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Spectroscopic and Theoretical Studies of Fluorescence Effects in 2-Methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole Induced by Molecular Aggregation.
J Fluoresc 2018; 28(1):65-77JF

Abstract

The article presents the results of fluorescence analyses of 2-methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole (MDFT) in an aqueous environment. MDFT dissolved in aqueous solutions with a pH value in the range from 1 to 4.5 yielded an interesting effect of two clearly separated fluorescence emissions. In turn, a single fluorescence was observed in MDFT dissolved in water solutions with a pH value from 4.5 to 12. As it was suggested in the previous investigations of other 1,3,4-thiadiazole compounds, these effects may be associated with conformational changes in the structure of the analysed molecule accompanied by aggregation effects. Crystallographic data showed that the effect of the two separated fluorescence emissions occurred in a conformation with the -OH group in the resorcyl ring bound on the side of the sulphur atom from the 1,3,4-thiadiazole ring. The hypothesis of aggregation as the mechanism involved in the change in the spectral properties at low pH is supported by the results of (Time-Dependent) Density Functional Theory calculations. The possibility of rapid analysis of conformational changes with the fluorescence spectroscopy technique may be rather important outcome obtained from the spectroscopic studies presented in this article. Additionally, the presented results seem to be highly important as they can be easily observed in solutions and biologically important samples.

Authors+Show Affiliations

Department of Biophysics, University of Life Sciences in Lublin, Akademicka 13, 20-950, Lublin, Poland. arkadiusz.matwijczuk@up.lublin.pl.Department of Physical Biochemistry, Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, Gronostajowa 7, 30-387, Krakow, Poland.Department of Theoretical Chemistry, Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060, Kraków, Poland.Department of Theoretical Chemistry, Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060, Kraków, Poland.Department of Chemistry, University of Life Sciences in Lublin, Akademicka 15, 20-950, Lublin, Poland.Departament of Chemistry, Jagiellonian University, Ingardena 3, 30-060, Kraków, Poland.Department of Chemistry, University of Life Sciences in Lublin, Akademicka 15, 20-950, Lublin, Poland. Institute of Industrial Organic Chemistry, Annopol 6, 03-236, Warsaw, Poland.Department of Cell Biology, Institute of Biology, Maria Curie-Skłodowska University, Akademicka 19, 20-033, Lublin, Poland. mariusz.gagos@poczta.umcs.lublin.pl.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28889356

Citation

Matwijczuk, Arkadiusz, et al. "Spectroscopic and Theoretical Studies of Fluorescence Effects in 2-Methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole Induced By Molecular Aggregation." Journal of Fluorescence, vol. 28, no. 1, 2018, pp. 65-77.
Matwijczuk A, Górecki A, Makowski M, et al. Spectroscopic and Theoretical Studies of Fluorescence Effects in 2-Methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole Induced by Molecular Aggregation. J Fluoresc. 2018;28(1):65-77.
Matwijczuk, A., Górecki, A., Makowski, M., Pustuła, K., Skrzypek, A., Waś, J., ... Gagoś, M. (2018). Spectroscopic and Theoretical Studies of Fluorescence Effects in 2-Methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole Induced by Molecular Aggregation. Journal of Fluorescence, 28(1), pp. 65-77. doi:10.1007/s10895-017-2175-2.
Matwijczuk A, et al. Spectroscopic and Theoretical Studies of Fluorescence Effects in 2-Methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole Induced By Molecular Aggregation. J Fluoresc. 2018;28(1):65-77. PubMed PMID: 28889356.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Spectroscopic and Theoretical Studies of Fluorescence Effects in 2-Methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole Induced by Molecular Aggregation. AU - Matwijczuk,Arkadiusz, AU - Górecki,Andrzej, AU - Makowski,Marcin, AU - Pustuła,Katarzyna, AU - Skrzypek,Alicja, AU - Waś,Joanna, AU - Niewiadomy,Andrzej, AU - Gagoś,Mariusz, Y1 - 2017/09/09/ PY - 2017/06/02/received PY - 2017/08/30/accepted PY - 2017/9/11/pubmed PY - 2017/9/11/medline PY - 2017/9/11/entrez KW - 1,3,4-Thiadiazole KW - DFT calculations KW - Molecular aggregation KW - Molecular spectroscopy KW - The effect of two fluorescence emission bands SP - 65 EP - 77 JF - Journal of fluorescence JO - J Fluoresc VL - 28 IS - 1 N2 - The article presents the results of fluorescence analyses of 2-methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole (MDFT) in an aqueous environment. MDFT dissolved in aqueous solutions with a pH value in the range from 1 to 4.5 yielded an interesting effect of two clearly separated fluorescence emissions. In turn, a single fluorescence was observed in MDFT dissolved in water solutions with a pH value from 4.5 to 12. As it was suggested in the previous investigations of other 1,3,4-thiadiazole compounds, these effects may be associated with conformational changes in the structure of the analysed molecule accompanied by aggregation effects. Crystallographic data showed that the effect of the two separated fluorescence emissions occurred in a conformation with the -OH group in the resorcyl ring bound on the side of the sulphur atom from the 1,3,4-thiadiazole ring. The hypothesis of aggregation as the mechanism involved in the change in the spectral properties at low pH is supported by the results of (Time-Dependent) Density Functional Theory calculations. The possibility of rapid analysis of conformational changes with the fluorescence spectroscopy technique may be rather important outcome obtained from the spectroscopic studies presented in this article. Additionally, the presented results seem to be highly important as they can be easily observed in solutions and biologically important samples. SN - 1573-4994 UR - https://www.unboundmedicine.com/medline/citation/28889356/Spectroscopic_and_Theoretical_Studies_of_Fluorescence_Effects_in_2-Methylamino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole_Induced_by_Molecular_Aggregation L2 - https://doi.org/10.1007/s10895-017-2175-2 DB - PRIME DP - Unbound Medicine ER -