Preparation of Benzothiazolyl-Decorated Nanoliposomes
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 carrie...
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doaj-7d108859d5f64cf69708e7ffaeead5302020-11-24T21:46:51ZengMDPI AGMolecules1420-30492019-04-01248154010.3390/molecules24081540molecules24081540Preparation of Benzothiazolyl-Decorated NanoliposomesSpyridon Mourtas0Panayiota Christodoulou1Pavlos Klepetsanis2Dimitrios Gatos3Kleomenis Barlos4Sophia G. Antimisiaris5Laboratory of Pharmaceutical Technology, Dept. of Pharmacy, School of Health Sciences, University of Patras, 26510 Rio, GreeceLaboratory of Pharmaceutical Technology, Dept. of Pharmacy, School of Health Sciences, University of Patras, 26510 Rio, GreeceLaboratory of Pharmaceutical Technology, Dept. of Pharmacy, School of Health Sciences, University of Patras, 26510 Rio, GreeceDepartment of Chemistry, University of Patras, 26510 Rio Patras, GreeceDepartment of Chemistry, University of Patras, 26510 Rio Patras, GreeceLaboratory of Pharmaceutical Technology, Dept. of Pharmacy, School of Health Sciences, University of Patras, 26510 Rio, GreeceAmyloid 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.https://www.mdpi.com/1420-3049/24/8/1540amyloid βtargetingbenzothiazolesfunctionalizationnanoliposomes |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Spyridon Mourtas Panayiota Christodoulou Pavlos Klepetsanis Dimitrios Gatos Kleomenis Barlos Sophia G. Antimisiaris |
spellingShingle |
Spyridon Mourtas Panayiota Christodoulou Pavlos Klepetsanis Dimitrios Gatos Kleomenis Barlos Sophia G. Antimisiaris Preparation of Benzothiazolyl-Decorated Nanoliposomes Molecules amyloid β targeting benzothiazoles functionalization nanoliposomes |
author_facet |
Spyridon Mourtas Panayiota Christodoulou Pavlos Klepetsanis Dimitrios Gatos Kleomenis Barlos Sophia G. Antimisiaris |
author_sort |
Spyridon Mourtas |
title |
Preparation of Benzothiazolyl-Decorated Nanoliposomes |
title_short |
Preparation of Benzothiazolyl-Decorated Nanoliposomes |
title_full |
Preparation of Benzothiazolyl-Decorated Nanoliposomes |
title_fullStr |
Preparation of Benzothiazolyl-Decorated Nanoliposomes |
title_full_unstemmed |
Preparation of Benzothiazolyl-Decorated Nanoliposomes |
title_sort |
preparation of benzothiazolyl-decorated nanoliposomes |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2019-04-01 |
description |
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. |
topic |
amyloid β targeting benzothiazoles functionalization nanoliposomes |
url |
https://www.mdpi.com/1420-3049/24/8/1540 |
work_keys_str_mv |
AT spyridonmourtas preparationofbenzothiazolyldecoratednanoliposomes AT panayiotachristodoulou preparationofbenzothiazolyldecoratednanoliposomes AT pavlosklepetsanis preparationofbenzothiazolyldecoratednanoliposomes AT dimitriosgatos preparationofbenzothiazolyldecoratednanoliposomes AT kleomenisbarlos preparationofbenzothiazolyldecoratednanoliposomes AT sophiagantimisiaris preparationofbenzothiazolyldecoratednanoliposomes |
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