Office: MH-582C
Phone:(657) 278-4252
Email:
kbillingsley@fullerton.edu
Lab: DBH-179
Phone: (657) 278-5295
Kelvin Billingsley
Associate Professor Organic & Bioorganic Chemistry
Research Interests
The foundation of our research 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 magnetic resonance imaging to discover and study new questions in cancer.
Education
Postdoctoral Stanford University, Medicinal Chemistry/Radiology
Ph.D. M.I.T., Organic Chemistry
B.S. Univ. South Carolina, Chemistry
Selected Publications
Hackett, E.; Shah, B.; Cheng, B.; LaGue, E.; Vemireddy, V.; Mendoza, M.; Bing, C.; Bachoo, R.; Billingsley, K.; Chopra, R.; Park, J. M. Probing Cerebral Metabolism with Hyperpolarized 13C Imaging after Opening the Blood-Brain Barrier with Focused Ultrasound. ACS Chem. Neuro. 2021, 12, 2820–2828.
Leister, J.; Chao, D.; Billingsley, K.* Palladium-Catalyzed Prenylation of (Hetero)Aryl Boronic Acids. Tetrahedon Lett. 2021, 66, 152800.
Tran, U.; Zhang, G. C.; Eom, R.; Billingsley, K.;* Ondrus, A. E.* Small Molecule Intervention in a Protein Kinase C–Gli Transcription Factor Axis. ACS Chem. Biol. 2020, 15, 1321–1327.
Mendoza, M.; Eom, R.; Salas, C.; Haynes-Smith, J.; Billingsley, K.* The Synthesis and Biological Evaluation of Novel Indolactam Alkaloids. Synthesis, 2019, 51, 4443–4451.
Mendoza, M.; Rao, N.; Tran, U.; Castaneda, C.; Billingsley, K.* The Total Synthesis of (–)-Indolactam I. Tetrahedron 2019, 75, 4337–4342.
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.
Courses Regularly Taught
CHEM 301A Organic Chemistry
Courses Taught
CHEM 301A/B Organic Chemistry
CHEM 306A Organic Chemistry Lab
CHEM 431 Advanced Organic Chemistry
CHEM 531 Organic Reactions Mechanisms
CHEM 535 Organic Synthesis
CHEM 537 Organic Spectroscopy
Fall 2022 Office Hours
Tue 10am-11am or by appointment.
