Chemistry Commons^™

Heteroacene-Based Amphiphile As A Molecular Scaffold For Bioimaging Probes, Tharindu A. Ranathunge, Mahesh Loku Yaddehige, Jordan H. Varma, Cameron Smith, Jay Nguyen, Iyanuoluwani Owolabi, Wojciech Kolodziejczyk, Nathan I. Hammer, Glake Hill, Alex Flynt, Davita L. Watkins

Faculty Publications

The challenges faced with current fluorescence imaging agents have motivated us to study two nanostructures based on a hydrophobic dye, 6H-pyrrolo[3,2-b:4,5-b’]bis [1,4]benzothiazine (TRPZ). TRPZ is a heteroacene with a rigid, pi-conjugated structure, multiple reactive sites, and unique spectroscopic properties. Here we coupled TRPZ to a tert-butyl carbamate (BOC) protected 2,2-bis(hydroxymethyl)propanoic acid (bisMPA) dendron via azide-alkyne Huisgen cycloaddition. Deprotection of the protected amine groups on the dendron afforded a cationic terminated amphiphile, TRPZ-bisMPA. TRPZ-bisMPA was nanoprecipitated into water to obtain nanoparticles (NPs) with a hydrodynamic radius that was <150 nm. For comparison, TRPZ-PG was encapsulated in pluronic-F127 (Mw …