We report here on three oligopeptide amphiphiles (OPA1-3) with different unsaturated double bonds, which self-assemble into shape-specific nanostructures. It was found that OPA1 with saturated hydrophobic tail self-assembled into conventional cylindrical nanofibers, while the unsaturated OPA2-3 molecules self-organized into helical nanoarchitectures. Due to the different double bond numbers in hydrophobic tails of OPA2-3, the helical pitch and width of their self-assemblies varied. Specially, linoleic acid-bearing OPA3 could be oxidized by lipoxidase to create hydroperoxide-containing OPA4, which further generated singlet oxygen ( 1 O 2 ) in the presence of catalytic iron (II) ion. The established system may provide a self-deliverable nanoplatform for 1 O 2 -mediated cancer treatment.
Results and DiscussionFirstly, three oligopeptide amphiphiles (OPA1-3) were synthesized manually by Fmoc-based solid phase synthesis. To obtain OPA4, OPA3 with linolic acid group was oxidized by lipoxidase. [20] The molecular weights of OPA1-4 were measured by matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS) ( Figure S1, Supporting [a] J.