David Smithrud

David B. Smithrud

Associate Professor

Associate Professor

Crosley Tower

603

A&S Chemistry - 0172

Professional Summary

David Smithrud is currently an Associate Professor of Chemistry at the University of Cincinnati. He received his BS degree in chemistry at the University of Washington. From there, he attended the University of California, Los Angeles and received his PhD. Under the guidance of Prof. Diederich, he developed synthetic host-guest complexes; with special emphasis on the effect solvents have on complexation. He joined Prof. Benkovic's group at the Pennsylvania State University. As a post-doctoral student and NIH fellow, he further investigated and exploited molecular recognition events through the development of catalytic antibodies. These studies included constructing phage display libraries of M13 and lambda bacteriophages, synthesizing haptens, and performing molecular cloning and kinetic analysis. He joined the Chemistry Department at UC. Our research group uses mimetic chemistry to investigate the intricate interplay that exist between functional groups at protein binding domains in order to determine the underlying forces that give proteins their unique ability to recognize molecules and to develop novel synthetic devices. This research has produced novel binding agents, cell transport agents, and compounds that bind the major groove of DNA.

Education

PhD: University of California, Los Angeles 1992

Research and Practice Interests

• Molecular recognition
• Cell transport
• DNA binding agents
• Peptidomimetics
• Host-Guest chemistry
• Catalysis
• Synthesis

Abbreviated Publications

Peer Reviewed Publications

David B. Smithrud, Xiaoyang Wang, Pheruza Tarapore, and Shuk-mei Ho “Crown Ether Host-Rotaxanes as Cytotoxic Agents” J. Med. Chem. Lett., 2013, 4 (1), pp 27–31

Haque, F; Lunn, J.; Fang, H.; Smithrud, D.; Guo, P. X. “Real-Time Sensing and Discrimination of Single Chemicals Using the Channel of Phi29 DNA Packaging Nanomotor” ACS NANO, 2012, 6, 3251-3261.

Wang X.; Smithrud,D. B. “Pt-rotaxanes as cytotoxic agents” Bioorg. Med. Chem. Lett., 2011, 21, 6880-6883.

Wang Xiaoyang; Smithrud David B. “Pt-rotaxanes as cytotoxic agents” Bioorganic & Medicinal Chemistry Letters, 2011  Volume: 21   Issue: 22   Pages: 6880-6883

Wang, Xiaoyang, Zhu, Jing, & Smithrud, David B (2010). Synthesis and investigation of host-[2]rotaxanes that bind metal cations. The Journal of organic chemistry, 75(10), 3358-70.

Zhu, Jing, McFarland-Mancini, Molly, Drew, Angela F, & Smithrud, David B (2009). Host-rotaxanes with oligomeric axles are intracellular transport agents. Bioorganic & medicinal chemistry letters, 19(2), 520-3.

Zhu, Jing, House, Brian E, Fleck, Erin, Isaacsohn, Idit, Drew, Angela F, & Smithrud, David B (2007). A host-rotaxane derivatized with carboxylic acids efficiently delivers a highly cationic fluoresceinated peptide. Bioorganic & medicinal chemistry letters, 17(18), 5058-62.

Wang, Xiaoyang, Bao, Xiaofeng, McFarland-Mancini, Molly, Isaacsohn, Idit, Drew, Angela F, & Smithrud, David B (2007). Investigation of the intracellular delivery of fluoresceinated peptides by a host-[2]rotaxane. Journal of the American Chemical Society, 129(23), 7284-93.

Bao, Xiaofeng, Isaacsohn, Idit, Drew, Angela F, & Smithrud, David B (2007). Determining the binding and intracellular transporting abilities of a host-[3]rotaxane. The Journal of organic chemistry, 72(11), 3988-4000.

Zhu, J.; Smithrud, D. B. "Host-Rotaxanes Model Proteins that Promote Ligand Association through a Favorable Change in Configurational Entropy". Org. Biomol. Chem. (2007), 5, 2992-2999.

Zhu, J.; House, B.; Fleck, E.; Isaacsohn I.; Drew, A. F.; Smithrud, D. B. "A host-rotaxane derivatized with carboxylic acids efficiently delivers a highly cationic fluoresceinated peptide". Bioorg. Med. Chem. Lett. (2007), 17, 5058-5062.

Wang, X.; Bao, X.; McFarland-Mancini, M.; Isaacsohn, I.; Drew, A. F.; Smithrud, D. B. "Investigation of the Intracellular Delivery of Fluoresceinated Peptides by a Host-[2]Rotaxane". J. Am. Chem. Soc. (2007), 129, 7284-7293.

Bao, X.; Isaacsohn, I.; Drew, A. F.; Smithrud, D. B. "Determining the Binding and Intracellular Transporting Abilities of a Host-[3]Rotaxane". J. Org. Chem. (2007), 72, 3988-4000.

Zhu, Jing, & Smithrud, David B (2007). Host-rotaxanes model proteins that promote ligand association through a favorable change in configurational entropy. Organic & biomolecular chemistry, 5(18), 2992-9.

Bao, X.; Isaacsohn, I.; Drew, A. F.; Smithrud, D. B. "Determining the intracellular transport mechanism of a cleft-[2]rotaxane". J. Am. Chem. Soc. (2006), 128, 12229-12238.

Bao, Xiaofeng, Isaacsohn, Idit, Drew, Angela F, & Smithrud, David B (2006). Determining the intracellular transport mechanism of a cleft-[2]rotaxane. Journal of the American Chemical Society, 128(37), 12229-38.

Fotins, Juris, & Smithrud, David B (2005). Creation and investigation of protein-core mimetics with parallel and antiparallel aligned amino acids. The Journal of organic chemistry, 70(11), 4452-9.

Smithrud, D. B.; Fotins, J. "Creation and investigation of protein-core mimetics with parallel and antiparallel aligned amino acids". J. Org. Chem. (2005), 70, 4452-4459.

Dvornikovs, V.; House, B. E.; Kaetzel, M.; Dedman, J. R.; Smithrud, D. B. "Host-[2]Rotaxanes as Cellular Transport Agents". J. Am. Chem. Soc. (2003), 125, 8290-8301.

Smukste, I.; House, B. E.; Smithrud, D. B. "Host-[2]Rotaxane: the Advantage of Converging Functional Groups for Guest Recognition". J. Org. Chem. (2003), 68, 2559-2571.

Smukste, I.; Smithrud, D. B. "Structure-Function Relationship of Amino Acid-[2]Rotaxanes". J. Org. Chem. (2003), 68, 2547-2558.

Turk, J. A.; Smithrud, D. B. "Synthesis and Evaluation of Peptidomimetics that Bind DNA". Bioorg. Med. Chem. (2003), 11, 2355-2365.

Dvornikovs, Vadims, House, Brian E, Kaetzel, Marcia, Dedman, John R, & Smithrud, David B (2003). Host-[2]rotaxanes as cellular transport agents. Journal of the American Chemical Society, 125(27), 8290-301.

Turk, Jeffrey A, & Smithrud, David B (2003). Synthesis and evaluation of peptidomimetics that bind DNA. Bioorganic & medicinal chemistry, 11(10), 2355-65.

Smukste, Inese, House, Brian E, & Smithrud, David B (2003). Host-[2]rotaxane: advantage of converging functional groups for guest recognition. The Journal of organic chemistry, 68(7), 2559-71.

Smukste, Inese, & Smithrud, David B (2003). Structure-function relationship of amino acid-[2]rotaxanes. The Journal of organic chemistry, 68(7), 2547-58.

Dvornikovs, Vadims, & Smithrud, David B (2002). Investigation of synthetic hosts that model cation-pi sites found at protein binding domains. The Journal of organic chemistry, 67(7), 2160-7.

Thompson, Samuel E, & Smithrud, David B (2002). Carboxylates stacked over aromatic rings promote salt bridge formation in water. Journal of the American Chemical Society, 124(3), 442-9.

Turk, J A, & Smithrud, D B (2001). Synthesis and physical properties of protein core mimetics. The Journal of organic chemistry, 66(25), 8328-35.

Zehnder, D W, & Smithrud, D B (2001). Facile synthesis of rotaxanes through condensation reactions of DCC-[2]rotaxanes. Organic letters, 3(16), 2485-7.

Smithrud, D B, Benkovic, P A, Benkovic, S J, Roberts, V, Liu, J, Neagu, I, Iwama, S, Phillips, B W, Smith, A B, & Hirschmann, R (2000). Cyclic peptide formation catalyzed by an antibody ligase. Proceedings of the National Academy of Sciences of the United States of America, 97(5), 1953-8.

Smithrud, D B, & Benkovic, S J (1997). The state of antibody catalysis. Current opinion in biotechnology, 8(4), 459-66.

Stewart, J D, Krebs, J F, Siuzdak, G, Berdis, A J, Smithrud, D B, & Benkovic, S J (1994). Dissection of an antibody-catalyzed reaction. Proceedings of the National Academy of Sciences of the United States of America, 91(16), 7404-9.

David B. Smithrud and Allan R. Pinhas Pencil-Paper Learning should be Combined with Online Homework Software J. Chem. Educ., 2015, 92 (12), pp 1965–1970

David B. Smithrud and Lucas A. Powers “A Versatile Axle for the Construction of Dissasemblage Rotaxanes” Molecules, 2016, 21, 1043

David B. Smithrud, Lucas Powers, Jennifer Lunn, Scott Abernathy, Michael Peschka, Shuk-mei Ho, and Pheruza Tarapore Ca2+ Selective Host Rotaxane Is Highly Toxic Against Prostate Cancer Cells
ACS Medicinal Chemistry Letters 2017 8 (2), 163-167 

A.M. D'Souza, Y. Jiang, A. Cast, L. Valanejad, M. Wright, K.Lewis, M. Kumbaji, S. Shah, D. Smithrud, R. Karns, S. Shin, N.Timchenko “Gankyrin promotes tumor-suppressor protein degradation to drive hepatocyte proliferation Cell Mol Gastroenterol Hepatol, 6 (2018), pp. 239-255

D'souza, A., A. Cast, M. Kumbaji, L.V. Kiefer, K. Glaser, S. Sheeniza, D. Smithrud, A. Bondoc and N. Timchenko 2018. Inhibition of gankyrin as a therapeutic approach for pediatric liver cancer. Pediatric Blood & Cancer. 65, S357-S357

D'Souza, A. M., A. Cast, M. Kumbaji, M. Rivas, R. Gulati, M. Johnston, D. Smithrud, J. Geller and N. Timchenko 2021. Small molecule Cjoc42 improves chemo-sensitivity and increases levels of tumor suppressor proteins in hepatoblastoma cells and in mice by inhibiting oncogene gankyrin. Frontiers in Pharmacology. 12, 580722.

Book Chapter

Smithrud, D. B.; Benkovic, S. J. "Perspectives in Supramolecular Chemistry". In Macrocycles and Antibodies as Catalysts; John Wiley & Sons Ltd.

Publications

Peer Reviewed Publications

Smithrud,David B., Powers,Lucas, Lunn,Jennifer, Abernathy,Scott, Peschka,Michael, Ho,Shuk-mei, Tarapore,Pheruza (2017. ) Ca2+ Selective Host Rotaxane Is Highly Toxic Against Prostate Cancer Cells .Acs Medicinal Chemistry Letters, , 8 (2 ) ,163 -167

Presentations

Poster Presentations

Powers, L.; Smithrud, D. B. (2013. ) Synthesis of Targeted Contrast Agents Based on Rotaxane Architecture .Oesper Symposium, University of Cincinnati. . Level:University

Powers, L.; Smithrud, D. B. (2014. ) Synthesis of Targeted Contrast Agents Based on Rotaxane Architecture .Oesper Symposium, University of Cincinnati. . Level:University

Powers, L.; Smithrud, D. B. (2015. ) Synthesis of Targeted Contrast Agents Based on Rotaxane Architecture .Oesper Symposium, University of Cincinnati. . Level:University

Paper Presentations

Lucas Powers and David Smithrud (01-05-2017. ) Novel MRI Imaging Agent Based on Rotaxane Architecture .Cincinnati. UC. Level:University

Service

University Research Council (Engineering/Physical Sciences ) Committee Chair Type:University/College Service Level:University 01-2013 -12-2013

Chemistry (Safety ) Committee Chair Type:Departmental Service Level:Department 01-2013 -12-2013

(Undergraduate Curriculum Committee ) Committee Member Type:Departmental Service Level:Department 01-2013 -12-2013

Molecules Type:Editorial Service Level:International 06-2013 -12-2013

University Research Council (Engineering/Physical Sciences Committee ) Committee Chair Type:University/College Service Level:University 01-01-2015 -12-31-2015

Chemistry (Chemistry Safety ) Committee Chair Type:Departmental Service Level:Department 01-01-2015 -12-31-2015

Chemistry Department (Undergraduate Curriculum ) Committee Member Type:Departmental Service Level:Department 01-01-2015 -12-31-2015

Molecules (special edition on rotaxanes ) Special Interest Group Chair Type:Editorial Service Level:International 01-01-2014 -12-31-2014

Molecules (special edition on host-guest chemsitry ) Special Interest Group Chair Type:Editorial Service Level:International 01-01-2014 -12-31-2014

Cincinnati Cancer Center Member Type:University/College Service Level:University 01-07-2014 -To Present

(Chemistry Safety Committee ) Committee Chair Type:Departmental Service Level:Department

(Undergraduate Curriculum Committee ) Committee Member Type:Departmental Service Level:Department

(University Research Council ) Committee Chair Type:University/College Service Level:College

University Cincinnati Cancer Center Member Type:University/College Service Level:University

Faculty Senate (Committee on Committees ) Committee Chair Type:University/College Service Level:College

Faculty Senate (Committee on Committees ) Committee Chair Type:University/College Service Level:College

(Safety Committee ) Committee Chair Type:Departmental Service Level:Department

(University Research Council ) Committee Chair Type:University/College Service Level:University

(Undergraduate Curriculum Committee ) Committee Member Type:Departmental Service Level:Department

(University Cincinnati Cancer Center ) Member Type:University/College Service Level:University

(Faculty Senate Committee on Elections ) Committee Chair Type:University/College Service Level:College

(Safety Committee ) Committee Chair Type:Departmental Service Level:Department

University Research Council Committee Chair Type:University/College Service Level:University

(Undergraduate Curriculum Committee ) Committee Member Type:Departmental Service Level:Department

(University Cincinnati Cancer Center ) Member Type:University/College Service Level:University

Keywords

biological, drug design, organic

Professional Affiliation

American Chemical Society

Courses Taught

Level:Both

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2040 ORGANIC CHEMISTRY I Level:Undergraduate

Organic Chemistry Level:Undergraduate

Organic Chemistry Level:Undergraduate

Organic Chemistry Level:Undergraduate

Chem8051 Level:Both

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2040 ORGANIC CHEMISTRY I Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

CHEM 8051 Level:Graduate

CHEM2041 Level:Undergraduate

CHEM2041 Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

15-CHEM-762 ADV SYN ORG CHEM adv syn org chem Level:Both

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2040 ORGANIC CHEMISTRY I Level:Undergraduate

-CHEM-1040 GEN CHEM I Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

-CHEM-2041 ORGANIC CHEMISTRYII Level:Undergraduate

ad syn chem Level:Both

Faculty Development Activities

5/3/2015 12:00:00 AM -5/8/2015 12:00:00 AM Organic in the Great Gateways and Large Enrollment Course Design Type:Workshop