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Issue 31, 2014
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Syntheses and characterization of liposome-incorporated adamantyl aminoguanidines

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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.

Graphical abstract: Syntheses and characterization of liposome-incorporated adamantyl aminoguanidines

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Article information


Submitted
19 Mar 2014
Accepted
20 Jun 2014
First published
02 Jul 2014

Org. Biomol. Chem., 2014,12, 6005-6013
Article type
Paper
Author version available

Syntheses and characterization of liposome-incorporated adamantyl aminoguanidines

M. Šekutor, A. Štimac, K. Mlinarić-Majerski and R. Frkanec, Org. Biomol. Chem., 2014, 12, 6005
DOI: 10.1039/C4OB00592A

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