Synthesis, characterization and the anticancer activity of six lanthanides(III) complexes with 5,7-dihalogenated-8-quino
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Synthesis, characterization and the anticancer activity of six lanthanides(III) complexes with 5,7‑dihalogenated‑8‑quinolinol and 2,2’‑bipyridine derivatives Rong Wang1 · Bi‑Qun Zou2,3 · Qi‑Pin Qin1,2 · Zhen‑Feng Wang1 · Ming‑Xiong Tan1 · Hong Liang2 Received: 30 January 2020 / Accepted: 15 May 2020 © Springer Nature Switzerland AG 2020
Abstract Six new lanthanide(III) complexes, namely [GdIII(QL1)3(BL1)] (Gd1), [GdIII(QL1)3(BL2)] (Gd2), [LuIII(QL2)2(BL3) (NO3)] (Lu1), [LuIII(QL2)2(BL2)(NO3)] (Lu2), [YbIII(QL3)2(BL2)(NO3)] (Yb1), and [YbIII(QL4)2(BL2)(NO3)] (Yb2) coordinated with 5,7-dibromo-8-quinolinol (H-QL1), 5,5′-dimethyl-2,2′-bipyridyl (BL1), 4,4′-di-tert-butyl-2,2′-bipyridine (BL2), 5,7-dibromo-2-methylquinolin-8-ol (H-QL2), 2,2′-bipyridine (BL3), 5,7-dichloro-8-hydroxyquinoline (H-QL3), and 5,7-dichloro-8-hydroxy-2-methylquinoline (H-QL4), were prepared. The L nIII complexes Gd1, Gd2, Lu1, Lu2, Yb1 and Yb2 showed high cytotoxicity toward cervical (HeLa), ovarian (SK-OV-3) and lung (NCI-H460) cancer cells with I C50 values from 0.18 ± 0.14 to 8.02 ± 1.71 μM. In addition, Yb1 and Yb2 impaired mitochondrial functions, decreased mitochondrial membrane potential, and altered the levels of mitochondrial related-proteins. The apoptosis-inducing capability was in the order of Yb2 > Yb1. Such observed differences in biological activities could be caused by the electronic effect of the methyl group of H-QL4 in Yb2.
Introduction The successful clinical use of cisplatin (cis-[PtCl2(NH3)2) and its related chemotherapeutic agents have inspired the research on other metal anti-tumor agents [1–9]. Recently, Rong Wang and Bi-Qun Zou contributed equally to this work. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11243-020-00399-4) contains supplementary material, which is available to authorized users. * Qi‑Pin Qin [email protected] * Ming‑Xiong Tan [email protected] 1
Guangxi Key Lab of Agricultural Resources Chemistry and Biotechnology, School of Chemistry and Food Science, Yulin Normal University, 1303 Jiaoyudong Road, Yulin 537000, People’s Republic of China
2
State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, People’s Republic of China
3
Department of Chemistry, Guilin Normal College, 9 Feihu Road, Gulin 541001, People’s Republic of China
lanthanide(III) compounds have received widespread attention because of their anti-cancer activities. Many such agents have been reported, such as near-infrared (NIR) Y bIII comIII plexes [10], quinolinoline L n complexes [11, 12], couIII marins Ln complexes [13–16], hesperetin-4-one-(benzoyl) hydrazone LnIII complexes [17], pyrenyl-terpyridine L nIII complexes [18], methylphosphonic acid Sm and Ho complexes [19], pyrrole-polyamide dimer-based CeIV complexes [20], and pentaphyrin LuIII complexes [21]. More recently, a number of 8-hydroxy-quinoline (8-HQ) metal complexe
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