New reagents for immunofluorescence analysis of carbazole series containing fluorinated β-dicarbonyl fragments and carboxylic substituent groups separated by spacers of different lengths from the light-gathering carbazole scaffold have been developed. The markers in complex with Eu3+ ions possess stability in the aqueous phase, intense and prolonged luminescence (τ 550 - 570 μs) with characteristic emission maxima in the region of 615 nm and excitation wavelengths in the region of 380 - 390 nm, which distinguishes them from most of the analogs used. In the study of marker conjugation with streptavidin, a reagent containing 4 - 5 europium labeling complexes based on spacer-containing carbazole tetraketone was obtained. The marker-doped silicate nanoparticles exhibit intense and long-lived luminescence in the characteristic region.
References
[1]
Hagan, A.K. and Zuchner, T. (2011) Lanthanide-Based Time-Resolved Luminescence Immunoassays. Analytical and Bioanalytical Chemistry, 400, 2847-2864. http://dx.doi.org/10.1007/s00216-011-5047-7
[2]
Kricka, L.J. and Park, J.Y. (2014) Assay Principles in Clinical Pathology. Pathobiology of Human Disease, 3207-3221. http://dx.doi.org/10.1016/b978-0-12-386456-7.06302-4
[3]
Yuan, J. and Matsumoto, K. (1996) Synthesis of a New Tetradentate Β-Diketonate-Europium Chelate That Can Be Covalently Bound to Proteins in Time-Resolved Fluorometry. Analytical Sciences, 12, 695-699. https://doi.org/10.2116/analsci.12.695
[4]
Romanov, D.V., Vasil'ev, N.V., Lyamin, A.I., Ivanovskaya, N.P. and Osin, N.S. (2006) Synthesis of Fluorine-Containing Tetraketones and Diketo Esters and Luminescence-Spectral Properties of Their Complexes with Lanthanide Ions. Russian Chemical Bulletin, 55, 276-280. https://doi.org/10.1007/s11172-006-0248-5
[5]
Zhang, L., Wang, Y.J., Ye, Z.Q., Jin, D.Y. and Yuan, J.L. (2012) New Class of Tetradentate β-Diketonate-Europium Complexes That Can Be Covalently Bound to Proteins for Time-Gated Fluorometric Application. Bioconjugate Chemistry, 23, 1244-1251. https://doi.org/10.1021/bc300075t
[6]
Taydakov, I.V., Akkuzina, A.A., Avetisov, R.I., Khomyakov, A.V., Saifutyarov, R.R. and Avetissov, I. Ch. (2016) Effective electroluminescent materials for OLED Applications Based on Lanthanide 1.3-Diketonates Bearing Pyrazole Moiety. Journal of Luminescence, 177, 31-39. https://doi.org/10.1016/j.jlumin.2016.04.017
[7]
Nehra, K., Dalal, A., Hooda, A., Bhagwan, Sh., Kumar, S.R., Mari, B., et al. (2022) Lanthanides Β-Diketonate Complexes as Energy-Efficient Emissive Materials: A Review. Journal of Molecular Structure, 1249, Article ID: 131531. https://doi.org/10.1016/j.molstruc.2021.131531
[8]
Vasil’ev, N., Romanov, D. Ivanovskaya, N. and Osin, N. (2005) Complexing Dibenzene-Containing Five-Membered Cyclic Compounds Containing Two Symmetrical beta-Dicarbonyl Substituents with Fluorinated Radicals. RU Patent No. 2296756.
[9]
Pugachyov, D.E., Kostryukova, T.S., Ivanovskaya, N.P., Lyamin, A.I., Romanov, D.V., Moiseyev, S.V., et al. (2019) Fused Fluorinated Bis-β-Diketones and Luminescent-Spectral Properties of Their Complexes with Europium. Russian Journal of General Chemistry, 89, 965-970. https://doi.org/10.1134/S1070363219050165
[10]
Kostryukova, T.S., Vasil'ev, N.V., Ivanovskaya, N.P., Zatonskii, G.V. and Osin, N.S. (2015) A Label for Immunofluorescence Analysis Based on Europium Complexes With Fluorinated Β-Diketone of the Carbazole Series. Russian Journal of Bioorganic Chemistry, 41, 186-191. https://doi.org/10.7868/S0132342315010091
[11]
Wu, F.B. and Zhang, C. (2002) A New Europium Β-Diketone Chelate for Ultrasensitive Time-Resolved Fluorescence Immunoassays. Analytical Biochemistry, 311, 57-67. https://doi.org/10.1016/s0003-2697(02)00390-1
[12]
Ratner, V., Khomutov, O., Karpenko, N., Filjakova, V. and Pashkevich K. (1995) Method of Synthesis of Fluorine-Containing β-Diketones. RU Patent No. 2100345 C1.
[13]
Qina, Z., Yua, J., Zhylkob, V., and Daic, L. (2021) Preparation and Photoluminescence of Europium(III) Complexes with TPPO as Neutral Ligand. Russian Journal of Applied Chemistry, 94, 1147-1152. https://doi.org/10.1134/S1070427221080164
[14]
Plant, S.G.P., Rogers K.M. and Williams S.B.C. (1935) The Friedel and Crafts Reaction in the Carbazole Series. Journal of the Chemical Society, 65, 741-752. https://doi.org/10.1039/JR9350000741
[15]
Armarego, W.L.F. and Chai, C.L.L. (2012) Purification of Laboratory Chemicals. 7th Edition, Butterworth-Heinemann, Oxford; Waltham, MA. https://shop.elsevier.com/books/purification-of-laboratory-chemicals/armarego/978-0-12-382161-4
