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Solution chemical properties of two bidentate pyrazolyl thiosemicarbazones 2-((3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinecarbothioamide (Me-pyrTSC), 2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)hydrazinecarbothioamide (Ph-pyrTSC), stability of their Cu(II) and Ru(η 6 -p-cymene) complexes were characterized in aqueous solution (with 30% DMSO) by the combined use of UV-visible spectrophotometry, 1 H NMR spectroscopy and electrospray ionization mass spectrometry in addition to their solid phase isolation. The solid phase structures of Me-pyrTSC∙H 2 O, [Ru(η 6 -p-cymene)(Me-pyrTSC)Cl]Cl and [Cu(Ph-pyrTSCH -1 ) 2 ] were determined by single crystal X-ray diffraction. High stability mononuclear Ru(η 6 -p-cymene) complexes with (N,S) coordination mode are formed in the acidic pH range, and increasing the pH the predominating dinuclear [(Ru(η 6 -p-cymene)) 2 (L) 2 ] 2+ complex with μ 2 -bridging sulphur donor atoms is formed (where L - is the deprotonated thiosemicarbazone). [CuL] + and [CuL 2 ] complexes show much higher stability compared to that of complexes of the reference compound benzaldehyde thiosemicarbazone. [CuL 2 ] complexes predominate at neutral pH. Me-pyrTSC and Ph-pyrTSC exhibited moderate cytotoxicity against human colonic adenocarcinoma cell lines (IC 50  = 33-76 μM), while their complexation with Ru(η 6 -p-cymene) (IC 50  = 11-24 μM) and especially Cu(II) (IC 50  = 3-6 μM) resulted in higher cytotoxicity. Cu(II) complexes of the tested thiosemicarbazones were also cytotoxic in three breast cancer and in a hepatocellular carcinoma cell line. No reactive oxygen species production was detected and the relatively high catalase activity of SUM159 breast cancer cells was decreased upon addition of the ligands and the complexes. In the latter cell line the tested compounds interfered with the glutathione synthesis as they decreased the concentration of this cellular reductant.

Titel:	Solution equilibrium, structural and cytotoxicity studies on Ru(η <superscript>6</superscript> -p-cymene) and copper complexes of pyrazolyl thiosemicarbazones.
Autor/in / Beteiligte Person:	Dömötör, O ; Kiss, MA ; Gál, GT ; May, NV ; Spengler, G ; Nové, M ; Gašparović, AČ ; Frank, É ; Enyedy, ÉA
Zeitschrift:	Journal of inorganic biochemistry, Jg. 202 (2020), S. 110883
Veröffentlichung:	New York, Elsevier., 2020
Medientyp:	academicJournal
ISSN:	1873-3344 (electronic)
DOI:	10.1016/j.jinorgbio.2019.110883
Schlagwort:	Apoptosis Breast Neoplasms pathology Carcinoma, Hepatocellular pathology Cell Proliferation Copper chemistry Cymenes chemistry Female Humans Liver Neoplasms pathology Pyrazoles chemistry Ruthenium chemistry Thiosemicarbazones chemistry Tumor Cells, Cultured Antineoplastic Agents chemistry Antineoplastic Agents pharmacology Breast Neoplasms drug therapy Carcinoma, Hepatocellular drug therapy Coordination Complexes chemistry Liver Neoplasms drug therapy Organometallic Compounds chemistry
Sonstiges:	Nachgewiesen in: MEDLINE Sprachen: English Publication Type: Journal Article; Research Support, Non-U.S. Gov't Language: English [J Inorg Biochem] 2020 Jan; Vol. 202, pp. 110883. <i>Date of Electronic Publication: </i>2019 Oct 22. MeSH Terms: Antineoplastic Agents / chemistry ; Antineoplastic Agents / pharmacology ; Breast Neoplasms / drug therapy ; Carcinoma, Hepatocellular / drug therapy ; Coordination Complexes / chemistry ; Liver Neoplasms / drug therapy ; Organometallic Compounds / *chemistry ; Apoptosis ; Breast Neoplasms / pathology ; Carcinoma, Hepatocellular / pathology ; Cell Proliferation ; Copper / chemistry ; Cymenes / chemistry ; Female ; Humans ; Liver Neoplasms / pathology ; Pyrazoles / chemistry ; Ruthenium / chemistry ; Thiosemicarbazones / chemistry ; Tumor Cells, Cultured Contributed Indexing: Keywords: Cytotoxicity; Metal complexes; Solution stability; Thiosemicarbazones; X-ray crystal structures Substance Nomenclature: 0 (Antineoplastic Agents) ; 0 (Coordination Complexes) ; 0 (Cymenes) ; 0 (Organometallic Compounds) ; 0 (Pyrazoles) ; 0 (Thiosemicarbazones) ; 1G1C8T1N7Q (4-cymene) ; 3QD5KJZ7ZJ (pyrazole) ; 789U1901C5 (Copper) ; 7UI0TKC3U5 (Ruthenium) Entry Date(s): Date Created: 20191106 Date Completed: 20210127 Latest Revision: 20210127 Update Code: 20231215

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Solution equilibrium, structural and cytotoxicity studies on Ru(η <superscript>6</superscript> -p-cymene) and copper complexes of pyrazolyl thiosemicarbazones.