Investigation of the complexation activity of pyrimidine-2,4(1H,3H)-dithione with Pd (II) and biological activity of the newly formed complex Investigation of the complexation activity of pyrimidine-2,4(1H,3H)-dithione
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This article describes the synthesis of a new Pd (II) complex by using 2,4-dithiouracil (2,4-DTu) as a starting reagent and its structure elucidation. The coordination compound was analyzed by several methods, including melting point determination, UV-Vis, 1H NMR-solution state, 1H- and 13C-NMR solid state, HSQC, 1H-1H COSY, ATR and Raman spectroscopy. The metal complex was formed by mixing aqueous solutions of metal salts with the ligand dissolved in DMSO and water, along with NaOH, in a metal-to-ligand-to-base ratio of 1:4:2. Furthermore, the compound's antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as yeasts, was assessed. It should be noted that for the first time a biologically active mixed ligand complex of Pd (II) with 2,4-DTu and 2-Tu was obtained. The ligands 2,4-DTu and 2-thiouracil (2-Tu) are bidentately coordinated to Pd(II) through a deprotonated nitrogen atom and the adjacent heteroatom—sulfur or oxygen, respectively. Tentative structures of the Pd(II) complexes are proposed, in which DMSO-h₆ and H₂O may be located either in the inner or outer coordination sphere. The new Pd(II) complex exhibited a coordination number of 6 or 4, respectively. The newly formed coordination compound of the corresponding pyrimidine-based ligands, i.e. 2,4-dithiouracil and 2-thiouracil, with Pd (II) demonstrated the strongest activity against Staphylococcus aureus. It, also, showed a significant improvement in its antifungal activity in comparison with free ligand 2,4-dithiouracil.
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Keller B., Sankreacha R., Rakovitch E., O’Brien P., Pignol J.P. A permanent breast seed implant as partial breast radiation therapy for early-stage patients: a comparison of palladium-103 and iodine-125 isotopes based on radiation safety considerations. International Journal of Radiation Oncology, Biology, Physics, 2005, 62(2): 358-365, https://doi.org/10.1016/j.ijrobp.2004.10.014
Khan B.T., Bhatt J., Najmuddin K., Shamsuddin S., Annapoorna K. Synthesis, antimicrobial, and antitumor activity of a series of palladium(II) mixed ligand complexes. Journal of Inorganic Biochemistry, 1991, 44(1): 55-63. https://doi.org/10.1016/0162-0134(91)80061-l
Kielhorn J., Melber C., Keller D., Mangelsdorfa I. Palladium - A review of exposure and effects to human health. International Journal of Hygiene and Environmental Health, 2002, 205(6): 417-432. https://doi.org/10.1078/1438-4639-00180
Kuzovlev A.S., Savinkina E.V., Chernyshev V.V., Grigoriev M.S., Volov A.N. Copper and palladium complexes with substituted pyrimidine-2-thiones and 2-thiouracils: Syntheses, spectral characterization and X-ray crystallographic study. Journal of Coordination Chemistry, 2015, 69(3): 508-521. https://doi.org/10.1080/00958972.2015.1123696
Lloyd J.R., Yong P., Macaskie L.E. Enzymatic recovery of elemental palladium by using sulfate-reducing bacteria. Applied and Environmental Microbiology, 1998, 64(11): 4607-9. https://doi.org/10.1128/AEM. Paisii Hilendarski 64.11.4607-4609.1998
Lusty J.R., Chan H.S.O., Peeling J. The Synthesis and characterisation of dithiouracil complexes of Rhodium (III), Iridium (III), Palladium (III) and Platinum (II). Transition Metal Chemistry, 1983, 8(12): 343-345. https://doi.org/10.1007/BF00618568
Lusty J. R., Peeling J., Abdel-Aal M.A. Complexes of 6-methyl-2-thiouracil with rhodium, iridium, platinum and palladium. Inorganic Chimistry Acta, 1981, 56: 21-26. https://doi.org/10.1016/S0020-1693(00)88542-4
Marinova P., Burdzhiev N., Blazheva D., Slavchev A. Synthesis and antibacterial studies of a new Au(III) complex with 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1h)-one. Molbank, 2024, 2024(2): M1827. https://doi.org/10.3390/M1827
Marinova P., Hristov M., Tsoneva S., Burdzhiev N., Blazheva D., Slavchev A., Varbanova E., Penchev P. Synthesis, characterization, and antibacterial studies of new Cu(II) and Pd(II) complexes with 6-methyl-2-thiouracil and 6-propyl-2-thiouracil. Applied Science, 2023, 13(24): 13150. https://doi.org/10.3390/app132413150
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Marinova P., Tsoneva S., Frenkeva M., Blazheva D., Slavchev A., Penchev P. New Cu (II), Pd (II) and Au (III) complexes with 2-thiouracil: Synthesis, Characteration and Antibacterial Studies, Russian Journal of General Chemistry, 2022, 92(8): 1578-1584. https://doi.org/10.1134/S1070363222080278
Marinova P.E., Tamahkyarova K.D. Synthesis and biological activities of some metal complexes of 2-thiouracil and its derivatives: A review. Compounds, 2024, 4(1): 186-213. https://doi.org/10.3390/compounds4010010
Marques M.P.M. Platinum and palladium polyamine complexes as anticancer agents: The structural factor. International Scholarly Research Notices, 2013, 2: 287353. https://doi.org/10.1155/2013/287353
Megremis S., Carey C.M. Corrosion and tarnish of dental alloys. In: Corrosion: Environments and Industries (S.D. Cramer, B.S. Covino Jr. Eds.), ASM Handbook, ASM International. 2006, pp. 891-921. ISBN 978-1-62708-184-9. https://doi.org/10.31399/asm.hb.v13c.a0004209
Novakov I.A., Orlinson B.S., Navrotskii M.B. Desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes and 2-haloacetonitriles. Russian Journal of Organic Chemistry, 2005, 41(4): 607-609. https://doi.org/10.1007/s11178-005-0211-1
Ólmez H., Yeşilel O.Z., Içbudak H. Thermal studies on solid complexes of uracil with some divalent transition metal ions. Journal of Thermal Analysis and Calorimetry, 2001, 63(1): 105-116. https://doi.org/10.1023/A:1010184319600
Rapp R.P. Changing strategies for the management of invasive fungal infections. Pharmacotherapy: The Journal of Human Pharmacology and Drug Therapy, 2004, 24(2P2): 4S-28S. https://doi.org/10.1592/phco.24.3.4S.33151
Ravindra K., Bencs L., van Grieken R. Platinum group elements in the environment and their health risk. Science of the Total Environment, 2004, 318(1-3): 1-43. https://doi.org/10.1016/S0048-9697(03)00372-3
Remoudaki E, Tsezos M, Hatzikioseyian A, Karakoussis Y. Mechanism of palladium biosorption by microbial biomass. The effects of metal ionic speciation and solution co-ions. Process Metallurgy, 1999, 9: 449-62. https://doi.org/10.1016/S1572-4409(99)80134-5
Rushforth R. Palladium in restorative dentistry. Platinum Metals Review, 2004, 48(1): 30-31. https://doi.org/10.1595/003214004X4813031
Scovell W.H. Kinetics and mechanism of methyl transfer from methylcobalamin to palladium (II). Journal of the American Chemical Society, 1974, 96(5): 3451-3456. https://doi.org/10.1021/JA00818A018
Shaheen F., Badashah A., Gielen M., Marchio L., de Vos D., Khosa M.K. Synthesis, characterization and in vitro cytotox-icity of homobimetallic complexes of palladium (II) with 2-thiouracil ligands. Crystal structure of [Pd2(TU)(PPh3)3Cl2]. Applied Organometallic Chemistry, 2007, 21(8): 626-632. https://doi.org/10.1002/aoc.1227
Srivastava A. Palladium metal complexes as platforms for anti tumor therapy. Journal of Xi'an Shiyou University, 2021, 17(6): 1716-27. Available at: https://www.xisdxjxsu.asia/V17I6-27.pdf
Szłyk E., Grodzicki A., Pazderski L., Wojtczak A., Chatłas J., Wrzeszcz G., Sitkowski J., Kamieński B. Palladium (II) chloride complexes with 1,2,4-triazolo[1,5-a] pyrimidines: X-ray, 15N-1H NMR and 15N CP MAS studies. Journal of the Chemical Society, Dalton Transactions, 2000, 6: 867-872. https://doi.org/10.1039/A908469J
Wataha J.C., Shor K. Palladium alloys for biomedical devices. Expert review of medical devices, 2010, 7(4): 489-501. https://doi.org/10.1586/erd.10.25
Weiss J.T, Dawson J.C., Macleod K.G., Rybski W., Fraser C., Torres-Sanchez C., Patton E.E., Bradley M., Carragher N.O. Unciti-Broceta A. Extracellular palladium-catalysed dealkylation of 5-fluoro-1-propargyl-uracil as a bioorthogonally activated prodrug approach. Nature Communications, 2014, 5(2): 3277. https://doi.org/10.1038/n Paisii Hilendarski comms4277
Wu S., Song R., Liu T., Li C. Antifungal therapy: Novel drug delivery strategies driven by new targets. Advanced Drug Delivery Reviews 2023, 199(8): 114967. https://doi.org/10.1016/j.addr.2023.114967
Yong P, Rowson N.A, Farr J.P.G, Harris I.R, Macaskie L.E. Bioaccumulation of palladium by Desulfovibrio desulfuricans. Journal of Chemical Technology and Biotechnology, 2002, 77(5): 593-601. https://doi.org/10.1002/jctb.606
Zalevskaya O.A., Gur’eva Yа. A., Kutchin A.V. Palladium complexes as promising antimicrobial agents. Russian Chemical Reviews, 2023, 92(9): RCR5093. https://doi.org/10.59761/RCR5093
Zhang X., Cheng G., Xing X., Liu J., Cheng Y., Ye T., Wang Q., Xiao X., Li Z., Deng H. Near-infrared light triggered porous AuPd alloy nanoparticles to produce mild localized heat to accelerate bone regeneration. The Journal of Physical Chemistry Letters, 2019, 10(15): 4185-4191. https://doi.org/10.1021/acs.jpclett.9b01735
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How to Cite
MARINOVA, Petya et al.
Investigation of the complexation activity of pyrimidine-2,4(1H,3H)-dithione with Pd (II) and biological activity of the newly formed complex.
Food Science and Applied Biotechnology, [S.l.], v. 9, n. 1, p. 173-183, mar. 2026.
ISSN 2603-3380.
Available at: <https://www.ijfsab.com/index.php/fsab/article/view/532>. Date accessed: 19 may 2026.
doi: https://doi.org/10.30721/fsab2026.v9.i1.532.