vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/2227-2925-2021-11-4-651-662vuzbiochemi-715Research ArticleФИЗИКО-ХИМИЧЕСКАЯ БИОЛОГИЯPHYSICOCHEMICAL BIOLOGYСинтез, антимикробная и антифунгицидная активность комплексов платины (II) и палладия (II)Platinum (II) and palladium (II) complexes: synthesis, antimicrobial and antifungal activityhttps://orcid.org/0000-0003-1885-2060СалищеваО. В.SalishchevaO. V.

Олеся Владимировна Салищева, к.х.н., доцент

650000, г. Кемерово, ул. Красная, 6

Olesya V. Salishcheva, Cand. Sci. (Chemistry), Associate Professor

6, Krasnaya Str., Kemerovo, 650000

salishchevaov@mail.ruhttps://orcid.org/0000-0002-5630-3196ПросековА. Ю.ProsekovA. Yu.

Александр Юрьевич Просеков, д.т.н., член-корреспондент РАН, ректор

650000, г. Кемерово, ул. Красная, 6

Alexander Yu. Prosekov, Dr. Sci. (Engineering), Professor, Corresponding Member of the Russian Academy of Sciences, Rectior

6, Krasnaya Str., Kemerovo, 650000

rector@kemsu.ruhttps://orcid.org/0000-0002-9874-5355МолдагуловаН. Е.MoldagulovaN. E.

Наталья Евгеньевна Молдагулова, к.х.н., доцент

650000, г. Кемерово, ул. Красная, 6

Natalya E. Moldagulova, Cand. Sci. (Chemistry), Associate Professor

6, Krasnaya Str., Kemerovo, 650000

olimpkemtipp@mail.ruhttps://orcid.org/0000-0001-7226-4732ПугачевВ. М.PugachevV. M.

Валерий Михайлович Пугачев, к.х.н., доцент

650000, г. Кемерово, ул. Красная, 6

Valery M. Pugachev, Cand. Sci. (Chemistry), Associate Professor

6, Krasnaya Str., Kemerovo, 650000

vm1707@mail.ruКемеровский государственный университетРоссияKemerovo State UniversityRussian Federation202110012022114651662Copyright © Салищева О.В., Просеков А.Ю., Молдагулова Н.Е., Пугачев В.М., 20222022Салищева О.В., Просеков А.Ю., Молдагулова Н.Е., Пугачев В.М.Salishcheva O.V., Prosekov A.Y., Moldagulova N.E., Pugachev V.M.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vuzbiochemi.elpub.ru/jour/article/view/715

Целью работы являлись синтез и исследование биологической активности моноядерных и биядерных комплексов платины (II) и палладия (II), содержащих концевые и мостиковые нитрит-лиганды, в отношении тест-культур Bacillus subtilis B4647, Aspergillus brasiliensis (niger) F679, Pseudomonas aeruginosa B8243, Escherichia сoli. Путем взаимодействия моноядерных комплексов платины (II) и палладия (II) синтезированы димерные комплексы с нитритными лигандами. Состав и строение комплексов были установлены методами элементного анализа, кондуктометрии, потенциометрии, криоскопии, ИК-спектроскопии, рентгенофазового и рентгенофлуоресцентного анализа. Установлен способ координации нитритных лигандов с центральным атомом. Антимикробные и противофунгицидные свойства оценивали по способности синтезированных комплексов подавлять жизнедеятельность бактерий и грибов методом диффузии в агаре и методом разведения в пробирке. Значения минимальной ингибирующей концентрации и минимальной бактерицидной концентрации комплексов, при которых наблюдается подавление видимого роста микроорганизмов и грибов и бактерицидный эффект действия комплексов, варьировались в диапазоне 62,5–125 мкмоль/дм3. Полученные результаты показали высокую активность биядерного комплекса палладия (II) неэлектролитного типа и биядерного комплекса платины (II) катионного типа. Биядерные комплексы платины и палладия в отличие от моноядерных проявляют более высокую антибактериальную активность. Эффективность антибактериального действия комплекса-неэлектролита палладия в отношении бактерий Bacillus subtilis, Escherichia coli и грибов Aspergillus niger была более выраженной. Исключение составляет антимикробная активность комплекса палладия в отношении Pseudomonas aeruginosa, которая сопоставима с активностью катионного биядерного комплекса платины. Изменяя структуру комплекса, состав и заряд внутренней сферы, число координационных центров, природу и дентатность лигандов, можно достичь более высокого токсического эффекта комплексов в отношении бактерий и грибков.

The study aims to synthesize and examine the biological activity of mono- and binuclear platinum (II) and palladium (II) complexes containing terminal and bridging nitrite ligands against the test cultures of Bacillus subtilis B4647, Aspergillus brasiliensis (niger) F679, Pseudomonas aeruginosa B8243, and Escherichia coli. Through the interaction of mononuclear platinum (II) and palladium (II) complexes, dimeric complexes having nitrite ligands were synthesized. The composition and structure of these complexes were established using elemental analysis, conductometry, potentiometry, cryoscopy, infrared spectroscopy, X-ray diffraction analysis, and X-ray fluorescence analysis. A way to coordinate nitrite ligands with the central atom was established. Antimicrobial and antifungal properties were evaluated according to the capability of the synthesized complexes to inhibit the activity of bacteria and fungi via diffusion in agar and in vitro dilution. The minimum inhibitory and bactericidal concentrations of the complexes suppressing the visible growth of microorganisms and fungi, as well as exhibiting their bactericidal effect, ranged from 62.5–125 μmol/dm3. The obtained results revealed a high activity of the palladium (II) binuclear complex of the non-electrolytic type and the platinum (II) binuclear complex of the cationic type. Unlike mononuclear complexes, palladium and platinum binuclear complexes demonstrate higher antibacterial activity. Antibacterial effectiveness exhibited by the palladium complex of the non-electrolytic type against bacteria Bacillus subtilis and Escherichia coli, as well as fungi Aspergillus niger, is more pronounced. The only exception is the antimicrobial activity of the palladium complex against Pseudomonas aeruginosa, which is comparable to that of the binuclear platinum complex of the cationic type. By changing the structure of the complex, the composition and charge of the inner sphere, the number of coordination centers, as well as the nature and denticity of ligands, it is possible to achieve a higher toxic effect of the complexes against bacteria and fungi.

комплексы платиныкомплексы палладиянитритные лигандыантимикробные свойстваplatinum complexespalladium complexesnitrite ligandsantimicrobial propertiesReferencesSalishcheva O. V., Prosekov A. Yu. Antimicrobial activity of mono- and polynuclear platinum and palladium complexes // Foods and Raw Materials. 2020. Vol. 8, no. 2. P. 298–311. https://doi.org/10.21603/2308-4057-2020-2-298-311.Salishcheva O. V., Prosekov A. Yu. Antimicrobial activity of mono- and polynuclear platinum and palladium complexes. Foods and Raw Materials. 2020;8(2):298–311. https://doi.org/10.21603/2308-4057-2020-2-298-311.Солодухина О. А., Верлан Н. В., Кочки на Е. О., Рожкова Н. Ю. Данные мониторинга безопасности антибактериальных препаратов в клинической практике // Известия вузов. Прикладная химия и биотехнология. 2018. Т. 8. N 2. С. 117–124. https://doi.org/0.21285/2227-2925-2018-8-2-117-124.Solodukhina O. A., Verlan N. V., Kochkina E. O., Rоzhkova N. U. Данные мониторинга безопасности антибактериальных препаратов в клинической практике. Izvestiya Vuzov. Prikladnaya Khimiya i Biotekhnologiya = Proceedings of Universities. Applied Chemistry and Biotechnology. 2018;8(2):117–124. (In Russian). https://doi.org/0.21285/2227-2925-2018-8-2-117-124.Фролова Ю. В., Кирш И. А., Безнаева О. В., Помогова Д. А., Тихомиров А. А. Создание упаковочных полимерных материалов с антимикробными свойствами // Известия вузов. Прикладная химия и биотехнология. 2017. Т. 7, N 3. С. 145–152. https://doi.org/10.21285/2227-2925-2017-7-3-145-152.Frolova Y. V., Kirsh I. A., Beznaeva O. V., Pomogova D. A., Tikhomirov A. A. Creation of polymeric packaging materials with antimicrobial properties. Izvestia Vuzov. Prikladnaya Khimia i Biotekhnologiya = Proceedings of Universities. Applied Chemistry and Biotechnology. 2017;7(3):145–152. (In Russian). https://doi.org/10/21285/2227-2925-2017-7-3-145-15Прозорова Г. Ф., Поздняков А. С., Иванова А. А., Емельянов А. И., Фадеева Т. В., Ермакова Т. Г. Биологическая активность полимерного серебросодержащего нанокомпозита // Известия вузов. Прикладная химия и биотехнология. 2018. Т. 8, N 2. С. 63–68. https://doi.org/10.21285/2227-2925-2018-8-2-63–68.Prozorova G. F., Pozdnyakov A. S., Ivanova A. A., Emel’yanov A. I., Fadeeva T. V., Ermakova T. G. The biological activity of polymer silver-containing nanocomposites. Izvestiya Vuzov. Prikladnaya Khimiya I Biotekhnologiya = Proceedings of Universities. Applied Chemistry and Biotechnology. 2018;8(2):63–68. (In Russian). https://doi.org/10.21285/2227-2925-2018-8-2-63-68.Прозорова Г. Ф., Коржова С. А., Мазяр И. В., Беловежец Л. А., Кузнецова Н. П., Емельянов А. И. [и др.]. Синтез и свойства новых сополимер-Ag(0) нанокомпозитов // Известия вузов. Прикладная химия и биотехнология. 2019. Т. 9, N 1. С. 22–27. https://doi.org/10.21285/2227-2925-2019-9-1-22-27.Prozorova G. F., Korzhova S. A., Mazyar I. V., Belovezhets L. A., Kuznetsova N. P., Emel'yanov A. I., et al. Synthesis and properties of novel copoly mer-Ag(0) nanocomposites. Izvestiya Vuzov. Prikladnaya Khimiya i Biotekhnologiya = Proceedings of Universities. Applied Chemistry and Biotechnology. 2018;9(1):22–27. (In Russian). https://doi.org/10.21285/2227-2925-2019-9-1-22-27.Fanelli M., Formica M., Fusi V., Giorgi L., Micheloni M., Paoli P. New trends in platinum and palladium complexes as antineoplastic agents // Coordination Chemistry Reviews. 2016. Vol. 310. P. 41–79. https://doi.org/10.1016/j.ccr.2015.11.004.Fanelli M., Formica M., Fusi V., Giorgi L., Micheloni M., Paoli P. New trends in platinum and palladium complexes as antineoplastic agents. Coordination Chemistry Reviews. 2016;310:41–79. https://doi.org/10.1016/j.ccr.2015.11.004.Sabounchei S. J., Shahriary P., Gholiee Y., Salehzadeh S., Khavasi H. R., Chehregani A. Platinum and palladium complexes with 5-methyl-5-(2-pyridyl)-2,4- imidazolidenedione: Synthesis, crystal and molecular structure, theoretical study, and pharmacological investigation // Inorganica Chimica Acta. 2014. Vol. 409(B). P. 265–275. https://doi.org/10.1016/j.ica.2013.09.051.Sabounchei S. J., Shahriary P., Gholiee Y., Salehzadeh S., Khavasi H. R., Chehregani A. Platinum and palladium complexes with 5-methyl-5-(2-pyridyl)-2,4- imidazolidenedione: Synthesis, crystal and molecular structure, theoretical study, and pharmacological investigation. Inorganica Chimica Acta. 2014;409(B):265–275. https://doi.org/10.1016/j.ica.2013.09.051.Stojković D. L., Jevtić V. V., Vuković N., Vukić M., Čanović P., Zarić M.M., et al. Synthesis, characterization, antimicrobial and antitumor reactivity of new palladium (II) complexes with methionine and tryptophane coumarine derivatives // Journal of Molecular Structure. 2018. Vol. 1157. P. 425–433. https://doi.org/10.1016/j.molstruc.2017.12.095.Stojković D. L., Jevtić V. V., Vuković N., Vukić M., Čanović P., Zarić M.M., et al. Synthesis, characterization, antimicrobial and antitumor reacti vity of new palladium (II) complexes with methionine and tryptophane coumarine derivatives. Journal of Molecular Structure. 2018;1157:425–433. https://doi.org/10.1016/j.molstruc.2017.12.095.Rani S., Kumar S., Chandra S. Spectroscopic and biological approach in the characterization of a novel 14-membered [N4] macrocyclic ligand and its Palladium (II), Platinum (II), Ruthenium (III) and Iridium (III) complexes // Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014. Vol. 118. P. 244–250. https://doi.org/10.1016/j.saa.2013.08.079.Rani S., Kumar S., Chandra S. Spectroscopic and biological approach in the characterization of a novel 14-membered [N4] macrocyclic ligand and its Palladium (II), Platinum (II), Ruthenium (III) and Iridium (III) complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014;118:244–250. https://doi.org/10.1016/j.saa.2013.08.079.Zhang X., Liu D., Lv F., Yu B., Shen Y., Cong H. Recent advances in ruthenium and platinum based supramolecular coordination complexes for antitumor therapy // Colloids Surf B Biointerfaces. 2019. Vol. 182. P. 110373. https://doi.org/10.1016/j.colsurfb.2019.110373.Zhang X., Liu D., Lv F., Yu B., Shen Y., Cong H. Recent advances in ruthenium and platinum based supramolecular coordination complexes for antitumor therapy. Colloids Surf B Biointerfaces. 2019;182:110373. https://doi.org/10.1016/j.colsurfb.2019.110373.Bakalova A. G., Buyukliev R. T., Nikolova R. P., Shivachev B. L., Mihaylova R. A., Konstantinov S.M. Synthesis, Spectroscopic properties, crystal structure and biological evaluation of new platinum complexes with 5-methyl-5-(2-thiomethyl)ethyl hydantoin // Anti-Cancer Agents in Medicinal Chemistry. 2019. Vol. 19, no. 10. P. 1243–1252. https://doi.org/10.2174/1871520619666190214103345.Bakalova A. G., Buyukliev R. T., Nikolova R. P., Shivachev B. L., Mihaylova R. A., Konstantinov S. M. Synthesis, Spectroscopic properties, crystal structure and biological evaluation of new platinum complexes with 5-methyl-5-(2-thiomethyl)ethyl hydantoin. Anti-Cancer Agents in Medicinal Chemistry. 2019;19(10):1243–1252. https://doi.org/10.2174/1871520619666190214103345.Radić G. P., Glodović V. V., Ratković Z. R., Garcia-Granda S., Roces F. L., Menéndez T. L., et al. Synthesis, characterization and antimicrobial activity of novel platinum (IV) and palladium (II) complexes with meso-1,2-diphenyl-ethylenediamine- N,N'-di-3-propanoic acid – Crystal structure of H2-1,2-dpheddp·2HCl·H2O // Journal of Molecular Structure. 2012. Vol. 1029. P. 180–186. https://doi.org/10.1016/j.molstruc.2012.07.007Radić G. P., Glodović V. V., Ratković Z. R., Garcia-Granda S., Roces F. L., Menéndez T. L., et al. Synthesis, characterization and antimicrobial activity of novel platinum (IV) and palladium (II) complexes with meso-1,2-diphenyl-ethylenediamine- N,N'-di-3-propanoic acid – Crystal structure of H2-1,2-dpheddp·2HCl·H2O. Journal of Molecular Structure. 2012;1029:180–186. https://doi.org/10.1016/j.molstruc.2012.07.007Lunagariya M. V., Thakor K. P., Waghe la B. N., Pathak C., Patel M. N. Design, synthesis, pharmacological evaluation and DNA interaction studies of binuclear Pt(II) complexes with pyrazolo[1,5-a]pyrimidine scaffold // Applied Organometallic Chemistry. 2018. Vol. 32, no. 4. P. e4222. https://doi.org/10.1002/aoc.4222.Lunagariya M. V., Thakor K. P., Waghela B. N., Pathak C., Patel M. N. Design, synthesis, pharmacological evaluation and DNA interaction studies of binuclear Pt(II) complexes with pyrazolo[1,5-a]pyrimidine scaffold. Applied Organometallic Chemistry. 2018;32(4):e4222. https://doi.org/10.1002/aoc.4222.Corduneanu O., Paquim A. M. C., Diculescu V., Fiuza S., Marques M. P. M., Oliveira-Brett A. M. DNA Interaction with Palladium Chelates of Biogenic Polyamines Using Atomic Force Microscopy and Voltammetric Characterization // Analytical Chemistry. 2010. Vol. 82, no. 4. P. 1245–1252. https://doi.org/10.1021/ac902127d.Corduneanu O., Paquim A. M. C., Diculescu V., Fiuza S., Marques M. P. M., Oliveira-Brett A. M. DNA Interaction with Palladium Chelates of Biogenic Poly-amines Using Atomic Force Microscopy and Voltammetric Characterization. Analytical Chemistry. 2010;82(4):1245– 1252. https://doi.org/10.1021/ac902127d.Juribašić M., Molčanov K., Kojić-Prodić B., Bellotto L., Kralj M., Zani F., et al. Palladium (II) complexes of quinolinylaminophosphonates: Synthesis, structural characterization, antitumor and antimicrobial activity // Journal of Inorganic Biochemistry. 2011. Vol. 105, no. 6. P. 867–879. https://doi.org/10.1016/j.jinorgbio.2011.03.011.Juribašić M., Molčanov K., Kojić-Prodić B., Bellotto L., Kralj M., Zani F., et al. Palladium (II) complexes of quinolinylaminophosphonates: Synthesis, structural characterization, antitumor and antimicrobial activity. Journal of Inorganic Bio chemistry. 2011;105(6):867–879. https://doi.org/10.1016/j.jinorgbio.2011.03.011.Potočňák I., Drweesh S. A., Farkasová V., Lüköová A., Sabolová D., Radojević I. D., et al. Low-dimensional compounds containing bioactive ligands. Part IX: Synthesis, structures, spectra, in vitro antimicrobial and anti-tumor activities and DNA binding of Pd (II) complexes with 7-bromo-quinolin-8-ol // Polyhedron. 2017. Vol. 135. P. 195–205. https://doi.org/10.1016/j.poly.2017.07.008.Potočňák I., Drweesh S. A., Farkasová V., Lüköová A., Sabolová D., Radojević I. D., et al. Low-dimensional compounds containing bioactive ligands. Part IX: Synthesis, structures, spectra, in vitro antimicrobial and anti-tumor activities and DNA binding of Pd (II) complexes with 7-bromo-quinolin-8-ol. Polyhedron. 2017;135:195–205. https://doi.org/10.1016/j.poly.2017.07.008.Naglah A. M., Al-Omar M. A., Almehizia A. A., AlKahtani H. M., Bhat M. A., Al-Shakliah N. S., et al. Synthesis, thermogravimetric, and spectroscopic characterizations of three palladium metal (II) ofloxacin drug and amino acids mixed ligand complexes as advanced antimicrobial materials // Journal of Molecular Structure. 2021. Vol. 1225, no. 4. Article no. 129102. https://doi.org/10.1016/j.molstruc.2020.129102.Naglah A. M., Al-Omar M. A., Almehizia A. A., AlKahtani H. M., Bhat M. A., Al-Shakliah N. S., et al. Synthesis, thermogravimetric, and spectroscopic characterizations of three palladium metal (II) ofloxacin drug and amino acids mixed ligand complexes as advanced antimicrobial materials. Journal of Molecular Structure. 2021;1225(4). Article no. 129102. https://doi.org/10.1016/j.molstruc.2020.129102.Rubino S., Pibiri I., Minacori Ch., Alduina R., Di Stefano V., Orecchio S., et al. Synthesis, structural characterization, antiproliferative and antimicrobial activity of binuclear and mononuclear Pt (II) complexes with perfluoroalkyl-heterocyclic ligands // Inorganica Chimica Acta. 2018. Vol. 483. P. 180– 190. https://doi.org/10.1016/j.ica.2018.07.039.Rubino S., Pibiri I., Minacori Ch., Alduina R., Di Stefano V., Orecchio S., et al. Synthesis, structural characterization, antiproliferative and antimicrobial activity of binuclear and mononuclear Pt (II) complexes with perfluoroalkyl-heterocyclic ligands. Inorganica Chimica Acta. 2018;483:180–190. https://doi.org/10.1016/j.ica.2018.07.039.Rubino S., Busà R., Attanzio A., Alduina R., Di Stefano V., Girasolo M. A., et. al. Synthesis, properties, antitumor and antibacterial activity of new Pt (II) and Pd (II) complexes with 2,2′-dithiobis(benzothiazole) ligand // Bioorganic and Medicinal Chemistry. 2017. Vol. 25, no. 8. P. 2378– 2386. https://doi.org/10.1016/j.bmc.2017.02.067.Rubino S., Busà R., Attanzio A., Alduina R., Di Stefano V., Girasolo M. A., et. al. Synthesis, properties, antitumor and antibacterial activity of new Pt (II) and Pd (II) complexes with 2,2′-dithiobis(benzothiazole) ligand. Bioorganic and Medicinal Chemistry. 2017;25(8):2378–2386. https://doi.org/10.1016/j.bmc.2017.02.067.Littlefield Sh. L., Baird M. C., Anagnostopoulou A., Raptis L. Synthesis, characterization and Stat3 inhibitory properties of the prototypical platinum (IV) anticancer drug, [PtCl3(NO2)(NH3)2] (CPA-7) // Inorganic Chemistry. 2008. Vol. 47, no. 7. P. 2798–2804. https://doi.org/10.1021/ic702057q.Littlefield Sh. L., Baird M. C., Anagnostopoulou A., Raptis L. Synthesis, characterization and Stat3 inhibitory properties of the prototypical platinum (IV) anticancer drug, [PtCl3(NO2)(NH3)2] (CPA-7). Inorganic Chemistry. 2008;47(7):2798–2804. https://doi.org/10.1021/ic702057q.Gel'fman M. I., Salishcheva O. V., Moldagulova N. E. Synthesis and kinetic studies of non-electrolytic binuclear platinum and palladium bromide complexes // Russian Journal of Inorganic Chemistry. 2005. Vol. 50, no. 7. P. 999–1003.Gel'fman M. I., Salishcheva O. V., Moldagulova N. E. Synthesis and kinetic studies of nonelectrolytic binuclear platinum and palladium bromide complexes. Russian Journal of Inorganic Chemistry. 2005;50(7):999–1003.Khranenko S. P., Kuratieva N. V., Plyusnin P. E., Gromilov S. A. Two crystal modifications of [Pden(NO2)2]. Synthesis, structure, and thermal properties // Journal of Structural Chemistry. 2014. Vol. 55, no. 2. P. 299–305. https://doi.org/10.1134/S0022476614020164.Khranenko S. P., Kuratieva N. V., Plyusnin P. E., Gromilov S. A. Two crystal modifications of [Pden(NO2)2]. Synthesis, structure, and thermal properties. Journal of Structural Chemistry. 2014;55(2):299–305. https://doi.org/10.1134/S0022476614020164.Накамото К. ИК-спектры и спектры КР неорганических и координационных соединений / пер с англ. Л. В. Христенко; под ред. Ю. А. Пентина. М.: Мир, 1991. 536 с.Nakamoto K. Infrared and Raman spectra of inorganic and coordination compounds. 4th ed. New York: John Wiley and sons. (Russ. ed.: Nakamoto K. IK-spektry i spektry KR neorganicheskikh i koordinatsionnykh soedinenii. Moscow: Mir, 1991. 536 p.)Sabounchei S. J., Shahriary P., Salehzadeh S., Gholiee Y., Chehregani A. Spectroscopic, theoretical, and antibacterial approach in the characterization of 5-methyl-5-(3-pyridyl)-2,4-imidazolidenedione ligand and of its platinum and palladium complexes // Comptes Rendus Chimie. 2015. Vol. 18, no. 5. P. 564–572. https://doi.org/10.1016/j.crci.2014.04.013.Sabounchei S. J., Shahriary P., Salehzadeh S., Gholiee Y., Chehregani A. Spectroscopic, theoretical, and antibacterial approach in the characterization of 5-methyl-5-(3-pyridyl)-2,4-imidazolidenedione ligand and of its platinum and palladium complexes. Comptes Rendus Chimie. 2015;18(5):564–572. https://doi.org/10.1016/j.crci.2014.04.013.Hubbard R. D., Fidanze S. Alkylating and platinum antitumor compounds // Comprehensive Medicinal Chemistry. 2006. Vol. 7. P. 129–148. https://doi.org/10.1016/B0-08-045044-X/00207-8.Hubbard R. D., Fidanze S. Alkylating and platinum antitumor compounds. Comprehensive Medicinal Chemistry. 2006;7:129–148. https://doi.org/10.1016/B0-08-045044-X/00207-8.Poklar N., Pilch D. S., Lippard S. J., Red-ding E. A., Dunham S. U., Breslauer K. J. Influence of cisplatin intrastrand crosslinking on the conformation, thermal stability, and energetics of a 20-mer DNA duplex // Proceedings of the National Academy of Sciences of USA. 1996. Vol. 93, no. 15. P. 7606– 7615. https://doi.org/10.1073/pnas.93.15.7606.Poklar N., Pilch D. S., Lippard S. J., Red-ding E. A., Dunham S. U., Breslauer K. J. Influence of cisplatin intrastrand crosslinking on the conformation, thermal stability, and energetics of a 20-mer DNA duplex. Proceedings of the National Academy of Sciences of USA. 1996;93(15):7606–7615. https://doi.org/10.1073/pnas.93.15.7606.Corduneanu O., Chiorcea-Paquim A.-M., Fiuza S. M., Marques M. P. M., Oliveira-Brett A. M. Poly-nuclear palladium complexes with biogenic polyamines: AFM and Voltammetric Characterization // Bioelectrochemistry. 2010. Vol. 78, no. 2. P. 97–105. https://doi.org/10.1016/j.bioelechem.2009.08.003.Corduneanu O., Chiorcea-Paquim A.-M., Fiuza S. M., Marques M. P. M., Oliveira-Brett A. M. Polynuclear palladium complexes with biogenic polyamines: AFM and Voltammetric Characterization. Bioelectrochemistry. 2010;78(2):97–105. https://doi.org/10.1016/j.bioelechem.2009.08.003.

The authors declare that there are no conflicts of interest present.