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Development of Novel Far-Red to Near-Infrared Fluorophores for Chemical Biology Applications
Fluorophores are substances capable of absorbing one wavelength of light and reemitting a photon at a longer wavelength. These molecules are extensively used as optical “paints” in tracing otherwise invisible structures and biological process. Fluorophores that excite and emit light within the near-infrared (NIR) window (650 nm–900 nm) are of particular interest as NIR light mitigates issues associate with light scattering and background fluorescence from native occurring, enabling deeper tissue penetration for in vivo imaging applications. Existing NIR fluorophores typically have large molecular weights, poor chemical or photostability and low brightness (ϵ × &phis;). This thesis describes a series of NIR fluorophores that overcome these issues and could potentially be used to investigate biological systems. Initial efforts focusing on sensor development, protein labeling, selective cytotoxicity, and drug delivery are described. ^ This thesis starts with a brief history of fluorescence, focusing on the design of small molecule NIR fluorophores (Chapter 1). Next, we describe our efforts to design a novel NIR fluorophore scaffold termed Nebraska Red (Chapter 2). This new scaffold is applied to generate selective cytotoxicity (Chapter 3), protein labeling (Chapter 4) and general payload release reagents (Chapter 5). Building off of this work, a new strategy to design ratiometric sensors, termed chemoselective alteration of fluorophore scaffolds (CAFS) is described (Chapter 6). A conclusion chapter (Chapter 7) is given to summarize the work that has been done in this thesis and discuss the future directions. ^
Zhou, Xinqi, "Development of Novel Far-Red to Near-Infrared Fluorophores for Chemical Biology Applications" (2018). ETD collection for University of Nebraska - Lincoln. AAI10846658.