McMicken College of Arts & SciencesMcMicken College of Arts & SciencesUniversity of Cincinnati

McMicken College of Arts & Sciences

Department of Chemistry

Department of Chemistry

Faculty and Staff Directory

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David B. Smithrud

Title: Associate Professor
Office: 603 Crosley Tower
Tel: 513-556-9254
Email: david.smithrud@uc.edu
Web: http://www.che.uc.edu/fac_staff/smithrud.html

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&39;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 Information

Research Interests

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

Research Support

  • (PI), Smithrud, David, Cellular Transport Agents: Applications and Mechanism, National Science Foundation. (CHE-0400539-01), $228,000.00. 08/15/2004 to 07/31/2008. Status: Closed.
  • (PI), Smithrud, David, Developing a Novel Anticancer Thereapy: Cellular Deliverey and Trageting, Wendy Will Case Cancer Fund, Inc.. (OSP 04182), $25,000.00. 07/01/2004 to 06/30/2005. Status: Closed.
  • (PI), Smithrud, David, Analyte Selective Hosts for Sample Identification and Sensor Development, American Chemical Society - National Chapter. (NCE), $80,000.00. 06/01/2002 to 08/31/2005. Status: Closed.
  • (Collaborator), Ahn, Chong; Guo, Peixuan; Smithrud, David, Phi29 Motor Nanopore for Single Molecule Sensing and dsDNA Fingerprinting, National Institute of Biomedical Imaging and Bioengineering. (R01 EB012135), $228,226.00. 04/01/2011 to 01/15/2012. Status: Closed.
  • (PI), Ho, Shuk Mei; Lee, Jing-Huei; Smithrud, David, Smart, Enzyme-Activated MRI Contrast Agents for Cancer Detection, National Institute of Biomedical Imaging and Bioengineering. (R21EB012122), $379,077.00. 04/01/2012 to 03/31/2014. Status: Active.
  • (PI), Ho, Shuk Mei; Lee, Jing-Huei; Smithrud, David, Smart, Enzyme-Activated MRI Contrast Agents for Cancer Detection, National Institute of Biomedical Imaging and Bioengineering. (R21EB012122), $379,077.00. 04/01/2012 to 03/31/2015. Status: Active.
  • (co-PI), Pheruza Tarapore, Shuk-Mei Ho, David Smithrud, Detecting ovarian cancers with tissue-specific MRI contrast agents, UC Provost’s Pilot Research Program. 40,000. 01-2013 to 12-2013. Status: Completed.
  • (co-PI), Pheruza Tarapore and David Smithrud, Novel methods to combat androgen resistant prostate cancer, UC. 01/09/2016 to 06/30/2017. Status: Active.

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

Book Chapter

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

Presentations & Lectures

Invited Presentations

  • Smithrud D. B. (10/04/2013). Cellular Transport Agents: what are they and what to do with them Cleveland State University.

Poster Presentations

  • Powers, L.; Smithrud, D. B. (2013). Synthesis of Targeted Contrast Agents Based on Rotaxane Architecture Oesper Symposium, University of Cincinnati.
  • Powers, L.; Smithrud, D. B. (2014). Synthesis of Targeted Contrast Agents Based on Rotaxane Architecture Oesper Symposium, University of Cincinnati.
  • Powers, L.; Smithrud, D. B. (2015). Synthesis of Targeted Contrast Agents Based on Rotaxane Architecture Oesper Symposium, University of Cincinnati.

Experience & Service

Service

  • Committee Chair, University Research Council Engineering/Physical Sciences, 01-2013 to 12-2013
  • Committee Chair, Chemistry Safety, 01-2013 to 12-2013
  • Committee Member, Undergraduate Curriculum Committee, 01-2013 to 12-2013
  • Molecules 06-2013 to 12-2013
  • Committee Chair, University Research Council Engineering/Physical Sciences Committee, 01/01/2015 to 12/31/2015
  • Committee Chair, Chemistry Chemistry Safety, 01/01/2015 to 12/31/2015
  • Committee Member, Chemistry Department Undergraduate Curriculum, 01/01/2015 to 12/31/2015
  • Special Interest Group Chair, Molecules special edition on rotaxanes, 01/01/2014 to 12/31/2014
  • Special Interest Group Chair, Molecules special edition on host-guest chemsitry, 01/01/2014 to 12/31/2014
  • Member, Cincinnati Cancer Center 01/07/2014 to Present
  • Committee Chair, Chemistry Safety Committee,
  • Committee Member, Undergraduate Curriculum Committee,
  • Committee Chair, University Research Council,
  • Member, University Cincinnati Cancer Center
  • Committee Chair, Faculty Senate Committee on Committees,

Other Experience and Professional Memberships

  • American Chemical Society,

Courses Taught

  • null
    Level: Both
    Term: 13SS

  • -CHEM-2041 ORGANIC CHEMISTRYII
    Level: Undergraduate
    Term: 13US

  • -CHEM-2040 ORGANIC CHEMISTRY I
    Level: Undergraduate
    Term: 13FS

  • Organic Chemistry
    Organic Chemistry
    Level: Undergraduate
    Term: 14SS

  • Organic Chemistry
    Organic Chemistry
    Level: Undergraduate
    Term: 14US

  • Organic Chemistry
    Organic Chemistry
    Level: Undergraduate
    Term: 14FS

  • Chem8051
    Level: Both
    Term: 15SS

  • -CHEM-2041 ORGANIC CHEMISTRYII
    Level: Undergraduate
    Term: 15US

  • -CHEM-2040 ORGANIC CHEMISTRY I
    Level: Undergraduate
    Term: 15FS

  • -CHEM-2041 ORGANIC CHEMISTRYII
    Level: Undergraduate

  • -CHEM-2041 ORGANIC CHEMISTRYII
    Level: Undergraduate
    Term: 16US

  • CHEM 8051
    Level: Graduate
    Term: 16FS