A curcumin-based TPA four-branched copper(II) complex probe for in vivo early tumor detection

Pi, Zifeng; Wang, Jiafeng; Jiang, Bo; Cheng, Gang; Su, Zhou

doi:10.1016/j.msec.2014.10.061

Cited by 24 publications

(16 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…24 Curcumin complexes have been described for all metals in the Groups 7-12 except for osmium. By far the most papers in this area deal with copper curcumin complexes, [25][26][27] followed by zinc, [28][29][30] nickel, 31 iron, 10,31 manganese, 32,33 and ruthenium 34,35 species. For the remaining middle and late transition metals, the number of well-characterized curcumin complexes is significantly smaller.…”

Section: How To Prepare and Characterize Metal Curcumin Complexesmentioning

confidence: 99%

“…The results clearly demonstrate that the solubility of homoleptic metal curcumin complexes can be significantly improved by blocking the phenolic -OH groups of the parent curcumin ligand. 25,26 2. The second potentially successful approach is the synthesis of heteroleptic complexes containing suitable spectator ligands in addition to curcumin.…”

Section: How To Prepare and Characterize Metal Curcumin Complexesmentioning

confidence: 99%

“…Compared with single-photon absorbing materials, the molecular excitation by the simultaneous absorption of two photons presents several advantages that include high confined excitation capacity, intrinsic three-dimension resolution, and the possibility of imaging at an increased penetration depth in tissue, with reduced photo-damage and background fluorescence. 25,42 In this context, the linear photophysical properties, two-photon absorption, and photostability behavior of the copper complexes Cu(Et 2 Curc) 2 (dioxane) and Cu(Bu 2 Curc) 2 have been investigated. The experimental results showed that the complexes exhibit a large two-photon absorption crosssection in the near-infrared region, high quantum yield and photostability and low cytotoxicity.…”

Section: Other Medicinal Applications Of Metal Curcumin Complexesmentioning

confidence: 99%

See 2 more Smart Citations

Metal complexes of curcumin – synthetic strategies, structures and medicinal applications

et al. 2015

View full text Add to dashboard Cite

This Tutorial Review presents an overview on the synthesis, characterization and applications of metal complexes containing curcumin (=1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) and its derivatives as ligands. Innovative synthetic strategies leading to soluble and crystallizable metal curcumin complexes are outlined in detail. Special emphasis is placed on the highly promising and exciting medicinal applications of metal curcumin complexes, with the three most important areas being anticancer activity and selective cytotoxicity, anti-Alzheimer's disease activity, and antioxidative/neuroprotective effects. Overall, this Tutorial Review provides the first general overview of this emerging and rapidly expanding field of interdisciplinary research.

show abstract

Section: How To Prepare and Characterize Metal Curcumin Complexesmentioning

confidence: 99%

Section: How To Prepare and Characterize Metal Curcumin Complexesmentioning

confidence: 99%

Section: Other Medicinal Applications Of Metal Curcumin Complexesmentioning

confidence: 99%

See 1 more Smart Citation

Metal complexes of curcumin – synthetic strategies, structures and medicinal applications

et al. 2015

View full text Add to dashboard Cite

show abstract

“…It has been widely studied for its multiple medicinal properties, e.g., antimicrobial, antioxidant, antibacterial, and anti-inflammatory, including anticancer activity, Alzheimer and infectious diseases [1,2,3,4,5,6,7]. However, the low solubility of curcumin in water, and its rapid metabolism and excretion, are related to a poor bioavailability that limits the scope of its potential benefits in living organisms [1,8,9,10,11,12]. Curcumin and curcuminoids, both natural and synthetic, are examples of β-diketone ligands capable of binding to a variety of metals to produce stable complexes [1,2].…”

Section: Introductionmentioning

confidence: 99%

Full Structural Characterization of Homoleptic Complexes of Diacetylcurcumin with Mg, Zn, Cu, and Mn: Cisplatin-level Cytotoxicity in Vitro with Minimal Acute Toxicity in Vivo

et al. 2019

View full text Add to dashboard Cite

At the present time, scientists place a great deal of effort worldwide trying to improve the therapeutic potential of metal complexes of curcumin and curcuminoids. Herein, the synthesis of four homoleptic metal complexes with diacetylcurcumin (DAC), using a ligand designed to prevent the interaction of phenolic groups, rendering metal complexes through the β-diketone functionality, is reported. Due to their physiological relevance, we used bivalent magnesium, zinc, copper, and manganese for complexation with DAC. The resulting products were characterized by ultraviolet-visible (UV-Vis), fluorescence spectroscopy, infrared spectroscopy (IR), liquid and solid-state nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), magnetic moment, mass spectrometry (MS), single crystal, and powder X-ray diffraction (SCXRD and PXRD). Crystallization was achieved in dimethylsulfoxide (DMSO) or N,N-dimethylformamide (DMF) as triclinic systems with space group P-1, showing the metal bound to the β-diketone function, while the 1H-NMR confirmed the preference of the enolic form of the ligand. Single crystal data demonstrated a 1:2 metal:ligand ratio. The inhibition of lipid peroxidation was evaluated using the thiobarbituric acid reactive substance assay (TBARS). All four metal complexes (Mg, Zn, Cu, and Mn) exhibited good antioxidant effect (IC50 = 2.03 ± 0.27, 1.58 ± 0.07, 1.58 ± 0.15 and 1.24 ± 0.10 μM respectively) compared with butylated hydroxytoluene (BHT) and α-tocopherol. The cytotoxic activity in human cancer cell lines against colon adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and lung adenocarcinoma (SKLU-1) was found comparable ((DAC)2Mg), or ca. 2-fold higher ((DAC)2Zn) than cisplatin. The acute toxicity assays indicate class 5 toxicity, according to the Organization for Economic Co-operation and Development (OECD) guidelines at doses of 3 g/kg for all complexes. No mortality or changes in the behavior of animals in any of the treated groups was observed. A therapeutic potential can be envisaged from the relevant cytotoxic activity upon human cancer cell lines in vitro and the undetected in vivo acute toxicity of these compounds.

show abstract

“…Such property has precluded the use of single crystal X-ray diffraction as a characterization technique [1,4,8,9,10]. As a consequence, the studies of metal complexes of curcumin and related compounds are more focused on their biological properties [8,9,10,11,12,13,14,15,16,17,18,19,20,21] rather than in detailed structural characterizations [8,9,10].…”

Section: Introductionmentioning

confidence: 99%

A New Family of Homoleptic Copper Complexes of Curcuminoids: Synthesis, Characterization and Biological Properties

et al. 2019

View full text Add to dashboard Cite

We report herein the synthesis and crystal structures of five new homoleptic copper complexes of curcuminoids. The scarcity of reports of homoleptic complex structures of curcuminoids is attributed to the lack of crystallinity of such derivatives, and therefore, their characterization by single crystal X-ray diffraction is rare. The ligand design suppressing the phenolic interaction by esterification or etherification has afforded a significant increase in the number of known crystal structures of homoleptic metal complexes of curcuminoids revealing more favorable crystallinity. The crystal structures of the present new copper complexes show four-fold coordination with a square planar geometry. Two polymorphs were found for DiBncOC-Cu when crystallized from DMF. The characterization of these new complexes was carried out using infrared radiation (IR), nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), and single crystal X-ray diffraction (SCXRD) and the antioxidant and cytotoxic activity of the obtained complexes was evaluated.

show abstract

A curcumin-based TPA four-branched copper(II) complex probe for in vivo early tumor detection

Cited by 24 publications

References 46 publications

Metal complexes of curcumin – synthetic strategies, structures and medicinal applications

Metal complexes of curcumin – synthetic strategies, structures and medicinal applications

Full Structural Characterization of Homoleptic Complexes of Diacetylcurcumin with Mg, Zn, Cu, and Mn: Cisplatin-level Cytotoxicity in Vitro with Minimal Acute Toxicity in Vivo

A New Family of Homoleptic Copper Complexes of Curcuminoids: Synthesis, Characterization and Biological Properties

Contact Info

Product

Resources

About