Biological activity and coordination modes of copper(ii) complexes of Schiff base-derived coumarin ligands

Creaven, Bernadette S.; Czeglédi, Eszter; Devereux, Michael; Enyedy, Éva A.; Kia, Agnieszka Foltyn-Arfa; Karcz, Dariusz; Kellett, Andrew; McClean, Siobhán; Nagy, Nóra Veronika; Noble, Andy; Rockenbauer, Antal; Szabó-Plánka, Terézia; Walsh, Maureen

doi:10.1039/c0dt00068j

Cited by 67 publications

(48 citation statements)

References 34 publications

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“…Schiff bases play an important role in biological [1][2][3] and coordination chemistry [4][5][6]. Recently, we have reported the crystal structures of afew Schiff bases and their complexes with metal atoms [7,8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N′-(5-bromo-2-methoxybenzylidene)-3- methylbenzohydrazide, C16H15BrN2O2

Wang¹,

Li²,

Ruan³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of N′-(5-bromo-2-methoxybenzylidene)-3- methylbenzohydrazide, C16H15BrN2O2

Wang¹,

Li²,

Ruan³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Their in vitro effects are clearly expressed . Recently, Creaven et al reported the antibacterial and anticancer activities, coordination modes of copper(II) complexes of Schiff based-derived coumarin ligands (Creaven et al, 2010). Therefore, these coumarin-metal compounds have potential to develop as anticancer drugs, which provides hope for the pursuit of non-platinum anticancer drugs.…”

Section: Other Tcm Active Ingredient-metal Based Anticancer Agents 2mentioning

confidence: 99%

Traditional Chinese Medicine Active Ingredient-Metal Based Anticancer Agents

Chen¹,

Liang²,

Liu³

2012

Recent Advances in Theories and Practice of Chinese Medicine

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“…In recent years, the successful development of metalbased pharmaceuticals, including copper anticancer agents, has attracted more attention on metal complexes in cancer treatment (1)(2)(3). Studies have shown that the copper complexes, such as dithiocarbamate (4,5), 8-hydroxyquinoline (6), clioquinol (7) and some Schiff base copper coordination compounds (8)(9)(10), exert promising anticancer activity by targeting the ubiquitinproteasome pathway (UPP) in preclinical trials.…”

Section: Introductionmentioning

confidence: 99%

Anticancer activity and computational modeling of ternary copper (II) complexes with 3-indolecarboxylic acid and 1,10-phenanthroline

Zhang

Wang

et al. 2016

International Journal of Oncology

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Abstract. Metal-containing compounds have been extensively studied for many years as potent proteasome inhibitors. The 20S proteasome, the main component of the ubiquitin proteasome pathway, is one of the excellent targets in anticancer drug development. We recently reported that several copper complexes were able to inhibit cancer-special proteasome and induce cell death in human cancer cells. However, the involved molecular mechanism is not known yet. We therefore synthesized three copper complexes and investigated their abilities on inhibiting proteasome activity and inducting apoptosis in human breast cancer cells. Furthermore, we employed molecular dockings to analyze the possible interaction between the synthetic copper complexes and the β5 subunit of proteasome which only reflects the chymotrypsin-like activity. Our results demonstrate that three Cu(II) complexes possess potent proteasome inhibition capability in a dose-dependent and time-dependent manner in MDA-MB-231 human breast cancer cells. They could bind to the β5 subunit of the 20S proteasome, which consequently cause deactivation of the proteasome and tumor cell death. The present study is significant for providing important theoretical basis for design and synthesis of anticancer drugs with low toxicity, high efficiency and high selectivity. IntroductionMetal complexes have important applications in many aspects of life. In recent years, the successful development of metalbased pharmaceuticals, including copper anticancer agents, has attracted more attention on metal complexes in cancer treatment (1-3). Studies have shown that the copper complexes, such as dithiocarbamate (4,5), 8-hydroxyquinoline (6), clioquinol (7) and some Schiff base copper coordination compounds (8-10), exert promising anticancer activity by targeting the ubiquitinproteasome pathway (UPP) in preclinical trials.The UPP selectively mediates cellular protein degradation which regulates cell cycle progression, signal transduction, differentiation, proliferation and apoptosis (11). The tagged proteins are degraded by the 26S proteasome, a huge cylinderlike protein complex, consists of one 20S core particle and two 19S regulatory particles (12). The 20S core particle comprises four packed rings, and each ring consists of 7 distinct subunits: the outer two rings are α subunits, acting like a 'gate' and controlling which proteins may go through into the cylinder; the inner two rings are β subunits, which form a catalytically active protease and are responsible for protein degradation (13). In proteasome of mammal cells, all α and β subunits are distinct and only subunits β1, β2 and β5 are catalytically active, which are responsible for caspase or peptidyl-glutamyl peptide-hydrolyzing (PGPH)-like activity, trypsin-like and chymotrypsin (CT)-like, respectively (14-16).Previous research has demonstrated that the inhibition of proteasomal CT-like activity is closely associated with tumor cell apoptosis (17)(18)(19)(20). Therefore, it is no surprise that selective inhibition of proteaso...

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Biological activity and coordination modes of copper(ii) complexes of Schiff base-derived coumarin ligands

Cited by 67 publications

References 34 publications

Crystal structure of N′-(5-bromo-2-methoxybenzylidene)-3- methylbenzohydrazide, C16H15BrN2O2

Crystal structure of N′-(5-bromo-2-methoxybenzylidene)-3- methylbenzohydrazide, C16H15BrN2O2

Traditional Chinese Medicine Active Ingredient-Metal Based Anticancer Agents

Anticancer activity and computational modeling of ternary copper (II) complexes with 3-indolecarboxylic acid and 1,10-phenanthroline

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