The discovery and implementation of molecularly targeted imaging modalities has progressed considerably in recent years. Our interest centers on the design and synthesis of near-IR fluorophores, which are employed extensively in microscopy and in vivo optical imaging. One such agent, indocyanine green, is FDA approved and currently involved in over 100 active clinical trials, including over 20 for cancer diagnosis. Despite a central role in modern biology and medicine, the compounds employed in near-IR fluorescence techniques have changed little in recent decades. Using molecular design concepts borrowed from related fields (e.g. medicinal chemistry and natural product synthesis), we seek to develop new agents with improved utility for cancer-related imaging. Specifically, we are developing near-IR fluorophores, especially in the cyanine class, with improved fluorescence properties and chemical stability. At this stage, the focus of the lab centers on the development of concise, modular synthetic approaches to target molecules. We have identified a new target-fluorophore linking strategy that imparts dramatically improved stability. The compounds we prepare will be applied in a variety of contexts to enable improved readout of biological processes, particularly in the area of cancer diagnosis. We have developed key collaborations (Mitchell and Krishna) to enable our small molecule synthesis-oriented group to evaluate our agents in in vivo settings.

National Institute of Health (NIH)
National Cancer Institute (NCI)
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National Cancer Institute Division of Basic Sciences
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Michie, Megan S; Götz, Ralph; Franke, Christian et al. (2017) Cyanine Conformational Restraint in the Far-Red Range. J Am Chem Soc 139:12406-12409
Chan, Susanna T S; Nani, Roger R; Schauer, Evan A et al. (2016) Characterization and Synthesis of Eudistidine C, a Bioactive Marine Alkaloid with an Intriguing Molecular Scaffold. J Org Chem 81:10631-10640
Patel, Nayan J; Chen, Yihui; Joshi, Penny et al. (2016) Effect of Metalation on Porphyrin-Based Bifunctional Agents in Tumor Imaging and Photodynamic Therapy. Bioconjug Chem 27:667-80
Sato, Kazuhide; Gorka, Alexander P; Nagaya, Tadanobu et al. (2016) Effect of charge localization on the in vivo optical imaging properties of near-infrared cyanine dye/monoclonal antibody conjugates. Mol Biosyst 12:3046-56
Gorka, Alexander P; Schnermann, Martin J (2016) Harnessing cyanine photooxidation: from slowing photobleaching to near-IR uncaging. Curr Opin Chem Biol 33:117-25
Sato, Kazuhide; Gorka, Alexander P; Nagaya, Tadanobu et al. (2016) Role of Fluorophore Charge on the In Vivo Optical Imaging Properties of Near-Infrared Cyanine Dye/Monoclonal Antibody Conjugates. Bioconjug Chem 27:404-13
Nani, Roger R; Shaum, James B; Gorka, Alexander P et al. (2015) Electrophile-integrating Smiles rearrangement provides previously inaccessible C4'-O-alkyl heptamethine cyanine fluorophores. Org Lett 17:302-5
Gorka, Alexander P; Nani, Roger R; Schnermann, Martin J (2015) Cyanine polyene reactivity: scope and biomedical applications. Org Biomol Chem 13:7584-98
Sato, Kazuhide; Nagaya, Tadanobu; Nakamura, Yuko et al. (2015) Impact of C4'-O-Alkyl Linker on in Vivo Pharmacokinetics of Near-Infrared Cyanine/Monoclonal Antibody Conjugates. Mol Pharm 12:3303-11
Schnermann, Martin J; Shenvi, Ryan A (2015) Syntheses and biological studies of marine terpenoids derived from inorganic cyanide. Nat Prod Rep 32:543-77

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