Synthesis of 3,7-diacyl-1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonane derivatives as promising lipid bilayer modifiers

Novel 3,7-bis(dialkylaminoacetyl)-1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonanes were synthesized, which can undergo conformational reorganization under the change of solvent polarity, protonation (the change of pH) or complexation with LaCl3. These compounds are capable of being embedded into the lipo...

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Bibliographic Details
Published in:Tetrahedron 2019-08, Vol.75 (33), p.4444-4450
Main Authors: Veremeeva, Polina N., Grishina, Irina V., Zaborova, Olga V., Averin, Alexei D., Palyulin, Vladimir A.
Format: Article
Language:English
Subjects:
3,7-Diazabicyclo[3.3.1]nonanes
Conformational switches
Liposomes
Nanocontainers
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Summary:Novel 3,7-bis(dialkylaminoacetyl)-1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonanes were synthesized, which can undergo conformational reorganization under the change of solvent polarity, protonation (the change of pH) or complexation with LaCl3. These compounds are capable of being embedded into the liposomal membranes and can serve as molecular switches for the development of stimulus-sensitive liposomal containers. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.06.009