Nanostructured nonionic thymidine nucleolipid self-assembly materials

Xavier Mulet, Thomas Kaasgaard, Charlotte Conn, Lynne Waddington, Danielle Kennedy, Asoka Weerawardena, Calum Drummond

Research output: Contribution to journalArticleResearchpeer-review

12 Citations (Scopus)


Three nucleoside lipids have been synthesized: 30-oleoylthymidine, 30,50-dioleoylthymidine, and 30-phytanoylthymidine. Differential scanning calorimetry and X-ray diffraction have been employed to characterize the physical properties of these neat lipids. Polarizing optical microscopy, small-angle X-ray scattering, and cryo-transmission electron microscopy techniques have been used to investigate the phase behavior in aqueous systems. Both oleoyl-based nucleoside lipids adopted a lamellar crystalline phase in the neat form at room temperature, and the phytanoyl derivative exhibited a fluid isotropic phase. Under excess water conditions, the presence of one branched (phytanoyl) or one unsaturated (oleoyl) chain promoted the formation of a liquid-crystalline lamellar phase at physiological temperatures. In contrast, the 30,50-dioleoylthymidine derivative is nonswelling and does not exhibit lyotropic liquid-crystalline phase behavior. The nucleolipidsa?? propensity for DNA-type binding and recognition has been evaluated by using a monolayer system to measure surface pressure-area isotherms in a Langmuir trough and indicates that the nucleoside base is available for nonspecific hydrogen bonding in the monolayer liquid expanded state for the single-chain nucleolipids but not for the dual-chain amphiphile.
Original languageEnglish
Pages (from-to)18415 - 18423
Number of pages9
Issue number23
Publication statusPublished - 2010

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