Structural and biological evaluation of some loloatin C analogues

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 17, 2009, Pages 6233-6240

  Tuin, Adriaan W ^a   Grotenbreg, Gijsbert M ^a   Spalburg, Emile ^b   de Neeling, Albert J ^b   Mars Groenendijk, Roos H ^c   van der Marel, Gijsbert A ^a   Noort, Daan ^c   Overkleeft, Herman S ^a   Overhand, Mark ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b NATIONAL INSTITUTE FOR PUBLIC HEALTH AND THE ENVIRONMENT   (Netherlands)

^c TNO   (Netherlands)

Author keywords

Cationic antimicrobial peptide; Loloatin C; Structure activity relationship; Sugar amino acid

Indexed keywords

LOLOATIN C; POLYPEPTIDE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HEMOLYSIS; HUMAN; HUMAN TISSUE; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; ERYTHROCYTES; HEMOLYSIS; HUMANS; MICROBIAL SENSITIVITY TESTS; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP;

NEGIBACTERIA; POSIBACTERIA;

EID: 68649090209     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.07.049     Document Type: Article

References (20)

1. Gerard J.M., Haden P., Kelly M.T., and Anderson R.J. J. Nat. Prod. 62 (1999) 80
2. Scherkenbeck J., Chen H., and Haynes R.K. Eur. J. Org. Chem. (2002) 2350
3. Selected examples include:. Stern A., Gibbons W.A., and Graig L.C. Proc. Natl. Acad. Sci. U.S.A. 61 (1968) 734
4. Gibbons W.A., Némethy G., Stern A., and Graig L.C. Proc. Natl. Acad. Sci. U.S.A. 67 (1970) 239
5. Jones C.R., Kuo M., and Gibbons W.A. J. Biol. Chem. 254 (1979) 10307
6. Krauss E.M., and Chan S.I. J. Am. Chem. Soc. 104 (1982) 6953
7. Mihailescu D., and Smith J.C. J. Phys. Chem. B 103 (1999) 1586
8. Chen H., Haynes R.K., Scherkenbeck J., Sze K.H., and Zhu G. Eur. J. Org. Chem. (2004) 31
9. Chen H., and Guo X.-K. Chin. J. Struct. Chem. 24 (2005) 273
10. dPhe-Asn sequence in a α-helical turn. See:. Rose G.D., Gierasch L.M., and Smith J.A. Adv. Prot. Chem. 37 (1985) 1-109
11. Reviewed in:. Povey J.F., Mark Smales C., Hassard S.J., and Howard M.J. J. Struct. Biol. 157 (2007) 329-338
12. Stöckle M., Voll G., Günther R., Lohof E., Locardi E., Gruner S., and Kessler H. Org. Lett. 4 (2002) 2501-2504
13. van Well R.M., Marinelli L., Altona C., Erkelens K., Siegal G., van Raaij M., Llamas-Saiz A.L., Kessler H., Novellino E., Lavecchia A., van Boom J.H., and Overhand M. J. Am. Chem. Soc. 125 (2003) 10822-10829
14. Grotenbreg G.M., Buizert A.E.M., Llamas-Saiz A.L., Spalburg E., van Hooft P.A., de Neeling A.J., Noort D., van Raaij M.J., van der Marel G.A., Overkleeft H.S., and Overhand M. J. Am. Chem. Soc. 128 (2006) 7559-7565
15. Wüthrich K. NMR of Proteins and Nucleic Acids (1986), John Wiley & Sons, New York
16. Wishart D.S., Sykes B.D., and Richards F.M. Biochemistry 31 (1992) 1647-1651
17. Ding Y., Qin C., Guo Z., Niu W., Zhang R., and Li Y. Chem. Biodivers. 4 (2007) 2827-2834
18. Compounds 8, 10, 11 and 12 did not fully dissolve for the hemolytical assay in up to 30% DMSO. Since their antimicrobial activities were also low, the solubility issue was not further pursued.
19. Olsen J.V., de Godoy L.M.F., Li G.Q., Macek B., Mortensen P., Pesch R., Makarov A., Lange O., Horning S., and Mann M. Mol. Cell. Proteomics 4 (2005) 2010-2021
20. Kaiser E., Colescott R.L., Bossering C.D., and Cook P.I. Anal. Biochem. 34 (1970) 595