Synthesis of Pyrrolidinyl PNA Containing Ir-Complex
Abstract
Iridium complex is a promising organometallic compound for bio-photophysical studies which have a large Stroke shift, long emissive lifetimes, and high quantum yields in visible range. Synthesis of pyrrolidinyl peptide nucleic acid (acpcPNA) containing [Ir(ppy)2(4’-methyl-2,2’-bipyridine-4-carboxylic acid)](PF6) or Ir-acpcPNA was studied in this research as a candidate probe for DNA detection in Fluorescence In Situ Hybridization (FISH) technique. The coupling condition for labeling Ir-COOH with linker was HATU/DIEA and DCC/NHS and gave 52 and 48 %yield, respectively. However, the coupling reaction between acpcPNA and Ir-COOH with HATU/DIEA condition gave low yield. For condition of DCC/NHS, Ir-acpcPNA product cannot be observed but the mass signal of decomposition of PNA was found. For this phenomenon, we assumed that iridium complexes can act as a catalyst for water oxidation, cause the decomposition of PNA. So, iridium complexes may be applied to use for PNA degradation within target cells. Keywords : pyrrolidinyl PNA, iridium, fluorescent, biomarkerReferences
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Gross, A., Husken, N., Schur, J., Raszeja, L., Ott, I. and Metzler-Nolte, N. (2012). A Ruthenocene-PNA Bioconjugate-Synthesis, Characterization, Cytotoxicity, and AAS-Detected Cellular Uptake. Bioconjugate Chem., 23, 1764-1774.
Koh, W. (2015). Peptide Nucleic Acid (PNA) and Its Applications. Retrieved February 10, 2018, from http://121.254.169.23/bbs/ndata/pn_ref/pn_ref_1227242202.pdf.
Nielsen, P. E. (1999). Peptide nucleic acid. A molecule with two identities. Acc. Chem. Res., 32, 624-630.
Reisberg, S., Dang, LA., Nguyen, QA., Piro, B., Noel, V., Nielsen, PE. (2008). Label-free DNA electrochemical sensor based on a PNA-functionalized conductive polymer. Talanta, 76(1), 206-210.
Sabale, P. M., Georgea, J. T. and Srivatsan, S. G. (2014). A base-modified PNA–graphene oxide platform as a turn-on fluorescence sensor for the detection of human telomeric repeats. Nanoscale, 6, 10460-10469.
Schatz, P., Distler, J., Berlin, K. and Schuster, M. (2006). Novel method for high throughput DNA methylation marker evaluation using PNA-probe library hybridization and MALDI-TOF detection. Nucleic Acids Res., 34(8), 59.
Suparpprom, C., Srisuwannaket, C., Sangvanich, P., Vilaivan, T. (2005). Synthesis and oligodeoxynucleotide binding properties of pyrrolidinyl peptide nucleic acids bearing prolyl-2-aminocyclo-pentanecarboxylic acid (ACPC) backbones. Tetrahedron Lett., 46, 2833-2837.
Thomsen, J. M., Huang, D. L., Crabtree, R. H. and Brudvig, G. W. (2015) Iridium-based complexes for water oxidation. Dalton Trans., 44, 12452–12472.
Verheijen, J. C., van de Marel, G. A., van der Boom, J. H. and Metzler-Nolte N. (2000). Transition Metal Derivatives of Peptide Nucleic Acid (PNA) Oligomer-Synthesis, Characterization and DNA binding. Bioconjugate Chem., 11(6), 741-743.
Wang, L., Puodziukynaite, E., Vary, R. P., Grumstrup, E. M., Walczak, R. W., Zolotarskaya, O. Y. (2012). Competition between Ultrafast Energy Flow and Electron Transfer in a Ru(II)-Loaded Polyfluorene Light-Harvesting Polymer. J. Phys. Chem. Lett., 3 (17), 2453–2457.
Zhoa, N., Wu, Y., Wang, R., Shi, L. and Chen, Z. (2011). An Iridium(III) Complex of Oximated 2,2'-bipyridine as a Sensitive Phosphorescent. Analyst, 136, 2277-2282.
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2018-10-29
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บทความวิจัยจากการประชุมวิชาการระดับชาติ"วิทยาศาสตร์วิจัย"ครั้งที่ 10
