Antimicrobial compounds

Abstract

The present invention relates to a compound of formula (I) AA-AA-AA-R 1 -R 2 (I) wherein, in any order, 2 of said AA (amino acid) moieties are cationic amino acids and 1 of said AA is an amino acid with a lipophilic R group, the R group having 14-27 non-hydrogen atoms; R 1 is a N atom, which may be substituted by a branched or unbranched C 1 -C 10 alkyl or aryl group, which group may incorporate up to 2 heteroatoms selected from N, O and S; and R 2 is an aliphatic moiety having 2-20 non-hydrogen atoms, said moiety being linear, branched or cyclic. The invention further relates to formulations containing these compounds, solid supports having these compounds attached thereto, the use of these compounds in therapy, particularly as antimicrobial, anti-tumour or anti-biofilm agents and non-therapeutic uses of these compounds, particularly their use in inhibiting biofilm formation or removing a biofilm.

1 - 22 . (canceled) 
     
     
         23 . A compound of formula (II):
   AA 1 -AA 2 -AA 3 -R 1 -R 2   (II)
   wherein AA 1  and AA 3  are independently lysine, arginine, histidine or a cationic analogue of lysine, arginine or histidine, and AA 2  is tributyl tryptophan or a biphenylalanine derivative selected from the group consisting of Phe (4-(2′-naphthyl)), Phe (4-(1′-naphthyl)), Phe(4-4′-n-butylphenyl), Phe (4-4′-biphenyl) and Phe(4-4′-t-butylphenyl);   R 1  is a N atom, which may be substituted by a branched or unbranched C 1 -C 10  alkyl or aryl group, which group may incorporate up to 2 heteroatoms selected from N, O and S; and   
       R 2  is an aliphatic moiety having 2-20 non-hydrogen atoms, said moiety being linear, branched or cyclic. 
     
     
         24 . The compound of  claim 23 , wherein said compound is a peptide. 
     
     
         25 . The compound of  claim 23 , wherein R 1  is unsubstituted. 
     
     
         26 . The compound of  claim 23 , wherein R 2  comprises 3 to 6 non-hydrogen atoms. 
     
     
         27 . The compound of  claim 23 , wherein the non-hydrogen atoms of R 2  are carbon atoms. 
     
     
         28 . The compound of  claim 23 , wherein R 2  is a linear or branched alkyl group. 
     
     
         29 . The compound of  claim 28 , wherein said alkyl group is selected from the group consisting of ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl and isomers thereof, and hexyl and isomers thereof. 
     
     
         30 . The compound of  claim 23 , wherein —R 1 -R 2  together is selected from the group consisting of —NHCH(CH 3 ) 2 , —NH(CH 2 ) 5 CH 3 , —NH(CH 2 ) 3 CH 3 , —NH(CH 2 ) 2 CH 3 , —NHCH 2 CH(CH 3 ) 2 , —NHcyclohexyl and —NHcyclopentyl. 
     
     
         31 . A solid support having attached thereto the compound as claimed in  claim 23 . 
     
     
         32 . A method of treating a tumor in a subject, said method comprising the administration to a subject of the compound of  claim 23 . 
     
     
         33 . A method of inhibiting biofilm formation or removing a biofilm ex vivo, said method comprising contacting said biofilm with the compound of  claim 23 . 
     
     
         34 . A method of treating a bio-film associated infection in a subject, said method comprising the administration to a subject of the compound of  claim 23 .