Faculty and Student Publications
Document Type
Article
Publication Date
8-18-2021
Abstract
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 comparison, TRPZ-PG was encapsulated in pluronic-F127 (Mw = 12 kD), a polymer surfactant to afford NPs almost twice as large as those formed by TRPZ-bisMPA. Size and stability studies confirm the suitability of the TRPZ-bisMPA NPs for biomedical applications. The photophysical properties of the TRPZ-bisMPA NPs show a quantum yield of 49%, a Stokes shift of 201 nm (0.72 eV) and a lifetime of 6.3 ns in water. Further evidence was provided by cell viability and cellular uptake studies confirming the low cytotoxicity of TRPZ-bisMPA NPs and their potential in bioimaging.
Relational Format
journal article
Recommended Citation
Ranathunge, T. A., Yaddehige, M. L., Varma, J. H., Smith, C., Nguyen, J., Owolabi, I., Kolodziejczyk, W., Hammer, N. I., Hill, G., Flynt, A., & Watkins, D. L. (2021). Heteroacene-based amphiphile as a molecular scaffold for bioimaging probes. Frontiers in Chemistry, 9, 729125. https://doi.org/10.3389/fchem.2021.729125
DOI
10.3389/fchem.2021.729125
Accessibility Status
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