TY - JOUR
T1 - Synthesis of theophylline-based iridium(I) N-heterocyclic carbene complexes including fluorinated-thiophenolate ligands. Preliminary evaluation of their in vitro anticancer activity
AU - Eslava-Gonzalez, Itzel
AU - Valdés, Hugo
AU - Teresa Ramírez-Apan, María
AU - Hernandez-Ortega, Simón
AU - Rosario Zermeño-Ortega, Miriam
AU - Avila-Sorrosa, Alcives
AU - Morales-Morales, David
N1 - Publisher Copyright:
© 2020 Elsevier B.V.
PY - 2020/7/1
Y1 - 2020/7/1
N2 - A series of theophylline-based Ir(I) N-heterocyclic carbene complexes including fluorinated-thiolate ligands have been prepared and fully characterized. The molecular structures of the complexes [(NHC)Ir(SC6F5)(COD)] (3a) and [(NHC)Ir(SC6F4H-4)(COD)] (3b) were unambiguously determined by single crystal X-ray diffraction analysis. Both compounds were isostructural, having the theophylline-imidazolylidene ligand coordinated to the metal center and completing the coordination sphere with a 1,5-COD and thiophenolate ligands. Interestingly, both complexes exhibit both inter- and intra-molecular π–stacking interactions between the fluorinated ring of the thiolate and the theophylline-based NHC ligand. Furthermore, for the series of Ir(I) NHC complexes preliminary in vitro anticancer activity experiments were performed on six human cancer cell-lines, i.e. glia cells of nervous central system (U-251), prostate (PC-3), leukemia (K-562), colon (HCT-15), breast (MCF-7) and lung (SKLU-1). Being complex (3) the one showing the best performance (compared to cisplatin) against PC-3 and SKLU-1 with IC50 values of 7.8 ± 0.4 μM and 10.7 ± 0.7 μM, respectively.
AB - A series of theophylline-based Ir(I) N-heterocyclic carbene complexes including fluorinated-thiolate ligands have been prepared and fully characterized. The molecular structures of the complexes [(NHC)Ir(SC6F5)(COD)] (3a) and [(NHC)Ir(SC6F4H-4)(COD)] (3b) were unambiguously determined by single crystal X-ray diffraction analysis. Both compounds were isostructural, having the theophylline-imidazolylidene ligand coordinated to the metal center and completing the coordination sphere with a 1,5-COD and thiophenolate ligands. Interestingly, both complexes exhibit both inter- and intra-molecular π–stacking interactions between the fluorinated ring of the thiolate and the theophylline-based NHC ligand. Furthermore, for the series of Ir(I) NHC complexes preliminary in vitro anticancer activity experiments were performed on six human cancer cell-lines, i.e. glia cells of nervous central system (U-251), prostate (PC-3), leukemia (K-562), colon (HCT-15), breast (MCF-7) and lung (SKLU-1). Being complex (3) the one showing the best performance (compared to cisplatin) against PC-3 and SKLU-1 with IC50 values of 7.8 ± 0.4 μM and 10.7 ± 0.7 μM, respectively.
KW - Cancer
KW - Cytotoxic activity
KW - Iridium complexes
KW - N-heterocyclic carbene
KW - Theophylline complex
KW - Thiolate complexes
KW - Xanthines
UR - http://www.scopus.com/inward/record.url?scp=85082121598&partnerID=8YFLogxK
U2 - 10.1016/j.ica.2020.119588
DO - 10.1016/j.ica.2020.119588
M3 - Artículo
AN - SCOPUS:85082121598
SN - 0020-1693
VL - 507
JO - Inorganica Chimica Acta
JF - Inorganica Chimica Acta
M1 - 119588
ER -