121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-460
Subject An Oxazolidinoindole-Based NIR Two Photon Probe for Mitochondria
Authors Jae-Hyeok Do, Hae-Jo Kim1,*
Department of chemistry, Hankuk University of Foreign Studies, Korea
1Department of Chemistry, Hankuk University of Foreign Studies, Korea
Abstract Background: Development of a method to control the function of a compound in a spatiotemporal manner is indispensable in the field of biological chemistry and drug delivery system. Ultraviolet (UV) irradiation-induced bond cleavage reaction or conformational change of backbone has been applied in order to control the function of a molecule. However, due to its low short wavelength, UV light exhibits limited penetration depth in biological tissues and can possibly cause tissue damage, which hampers the application of UV light for the treatment of internal tumors.1,2 Near-infrared (NIR) two-photon photolysis can overcome these problems. As already known, two-photon microscopy has advantage of spatial concentrativeness and high permeability than one-photon microscopy. NIR light is more harmless to living organisms than UV light. Combining with these two advantages, NIR two photon was used as driving force for probe's intramolecular photolysis.3,4 For targeting mitochondria, triphenylphosphonium is used as a biomarker for cellular mitochondria.5 Materials and Method: Chemical probe was prepared according to the standard method in the lab and all starting reagents purchased from the chemical suppliers. Result: The NIR two photon probe based on oxazolidinoindole was designed to function through photolysis. Conformational cleavage occurs and oxazolidinoindole phenol fragment changes into hydroxyethylindolium phenolate, emitting a green light in the range of 570 nm.6 Conclusion: Latent NIR two photon probe was successfully photolysised and emitted a green light in the range of 570 nm. Reference: 1 Shigenaga, A.; Yamamoto, J.; Sumikawa, Y.; Furuta, T.; Otaka, A. Tetrahedron. Lett. 2010, 51, 2868. 2 Yang, Y.; Yang, Y. F.; Xie, X. Y.; Wang, Z. Y.; Gong, W.; Zhang, H.; Li, Y.; Yu, F. L.; Li, Z. P.; Mei, X.G. Biomat. 2015, 48, 84. 3 Weissleder, R. Nat. Biotechnol. 2001, 19, 316.6. 4 Hambley, T. W.; Hait, W. N. Cancer. Res. 2009, 69, 1259. 5 Murphy, M. P.; Smith, R. A. J. Annu. Rev. Pharmacol. Toxicol. 2007, 47, 629 . 6 Kim, C. Y.; Kang, H. J.; Chung, S. J.; Kim, H.-K.; Na, S.-Y.; Kim, H.-J. Anal. Chem. 2016, 88, 7178.
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