Poster - 17-09-14
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The document summarizes an investigation into the binding of fusidic acid within the spliceosome. Fusidic acid was found to inhibit the spliceosome, the large protein complex responsible for splicing pre-mRNA into mRNA. To better understand how fusidic acid binds, the researchers synthesized probes by attaching photo-reactive groups to fusidic acid. Upon activation, the probes would covalently bind to the binding site on the spliceosome. Analysis of the resulting complex using mass spectrometry could then provide insights into the binding site of fusidic acid within this important protein complex.
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Reactive Oxygen Species,Reactive Nitrogen Species and Redox Signaling
Reactive Oxygen Species,Reactive Nitrogen Species and Redox Signaling
Sinulasulfoxide and sinulasulfone, sulfur containing alkaloids from the
Sinulasulfoxide and sinulasulfone, sulfur containing alkaloids from the
Expression of genetic material : From Transcription to Translation
Expression of genetic material : From Transcription to Translation
Poster - 17-09-14
- 1. ARRESTING THE SPLICEOSOME: Investigating the Binding of Fusidic Acid within the Spliceosome Robert J. Soltysiaka, Alexander M. Bowena Steven J. Hartea, David J. Berrisforda, Ray T. O’Keefeb and Roger C. Whiteheada aSchool of Chemistry, Oxford Road, University of Manchester, M13 9PL, UK. bFaculty of Life Sciences, University of Manchester, M13 9PT, UK • The central dogma of biology states that DNA is transcribed within the nucleus to give RNA. • The RNA is then exported into the cytosol, before being translated by the ribosome to give proteins. • Splicing is the final step of transcription.1 • Splicing consists of two transesterification reactions converting pre-mRNA to mRNA. • These reactions removes the non-coding nucleotide sequences (introns) from the coding nucleotide sequences (exons). • During these reactions the exons are also coupled together and the introns ejected as a “lariat complex”.2 • Errors or disruptions in splicing can result in incorrectly formed mRNA, which can play a part in many diseases, including cancer. It is for this reason inhibition of the spliceosome is of interest as a potential cancer therapy. Introduction to Splicing The Spliceosome • The spliceosome is a large, highly dynamic protein complex, consisting of 5 snRNPs (small nuclear RiboNucleoProteins), which assemble around the pre-mRNA and separate after splicing.3 • It is thought to act in a catalytic manner during splicing, by positioning pre-mRNA to allow the transesterification reactions to occur. The Splicing Cycle Fusidic Acid • Previous methods of inhibiting the spliceosome have involved using small molecules to inhibit individual proteins, thus impeding splicing. A B • The focus of the project is on SNU114, a protein within the U5 snRNP. • To find a suitable compound a homologue for U5 was first found: EF-G (Elongation Factor G, shown left, with fusidic acid binding). • By screening small molecule inhibitors of EF-G we found fusidic acid, a steroid, which showed some efficacy in inhibiting the spliceosome.4 Elucidation of the Binding Site • Little is known about the binding site or mechanism of fusidic acid and SNU114. • For this reason it was decided to attach a photo-reactive “probe” to fusidic acid to investigate. • The probe would covalently bond to the area surrounding the binding site when activated. Synthesis • Benzophenone: • Trifluoromethyldiazirine: • Fusidic acid probes: (a) Benzoyl chloride, AlCl3. (b) AcOH, H2SO4, CrO3 (c) Amine linker, DCC, DCM. (n = 1, 1.5, 2, 4) (a) i) Mg, Et2O ii) CF3CO2Et. (b) NH2OH.HCl, EtOH, py. (c) p-TsCl, DMAP, Et3N, DCM. (d) NH3, DCM. (e) TMSOTf, DCM, Et3N. (f) n- BuLi, CO2. (g) I2, Et3N. (h) as above with (c). (a) Chloromethyl pivalate, Et3N, DMF. (b) Succinic anhydride, DMAP, py. (c) Linker-R, DCC, DMAP, DCM. (n = 1, 1.5, 2, 4) R = References 1. Nilsen, T. W. Bioessays 2003, 25, 1147-1149. 2. (i) Stryer, L.; Berg, J. M.; Tymoczko, J. L. Biochemistry; 6th ed.; W. H. Freeman and Company 2007. (ii) Jurica, M. S.; Moore, M. J. Methods 2002, 28, 336-345. 3. (i) Newman, A. J.; Nagai, K. Current Opinion in Structural Biology 2010, 20, 82-89. (ii) Nilsen, T. W. Molecular Cell 2002, 9, 8-9. (iii) Staley, J. P.; Guthrie, C. Cell 1998, 92, 315-326. 4. Harte, S. J. PhD Thesis, University of Manchester, 2012. • The resulting complex could be broken down into fragments which could be analysed by mass spectrometry to give a clearer picture of the binding site. • Two probes were chosen, benzophenone and trifluoromethyldiazirine: