrob. Agents Chemother. 54 2010 4049 4058
2. G.G. Perron, M. Zasloff, and G. Bell Experimental evolution of resistance to an antimicrobial peptide Proc. Biol. Sci. 273 2006 251 256 (Pubitemid 46768100)
3. A.T. Yeung, S.L. Gellatly, and R.E. Hancock Multifunctional cationic host defence peptides and their clinical applications Cell. Mol. Life Sci. 68 2011 2161 2176
4. H. Tsubery, I. Ofek, S. Cohen, and M. Fridkin N-Terminal modifications of Polymyxin B nonapeptide and their effect on antibacterial activity Peptides 22 2001 1675 1681 (Pubitemid 32918247)
5. J.N. Steenbergen, J. Alder, G.M. Thorne, and F.P. Tally Daptomycin: a lipopeptide antibiotic for the treatment of serious Gram-positive infections J. Antimicrob. Chemother. 55 2005 283 288 (Pubitemid 40425449)
6. N.P. Chongsiriwatana, T.M. Miller, M. Wetzler, S. Vakulenko, A.J. Karlsson, S.P. Palecek, S. Mobashery, and A.E. Barron Short alkylated peptoid mimics of antimicrobial lipopeptides Antimicrob. Agents Chemother. 55 2011 417 420
7. D. Avrahami, and Y. Shai Bestowing antifungal and antibacterial activities by lipophilic acid conjugation to d, l-amino acid-containing antimicrobial peptides: a plausible mode of action Biochemistry 42 2003 14946 14956 (Pubitemid 37553525)
8. A. Majerle, J. Kidric, and R. Jerala Enhancement of antibacterial and lipopolysaccharide binding activities of a human lactoferrin peptide fragment by the addition of acyl chain J. Antimicrob. Chemother. 51 2003 1159 1165 (Pubitemid 36622072)
9. P. Mak, J. Pohl, A. Dubin, M.S. Reed, S.E. Bowers, M.T. Fallon, and W.M. Shafer The increased bactericidal activity of a fatty acid-modified synthetic antimicrobial peptide of human cathepsin G correlates with its enhanced capacity to interact with model membranes Int. J. Antimicrob. Agents 21 2003 13 19 (Pubitemid 36043970)
10. N.A. Lockwood, J.R. Haseman, M.V. Tirrell, and K.H. Mayo Acylation of SC4 dodecapeptide increases bacterial potency against Gram-positive bacterial, including drug resistant strains Biochem. J. 378 2004 93 103 (Pubitemid 38299547)
11. A. Makovitzki, D. Avrahami, and Y. Shai Ultrashort antibacterial and antifungal lipopeptides Proc. Natl. Acad. Sci. U. S. A. 103 2006 15997 16002 (Pubitemid 44657581)
12. A. Makovitzki, J. Baram, and Y. Shai Antimicrobial lipopolypeptides composed of palmitoyl di- and tricationic peptides: in vitro and in vivo activities, self-assembly to nanostructures, and a plausible mode of action Biochemistry 47 2008 10630 10636
13. A.F. Chu-Kung, K.N. Bozzelli, N.A. Lockwood, J.R. Haseman, K.H. Mayo, and M. Tirrell Promotion of peptide antimicrobial activity by fatty acid conjugation Bioconjug. Chem. 15 2004 530 535 (Pubitemid 38657858)
14. G. Laverty, M. McLaughlin, C. Shaw, S.P. Gorman, and B.F. Gilmore Antimicrobial activity of short, synthetic cationic lipopeptides Chem. Biol. Drug Des. 75 2010 563 569
15. C.J. Arnusch, H.B. Albada, M. Van Vaardegem, R.M.J. Liskamp, H.-G. Sahl, Y. Shadkchan, N. Osherov, and Y. Shai Trivalent ultrashort lipopeptides are potent pH dependent antifungal agents J. Med. Chem. 55 2012 1296 1302
16. A. Tossi, L. Sandri, and A. Giangaspero Amphipathic, alpha-helical antimicrobial peptides Biopolymers 55 2000 4 30
17. N.K. Brogden, and K.A. Brogden Will new generations of modified antimicrobial peptides improve their potential as pharmaceuticals? Int. J. Antimicrob. Agents 38 2011 217 225
18. J. Pernak, J. Rogoza, and I. Mirska Synthesis and antimicrobial activities of new pyridinium and benzimidazolium chlorides Eur. J. Med. Chem. 36 2001 313 320 (Pubitemid 32675223)
19. H. Turkmen, N. Ceyhan, N. Ulku Karabay Yavasoglu, G. Ozdemir, and B. Cetinkaya Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a] pyridinium bromides with varying benzyl substituents Eur. J. Med. Chem. 46 2011 2895 2900
20. V. Sambhy, B.R. Peterson, and A. Sen Antibacterial and hemolytic activities of pyridinium polymers as a function of the spatial relationship between the positive charge and the pendant alkyl tail Angew. Chem. Int. Ed. 47 2008 1250 1254
21. L. Kardas-Sloma, P.Y. Boelle, L. Opatowski, C. Brun-Buisson, D. Guillemot, and L. Temime Impact of antibiotic exposure patterns on selection of community-associated methicillin-resistant Staphylococcus aureus in hospital settings Antimicrob. Agents Chemother. 55 2011 4888 4895
22. D. Takahashi, S.K. Shukla, O. Prakash, and G. Zhang Structural determinants of host defense peptides for antimicrobial activity and target cell selectivity Biochimie 92 2010 1236 1241
23. J. Svenson, W. Stensen, B.O. Brandsdal, B.E. Haug, J. Monrad, and J.S. Svendsen Antimicrobial peptides with stability toward tryptic degradation Biochemistry 47 2008 3777 3788 (Pubitemid 351431368)
24. W. Qian, F. Liu, and T.R. Burke Jr. Investigation of unanticipated alkylation at the N (π) position of a histidyl residue under Mitsunobu conditions and synthesis of orthogonally protected histidine analogues J. Org. Chem. 76 2011 8885 8890