Investigating the delivery mechanism of fluoresceinated peptides via a host-[2]rotaxane

ORGN 448

Xiaoyang Wang, wanxy@email.uc.edu and David B. Smithrud, David.Smithrud@uc.edu. Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221
Host-rotaxanes (HR's) are promising protein binding domains mimics. We recently discovered that the amount of material delivered by a HR is concentration dependent and largely temperature and ATP independent, which suggests that a passive mechanism is involved. Extraction and U-tube studies were used to model the transport process. The result showed that fluorescein-Ala-Gln-Glu-Ala-Val can be released from an HR into an aqueous phase, an HR can transport a greater than a stoichiometric amount of Fl-AQEAV through a CHCl3 phase, and that an acidic proton is necessary for transport into a CHCl3 phase. The next generation of transporters will increase the binding energy of host-guest complexes through a more hydrophobic binding domain. Charged groups on the axle are shielded via a "Z" or an "I" shaped pocket. More stable host-guest complexes will enable the transporters to operate at a lower concentration of components, and thus, be more efficient intracellular delivery devices.
 

New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Sci-Mix

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007