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20-(S)-Camptothecin (CPT)-conjugated dipeptides are reported that preassemble into nanotubes with diameters ranging from 80-120 nm. These nanoassemblies maintain a high (∼47 %) drug loading and exhibit greater drug stability (i.e., resistance to lactone hydrolysis), and consequently greater efficacy against several human cancer cells (HT-29, A549, H460, and(More)
The self-assembly of bolaamphiphile 1 into nanotubes containing a nanostructured electron donor/acceptor heterojunction is reported. In 10% MeOH/H(2)O, the tetraphenylporphyrin (TPP) and 1,4,5,8-naphthalenetetracarboxylic acid diimide chromophores engage in strong J-type π-π interactions within monolayer rings that further stack into the nanotube(More)
A simple, low molecular weight camptothecin-lysine conjugate is reported to self-assemble into nanotubes with diameters of 70-100nm and a drug loading level of 60.5%. The nanotubes exhibited promising in vitro cytotoxicity against cancer cell lines A549, NCI-H460 and NCI-H23. The release of active camptothecin was highly dependent on conjugate(More)
Full details of studies leading to the total synthesis of the teicoplanin aglycon are provided. Key elements of the first generation approach (26 steps from constituent amino acids, 1% overall) include the coupling of an EFG tripeptide precursor to the common vancomycin/teicoplanin ABCD ring system and sequential DE macrocyclization of the 16-membered ring(More)
The self-assembly of small molecules provides a potentially powerful method to create functional nanomaterials for many applications ranging from optoelectronics to oncology. However, the design of well-defined nanostructures via molecular assembly is a highly empirical process, which severely hampers efforts to create functional nanostructures using this(More)
We report a mild, iridium-catalyzed borylation of aromatic polysulfone with bis(pinacolato)diboron [B(2)(pin)(2)] to form the corresponding borylated polysulfones up to high concentrations with nearly constant efficiency. The Suzuki-Miyaura cross-coupling reactions of the borylated polysulfones with functionalized aryl bromides allows installation of(More)
The construction of an n-p heterojunction through the self-assembly of a dyad based on tetraphenylporphyrin (TPP) and 1,4,5,8-naphthalenedimide (NDI) (1) is described. Proton transfer from the lysine head group of 1 to the porphyrin ring occurs concomitantly with self-assembly into 1D nanorods in CHCl3. TEM and AFM studies showed that the nanorods are(More)
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