Abstract
5-Fluorouracil is a well-known and widely used drug in medical practice for the treatment of cancer. However, there is no analytical review in the literature on the synthesis of 5-fluorouracil and its prodrugs, the properties of these compounds and the factors affecting their metabolism. In the present mini review, we made an attempt to summarize and analyze available material on these issues.
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G. M. Blackburn, M. J. Gait, D. Loakes, D. M. Williams, Nucleic Acids in Chemistry and Biology, Royal Society of Chemistry, Cambridge, 2006, 470 p.
C. Heidelberger, F. J. Ansfield, Cancer Res., 1963, 23, 1226.
H. Luellmann, K. Mohr, A. Ziegler, D. Bieger, Color Atlas of Pharmacology, 2nd ed., Thieme, Stuttgart—New York, 2000, 368 pp.
S. L. Guturov, N. N. Semenov, E. I. Zagrekova, Rus. Med. Zhurn. [Russ. Med. J.], 2001, 9, No. 22, 1017 (in Russian).
A. V. Semakov, A. A. Blinkov, G. P. Gaenko, A. G. Vostrova, J. G. Molotkovsky, Russ. J. Bioorg. Chem., 2013, 39, 299; DOI: https://doi.org/10.1134/S1068162013030138.
Yu. I. Murinov, S. A. Grabovskii, N. N. Kabal’nova, Russ. Chem. Bull., 2019, 68, 946; DOI: https://doi.org/10.1007/s11172-019-2505-4.
E. N. Knyazev, S. V. Nikulin, A. Yu. Khristichenko, T. N. Gerasimenko, O. V. Kindeeva, V. A. Petrov, G. A. Belyakova, D. V. Maltseva, Russ. Chem. Bull., 2019, 68, 2344; DOI: https://doi.org/10.1007/s11172-019-2709-7.
J.-P. Bégué, D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley, Hoboken, 2008, 365 pp.
A. Tressaud, G. Haufe, Fluorine and Health. Molecular Imaging, Biomedical Materials and Pharmaceuticals, Elsevier, Amsterdam, 2008, p. 553–778.
P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH, Weinheim, 2013, 320 pp.
R. Duschinsky, E. Pleven, C. Heidelberger, J. Am. Chem. Soc., 1957, 79, 4559; DOI: https://doi.org/10.1021/ja01573a087.
R. Duschinsky, T. Gabriel, W. Tautz, A. L. Nussbaum, M. Hoffer, E. Grunberg, J. H. Burchenal, J. J. Fox, Nucleosides, 1967, 37, 47.
Medicinal Chemistry of Nucleic Acids, Eds L.-H. Zhang, L. Xi, J. Chattopadhyaya, Wiley, Hoboken, 2011, 456 pp.
S. Hironao, Yu. Iida, K. Ikawa, Yo. Sawama, Ya. Monguchi, Yu. Kitade, Yo. Maki, H. Inoue, K. Hirota, Molecules, 2012, 17, 6519; DOI: https://doi.org/10.3390/molecules17066519.
J. Shelton, X. Lu, J. A. Hollenbaugh, J. Hyun. Ch. Franck, A. Raymond, F. Schinazi, Chem. Rev., 2016, 23, 14379; DOI: https://doi.org/10.1021/acs.chemrev.6b00209.
A. A. Markovich, V. A. Gorbunova, Rus. Med. Zhurn. [Russ. Med. J.], 2006, No. 14, 1016 (in Russian).
K. Ohkura, T. Sugaoi, M. Takahashi, K.-i. Seki, Heterocycles, 2007, 72, 691; DOI: https://doi.org/10.3987/COM-06-S(K)54.
Y. Shibamoto, L. Zhou, H. Hatta, M. Mori, Si. Nishimoto, Jpn. J. Cancer Res., 2000, 91, 433; DOI: https://doi.org/10.1111/j.1349-7006.2000.tb00963.x.
C. Liu, J. Wang, Y. Xie, H. Chen, MedChemComm, 2017, 8, 385–389; DOI: https://doi.org/10.1039/C6MD00536E.
D. E. Metzler, Biochemistry: the Chemical Reactions of Living Cell, Elsevier, New York, 1980, Vol. 1, 940 pp.
I. B. Chernikova, S. L. Khursan, L. V. Spirikhin, M. S. Yunusov, Russ. Chem. Bull., 2013, 62, 2445; DOI: https://doi.org/10.1007/s11172-013-0354-0.
I. B. Chernikova, S. L. Khursan, L. V. Spirikhin, M. S. Yunusov, Chem. Heterocycl. Compd., 2015, 51, 568; DOI: https://doi.org/10.1007/s10593-015-1737-y.
I. B. Chernikova, M. S. Yunusov, Russ. Chem. Bull., 2020, 69, 2159; DOI: https://doi.org/10.1007/s11172-020-3015-0.
I. B. Chernikova, L. V. Spirikhin, M. F. Abdullin, M. S. Yunusov, Chem. Nat. Compd., 2017, 53, 1141; DOI: https://doi.org/10.1007/s10600-017-2218-6.
T. B. Lozeron, M. P. Gordon, T. Gabriel, W. Tautz, R. Duschinsky, Biochemistry, 1964, 3, 1844; DOI: https://doi.org/10.1021/bi00900a009.
S. A. Giller, R. A. Zhuk, M. Yu. Lidak, Dokl. Akad. Nauk SSSR [Dokl. USSR Acad. Sci.], 1967, 176, 332 (in Russian).
O. Miyashita, K. Matsumura, H. Shimadzu, N. Hashimoto, Chem. Pharm. Bull., 1981, 29, 3181. DOI: https://doi.org/10.1248/cpb.29.3181.
I. B. Chernikova, S. L. Khursan, M. Yu. Eropkin, M. S. Yunusov, Pharm. Chem. J., 2019, 53, 108; DOI: https://doi.org/10.1007/s11094-019-01962-9.
I. B. Chernikova, M. S. Yunusov, A. G. Mustaphin, Russ. Chem. Bull., 2020, 69, 114; DOI: https://doi.org/10.1007/s11172-020-2731-9.
R. B. Diasio, B. E. Harris, Clin. Pharmacokinet., 1989, 16, 215; DOI: https://doi.org/10.2165/00003088-198916040.
Y. Isobe, M. Tobe, Y. Inoue, M. Isobe, M. Tsuchiya, H. Hayashi, Bioorg. Med. Chem., 2003, 11, 4933; DOI: https://doi.org/10.1016/j.bmc.2003.09.012.
J. P. Henderson, J. Byun, J. Takeshita, J. W. Heinecke, J. Biol. Chem., 2003, 278, 23522; DOI: https://doi.org/10.1074/jbc.M303928200.
J. Takeshita, J. Byun, T. Q. Nhan, D. K. Pritchard, S. Pennathur, S. M. Schwartz, A. Chait, J. W. Heinecke, J. Biol. Chem., 2006, 281, 3096; DOI: https://doi.org/10.1074/jbc.M509236200.
O. S. Tee, S. Banerjee, Can. J. Chem., 1979, 57, 626; DOI: https://doi.org/10.1139/v79-101.
I. B. Chernikova, M. S. Yunusov, Izv. Ufimsk. Nauchn. Tsentra RAN [Bull. Ufa Sci. Center of RAS], 2020, No. 1, 45; DOI: https://doi.org/10.31040/2222-8349-2020-0-1-45-49 (in Russian).
I. B. Chernikova, M. S. Yunusov, Vestn. Bashkirsk. Un-ta [Bull. Bashkir. Univ.], 2021, 26, 605; DOI: https://doi.org/10.33184/bulletin-bsu-2021.3.11 (in Russian).
V. G. Kasradze, I. B. Ignatyeva, R. A. Khusnutdinov, K. Yu. Suponitskii, M. Yu. Antipin, M. S. Yunusov, Chem. Heterocycl. Compd., 2012, 48, 1018; DOI: https://doi.org/10.1007/s10593-012-1094-z.
I. B. Chernikova, L. V. Spirikhin, A. N. Lobov, M. S. Yunusov, Chem. Nat. Compd., 2017, 53, 714; DOI: https://doi.org/10.1007/s10600-017-2097-x.
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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 1–5, January, 2022.
The work was carried out in the framework of the Russian state assignment to the Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences “Synthesis of biologically active heterocyclic and terpenoid compounds” (Research theme AAAA-A20-120012090026-9, Registration number 0246-2019-0027).
No human or animal subjects were used in this research.
The authors declare no competing interests.
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Chernikova, I.B., Yunusov, M.S. Synthesis and properties of fluorinated uracils as promising drugs for medicine. Russ Chem Bull 71, 1–5 (2022). https://doi.org/10.1007/s11172-022-3370-0
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DOI: https://doi.org/10.1007/s11172-022-3370-0