title: Syntheses and characterization of liposome-incorporated adamantyl aminoguanidines.
abstract: A series of mono and bis-aminoguanidinium adamantane derivatives has been synthesized and incorporated into liposomes. They combine two biomedically significant molecules, the adamantane moiety and the guanidinium group. The adamantane moiety possesses the membrane compatible features while the cationic guanidinium subunit was recognized as a favourable structural feature for binding to complementary molecules comprising phosphate groups. The liposome formulations of adamantyl aminoguanidines were characterized and it was shown that the entrapment efficiency of the examined compounds is significant. In addition, it was demonstrated that liposomes with incorporated adamantyl aminoguanidines effectively recognized the complementary liposomes via the phosphate group. These results indicate that adamantane derivatives bearing guanidinium groups might be versatile tools for biomedical application, from studies of molecular recognition processes to usage in drug formulation and cell targeting.
authors.affiliation: Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia. majerski@irb.hr.
authors.forename: Marina
authors.initials: M
authors.lastname: Šekutor
authors.forename: Adela
authors.initials: A
authors.lastname: Štimac
authors.forename: Kata
authors.initials: K
authors.lastname: Mlinarić-Majerski
authors.forename: Ruža
authors.initials: R
authors.lastname: Frkanec
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D002645:Chickens; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D008081:Liposomes / Q000737:chemistry*; D008858:Microscopy, Phase-Contrast; D008968:Molecular Conformation; D010316:Particle Size; D055672:Static Electricity; D034421:Sus scrofa; D013816:Thermodynamics
chemical_list: D006146:Guanidines; D008081:Liposomes; D000218:Adamantane; C004479:pimagedine