Design, synthesis and antimicrobial properties of non-hemolytic cationic α-cyclopeptoids

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 5, 2010, Pages 2010-2018

  Comegna, Daniela ^a   Benincasa, Monica ^b   Gennaro, Renato ^b   Izzo, Irene ^a   De Riccardis, Francesco ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Antibiotics; Cyclic peptoids; Solid phase synthesis

Indexed keywords

ALPHA CYCLOPEPTOID DERIVATIVE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; GLYCINE DERIVATIVE; LYSINE; N ALKYLGLYCINE DERIVATIVE; N ALKYLGLYCINE PEPTIDOMIMETIC DERIVATIVE; OLIGOMER; PROPIDIUM IODIDE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA; CANDIDA ALBICANS; CANDIDA FAMATA; CELL PERMEABILIZATION; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; CYCLIZATION; DRUG DESIGN; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FLOW CYTOMETRY; HEMOLYSIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CATIONS; CELL MEMBRANE PERMEABILITY; DRUG DESIGN; ERYTHROCYTES; HEMOLYSIS; HUMANS; MICROBIAL SENSITIVITY TESTS; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP;

CANDIDA ALBICANS; DEBARYOMYCES HANSENII;

EID: 77249136256     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.01.026     Document Type: Article

References (55)

1. Wu Y.-D., and Gellman S. Acc. Chem. Res. 41 (2008) 1231
2. In: Nielsen P.E. (Ed). Pseudo-Peptides in Drug Development (2004), Wiley-VCH, Weinheim
3. Giannis A., and Kolter T. Angew. Chem., Int. Ed. Engl. 32 (1993) 1244
4. Gante J. Angew. Chem., Int. Ed. Engl. 33 (1994) 1699
5. Hancock R.E.W., and Sahl H.-G. Nat. Biotechnol. 24 (2006) 1551
6. Zasloff M. Nature 415 (2002) 389
7. Shai Y. Biopolymers (Pept. Sci.) 66 (2002) 236
8. Matsuzaki K. Biochim. Biophys. Acta 1462 (1999) 1
9. Yang L., Weiss T.M., Lehrer R.I., and Huang H.W. Biophys. J. 79 (2000) 2002
10. Shai Y. Biochim. Biophys. Acta 1462 (1999) 55
11. Giuliani A., Pirri G., and Nicoletto S. Cent. Eur. J. Biol. 2 (2007) 1
12. Selsted M.E., and Ouellette A.J. Nat. Immunol. 6 (2005) 551
13. Yang D., Biragyn A., Hoover D.M., Lubkowski J., and Oppenheim J.J. Annu. Rev. Immunol. 22 (2004) 181
14. Porter E.A., Wang X., Lee H.-S., Weisblum B., and Gellman S.H. Nature 404 (2000) 565
15. Savage P.B. Eur. J. Org. Chem. (2002) 759
16. Ryge T.S., Frimodt-Møller N., and Hansen P.R. Chemotherapy 54 (2008) 152
17. Lai X.-Z., Feng Y., Pollard J., Chin J.N., Rybak M.Y., Bucki R., Epand R.F., Epand R.M., and Savage P.B. Acc. Chem. Res. (2008) 1233
18. Ryge T.S., and Hansen P.R. Bioorg. Med. Chem. 14 (2006) 4444
19. Chongsiriwatana N.P., Patch J.A., Czyzewski A.M., Dohm M.T., Ivankin A., Gidalevitz D., Zuckermann R.N., and Barron A.E. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 2794
20. Interesting examples are:. Motiei L., Rahimipour S., Thayer D.A., Wong C.-H., and Ghadiri M.R. Chem. Commun. (2009) 3693
21. Fletcher J.T., Finlay J.A., Callow J.A., and Ghadiri M.R. Chem. Eur. J. 13 (2007) 4008
22. Au V.S., Bremner J.B., Coates J., Keller P.A., and Pyne S.G. Tetrahedron 62 (2006) 9373
23. 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., and Ghadiri M.R. Nature 412 (2001) 452
24. Casnati A., Fabbi M., Pellizzi N., Pochini A., Sansone F., Ungaro R., Di Modugno E., and Tarzia G. Bioorg. Med. Chem. Lett. 6 (1996) 2699
25. Robinson J.A., Shankaramma C.S., Jetter P., Kienzl U., Schwendener R.A., Vrijbloed J.W., and Obrecht D. Bioorg. Med. Chem. 13 (2005) 2055
26. Craik D.J., Cemazar M., and Daly N.L. Curr. Opin. Drug Discovery Dev. 10 (2007) 176
27. Trabi M., and Craik D.J. Trend Biochem. Sci. 27 (2002) 132
28. Maulucci N., Izzo I., Bifulco G., Aliberti A., De Cola C., Comegna D., Gaeta C., Napolitano A., Pizza C., Tedesco C., Flot D., and De Riccardis F. Chem. Commun. (2008) 3927
29. Kwon Y.-U., and Kodadek T. Chem. Commun. (2008) 5704
30. Vercillo O.E., Andrade C.K.Z., and Wessjohann L.A. Org. Lett. 10 (2008) 205
31. Vaz B., and Brunsveld L. Org. Biomol. Chem. 6 (2008) 2988
32. Wessjohann L.A., Andrade C.K.Z., Vercillo O.E., and Rivera D.G. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems Vol. 10 (2007), Italian Society of Chemistry 24-53
33. Shin S.B.Y., Yoo B., Todaro L.J., and Kirshenbaum K. J. Am. Chem. Soc. 129 (2007) 3218
34. Hioki H., Kinami H., Yoshida A., Kojima A., Kodama M., Taraoka S., Ueda K., and Katsu T. Tetrahedron Lett. 45 (2004) 1091
35. Chatterjee J., Mierke D., and Kessler H. Chem. Eur. J. 14 (2008) 1508
36. Chatterjee J., Mierke D., and Kessler H. J. Am. Chem. Soc. 128 (2006) 15164
37. Nnanabu E., and Burgess K. Org. Lett. 8 (2006) 1259
38. Sutton P.W., Bradley A., Farràs J., Romea P., Urpì F., and Vilarrasa J. Tetrahedron 56 (2000) 7947
39. Sutton P.W., Bradley A., Elsegood M.R., Farràs J., Jackson R.F.W., Romea P., Urpì F., and Vilarrasa J. Tetrahedron Lett. 40 (1999) 2629
40. Unciti-Broceta A., Diezmann F., Ou-Yang C.Y., Fara M.A., and Bradley M. Bioorg. Med. Chem. 17 (2009) 959
41. Benincasa M., Scocchi M., Pacor S., Tossi A., Nobili D., Basaglia G., Busetti M., and Gennaro R. J. Antimicrob. Chemother. 58 (2006) 950
42. De Cola C., Licen S., Comegna D., Cafaro E., Bifulco G., Izzo I., Tecilla P., and De Riccardis F. Org. Biomol. Chem. 7 (2009) 2851
43. Clement N.R., and Gould J.M. Biochemistry 20 (1981) 1539
44. Kourie J.I., and Shorthouse A.A. Am. J. Physiol. Cell. Physiol. 278 (2000) C1063
45. Simon R.J., Kania R.S., Zuckermann R.N., Huebner V.D., Jewell D.A., Banville S.C., Ng S., Wang L., Rosenberg S., Marlowe C.K., Spellmeyer D.C., Tan R., Frankel A.D., Santi D.V., Cohen F.E., and Bartlett P.A. Proc. Natl. Acad. Sci. U.S.A. 89 (1992) 9367
46. Zuckermann R.N., Kerr J.N., Kent S.B.H., and Moos W.H. J. Am. Chem. Soc. 114 (1992) 10646
47. The N-fluorenylmethoxycarbonyl,N′-benzyloxyethyl glycine was synthesised in three steps, with an overall yield of 49%. See supporting information of Ref. 10a.
48. Pina-Vaz C., Sansonetty F., Rodrigues A.G., Costa-Oliveira S., Tavares C., and Martinez-de-Oliveira J. Clin. Microbiol. Infect. 7 (2001) 609
49. Craik D.J., Daly N.L., Saska I., Trabi M., and Rosengren K.J. J. Bacteriol. 185 (2003) 4011
50. Craik D.J., Cemazar M., Wang C.K., and Daly N.L. Biopolymers 84 (2006) 250
51. Tran D., Tran P., Roberts K., Osapay G., Schaal J., Ouellette A., and Selsted M.E. Antimicrob. Agents Chemother. 52 (2008) 944
52. Selsted M.E. Curr. Protein Pept. Sci. 5 (2004) 365
53. Benincasa M., Scocchi M., Podda E., Skerlavaj B., Dolzani L., and Gennaro R. Peptides 25 (2004) 2055
54. Podda E., Benincasa M., Pacor S., Micali F., Mattiuzzo M., Gennaro R., and Scocchi M. Biochim. Biophys. Acta 1760 (2006) 1732
55. Skerlavaj B., Benincasa M., Risso A., Zanetti M., and Gennaro R. FEBS Lett. 463 (1999) 58