Water soluble luminescent platinum terpyridine complexes with glycosylated acetylide and arylacetylide ligands: photoluminescent properties and cytotoxicities

Abstract

Platinum(II) terpyridine complexes with glycosylated acetylide and arylacetylide ligands bind to DNA with binding constants approximately 10(5) mol(-1) dm(3); the glycosylated arylacetylide complexes exhibit emission at lambda(max) approximately 620 nm in water and are up to approximately 100-times higher in potency than the clinical cisplatin drug in killing cancer cells.

Synthesis and Antibacterial Activities of Sugar-containing Platinum Ethynyl Complexes

“…As a result, the metabolism in the cell is stopped, and microorganism dies (Dai et al 2013). The anticancer and antibacterial activity of the gold ethynyl complexes were reported recently (Hikisz et al 2015), and previous report (Ma et al 2005) of the sugar-containing platinum ethynyl complexes demonstrated 100 times higher anticancer efficiency than cis platin. Hexose sugar-containing aryl ethynyl ligand 3 was formed by Sonogashira coupling reaction using N-(4-iodophenyl)-β-D-glucopyranosylamine 1 and trimethysilylacetylene, followed by the deprotection of trimethylsilyl group by K 2 CO 3 .…”

“…M-C σ-bonded and M-C π-bonded organometallic complexes with sugar moieties also demonstrated biosensing and medicinal activity (Monney et al 2013). According to present knowledge, sugar-containing M-C σ-bonded ethynyl complexes are scarce (Ma et al 2005).…”

“…As a consequence, these materials possess interesting properties such as optical nonlinearity, luminescence, liquid crystallinity (Long et al 2003). Compared to the application of conjugated organic PPEs in biology (Kim et al 2007, Dam et al 2002, Phillips 2008, Babudri et al 2003, Erdogan et al 2002, little attention is given to their organometallic analogues (Wong et al 2004, Ma et al 2005. However, metal coordination complexes with tunable properties, such as radioactivity, cytotoxicity or photophysical features, would be good candidates for biomedical application, e.g.…”

“…Carbohydrate complexes of platinum group metals (Pd, Pt, Rh, Ir), where carbohydrate is directly bonded to metal atom, have been reported (Steinborn et al 2000). In recent years, metal coordination complexes with sugar substituted chelating ligands were studied for the development of diagnostic tracers (Mindt et al 2006, Ferreira et al 2006, MRI contrast agents (Fulton et al 2006, Duimstra et al 2005 and therapeutic agents (Krishnamurthy et al 2008, Ott et al 2005, Ma et al 2005. M-C σ-bonded and M-C π-bonded organometallic complexes with sugar moieties also demonstrated biosensing and medicinal activity (Monney et al 2013).…”

Metal-based glycoconjugates and their potential in targeted anticancer chemotherapy

“…Remarkably, it proved up to 100-fold more active than cisplatin and 8-fold more cytotoxic than the corresponding non-glycosylated analogue [85]. Subsequent in-depth mechanistic studies revealed a strong interaction with ctDNA through a non-intercalating binding mode and the capability to induce preferential apoptosis rather than necrosis [86].…”