Synthesis, spectroscopic characterization, crystal structure and DNA docking studies of a new trans-platinum saccharinate complex containing aqua and dimethyl sulfoxide ligands

Yıl 2024, Cilt: 11 Sayı: 2, 683 - 690, 15.05.2024

Ceyda İçsel Yılmaz

https://doi.org/10.18596/jotcsa.1399962

Öz

A new trans-platinum complex, trans-[Pt(sac)2(H2O)(DMSO)] (sac= saccharinate; DMSO= dimethyl sulfoxide), was synthesized and characterized by elemental analysis, UV, FTIR, NMR spectroscopy and X-ray single-crystal diffraction. In the mononuclear complex, the platinum(II) cation was coordinated by two N-coordinated sac ligands in the trans position, the sulfur atom of the DMSO ligand, and an aqua ligand, forming a distorted square planar coordination geometry. The interaction of the platinum(II) complex with DNA was studied using molecular docking. The complex successively docked into the minor groove of DNA via intermolecular hydrogen bonds with the adenine, cytosine, and guanine bases.

Anahtar Kelimeler

Platinum(II) complex, saccharinate, X-ray crystallography, DNA docking

Kaynakça

• 1. Baran EJ, Yilmaz VT. Metal complexes of saccharin. Coord Chem Rev [Internet]. 2006 Aug;250(15–16):1980–99. Available from: <URL>.
• 2. Brabec V, Hrabina O, Kasparkova J. Cytotoxic platinum coordination compounds. DNA binding agents. Coord Chem Rev [Internet]. 2017 Nov;351:2–31. Available from: <URL>.
• 3. Cai L, Yu C, Ba L, Liu Q, Qian Y, Yang B, et al. Anticancer platinum‐based complexes with non‐classical structures. Appl Organomet Chem [Internet]. 2018 Apr 11;32(4):e4228. Available from: <URL>.
• 4. Jin S, Guo Y, Guo Z, Wang X. Monofunctional Platinum(II) Anticancer Agents. Pharmaceuticals [Internet]. 2021 Feb 7;14(2):133. Available from: <URL>.
• 5. Sharma R, Singh VJ, Chawla PA. Advancements in the Use of Platinum Complexes as Anticancer Agents. Anticancer Agents Med Chem [Internet]. 2022 Mar;22(5):821–35. Available from: <URL>.
• 6. Štarha P, Křikavová R. Platinum(IV) and platinum(II) anticancer complexes with biologically active releasable ligands. Coord Chem Rev [Internet]. 2024 Feb;501:215578. Available from: <URL>.
• 7. Henderson W, Nicholson BK, McCaffrey LJ. Platinum(II) and palladium(II) saccharinate complexes. Inorganica Chim Acta [Internet]. 1999 Feb;285(1):145–8. Available from: <URL>.
• 8. Al-Jibori SA, Al-Jibori GH, Al-Hayaly LJ, Wagner C, Schmidt H, Timur S, et al. Combining anti-cancer drugs with artificial sweeteners: Synthesis and anti-cancer activity of saccharinate (sac) and thiosaccharinate (tsac) complexes cis -[Pt(sac)2(NH3)2] and cis-[Pt(tsac)2(NH3)2]. J Inorg Biochem [Internet]. 2014 Dec;141:55–7. Available from: <URL>.
• 9. Cavicchioli M, Massabni AC, Castellano EE, Sabeh LPB, Costa-Neto CM. Synthesis and X-ray structure of the dinuclear platinum(II) complex with saccharin {K[Pt(sac)3(H2O)]·H2O}2: Studies on its antiproliferative activity in aqueous solution. Inorganica Chim Acta [Internet]. 2007 Jun;360(9):3055–60. Available from: <URL>.
• 10. Guney E, Yilmaz VT, Kazak C. Bis(saccharinato)palladium(II) and platinum(II) complexes with 2,2′-bipyridine: Syntheses, structures, spectroscopic, fluorescent and thermal properties. Polyhedron [Internet]. 2010 Mar;29(4):1285–90. Available from: <URL>.
• 11. Guney E, Yilmaz VT, Sengul A, Buyukgungor O. Platinum(II) and palladium(II) saccharinato complexes with 2,2′:6′,2″-terpyridine: Synthesis, characterization, crystal structures, photoluminescence and thermal studies. Inorganica Chim Acta [Internet]. 2010 Jan;363(2):438–48. Available from: <URL>.
• 12. Yilmaz VT, Ertem A, Guney E, Buyukgungor O. Palladium(II) and Platinum(II) Saccharinate Complexes with 2‐Aminomethylpyridine and 2‐Aminoethylpyridine: Synthesis, Characterization, Crystal Structures, and Thermal Properties. Zeitschrift für Anorg und Allg Chemie [Internet]. 2010 Mar 16;636(3–4):610–5. Available from: <URL>.
• 13. Guney E, Yilmaz VT, Buyukgungor O. Neutral and cationic palladium(II) and platinum(II) complexes of 2,2′-dipyridylamine with saccharinate: Syntheses, spectroscopic, structural, fluorescent and thermal studies. Inorganica Chim Acta [Internet]. 2010 Aug;363(11):2416–24. Available from: <URL>.
• 14. Guney E, Kaya Y, Yilmaz VT, Gumus S. Synthesis, experimental and theoretical characterization of palladium(II) and platinum(II) saccharinate complexes with 2-(2-pyridyl)benzimidazole. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2011 Sep;79(5):1171–8. Available from: <URL>.
• 15. Guney E, Yilmaz VT, Buyukgungor O. Palladium(II) and platinum(II) saccharinate complexes containing pyridine and 3-acetylpyridine: Synthesis, crystal structures, fluorescence and thermal properties. Polyhedron [Internet]. 2011 Aug;30(12):1968–74. Available from: <URL>.
• 16. Guney E, Yilmaz VT, Ari F, Buyukgungor O, Ulukaya E. Synthesis, characterization, structures and cytotoxic activity of palladium(II) and platinum(II) complexes containing bis(2-pyridylmethyl)amine and saccharinate. Polyhedron [Internet]. 2011 Jan;30(1):114–22. Available from: <URL>.
• 17. Ari F, Aztopal N, Icsel C, Yilmaz VT, Guney E, Buyukgungor O, et al. Synthesis, structural characterization and cell death-inducing effect of novel palladium(II) and platinum(II) saccharinate complexes with 2-(hydroxymethyl)pyridine and 2-(2-hydroxyethyl)pyridine on cancer cells in vitro. Bioorg Med Chem [Internet]. 2013 Nov;21(21):6427–34. Available from: <URL>.
• 18. Yilmaz VT, Icsel C, Turgut OR, Aygun M, Erkisa M, Turkdemir MH, et al. Synthesis, structures and anticancer potentials of platinum(II) saccharinate complexes of tertiary phosphines with phenyl and cyclohexyl groups targeting mitochondria and DNA. Eur J Med Chem [Internet]. 2018 Jul;155:609–22. Available from: <URL>.
• 19. Icsel C, Yilmaz VT, Cevatemre B, Aygun M, Ulukaya E. Structures and anticancer activity of chlorido platinum(II) saccharinate complexes with mono- and dialkylphenylphosphines. J Inorg Biochem [Internet]. 2019 Jun;195:39–50. Available from: <URL>.
• 20. Icsel C, Yilmaz VT, Cevatemre B, Aygun M, Ulukaya E. Cytotoxic platinum(II) complexes derived from saccharinate and phosphine ligands: synthesis, structures, DNA cleavage, and oxidative stress-induced apoptosis. JBIC J Biol Inorg Chem [Internet]. 2020 Feb 26;25(1):75–87. Available from: <URL>.
• 21. Icsel C, Yilmaz VT, Aygun M, Ulukaya E. Trans-Pd/Pt(II) saccharinate complexes with a phosphine ligand: Synthesis, cytotoxicity and structure-activity relationship. Bioorg Med Chem Lett [Internet]. 2020 May;30(9):127077. Available from: <URL>.
• 22. Icsel C, Yilmaz VT, Aygun M, Cevatemre B, Alper P, Ulukaya E. Palladium(II) and platinum(II) saccharinate complexes with bis(diphenylphosphino)methane/ethane: synthesis, S-phase arrest and ROS-mediated apoptosis in human colon cancer cells. Dalt Trans [Internet]. 2018;47(33):11397–410. Available from: <URL>.
• 23. Yilmaz VT, Icsel C, Aygun M, Erkisa M, Ulukaya E. Pd(II) and Pt(II) saccharinate complexes of bis(diphenylphosphino)propane/butane: Synthesis, structure, antiproliferative activity and mechanism of action. Eur J Med Chem [Internet]. 2018 Oct;158:534–47. Available from: <URL>.
• 24. Medici S, Peana M, Nurchi VM, Lachowicz JI, Crisponi G, Zoroddu MA. Noble metals in medicine: Latest advances. Coord Chem Rev [Internet]. 2015 Feb;284:329–50. Available from: <URL>.
• 25. Fanelli M, Formica M, Fusi V, Giorgi L, Micheloni M, Paoli P. New trends in platinum and palladium complexes as antineoplastic agents. Coord Chem Rev [Internet]. 2016 Mar;310:41–79. Available from: <URL>.
• 26. Alam MN, Huq F. Comprehensive review on tumour active palladium compounds and structure–activity relationships. Coord Chem Rev [Internet]. 2016 Jun;316:36–67. Available from: <URL>.
• 27. Paprocka R, Wiese-Szadkowska M, Janciauskiene S, Kosmalski T, Kulik M, Helmin-Basa A. Latest developments in metal complexes as anticancer agents. Coord Chem Rev [Internet]. 2022 Feb;452:214307. Available from: <URL>.
• 28. Keene FR, Smith JA, Collins JG. Metal complexes as structure-selective binding agents for nucleic acids. Coord Chem Rev [Internet]. 2009 Aug;253(15–16):2021–35. Available from: <URL>.
• 29. Pages BJ, Ang DL, Wright EP, Aldrich-Wright JR. Metal complex interactions with DNA. Dalt Trans [Internet]. 2015;44(8):3505–26. Available from: <URL>.
• 30. Sherman SE, Gibson D, Wang AHJ, Lippard SJ. Crystal and molecular structure of cis-[Pt(NH3)2[d(pGpG)]], the principal adduct formed by cis-diamminedichloroplatinum(II) with DNA. J Am Chem Soc [Internet]. 1988 Oct 1;110(22):7368–81. Available from: <URL>.
• 31. Smith JA, Keene FR, Li F, Collins JG. Noncovalent DNA Binding of Metal Complexes. In: Reedijk J, Poeppelmeier K, editors. Comprehensive Inorganic Chemistry II [Internet]. Elsevier; 2013. p. 709–50. Available from: <URL>.
• 32. Liu HK, Sadler PJ. Metal Complexes as DNA Intercalators. Acc Chem Res [Internet]. 2011 May 17;44(5):349–59. Available from: <URL>.
• 33. Britten JF, Lippert B, Lock CJL, Pilon P. Platinum(II) complexes with terminal hydroxo and aqua groups: crystal structures of hydroxo-cis-diammine(1-methylcytosine-N3)platinum(II) nitrate dihydrate, [Pt(OH)(NH3)2(C5H7N3O)]NO3.2H2O, and cis-diammineaqua(1-methylcytosine-N3)platinum(II) dinitrate hydrate, [Pt(NH3)2(H2O)(C5H7N3O)](NO3)2.H2O. Inorg Chem [Internet]. 1982 May 1;21(5):1936–41. Available from: <URL>.
• 34. Rochon FD, Melanson R. Molecular and crystal structure of a platinum(II) complex with aquo and sulfate ligands: aquo(N,N’-dimethylethylenediamine)(sulfato)platinum(II) hydrate. Inorg Chem [Internet]. 1987 Apr 1;26(7):989–92. Available from: <URL>.
• 35. Intini FP, Lanfranchi M, Natile G, Pacifico C, Tiripicchio A. Synthesis and Crystal Structure of a trans -Diaquabis(amidato) Complex of Platinum(II). Inorg Chem [Internet]. 1996 Jan 1;35(6):1715–7. Available from: <URL>.
• 36. Meinema HA, Verbeek F, Marsman JW, Bulten EJ, Dabrowiak JC, Krishnan BS, et al. The synthesis and characterization of 1,1-bis(aminomethyl)cyclohexaneplatinum(II) compounds and the crystal structure determination of 1,1-bis(aminomethyl)-cyclohexaneaquosulphatoplatinum(II) monohydrate. Inorganica Chim Acta [Internet]. 1986 Apr;114(2):127–35. Available from: <URL>.
• 37. Rath NP, Fallis KA, Anderson GK. Structure of trans-aquadichloro(triphenylphosphine)platinum(II). Acta Crystallogr Sect C Cryst Struct Commun [Internet]. 1993 Dec 15;49(12):2079–81. Available from: <URL>.
• 38. Deacon GB, Drago PR, Göbbels D, Wickleder MS, Meyer G. A Novel Alkene(alkyl)(aqua)(aryl)platinum(II) Complex - [Pt{CH(CH2C6F5)CH2CH2CH=CH2}(C6F5)(OH2)]. Zeitschrift für Anorg und Allg Chemie [Internet]. 2001 May;627(5):811–3. Available from: <URL>.
• 39. Price JH, Williamson AN, Schramm RF, Wayland BB. Palladium(II) and platinum(II) alkyl sulfoxide complexes. Examples of sulfur-bonded, mixed sulfur- and oxygen-bonded, and totally oxygen-bonded complexes. Inorg Chem [Internet]. 1972 Jun 1;11(6):1280–4. Available from: <URL>.
• 40. Rigaku Oxford Diffraction, CrysAlisPro Software System, Version 1.171.38.46, Rigaku Corporation, Oxford, UK, 2015.
• 41. Dolomanov O V., Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H. OLEX2 : a complete structure solution, refinement and analysis program. J Appl Crystallogr [Internet]. 2009 Apr 1;42(2):339–41. Available from: <URL>.
• 42. Sheldrick GM. SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr Sect A Found Adv [Internet]. 2015 Jan 1;71(1):3–8. Available from: <URL>.
• 43. Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr Sect C Struct Chem [Internet]. 2015 Jan 1;71(1):3–8. Available from: <URL>.
• 44. Trott O, Olson AJ. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem [Internet]. 2010 Jan 30;31(2):455–61. Available from: <URL>.
• 45. İçsel C. Synthesis, characterization and crystal structures of platinum(II) saccharinate complexes with 1,5-cyclooctadiene. Turkish J Chem [Internet]. 2020;44(3):736–45. Available from: <URL>.
• 46. Melanson R, Rochon FD. The Crystal Structure of cis -Dichlorobis(dimethylsulfoxide)platinum(II). Can J Chem [Internet]. 1975 Aug 15;53(16):2371–4. Available from: <URL>.
• 47. Olusegun MA, Reddy D, Jaganyi D. An investigation of comparative substitution behavior of bifunctional trans ‐platinum(II) complexes with symmetric and asymmetric alkylamine ligands. Int J Chem Kinet [Internet]. 2020 Dec 4;52(12):884–92. Available from: <URL>.