Nucleolipids: Natural Occurrence, Synthesis, Molecular Recognition, and Supramolecular Assemblies as Potential Precursors of Life and Bioorganic Materials

Abstract

Nucleolipids are hybrid molecules composed of a nucleobase, a nucleoside, a nucleotide or an oligonucleotide (either DNA or RNA), and a lipophilic moiety, which might be either simply a single- or double-chained alkyl (or alkenyl) moiety or a carbocyclic hydrocarbon such as cholesterol, a vitamin, or a bile acid. This review covers all aspects of nucleolipids, namely their natural occurrence, their synthesis, their molecular recognition, as well as aggregation behavior, either in aqueous or non-aqueous solution. Potential future aspects of nucleolipids in material sciences and for the elucidation of biochemical reactions in living cells are discussed.

Tunable Hydrophobicity in DNA Micelles: Design, Synthesis, and Characterization of a New Family of DNA Amphiphiles

“…[11] Another related class of amphiphiles is based on low-molecular-weight hydrophobic groups attached to ODNs or individual nucleotides. The latter are known as nucleolipids and have been extensively studied for their interactions with membranes, potential biomedical applications, [12] and their supramolecular organization, both into monolayers [13] and micelles. [14] The ability of these aggregates to carry information is limited by the presence of only individual nucleotides, but pyrimidine bases modified at the 5-position with a range of hydrophobic moieties have also been integrated into DNA sequences by using solid-phase synthesis.…”

Self-assembled nucleolipids: from supramolecular structure to soft nucleic acid and drug delivery devices

“…It may also be involved in the synthesis of phosphatidylinositol and cardiolipin, two components of mammalian cell membranes. Other naturally occurring nucleolipids, isolated from bacteria (tunicamycins, liposidomycins and septacidin) or marine sponges (agelasines), which elicit biological responses such as antimicrobial, antifungal, antiviral or antitumor activities, have also been reviewed by Rosemeyer (1). …”

Nucleic acid amphiphiles: synthesis and self-assembled nanostructures

“…This class of modified nucleic acids is covered in an excellent review. 12 First, the classification and techniques for the synthesis of amphiphilic oligonucleotides (AONs) will be introduced. Then their self-assembled structures and potential applications will be described.…”