Comparative study of the inclusion complexation of uracil and 5-fluorouracil with native and modified cyclodextrins: some theoretical and practical
Source abstract
Abstract
In this study, the inclusion complexes of α-, β-cyclodextrins and derivatives hydroxypropyl-α-, hydroxypropyl-β-cyclodextrins with uracil and the anti-cancer agent 5- fluorouracil were demonstrated by UV-Vis spectroscopy and quantum chemical calculations. The complexes stability constants and the thermodynamic parameters for the 1:1 stoichiometry inclusion complexes were obtained and compared. The thermodynamic analysis of the studied complexes showed that the inclusion reaction is an exothermic spontaneous reaction and is an enthalpy driven process for the temperature domain of 298K to 313K. Theoretical calculations were performed on complexes to examine the energetic quantities involved in the stability of the complexes. The correlation of the energy parameters obtained from experimental and theoretical data suggests a high affinity between cyclodextrins and both uracil and 5-fluorouracil molecules.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Drug Solubulity and Delivery Systems · Muon and positron interactions and applications · Enzyme Structure and Function
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (37)
Show source-provided references
1. [1] Wimmer, T. Cyclodextrins. Ullmann's Encyclopedia of Industrial Chemistry; Wacker-Chemie GmbH: Burghausen, Germany, 2012.
2. [2] B. G. Poulson, Q. A. Alsulami, A. Sharfalddin, E. F. El Agammy, F. Mouffouk, A. H. Emwas, L. Jaremko, M. Jaremko, Polysaccharides 3, 1 (2022); https://doi.org/10.3390/polysaccharides301000110.3390/polysaccharides3010001 ↗
3. [3] Sandilya AA, Natarajan U, Priya MH. Molecular View into the Cyclodextrin Cavity: Structure and Hydration. ACS Omega 5(40), 25655 (2020); https://doi.org/10.1021/acsomega.0c0276010.1021/acsomega.0c02760 ↗
4. [4] G. M. Miranda, V. O. R. E. Santos, J. R. Bessa, Y. C. F. Teles, S. C. M. A. Yahouédého, M. S. Goncalves, J. R. Ribeiro-Filho, Biomolecules 11(3), 361 (2021); https://doi.org/10.3390/biom1103036110.3390/biom11030361 ↗
5. [5] A. R. Katageri, M. A. Sheikh, International Research Journal of Pharmacy 3(1), 52 (2012), http://www.irjponline.com/admin/php/uploads/788_pdf.pdf
6. [6] B. D. Shewale, N.P. Sapkal, N. A. Raut, N. J. Gaikwad, R. A. Fursule, Indian Journal of Pharmaceutical Sciences 70(2), 255 (2008); https://doi.org/10.4103/0250-474X.4147010.4103/0250-474X.41470 ↗
7. [7] T. Loftsson, M. E. Brewster, H. Derendorf, N. Bodor, PZ Wissenschaft 136(1), 5 (1991)
8. [8] C. Focaccetti, A. Bruno, E. Magnani, D. Bartolini, E. Principi, K. Dallaglio, E. O. Bucci, G. Finzi, F. Sessa, D. M. Noonan, A. Albini, PLOS ONE 10(2), 1 (2015); https://doi.org/10.1371/journal.pone.011568610.1371/journal.pone.0115686 ↗
9. [9] M. Bartolotta, M. Buthelezi, Journal of Photochemistry and Photobiology A: Chemistry. 371, 382 (2018); https://doi.org/10.1016/j.jphotochem.2018.11.03710.1016/j.jphotochem.2018.11.037 ↗
10. [10] P. A. Wieczorkiewicz, T. M. Krygowski, H. Szatylowicz, Molecules 27(21), 7240 (2022); https://doi.org/10.3390/molecules2721724010.3390/molecules27217240 ↗
11. [11] G. J. Peters, C. J. van Groeningen, Annals of Oncology 2(7), 469 (1991); https://doi.org/10.1093/oxfordjournals.annonc.a05799410.1093/oxfordjournals.annonc.a057994 ↗
12. [12] R. Diasio, B. Harris, Clinical Pharmacokinetics 16, 215 (1989); https://doi.org/10.2165/00003088-198916040-0000210.2165/00003088-198916040-00002 ↗
13. [13] J. B. Parker, J. T. Stivers, Biochemistry 50(5), 612 (2011); https://doi.org/10.1021/bi101536k10.1021/bi101536k ↗
14. [14] S. Ghafouri-Fard, Soudeh, A. Atefe, T. A. Farhad, S. Hamed, F. Faranak, J. S. Alireza, B. Abbas, T. Mohammad, Frontiers in Oncology 11, 658636 (2021); https://doi.org/10.3389/fonc.2021.60898710.3389/fonc.2021.608987 ↗
15. [15] R. M. Haley, R. Gottardi, R. Langer, M. J. Mitchell, Drug Delivery and Translational Research 10(3), 661 (2020); https://doi.org/10.1007/s13346-020-00724-510.1007/s13346-020-00724-5 ↗
16. [16] D. L. Melnikova, Z. F. Badrieva, M. A. Kostin, C. Maller, M. Stas, A. Buczek, M. A. Broda, T. Kupka, A. M. Kelterer, P. M. Tolstoy, V. D. Skirda, Molecules 25(23), 5706 (2020); https://doi.org/10.3390/molecules2523570610.3390/molecules25235706 ↗
17. [17] L. Jin, Q. Liu, Z. Sun, X. Ni, M. Wei, Industrial & Engineering Chemistry Research 49, 11176 (2010); https://doi.org/10.1021/ie100990z[18] C. Di Donato , M. Lavorgna, R. Fattorusso, C. Isernia, M. Isidori, G. Malgieri, C. Piscitelli, C. Russo, L. Russo, R. Iacovino, Molecules. 21(12), 1644 (2016); https://doi.org/10.3390/molecules2112164410.3390/molecules21121644 ↗
18. [19] A. Neacsu, E. Pincu, G. Munteanu, C. Munteanu, V. Meltzer, Revista de Chimie. 68, 2756 (2017); https://doi.org/10.37358/RC.17.12.597110.37358/RC.17.12.5971 ↗
19. [20] I. V. Terekhova, R. S. Kumeev, G. A. Alper, A. Agafonov, Russian Journal of Physical Chemistry A 85, 1844 (2011); https://doi.org/10.1134/S003602441110029310.1134/S0036024411100293 ↗
20. [21] A. Buczek, M. Staś, C. Hebenstreit, C. Maller, M. Broda, T. Kupka, A. Kelterer, International Journal of Quantum Chemistry 121(5), e26487 (2020); https://doi.org/10.1002/qua.2648710.1002/qua.26487 ↗
21. [22] G. Raffaini, S. Elli, F. Ganazzoli, M. Catauro, Macromolecular symposia 404(1), 2100305 (2022); https://doi.org/10.1002/masy.20210029610.1002/masy.202100296 ↗
22. [23] J. Orgoványi, E. Oláh, K. H-Otta, E. Fenyvesi, Journal of Inclusion Phenomena and Macrocyclic Chemistry 63, 53 (2009); https://doi.org/10.1007/s10847-008-9488-310.1007/s10847-008-9488-3 ↗
23. [24] C. Y. Huang, Methods in Enzymology 87, 509 (1982); https://doi.org/10.1016/S0076-6879(82)87029-810.1016/S0076-6879(82)87029-8 ↗
24. [25] C. Tablet, I. Matei, M. Hillebrand, IntechOpen, 47 (2012); https://doi.org/10.5772/3428710.5772/34287 ↗
25. [26] A. Ashnagar, N. G. Naseri, B. Khanaki, E-Journal of Chemistry 4(44), 550 (2007); https://doi.org/10.1155/2007/50271810.1155/2007/502718 ↗
26. [27] N. Gharib Naseri, A. Ashnagar, F. Husseini, Scientia Iranica. 14(4), 308 (2007)
27. [28] M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, Journal of computational chemistry 14, 1347 (1993); https://doi.org/10.1002/jcc.54014111210.1002/jcc.540141112 ↗
28. [29] R. C. Binning, Jr., L. A. Curtiss, Journal of computational chemistry 11, 1206 (1990); https://doi.org/10.1002/jcc.54011101310.1002/jcc.540111013 ↗
29. [30] N. Markova, V. Enchev. I. Timtcheva, Journal of Physical Chemistry A 109(9), 1981 (2005); https://doi.org/10.1021/jp046132m10.1021/jp046132m ↗
30. [31] B. Khalili, M. Rimaz, Structural Chemistry 29, 681-702 (2018); https://doi.org/10.1007/s11224-017-1062-410.1007/s11224-017-1062-4 ↗
31. [32] H. Mohamed Ameen, S. Kunsági-Máté, B. Bognár, L. Szente, M. Poór, B. Lemli, Molecules 24(24), 4565 (2019); https://doi.org/10.3390/molecules2424456510.3390/molecules24244565 ↗
32. [33] J. He, Z. P. Zheng, Q. Zhu, F. Guo, J. Chen, Molecules 22(11), 1801 (2017); https://doi.org/10.3390/molecules2211180110.3390/molecules22111801 ↗
33. [34] P. Padhan, A. Sethy, P. K. Behera, Journal of Photochemistry and Photobiology A: Chemistry 337, 165 (2017); https://doi.org/10.1016/j.jphotochem.2017.01.01510.1016/j.jphotochem.2017.01.015 ↗
34. [35] M. Saroj, R. Payal, S. Jain, N. Sharma, R. Rastogi, Journal of Inclusion Phenomena and Macrocyclic Chemistry 90, 305 (2018); https://doi.org/10.1007/s10847-018-0782-410.1007/s10847-018-0782-4 ↗
35. [36] Z. Tang, C. A. Chang, Journal of Chemical Theory and Computation 14(1):303 (2018); https://doi.org/10.1021/acs.jctc.7b0089910.1021/acs.jctc.7b00899 ↗
36. [37] G. Schaftenaar, Molden, Available at: https://www.theochem.ru.nl/molden/
37. [38] S. Grimme, http://wires.wiley.com/WileyCDA/WiresArticle/wisId-WCMS30.html