Craig Seymour

Craig Seymour

Specialization in Biochemistry.
Research with Prof. Tim Macdonald.

Craig is from Centreville, Virginia and graduated from Westfield High School in nearby Chantilly. Since his second semester here at the University of Virginia, he has been conducting research in the Macdonald lab.  The Macdonald lab, in association with Dr. Hoffman of the UVA Medical School, works to improve the antibiotic, Nitazoxanide.

Although Nitazoxanide is prescribed for fighting Cryptosporidium parvum and Giardia lamblia, it is far from an ideal drug.  Nitazoxanide requires a massive dose in order to be effective as it is not efficiently absorbed by the body.  Additionally, they hope to make Nitazoxanide an effective treatment for bacterial infections.  Their group has published two papers on our efforts to improve the drug’s solubility and activity against bacteria by optimizing both the head and tail region of the drug (figure 1).       

Figure 1- Nitazoxanide divided into its two main groups: the head region, a 5-nitro-1,3-thiazole and the tail region, a phenyl ring with an orthoacetate ester.

Thus far, the data from Dr. Hoffman’s lab has shown that most modifications to the head region are not tolerated and that the 5-nitrothiazole is critical for activity.  During Craig’s fourth year, he has focused my research on the appendage of various quinolone antibiotics to form “hybrid” antibiotics.  These derivatives retain the active 5-nitrothiazole head group and replace the tail region with quinolone moieties. The high number of functional groups involved has made synthesis and purification difficult but there have been a number of compounds created and evaluated thus far with results that lend credence to the project.

Craig is very proud to work on this project, since it allows him to use his passion for organic chemistry to create antibiotics that are desperately needed.

After he graduates from UVA, Craig plans to follow his passion by going to graduate school for synthetic organic chemistry.  So far, he have been accepted by the University of Illinois: Urbana-Champaign, the University of Texas: Austin, North Carolina State University and the University of Pittsburgh.

Craig would like to thank the following people for their assistance with his degree the past four years:  Dr. Eric Ballard, Taylor Koerner, Dr. James East, Dr. Andrew Kennedy, Prof. Tim Macdonald, Prof. Dean Harman, Prof. Glenn McGarvey, the chemistry department staff, Jennifer Tomlinson, and, of course, my parents.

 

Publications

Ballard, T.E.; Wang, X.; Olekhnovich, I; Koerner, T; Seymour, C.; Salamoun, J.; Warthan, M.; Hoffman, P.S.; Macdonald, T.L. “Synthesis and Antimicrobial Evaluation of Nitazoxanide-Based Analogues: Identification of Selective and Broad Spectrum Activity”, ChemMedChem, 2011, 6, 362 – 377. DOI: 10.1002/cmdc.201000475.

Ballard, T.E.; Wang, X.; Olekhnovich, I.; Koerner, T.; Seymour, C.; Hoffman, P.S.; Macdonald, T. L. “Biological Activity of Modified and Exchanged 2-Amino-5-Nitrothiazole Amide Analogues of Nitazoxanide”, Bioorg. Med. Chem. Lett., 2010, 20, 3537 – 3539. DOI: 10.1016/j.bmcl.2010.04.126.