Cynthia M. Dupureur, Interim Department Chair
Undergraduate Program Overview
Degree Programs In Biochem and Biotech
Chemistry Tutoring Service
Undergraduate Scholarships and Awards
Research for Undergraduates
Chemistry & Biochemistry: Summer 2016
Graduate Program Overview
Application to Graduate Program
Graduate Student Seminars
Robert W. Murray Lecture
Visiting Speaker Seminars
Distinguished Alumni Lecture
Professor Gokel attended Tulane University, New Orleans, LA, B.S. chemistry, 1968, University of Southern California, Los Angeles, CA, Ph.D. chemistry with I. K. Ugi, 1971 and UCLA, where he did a postdoctoral fellowship with D.J. Cram, 1972-1974. He served at Penn State, Maryland and Miami prior to heading the Program in Chemical Biology, Washington University School of Medicine, St. Louis. He joined UM-St. Louis as Distinguished Professor in 2006 and also serves as Director of the Center for Nanoscience.
Synthetic cation and anion channels
During the past decade, our lab has developed and elaborated a class of synthetic ion channels called hydraphiles. We use diaza-18-crown-6 macrocycles as head groups and entry portals for ion conduction. Hydrophobic spacer chains connect the headgroups and impart the appropriate length for the hydraphile to span the bilayer. A third, central macrocycle acts as an "ion relay". . These compounds not only function as ion channels in membranes, they enhance the efficacy of FDA-approved antibiotics such as rifampicin, a first line drug used against TB, by up to 16-fold. .
Anion, particularly chloride, permeability is essential for volume, pH, and membrane potential regulation in all cells. We have developed a chloride-selective channel (shown). We are currently studying some very simple tris-arene molecules that have proved to be effective transformation and transfection agents. These non-toxic compounds enhance the transport of DNA across the cellular boundaries of bacteria, yeast, plants, and mammalian cells. Two lab members have founded a company called Genetix Fusion LLC that is developing this technology.
Molecular Capsules and Nanotubes
It has been known for more than a century that phenols and aldehydes react to form macrocycles. We have been developing the chemistry of amphiphilic nanocapsules and nanotubes for drug delivery. The pyrogallolarene compounds have a unique and nearly unexplored chemistry. We have found that they form ion channels and exhibit very unusual amphiphilic properties. The figure below shows a section of nanotube along with the adjacent tubes interlocked with it. The individual elements that form the nanotube also foster ion transport in natural membranes.
Selected Recent Publications
Hydraphiles enhance antimicrobial potency against Escherichia coli, Pseudomonas aeruginosa, and Bacillus subtilis,″ M. B. Patel, E. C. Garrad, A Stavri, M. R. Gokel, S. Negin, J. W. Meisel, Z. Cusumano and G. W. Gokel, Bioorg. & Med. Chem. 2016, 24, 2864
Biological Activity of Macrocyclic Cation Transporters,″ R. Cantwell, E. C. Garrad, M. R. Gokel, M. J. Hayes, J. W. Meisel, S. Negin, M. B. Patel and G. W. Gokel, Curr. Org. Chem. 2015, 19, 2229.
"The aqueous medium-dimethylsulfoxide conundrum in biological studies″, S. Negin, M. R. Gokel, M. B. Patel, S. L. Sedinkin, D. C. Osborn and G. W. Gokel, RSC Advances 2015, 5, 8088.
"Improved synthesis of benzyl hydraphile synthetic cation", N. S. Curvey, S. E. Luderer, J. K. Walker and G. W. Gokel, Synthesis, 2014, 46, 2771
"Hydraphile synthetic ion channels alter root architecture in Arabidopsis thaliana,” M. B. Patel, A. Stavri, N. S. Curvey and G. W. Gokel, Chem. Commun. 2014,, 50 11562
"Ion transport through bilayer membranes mediated by pyrogallolarenes ," S. Negin, R. Li, O. V. Kulikov, M. M. Daschbach and G. W. Gokel, Inorg. Chim. Acta 2014, 417, 177.
"Morphologies of branched-chain pyrogallolarenes in the solid state," O. V. Kulikov, S. Negin, N. P. Rath and G. W. Gokel, Supramolecular Chem. 2014, 26, 506.
"Synthetic ion channels: From pores to biological applications," G. W. Gokel and S. Negin, Acc. Chem. Res., 2013, 46, 2024.
"Properties of Long Alkyl-chained Resorcinarenes in Bilayers and on the Langmuir Trough," P. Ogirala, S. Negin, C. Agena, C. Schäfer, T. Geisler, J. Mattay, and G. W. Gokel, New J. Chem. 2013, 37, 105.
"Anion Complexation and Transport by Isophthalamide and Dipicolinamide Derivatives: DNA Plasmid Transformation in E. coli," J. L. Atkins, M. B. Patel, M. M. Daschbach, J. W. Meisel, and G. W. Gokel, J. Am. Chem. Soc., 2012, 134, 13546
"Aggregation and Supramolecular Membrane Interactions that Influence Anion Transport in Tryptophan-Containing Synthetic Peptides.," M. M. Daschbach, S. Negin, L. You, M. Walsh and G. W. Gokel, Chem. A Eur. J. 2012, 18, 7608.
"Rapid acyl migration between pyrogallyl 1,2- and 1,3-dipivaloates," Y. Shan, J. Liu, N. P. Rath and G. W. Gokel, Nat. Prod. Commun. 2012, 7, 333.
"Synthetic amphiphilic peptides that self assemble to memberane active anion transporters," G. W. Gokel and M. M. Daschbach, Anion Coord. Chem. 2012, pp. 465-519, (Ed: K. Bowman-James, A. Bianchi and E. Garcia-Espana).
"Synthetic memberane active amphiphiles," G. W. Gokel and S. Negin, Adv. Drug Delivery Rev. 2012, 64, 784.
"Pyrogalloarenes show highly Variable Amphiphilic Behavior at the Air-Water Interface Dependent Upon side Chain Length and Branching", M. M Daschbach, O. V. Kulikov, E. F. Long and G. W. Gokel, Chem. A Eur. J. 2011, 17, 8913