Faculty

Janarthanan Jayawickramarajah

Assistant Professor
Ph.D., 2005, The Universtiy of Texas at Austin

Office: 5027 Percival Stern Building
Email: jananj@tulane.edu
Phone: (504) 862-3580
Website:  Professor Jayawickramarajah Group

Discipline

Bio-Organic Chemistry, Nanobiotechnology, Molecular Recognition and Self-Assembly

Exquisitely controlled self-assembly in water is a key modality used by Nature to build highly functional biological systems. Research in the Jayawickramarajah group involves a highly interdisciplinary effort to develop bio-inspired functional molecules capable of undergoing specific molecular recognition events. A main thrust of our research is to study water compatible, self-assembling, synthetically functionalized oligomers that address contemporary problems.  We are currently focused on the following two research areas.

• Development of Stimuli Responsive Protein-Binders Based on DNA-Small Molecule Chimeras. This project focuses on the development of DNA-small molecule chimeras that are programmed to bind and inhibit salient protein targets only upon non-covalent activation by specific endogenous or externally introduced trigger molecules. The development of general mechanisms for the non-covalent transformation of inactive protein inhibitors into activated compounds in the presence of specific endogenous (or externally added) stimuli is envisioned to contribute to prodrug development.

• Development of Well-Defined Porphyrin Arrays in Water: Towards Photonic Nanostructures. This project concerns the development of photonic nanowires composed of self-assembled multi-porphyrins in water. In these assemblies, the individual chromophores are non p-aggregated and are placed, via molecular recognition, at well-defined positions. The generation of self-assembled multi-porphyrin containing photonic nanostructures in water is envisioned to have potential applications as synthetic light harvesting antennae, catalyst arrays, and chemo-responsive sensing materials.

As a result of our prepare-and-analyze philosophy, students in the laboratory will be versed in synthetic organic chemistry and chemical biology, as well as being proficient in a whole host of spectroscopic, microscopic, and analytical techniques.

Selected Publications

Harris, D. C.; Saks, B. R.; Jayawickramarajah, J. Protein-binding molecular switches via host-guest stabilized DNA hairpins. J. Am. Chem. Soc. 2011, 133, 7676-7679.

Mishur, R. J.; Griffin, M. E.; Battle, C. H.; Shan, B.; Jayawickramarajah, J. Molecular recognition and enhancement of aqueous solubility and bioactivity of CD437 by β-cyclodextrin. Bioorg. Med. Chem. Lett. 2011, 21, 857-860.

Battle, C.; Jayawickramarajah, J. Supramolecular approaches for inhibition of protein-protein and protein/DNA interactions in Supramolecular Chemistry: From Molecules to Nanomaterials; Gale, P., Steed, J., Eds. John Wiley & Sons: United Kingdom, 2010, Accepted.

Fathalla, M.; Li, S.-C.; Neuberger, A. Schmehl, R.; Diebold, U.; Jayawickramarajah, J. Straightforward Self-Assembly of Porphyrin Nanowires in Water: Harnessing Adamantane/β-Cyclodextrin Interactions J. Am. Chem. Soc. 2010, 132, 9966-9967.

(Highlighted in Nature Materials, Aug 2010, Vol. 9, p 605, and is the 8th most-read article in J. Am. Chem Soc. for August 2010).

Fathalla, M.; Jayawickramarajah, J. Configurational isomers of a stilbene linked bis(porphyrin) tweezer: Synthesis and fullerene binding studies. Eur. J. Org. Chem. 2009, 6095-6099. (picked as “Eurbest” article by the editors and is the one of the most-accessed articles in Eur. J. Org. Chem. for November 2009).

Pierce, S. E.; Wang, J.; Jayawickramarajah, J.; Hamilton, A. D.; Brodbelt, J. S. Examination of the effect of the annealing cation on higher order structures containing guanine or isoguanine repeats. Chem. Eur. J. 2009. 15, 11244-11255.

Fathalla, M.; Li, S.-C.; Diebold, U. Alb, A.; Jayawickramarajah, J. Water-soluble nanorods self-assembled via pristine-C60 and porphyrin moieties. Chem Comm. 2009, 4209-4211.

Fathalla, M.; Lawrence, C.; Zhang, N.; Sessler, J. L.; Jayawickramarajah, J. Base-pairing mediated non-covalent polymers Chem. Soc. Rev. 2009. 38, 1608-1620.

Rosenzweig, B. A.; Ross, N. T.; Tagore, D. M.; Jayawickramarajah, J.; Saraogi, l.; Hamilton, A. D. Multivalent protein binding and precipitation by self-assembling molecules on a DNA pentaplex scaffold. J. Am. Chem. Soc. 2009, 131, 5020-5021.

Harris, D. C.; Chu, X; Jayawickramarajah, J. Protein recognition via oligonucleotide-linked small molecules: Utilization of the hemin-binding aptamer. Supramol. Chem. 2009, 21, 316-323.

Harris, D. C.; Chu, X; Jayawickramarajah, J. DNA-small molecule chimera with responsive protein-binding ability. J. Am. Chem. Soc. 2008, 130, 14950-14951.

Pierce, S. E.; Sherman, C. L.; Jayawickramarajah, J.; Lawrence, C. M.; Sessler, J. L.; Brodbelt, J. S. ESI-MS characterization of a novel pyrrole-inosine nucleoside that interacts with guanine bases. Anal. Chim. Acta. 2008, 627, 129-135.

Jayawickramarajah, J.; Tagore, D. M.; Tsou, K.; Hamilton, A. D. Allosteric control of self-assembly: Modulating the formation of guanine quadruplexes through orthogonal aromatic interactions. Angew. Chem. Int. Ed. 2007, 46, 7583-7586. (picked as ‘hot-paper’ by the editors)

Tagore, D. M.; Sprinz, K. I.; Fletcher, S.; Jayawickramarajah, J.; Hamilton, A. D. Protein recognition and denaturation by self-assembling fragments on a quadruplex scaffold. Angew. Chem. Int. Ed. 2007, 46, 223-225. (picked as ‘hot-paper’ by the editors)

Torres, T.; Gouloumis, A.; Sanchez, D.; Jayawickramarajah. J.; Seitz, W.; Guldi, D. M.; Sessler, J. L. Photophysical characterization of a cytidine-guanosine tethered phthalocyanine-fullerene dyad. Chem. Comm. 2007, 292-294.

Sessler, J. L.; Lawrence, C.; Jayawickramarajah, J. Molecular recognition via base-pairing. Chem. Soc. Rev. 2007. 36, 314-325.

Sessler, J. L.; Jayawickramarajah, J.; Gouloumis, A.; Pantos, G. D.; Torres, T.; Guldi, D. M. Guanosine and fullerene derived de-aggregation of a new phthalocyanine-linked cytidine derivative. Tetrahedron 2006, 62, 2123-2131.

Sessler, J. L.; Jayawickramarajah, J. Functionalized base-pairs: versatile scaffolds for self-assembly. Chem. Comm. 2005, 15, 1939-1949.

Sessler, J. L.; Jayawickramarajah, J.; Gouloumis, A.; Torres, T.; Guldi, D. M.; Maldonado, S.; Stevenson, K. J. Synthesis and photophysics of a porphyrin-fullerene dyad assembled through Watson-Crick hydrogen bonding. Chem. Comm. 2005, 14, 1892-1894.

Sessler, J. L.; Jayawickramarajah, J.; Sherman, C. L.; Brodbelt, J. S. Enhancing Hoogsteen interactions: A pyrrole-containing purine nucleoside that competes with guanosine self-assembly. J. Am. Chem. Soc. 2004, 126, 11460-11461.

Sessler, J. L.; Jayawickramarajah, J.; Sathiosatham, M. Energy-and electron-transfer in supramolecular systems. In Encyclopedia of Supramolecular Chemistry; Atwood, J., Steed, J., Eds. Marcel Dekker: New York, 2004, pp 535-545.

Sessler, J. L.; Jayawickramarajah, J.; Sathiosatham, M.; Sherman, C. L.; Brodbelt, J. S. A novel guanosine-cytidine dinucleoside that self-assembles into a trimeric supramolecule. Org. Lett. 2003, 5, 2627-2630.