New fluorinated tetraketone derivatives of N-substituted carbazoles were synthesized and tested as ligands for fluorescence immunoassay. The spectral properties of the obtained heterocyclic tetraketones and their Eu(III) complexes were studied. The complexes showed longwave absorption at 360–380 nm, high extinction coefficient values, long lifetime of excited states, and intense luminescence, allowing to consider the use of such lanthanide complexes in immunofluorescence analysis.
Similar content being viewed by others
References
Yamada, S.; Miyoshi, F.; Kano, K.; Ogawa, T. Anal. Chim. Acta 1981, 127, 195.
Hemmilä, I. Clin. Chem. 1985, 31, 359.
Diamandis, E. P. Clin. Biochem. 1988, 21, 139.
Hemmilä, I. J. Alloys Compd. 1995, 225, 480.
Bekman, N. I.; Laricheva, S. Yu.; Pomelova, V. G.; Osin, N. S. Clinical laboratory diagnostics [in Russian] 2010, 12, 33.
Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, K. A., Jr.; Bünzli, J.-C. G.; Pecharsky, V. K.; Eds.; Elsevier, 2005, Vol. 35, Chapter 225, p. 226.
Hemmilä, I.; Mukkala, V.-M. Crit. Rev. Clin. Lab. Sci. 2001, 38, 441.
Comprehensive Inorganic Chemistry II: From Elements to Applications; Drozdov, A.; Kuzmina, N., Eds.; Elsevier, 2013, 2nd ed., Vol. 2, p. 511.
Utochnikova, V. V.; Kuz'mina, N. P. Coordination chemistry [in Russian] 2016, 42, 640.
Yuan, J.; Matsumoto, K. J. Pharm. Biomed. Anal. 1997, 15, 1397.
Wu, F.-B.; Han, S.-Q.; Zhang, C.; He, Y.-F. Anal. Chem. 2002, 74, 5882.
Romanov, D. V.; Lyamin, A. I.; Ivanovskaya, N. P.; Moiseev, S. V.; Zhedulov, A. E.; Osin, N. S.; Vasil'ev, N. V. RU patent 2296756.
He, P.; Wang, H. H.; Liu, S. G.; Shi, J. X.; Wang, G.; Gong, M. L. Inorg. Chem. 2009, 48, 11382.
Romanov, D. V.; Lyamin, A. I.; Ivanovskaya, N. P.; Zhedulov, A. E.; Osin, N. S.; Vasil'ev, N. V. RU patent 2373200.
Kostryukova, T. S.; Ivanovskaya, N. P.; Lyamin, A. I.; Romanov, D. V.; Osin, N. S.; Zatonsky, G. V.; Vasil'ev, N. V. Russ. J. Gen. Chem. 2012, 82, 455. [Zh. Obshch. Khim., 2012, 82, 462.]
Kostryukova, T. S.; Ivanovskaya, N. P.; Zatonsky, G. V.; Osin, N. S.; Vasil'ev, N. V. Russ. J. Bioorg. Chem. 2015, 41, 186. [Bioorg. Khim. 2015, 41, 212.]
Osin, N. S.; Pomelova, V. G.; Shlyakova, S. Yu.; Bulatov, А. А.; Osipova, T. А.; Sigal, E. R.; Koryazova, L. K.; Martynov, A. V. Biotekhnologiya 1997, 9–10, 49.
Stevens, S. T.; Tucker, S. H. J. Chem. Soc., Perkin. Trans. 1 1923, 123, 2140.
Cho, J.-H.; Ryu, Y.-S.; Oh, S.-H.; Kwon, J.-K.; Yum, E.-K. Bull. Korean Chem. Soc. 2011, 32, 2461.
de Montmollin, G.; de Montmollin, M. Helv. Chim. Acta 1923, 6, 94.
Mitchell, D. R; Plant, S. G. P. J. Chem. Soc. 1936, 1295.
Filyakova, V. I.; Karpenko, N. S.; Kuznetsova, O. A.; Pashkevich, K. I. Russ. J. Org. Chem. 1998, 34, 381. [Zh. Org. Khim. 1998, 34, 411.]
Paskevich, K. I.; Saloutin, V. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1981, 50, 180. [Usp. Khim. 1981, 50, 325.]
Structure Determination of Organic Compounds; Pretsch, E.; Bühlmann, P.; Badertscher, M., Eds.; Springer, 2000, p. 288.
Yuan, J.; Sueda, S.; Somazava, R.; Matsumoto, K.; Matsumoto, K. Chem. Lett. 2003, 32, 492.
Tsaryuk, V.; Zolin, V.; Legendziewicz, J. J. Lumin. 2003, 102-103, 744.
Hemmilä, I.; Mukkala, V.-M.; Latva, M.; Kiilholma, P. J. Biochem. Biophys. Methods 1993, 26, 283.
Latva, M.; Takalo, H.; Mukkala, V.-M.; Matachescu, C.; Rodriguez-Ubis, J. C.; Kankarea, J. J. Lumin. 1997, 75, 149.
Hemmilä, I.; Dakubu, S. US Patent 4565790.
Gordon, A. J.; Ford, R. A. The Chemist's Companion [Russian translation]; Mir: Moscow, 1976, p. 571.
Buu-Hoi; Ryer, R. Recl. Trav. Chim. Pays–Bas Belg. 1947, 66, 533.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(5), 528–534
Rights and permissions
About this article
Cite this article
Pugachov, D.E., Kostryukova, T.S., Zatonsky, G.V. et al. Fluorinated tetraketone derivatives of N-substituted carbazoles and their Eu(III) complexes for fluorescence immunoassay. Chem Heterocycl Comp 54, 528–534 (2018). https://doi.org/10.1007/s10593-018-2300-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-018-2300-4