New iron(III) complexes with 2-formylpyridine thiosemicarbazones: Synthetic aspects, structural and spectral analyses and cytotoxicity screening against MCF-7 human cancer cells

被引:6
作者
Fathy, Amany [1 ]
Ibrahim, Ahmed B. M. [2 ]
Abd Elkhalik, S. [1 ]
Villinger, Alexander [3 ]
Abbas, S. M. [1 ]
机构
[1] Beni Suef Univ, Fac Sci, Chem Dept, Bani Suwayf 62521, Egypt
[2] Assiut Univ, Fac Sci, Dept Chem, Assiut 71516, Egypt
[3] Univ Rostock, Inst Chem, Albert Einstein Str 3A, D-18059 Rostock, Germany
关键词
Tridentate ligands; Transition metals; Coordination compounds; X-ray diffraction; Cationic complexes; Anti-cancer activity; RIBONUCLEOTIDE REDUCTASE INHIBITOR; IRON CHELATORS; IN-VITRO; COPPER-COMPLEXES; PHASE-I; 3-AMINOPYRIDINE-2-CARBOXALDEHYDE THIOSEMICARBAZONE; 2-ACETYLPYRIDINE THIOSEMICARBAZONES; ISONICOTINOYL HYDRAZONE; BIOLOGICAL EVALUATION; ANTICANCER ACTIVITY;
D O I
10.1016/j.heliyon.2023.e13008
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
2-Formylpyridine thiosemicarbazone -iron (III) chelates [FeL2] Cl center dot 2H2O {L = L1 (C1) [HL1 = 4-(4-Nitrophenyl)-1-((pyridin-2-yl)methylene)thiosemicarbazide] and L = L2 (C2) [HL2 = 4-(2,5-Dimethoxyphenyl)-1-((pyridin-2-yl)methylene)thiosemicarbazide]} were prepared. The two ligand anions in each complex resulted in saturation of the iron coordination number and consequently the existence of these complexes as 1:1 electrolytes. As well, the iron in these complexes exhibits low-spin electronic configuration. X-ray crystallography of complex C1 indicated its triclinic crystal system and P 1 space group. In addition, it proved the ligation through a thiol sulfur atom and two nitrogen atoms of pyridine and azomethine groups. This is while the presence of two water molecules of crystallization in the complex structure was also indicated. The ligand HL1 was selected for cytotoxicity screening against human MCF-7, A-549, HEPG-2 and HCT-116 cancer cells and the most enhanced activities were detected against the breast cells. Against these cells, the compounds HL1, HL2, C1 and C2 induced cytotoxicity, respectively, with IC50 values of 52.4, 145.4, 34.3 and 62.0 mu M. However, against the healthy BHK cells, HL1 and HL2 caused cytotoxicity, respectively, with IC50 values of 54.8 and 110.6 mu M and cytotoxicity with percent viabilities of 56.7 and 55.4% of the BHK cells by the complexes (137.4 mu M of C1 and 131.9 mu M of C2) was determined. These activities against MCF-7 cells are less significant compared with the measured value for doxorubicin. But this standard is more toxic to normal cells than the thiosemicarbazones (IC50 (doxorubicin) = 9.66 mu M against MCF-7 cells and 36.42 mu M against BHK cells).
引用
收藏
页数:9
相关论文
共 70 条
[1]   The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[2]   Binuclear Cu(II) complex based on N-acetylanthranilic acid induces significant cytotoxic effect on three cancer cell lines [J].
Aly, Aref A. M. ;
Zidan, Amna S. A. ;
Ibrahim, Ahmed B. M. ;
Mosbah, Hanan K. ;
Mayer, Peter ;
Saber, Saber H. .
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1249
[3]  
[Anonymous], 2013, SAINT+
[4]   Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile [J].
Assaleh, Mohamed H. ;
Bjelogrlic, Snezana K. ;
Prlainovic, Nevena ;
Cvijetic, Ilija ;
Bozic, Aleksandra ;
Arandjelovic, Irena ;
Vukovic, Dragana ;
Marinkovic, Aleksandar .
ARABIAN JOURNAL OF CHEMISTRY, 2022, 15 (01)
[5]   Iron and the anaemia of chronic disease: a review and strategic recommendations [J].
Cavill, Ivor ;
Auerbach, Michael ;
Bailie, George R. ;
Barrett-Lee, Peter ;
Beguin, Yves ;
Kaltwasser, Peter ;
Littlewood, Tim ;
Macdougall, Iain C. ;
Wilson, Keith .
CURRENT MEDICAL RESEARCH AND OPINION, 2006, 22 (04) :731-737
[6]   Potent antitumor activity of novel iron chelators derived from di-2-pyridylketone isonicotinoyl hydrazone involves fenton-derived free radical generation [J].
Chaston, TB ;
Watts, RN ;
Yuan, J ;
Richardson, DR .
CLINICAL CANCER RESEARCH, 2004, 10 (21) :7365-7374
[7]  
Chaston TB, 2003, CLIN CANCER RES, V9, P402
[8]   Increasing the antibacterial activity of gallium(III) against Pseudomonas aeruginosa upon coordination to pyridine-derived thiosemicarbazones [J].
da Silva, Jeferson G. ;
Azzolini, Lucas S. ;
Wardell, Solange M. S. V. ;
Wardell, James L. ;
Beraldo, Heloisa .
POLYHEDRON, 2009, 28 (11) :2301-2305
[9]   Interaction of Triapine and related thiosemicarbazones with iron(III)/(II) and gallium(III): a comparative solution equilibrium study [J].
Enyedy, Eva A. ;
Primik, Michael F. ;
Kowol, Christian R. ;
Arion, Vladimir B. ;
Kiss, Tamas ;
Keppler, Bernhard K. .
DALTON TRANSACTIONS, 2011, 40 (22) :5895-5905
[10]   WinGX and ORTEP for Windows: an update [J].
Farrugia, Louis J. .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2012, 45 :849-854