Antibacterial activity of two alkylamines integrated an indane scaffold: mimicry of a complementary unit on magainin 2.
Based on the antibacterial activity of 9-phenylnonylamine (pC9a) against Escherichia coli (ATCC29522) and Staphylococcus aureus (ATCC25923), we have further tested the inhibitory ability of the growth of the bacteria by (+/-)1-(4-aminobutyl)-6-benzylindane (PM2) and (+/-)1-benzyl-6-(4-aminobutyl) indane (PM3), that is, two kinds of 1,6-disubstituted indanes. In an in vitro assay, they showed almost the same antibacterial activities against the bacteria as pC9a, as well as that of magainin 2 analogs (i.e., the peptides MSI-78 and 87-ISM), except in the case of 87-ISM against S. aureus. At the MIC (minimum inhibitory concentration) values, however, their killing rate of E. coli is actually quicker than pC9a. This indicates that an indane scaffold, used as a template to mimic a part of the alpha-helical structure of magainin 2, can accelerate the killing rate. At present, however, it is unknown whether either the hydrophobicity or the alpha-helical structure, or both, of the indane scaffold is involved in accelerating the rate. Moreover, these two indanes also showed stronger antibacterial activity against two strains of Helicobacter pylori (ATCC43526, ATCC43579) than either pC9a or magainin 2 related peptides.
Numao
N
N
Sagami Chemical Research Center, Kanagawa, Japan.
Iwahori
A
A
Hirota
Y
Y
Sasatsu
M
M
Kondo
I
I
Onimura
K
K
Sampe
R
R
Yamane
S
S
Itoh
S
S
Katoh
T
T
Kobayashi
S
S
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D023181:Antimicrobial Cationic Peptides; D004912:Erythrocytes / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D016480:Helicobacter pylori / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D007189:Indans / Q000737:chemistry / Q000494:pharmacology*; D054806:Magainins; D008826:Microbial Sensitivity Tests; D018716:Molecular Mimicry; D010455:Peptides / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D029867:Xenopus Proteins
C108248:1-(4-aminobutyl)-6-benzylindane; C108247:1-benzyl-6-(4-aminobutyl)indane; D000900:Anti-Bacterial Agents; D023181:Antimicrobial Cationic Peptides; D007189:Indans; D054806:Magainins; D010455:Peptides; D029867:Xenopus Proteins; C053301:magainin 2 peptide, Xenopus