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Programmed Recognition between Complementary Dinucleolipids To Control the Self‐Assembly of Lipidic Amphiphiles
Author(s) -
MoralesReina Sara,
Giri Chandan,
Leclercq Maxime,
VelaGallego Sonia,
Torre Isabel,
Castón José R.,
Surin Mathieu,
Escosura Andrés
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904217
Subject(s) - nucleobase , amphiphile , thymine , nucleic acid , chemistry , self assembly , molecular recognition , sequence (biology) , covalent bond , nucleotide , molecule , function (biology) , combinatorial chemistry , nanotechnology , dna , materials science , copolymer , biochemistry , organic chemistry , polymer , biology , evolutionary biology , gene
One of the major goals in systems chemistry is to create molecular assemblies with emergent properties that are characteristic of life. An interesting approach toward this goal is based on merging different biological building blocks into synthetic systems with properties arising from the combination of their molecular components. The covalent linkage of nucleic acids (or their constituents: nucleotides, nucleosides and nucleobases) with lipids in the same hybrid molecule leads, for example, to the so‐called nucleolipids. Herein, we describe nucleolipids with a very short sequence of two nucleobases per lipid, which, in combination with hydrophobic effects promoted by the lipophilic chain, allow control of the self‐assembly of lipidic amphiphiles to be achieved. The present work describes a spectroscopic and microscopy study of the structural features and dynamic self‐assembly of dinucleolipids that contain adenine or thymine moieties, either pure or in mixtures. This approach leads to different self‐assembled nanostructures, which include spherical, rectangular and fibrillar assemblies, as a function of the sequence of nucleobases and chiral effects of the nucleolipids involved. We also show evidence that the resulting architectures can encapsulate hydrophobic molecules, revealing their potential as drug delivery vehicles or as compartments to host interesting chemistries in their interior.