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Dr. Kelvin Billingsley

Assistant Professor Organic & Bioorganic Chemistry

Billingsley sm

Our research focuses on the discovery and application of new therapeutics, chemical probes and methods for organic synthesis.  Motivated by an interest in human health, our program is specifically directed towards areas of medical relevance, leveraging expertise in biomedical imaging and medicinal chemistry to develop new agents for the diagnosis and treatment of various diseases.

Office: MH-582C
Phone:(657) 278-4252
Lab:  DBH-179
Email: This email address is being protected from spambots. You need JavaScript enabled to view it.
Lab Website:billingsleyresearch.org


Courses Taught

  • CHEM 301A Organic Chemistry

Education

Postdoctoral Stanford University, Medicinal Chemistry/Radiology
Ph.D. M.I.T., Organic Chemistry
B.S. Univ. South Carolina, Chemistry


Research Interests

The foundation of our reserach is the development of chemical tools and methods with applications that span from medicinal chemistry to radiological sciences.  The lab takes an interdisciplinary approach, combining elements of organic synthesis, catalysis and biology, to address problems of clinical importance.  We maintain a fundamental interest in designing metal-catalyzed processes to construct structural motifs embodied in molecules of biological and therapeutic significance.  Using such chemical technologies, we are also developing molecular probes for hyperpolarized 13C MR and PET imaging to discover and study new questions in cancer and neurobiology. 


Selected Publications

Park, J. M.; Wu, M.; Datta, K.; Liu, S.-C.; Castillo, A.; Lough, H.; Spielman, D. M.; Billingsley, K.* Hyperpolarized Sodium [1-13C]-Glycerate as a Probe for Assessing Glycolysis In Vivo. J. Am. Chem. Soc. 2017, 139, 6629-6634.

Haynes-Smith, J.; Diaz, I.; Billingsley, K.* Modular Total Synthesis of Protein Kinase C Activator (–)-Indolactam V. Org. Lett. 2016, 18, 20082011.

Thomas, C.; Wu, M.; Billingsley, K.* An Amination-Oxidation Strategy for the Synthesis of Monoarylamines. J. Org. Chem. 2016, 81, 330-335.

Josan, S.; Billingsley, K.; Orduna, J.; Park, J. M.; Luong, R.; Yu, L.; Hurd, R.; Pfefferbaum, A.; Spielman, D.; Mayer, D. Assessing Inflammatory Liver Injury in an Acute CCl4 Model using Dynamic 3D Metabolic Imaging of Hyperpolarized [1-13C]-Pyruvate. NMR Biomed. 2015, 28, 1671-1677.

Loy, B. A.; Lesser, A. B.; Staveness, D.; Billingsley, K.; Cegelski, L.; Wender, P. A. Toward a Biorelevant Structure of Protein Kinase C Bound Allosteric Modulators: Design, Synthesis, and Evaluation of Labeled Bryostatin Analogs for Analysis with Solid-State REDOR NMR Spectroscopy. J. Am. Chem. Soc. 2015, 137, 3678-3685.

Billingsley, K.;* Josan, S.; Park, J. M.; Tee, S. S.; Spielman-Sun, E.; Hurd, R.; Mayer, D.; Spielman, D. Hyperpolarized [1,4-13C]Diethylsuccinate: A Potential DNP Substrate for In Vivo Metabolic Imaging. NMR Biomed. 2014, 27, 356-362.

Billingsley, K.;* Park, J. M.; Josan, S.; Hurd, R.; Mayer, D.; Spielman-Sun, E.; Nishimura, D.; Brooks, J. D.; Spielman, D. The Feasibility of Assessing Branched-Chain Amino Acid Metabolism in Cellular Models of Prostate Cancer with Hyperpolarized [1-13C]-Ketoisocaproate. Magn. Reson. Imaging 2014, 32, 791-795.

Düfert, M. A.; Billingsley, K.; Buchwald, S. L. Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation. J. Am. Chem. Soc. 2013, 135, 12877-12885.

Wender, P. A.; Billingsley, K. Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues. Synthesis 2013, 45, 1815-1824.

Josan, S.; Hurd, R.; Billingsley, K.; Senadheera. L; Park, J.; Yen, Y.-F.; Pfefferbaum, A.; Spielman, D.; Mayer, D. Effects of Isoflurane Anesthesia on Hyperpolarized 13C Metabolic Measurements in Rat Brain. Magn. Reson. Med. 2013, 70, 1117-1124.

Balaconis, M. K.; Billingsley, K.; Dubach, M.; Cash, K. J.; Clark, H. A. The Design and Development of Fluorescent Nano-Optodes for In Vivo Glucose Monitoring. J. Diabetes Sci. Technol. 2011, 5, 1650-1657.

Billingsley, K.; Balaconis, M. K.; Dubach, J. M.; Zhang, N.; Lim, E.; Francis, K. P.; Clark, H. A. Fluorescent Nano-Optodes for Glucose Detection. Anal. Chem. 2010, 82, 3707-3013.

Billingsley, K.; Buchwald, S. L. A General and Efficient Method for the Suzuki-Miyaura Coupling of 2-Pyridyl Nucleophiles. Angew. Chem. Int. Ed. 2008, 47, 4695-4698.

Billingsley, K.; Buchwald, S. L. An Improved System for the Palladium-Catalyzed Borylation of Aryl Halides with Pinacol Borane. J. Org. Chem. 2008, 73, 5589-5591.

Billingsley, K.; Barder, T. E.; Buchwald, S. L. Palladium-Catalyzed Borylation of Aryl Chlorides: Scope, Applications, and Computational Studies. Angew. Chem. Int. Ed. 2007, 46, 5359-5363.

Billingsley, K.; Buchwald, S. L. Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki-Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters. J. Am. Chem. Soc. 2007, 129, 3358-3366.

Billingsley, K.; Anderson, K. W.; Buchwald, S. L. A Highly Active Catalyst for Suzuki-Miyaura Cross-Coupling Reactions of Heteroaryl Compounds. Angew. Chem. Int. Ed. 2006, 45, 3484-3488.

Brizius, G.; Billingsley, K.; Smith, M. D.; Bunz, U. H. F. Conformational and Electronic Engineering of Twisted Diphenylacetylenes. Org. Lett. 2003, 5, 3951-3954.