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Zinc(II) Complexes of Acylpyrazolones Decorated with a Cyclohexyl Group Display Antiproliferative Activity Against Human Breast Cancer Cells
Author(s) -
Marchetti Fabio,
Nicola Corrado,
Pettinari Riccardo,
Pettinari Claudio,
Aiello Iolinda,
Deda Massimo,
Candreva Angela,
Morelli Sabrina,
Bartolo Loredana,
Crispini Alessandra
Publication year - 2020
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201900775
Subject(s) - chemistry , zinc , stereochemistry , crystallography , electron paramagnetic resonance , cytotoxicity , octahedron , medicinal chemistry , crystal structure , in vitro , organic chemistry , nuclear magnetic resonance , physics , biochemistry
Five‐ and six‐coordinated zinc(II) complexes, [Zn(Q R ) 2 (H 2 O)] ( 1–2 ) and [Zn(Q R ) 2 (L)] ( 3–8 ) {HQ R = 4‐R(C=O)‐5‐pyrazolones in general, in detail HQ C17 , R = –(CH 2 ) 16 CH 3 , HQ Cy , R = –C 6 H 11 ; L = bipy, tmeda or en} have been synthesized and characterized by IR, 1 H and 13 C NMR, UV/Visible spectroscopy, elemental analysis, TGA and ESI mass spectrometry. The square pyramidal complex [Zn(Q C17 ) 2 (H 2 O)] ( 1 ) has been structurally characterized, together with a trans octahedral [Zn(Q Cy ) 2 (EtOH) 2 ] ( 2b ) species obtained by recrystallization of [Zn(Q Cy ) 2 (H 2 O)] ( 2 ) from ethanol. Additionally, in both complexes [Zn(Q Cy ) 2 (bipy)] ( 4 ) and [Zn(Q C17 ) 2 (tmeda)] ( 5 ) structurally characterized by single crystal X ray diffraction, the same amount of Δ and Λ enantiomers are present, with the only difference related to the mutual disposition of the different type of the Q R coordinated oxygen atoms. The cytotoxicity of the complexes [Zn(Q Cy ) 2 (H 2 O)] ( 2 ), [Zn(Q Cy ) 2 (bipy)] ( 4 ) and [Zn(Q Cy ) 2 (en)] ( 8 ) has been evaluated in vitro against MCF‐7 human breast cancer cell line in a biohybrid membrane system. Results revealed that zinc complexes possess antiproliferative activity inducing apoptosis by activation of caspase‐3 and p‐JNK.