title: Effects of alkyl chain length of gallate on self-association and membrane binding.
abstract: Alkyl gallates are anticipated for their use as anti-bacterial and anti-viral agents. Although their pharmacological activities depend on their alkyl chain length, no mechanism has yet been clarified. As described herein, we investigated the membrane binding properties of a series of alkyl gallates using fluorescence measurement to elucidate their different pharmacological activities. Membrane binding of the alkyl gallates increased concomitantly with increasing alkyl chain length, except for cetyl gallate and stearyl gallate. Dynamic light scattering revealed that alkyl gallates with a long alkyl chain are prone to self-association in the solution. Membrane binding abilities of the alkyl gallates are correlated with anti-bacterial and anti-virus activities, as described in previous reports. The partition constants of the alkyl gallates to lipid membranes depend on the membrane components and the membrane phase. Self-association and lipid binding of the alkyl gallates might be primary biophysical factors associated with their pharmacological activities.
authors.affiliation: Institute of Applied Physics, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan.
authors.forename: Eisuke
authors.initials: E
authors.lastname: Takai
authors.forename: Atsushi
authors.initials: A
authors.lastname: Hirano
authors.forename: Kentaro
authors.initials: K
authors.lastname: Shiraki
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology; D005707:Gallic Acid / Q000031:analogs & derivatives* / Q000494:pharmacology; D007700:Kinetics; D008566:Membranes / Q000737:chemistry; D015394:Molecular Structure; D010743:Phospholipids / Q000737:chemistry*; D012995:Solubility
chemical_list: D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D010743:Phospholipids; D005707:Gallic Acid