Preparation of Benzothiazolyl-Decorated Nanoliposomes
1
Laboratory of Pharmaceutical Technology, Dept. of Pharmacy, School of Health Sciences, University of Patras, 26510 Rio, Greece
2
Institute of Chemical Engineering Sciences of the Foundation for Research and Technology Hellas (FORTH/IEC-HT), 26504 Rio Patras, Greece
3
Department of Chemistry, University of Patras, 26510 Rio Patras, Greece
4
CBL-Patras, Patras Industrial Area, Block 1, 25018 Patras, Greece
*
Author to whom correspondence should be addressed.
Academic Editor: Simona Rapposelli
Molecules 2019, 24(8), 1540; https://doi.org/10.3390/molecules24081540
Received: 16 March 2019
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Revised: 14 April 2019
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Accepted: 17 April 2019
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Published: 18 April 2019
(This article belongs to the Special Issue Neuroprotective Agents to Treat Dementias)
Amyloid β (Aβ) species are considered as potential targets for the development of diagnostics/therapeutics towards Alzheimer’s disease (AD). Nanoliposomes which are decorated with molecules having high affinity for Aβ species may be considered as potential carriers for AD theragnostics. Herein, benzothiazolyl (BTH) decorated nanoliposomes were prepared for the first time, after synthesis of a lipidic BTH derivative (lipid-BTH). The synthetic pathway included acylation of bis(2-aminophenyl) disulfide with palmitic acid or palmitoyl chloride and subsequent reduction of the oxidized dithiol derivative. The liberated thiols were able to cyclize to the corresponding benzothiazolyl derivatives only after acidification of the reaction mixture. Each step of the procedure was monitored by HPLC analysis in order to identify all the important parameters for the formation of the BTH-group. Finally, the optimal methodology was identified, and was applied for the synthesis of the lipid-BTH derivative. BTH-decorated nanoliposomes were then prepared and characterized for physicochemical properties (size distribution, surface charge, physical stability, and membrane integrity during incubation in presence of buffer and plasma proteins). Pegylated BTH-nanoliposomes were demonstrated to have high integrity in the presence of proteins (in comparison to non-peglated ones) justifying their further exploitation as potential theragnostic systems for AD.
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Keywords:
amyloid β; targeting; benzothiazoles; functionalization; nanoliposomes
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MDPI and ACS Style
Mourtas, S.; Christodoulou, P.; Klepetsanis, P.; Gatos, D.; Barlos, K.; Antimisiaris, S.G. Preparation of Benzothiazolyl-Decorated Nanoliposomes. Molecules 2019, 24, 1540. https://doi.org/10.3390/molecules24081540
AMA Style
Mourtas S, Christodoulou P, Klepetsanis P, Gatos D, Barlos K, Antimisiaris SG. Preparation of Benzothiazolyl-Decorated Nanoliposomes. Molecules. 2019; 24(8):1540. https://doi.org/10.3390/molecules24081540
Chicago/Turabian StyleMourtas, Spyridon, Panayiota Christodoulou, Pavlos Klepetsanis, Dimitrios Gatos, Kleomenis Barlos, and Sophia G. Antimisiaris. 2019. "Preparation of Benzothiazolyl-Decorated Nanoliposomes" Molecules 24, no. 8: 1540. https://doi.org/10.3390/molecules24081540
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