Novel tetrazole PtII and PdII complexes with enhanced water solubility: synthesis, structural characterization and evaluation of antiproliferative activity
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Tatiyana V. Serebryanskaya
, Alexander S. Lyakhov , Ludmila S. Ivashkevich , Yuri V. Grigoriev , Andreii S. Kritchenkov , Victor N. Khrustalev , Alexander G. Tskhovrebovand Oleg A. Ivashkevich
Abstract
Novel platinum(II) and palladium(II) chlorido complexes with tetrazole derivatives 1-(2-hydroxyethyl)tetrazole (het) and 1-[tris(hydroxymethyl)methyl]tetrazole (thm), viz. cis-[Pt(het)2Cl2], trans-[Pt(het)2Cl2], trans-[Pt(thm)2Cl2], trans-[Pd(het)2Cl2], and trans-[Pd(thm)2Cl2], were synthesized. The compounds were characterized by elemental and high-resolution electrospray ionization (HRESI) mass spectrometry, high-performance liquid chromatography (HPLC), 1H, 13C and 195Pt nuclear magnetic resonance (NMR) spectroscopy, thermal analyses, and Infrared (IR) spectroscopy. Molecular and crystal structures of trans-[PdL2Cl2] and trans-[PtL2Cl2] (L = het, thm) were established by single-crystal X-ray analysis. The complex cis-[Pt(het)2Cl2] was found to undergo cis–to–trans isomerization upon heating in acetonitrile solution and in the solid state. The synthesized complexes show rather high water solubility lying in the range of 2–10 mg/L.
Funding source: Russian Foundation for Basic Research
Award Identifier / Grant number: 20-53-00006
Funding source: Belarusian Foundation for Fundamental Research
Award Identifier / Grant number: X20P-066
Award Identifier / Grant number: 075-03-2020-223 (FSSF-2020-0017)
Acknowledgments
Funding for this research was provided by Russian Foundation for Basic Research (project number 20-53-00006) and Belarusian Foundation for Fundamental Research (grant X20P-066). We acknowledge the RUDN University Program 5-100. Funding for this research was provided by Ministry of Science and Higher Education of the Russian Federation (award no. 075-03-2020-223 (FSSF-2020-0017)).
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: Funding for this research was provided by Russian Foundation for Basic Research (project number 20-53-00006) and Belarusian Foundation for Fundamental Research (grant X20P-066). We acknowledge the RUDN University Program 5-100. Funding for this research was provided by Ministry of Science and Higher Education of the Russian Federation (award no. 075-03-2020-223 (FSSF-2020-0017)).
Competing interests: The authors declare no conflicts of interest regarding this article.
References
1. Komeda, S., Lin, Y. L., Chikuma, M. A tetrazolato-bridged dinuclear platinum(II) complex exhibits markedly high in vivo antitumor activity against pancreatic cancer. ChemMedChem 2011, 6, 987–990; https://doi.org/10.1002/cmdc.201100141.Search in Google Scholar PubMed
2. Komeda, S., Takayama, H., Suzuki, T., Odani, A., Yamori, T., Chikuma, M. Synthesis of antitumor azolato-bridged dinuclear platinum(II) complexes with in vivo antitumor efficacy and unique in vitro cytotoxicity profiles. Metallomics 2013, 5, 461–468; https://doi.org/10.1039/c3mt00040k.Search in Google Scholar PubMed
3. Serebryanskaya, T. V., Yung, T., Bogdanov, A. A., Shchebet, A., Johnsen, S. A., Lyakhov, A. S., Ivashkevich, L. S., Ibrahimava, Z. A., Garbuzenco, T. S., Kolesnikova, T. S., Melnova, N. I., Gaponik, P. N., Ivashkevich, O. A. Synthesis, characterization, and biological evaluation of new tetrazole-based platinum(II) and palladium(II) chlorido complexes - potent cisplatin analogues and their trans isomers. J. Inorg. Biochem. 2013, 120, 44–53; https://doi.org/10.1016/j.jinorgbio.2012.12.001.Search in Google Scholar PubMed
4. Serebryanskaya, T. V., Lyakhov, A. S., Ivashkevich, L. S., Schur, J., Frias, C., Prokop, A., Ott, I. Gold(I) thiotetrazolates as thioredoxin reductase inhibitors and antiproliferative agents. Dalton Trans. 2014, 44, 1161–1169; https://doi.org/10.1039/C4DT03105A.Search in Google Scholar
5. Popova, E. A., Serebryanskaya, T. V., Selivanov, S. I., Haukka, M., Panikorovsky, T. L., Gurzhiy, V. V., Ott, I., Trifonov, R. E., Kukushkin, V. Y. Water-soluble platinum(II) complexes featuring 2-alkyl-2H-tetrazol-5-ylacetic acids: synthesis, characterization, and antiproliferative activity. Eur. J. Inorg. Chem. 2016, 2016, 4659–4667; https://doi.org/10.1002/ejic.201600626.Search in Google Scholar
6. Yang, J., Xu, Y., Jiang, M., Zou, D., Yang, G., Shen, L., Zou, J. Photochemical property of two Ru(II) compounds based on 5-(2-pyrazinyl)tetrazole for cancer phototherapy by changing auxiliary ligand. J. Inorg. Biochem. 2019, 193, 124–129; https://doi.org/10.1016/j.jinorgbio.2019.01.015.Search in Google Scholar PubMed
7. Caporale, C., Ranieri, A. M., Paternoster, S., Bader, C. A., Falasca, M., Plush, S. E., Brooks, D. A., Stagni, S., Massi, M. Photophysical and biological properties of iridium tetrazolato complexes functionalised with fatty acid chains. Inorganics 2020, 8; https://doi.org/10.3390/inorganics8040023.Search in Google Scholar
8. Sorvina, A., Bader, C. A., Darby, J. R. T., Lock, M. C., Soo, J. Y., Johnson, I. R. D., Caporale, C., Voelcker, N. H., Stagni, S., Massi, M., Morrison, J. L., Plush, S. E., Brooks, D. A. Mitochondrial imaging in live or fixed tissues using a luminescent iridium complex. Sci. Rep. 2018, 8; https://doi.org/10.1038/s41598-018-24672-w.Search in Google Scholar PubMed PubMed Central
9. Caporale, C., Bader, C. A., Sorvina, A., MaGee, K. D. M., Skelton, B. W., Gillam, T. A., Wright, P. J., Raiteri, P., Stagni, S., Morrison, J. L., Plush, S. E., Brooks, D. A., Massi, M. Investigating intracellular localisation and cytotoxicity trends for neutral and cationic iridium tetrazolato complexes in live cells. Chem. Eur J. 2017, 23, 15666–15679; https://doi.org/10.1002/chem.201701352.Search in Google Scholar PubMed
10. Bader, C. A., Sorvina, A., Simpson, P. V., Wright, P. J., Stagni, S., Plush, S. E., Massi, M., Brooks, D. A. Imaging nuclear, endoplasmic reticulum and plasma membrane events in real time. FEBS Lett. 2016, 590, 3051–3060; https://doi.org/10.1002/1873-3468.12365.Search in Google Scholar PubMed
11. Voitekhovich, S. V., Serebryanskaya, T. V., Lyakhov, A. S., Gaponik, P. N., Ivashkevich, O. A. Copper(II), palladium(II) and platinum(II) chloride complexes with 5-amino-2-tert-butyltetrazole: synthesis, characterization and cytotoxicity. Polyhedron 2009, 28, 3614–3620; https://doi.org/10.1016/j.poly.2009.07.054.Search in Google Scholar
12. Ivashkevich, L. S., Serebryanskaya, T. V., Lyakhov, A. S., Gaponik, P. N. An X-ray powder diffraction study of cis-dichloridobis(2-methyl-2H-tetrazol-5-amine-ΚN(4))platinum(II), a tetrazole-containing analogue of cisplatin. Acta Crystallogr. C 2011, 67, m195–m198; https://doi.org/10.1107/s0108270111018063.Search in Google Scholar PubMed
13. Stetsenko, A. I., Presnov, M. A., Konovalova, A. L. The chemistry of antitumour platinum complexes. Russ. Chem. Rev. 1981, 50, 353–367; https://doi.org/10.1070/rc1981v050n04abeh002605.Search in Google Scholar
14. Mikhaylov, V. N., Sorokoumov, V. N., Liakhov, D. M., Tskhovrebov, A. G., Balova, I. A. Polystyrene-supported acyclic diaminocarbene palladium complexes in Sonogashira cross-coupling: stability vs. catalytic activity. Catalysts 2018, 8, 141; https://doi.org/10.3390/catal8040141.Search in Google Scholar
15. Aromí, G., Barrios, L. A., Roubeau, O., Gamez, P. Triazoles and tetrazoles: prime ligands to generate remarkable coordination materials. Coord. Chem. Rev. 2011, 255, 485–546; https://doi.org/10.1016/j.ccr.2010.10.038.Search in Google Scholar
16. Shannon, R. D. Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides. Acta Crystallogr. A 1976, 32, 751–767; https://doi.org/10.1107/s0567739476001551.Search in Google Scholar
17. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr. D 2009, 65, 148–155; https://doi.org/10.1107/s090744490804362x.Search in Google Scholar
18. Protas, A. V., Popova, E. A., Suslonov, V. V., Trifonov, R. E. Novel water soluble palladium(II) complexes featuring tetrazolylacetic acids and their esters. Polyhedron 2017, 124, 131–138; https://doi.org/10.1016/j.poly.2016.12.032.Search in Google Scholar
19. Popova, E. A., Protas, A. V., Mukhametshina, A. V., Ovsepyan, G. K., Suezov, R. V., Eremin, A. V., Stepchenkova, E. I., Tarakhovskaya, E. R., Fonin, A. V., Starova, G. L., Mikolaichuk, O. V., Porozov, Y. B., Gureev, M. A., Trifonov, R. E. Synthesis, biological evaluation and molecular docking studies on the DNA and BSA binding interactions of palladium(II) and platinum(II) complexes featuring amides of tetrazol-1-yl- and tetrazol-5-ylacetic acids. Polyhedron 2019, 158, 36–46; https://doi.org/10.1016/j.poly.2018.10.038.Search in Google Scholar
20. Voitekhovich, S. V., Serebryanskaya, T. V., Gaponik, P. N., Ivashkevich, L. S., Lyakhov, A. S., Ivashkevich, O. A. Preparation and characterization of the first coordination compounds of tetrazol-2-ylacetic acid. Inorg. Chem. Commun. 2010, 13, 949–951; https://doi.org/10.1016/j.inoche.2010.05.003.Search in Google Scholar
21. Khripun, A. V., Selivanov, S. I., Kukushkin, V. Y., Haukka, M. Hydrogen bonding patterns in pyrazole Pt(II- and IV) chloride complexes. Inorg. Chim. Acta. 2006, 359, 320–326; https://doi.org/10.1016/j.ica.2005.08.017.Search in Google Scholar
22. Khripun, A. V., Haukka, M., Kukushkin, V. Y. Directed synthesis of isomerically pure platinum pyrazole complexes. Russ. Chem. Bull. 2006, 55, 247–255; https://doi.org/10.1007/s11172-006-0245-8.Search in Google Scholar
23. MacDonald, F. M., Sadler, P. J. Studies of the cis-trans isomerism of some square-planar platinum(II) nitroimidazole complexes. Polyhedron 1991, 10, 1443–1448; https://doi.org/10.1016/s0277-5387(00)81281-4.Search in Google Scholar
24. Anderson, C., Beauchamp, A. Synthesis of the tetrachlorobis(5-nitroimidazole)ruthenium(III) anion and solution chemistry in water and methanol. Inorg. Chim. Acta. 1995, 233, 33–41; https://doi.org/10.1016/0020-1693(94)04400-p.Search in Google Scholar
25. Lyakhov, A. S., Mosalkova, A. P., Degtyarik, M. M., Ivashkevich, L. S., Gaponik, P. N. Trans-dichloridotetrakis-[1-(2-hydroxy-ethyl)-1H-tetrazole-ΚN 4]cobalt(II). Acta Crystallogr. Sect. E Struct. Rep. Online 2009, 65, m1397–m1398; https://doi.org/10.1107/s1600536809042263.Search in Google Scholar
26. Degtyarik, M. M., Gaponik, P. N., Naumenko, V. N., Lesnikovich, A. I., Nikanovich, M. V. Infrared spectroscopic study of copper(II) complexes with N-substituted tetrazoles. Spectrochim. Acta Part A Mol. Spectrosc. 1987, 43, 349–353; https://doi.org/10.1016/0584-8539(87)80116-2.Search in Google Scholar
27. Chen, Y., Guo, Z., Parsons, S., Sadler, P. J. Stereospecific and kinetic control over the hydrolysis of a sterically hindered platinum picoline anticancer complex. Chem. Eur J. 1998, 4, 672–676; https://doi.org/10.1002/(sici)1521-3765(19980416)4:4<672::aid-chem672>3.0.co;2-8.10.1002/(SICI)1521-3765(19980416)4:4<672::AID-CHEM672>3.0.CO;2-8Search in Google Scholar
28. Holford, J. Novel sterically hindered platinum complex AMD473 Pt. Br. J. Canc. 1998, 77, 366–373; https://doi.org/10.1038/bjc.1998.59.Search in Google Scholar
29. Gaponik, P. N., Karavai, V. P. Synthesis and properties of 1-(2-hydroxyethyl)tetrazole. Chem. Heterocycl. Compd. 1985, 21, 1172–1174; https://doi.org/10.1007/bf00515264.Search in Google Scholar
30. Gaponik, P. N., Karavai, V. P., Grigor’ev, Y. V. Synthesis of 1-substituted tetrazoles by heterocyclization of primary amines, orthoformic ester, and sodium azide. Chem. Heterocycl. Compd. 1985, 21, 1255–1258; https://doi.org/10.1007/bf00515224.Search in Google Scholar
31. Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Spagna, R. SIR2004: an improved tool for crystal structure determination and refinement. J. Appl. Crystallogr. 2005, 38, 381–388; https://doi.org/10.1107/s002188980403225x.Search in Google Scholar
32. Sheldrick, G. M. A. Short history of SHELX. Acta Crystallogr. A 2008, 64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar
33. Farrugia, L. J. ORTEP-3 for Windows - a version of ORTEP-III with a graphical user interface (GUI). J. Appl. Crystallogr. 1997, 30, 565; https://doi.org/10.1107/s0021889897003117.Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2020-0082).
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