Curcuminoids as potential new iron-chelating agents: spectroscopic, polarographic and potentiometric study on their Fe(III) complexing ability

Borsari, Marco; Ferrari, Erika; Grandi, Romano; Saladini, Monica

doi:10.1016/s0020-1693(01)00687-9

Cited by 180 publications

(137 citation statements)

References 25 publications

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“…Curcumin is able to bind ferrous and ferric ions through its hydroxyl and methoxyl group on the phenolic ring, and through its keto-enol moiety. 15,30) In terms of chelation ability, we noted that the number of double bonds in the heptadione linkage may influence the ligand conformation and binding ability of the molecules. The SAR for these compounds as pertains to the hydroxyl scavenging and iron chelating abilities still needs further investigation.…”

Section: Resultsmentioning

confidence: 99%

Electron Paramagnetic Resonance Study of the Free Radical Scavenging Capacity of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Morales

Sirijaroonwong

Yamanont

et al. 2015

Biological & Pharmaceutical Bulletin

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The quantitative free radical scavenging capacity of curcumin and its demethoxy derivatives (demethoxycurcumin (Dmc) and bisdemethoxycurcumin (Bdmc)) and hydrogenated derivatives (tetrahydrocurcumin (THC), hexahydrocurcumin (HHC) and octahydrocurcumin (OHC)) towards 1,1-diphenyl-2-picryl hydrazyl (DPPH), nitric oxide radical (NO), hydroxyl radical (HO · ) and superoxide anion radical (O 2 · ) were investigated by electron paramagnetic resonance (EPR) spectroscopy. One mole of the hydrogenated derivatives scavenged about 4 mol of the DPPH radical, while curcumin and Dmc scavenged about 3 mol of the DPPH radical. Curcumin and THC showed moderate scavenging activity towards NO, yielding 200 mmol of NO scavenged per 1 mol of the scavenger. In contrast, curcumin and its derivatives showed very low scavenging activity towards HO · and O 2 · , yielding approximately only 3-12 mmol scavenged per 1 mol of the tested compounds. Our results suggest that curcumin and its derivatives principally act as chain breaking antioxidants rather than as direct free radical scavengers. Furthermore, we showed that the ortho-methoxyphenolic group and the heptadione linkage of these molecules greatly contributed to their DPPH and NO scavenging activity.Key words curcumin; electron paramagnetic resonance; free radical scavenger; spin trapping Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione] is the primary biologically active constituent that is isolated from the spice, turmeric (Curcuma longa LINN). It shows various therapeutically beneficial activities, including anti-oxidant, anti-inflammatory, anti-cancer, and anti-viral activities 1,2) mediated through its interactions with several molecular targets such as enzymes, receptors, and transcription factors.3,4) As a potent anti-oxidant, several mechanisms have been proposed which describe the direct interaction of curcumin with reactive oxygen species (ROS) as well as its involvement in ROS-independent mechanisms (i.e., induction of antioxidant enzymes). 5,6) The structure-antioxidant activity relationship of curcumin and the compound it reduces has been demonstrated in both in vitro and in vivo models, for example, 1,1-diphenyl-2-picrylhydrazyl (DPPH) kinetic analysis, γ-radiolysis of rat liver microsomes, 7) 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH)-induced low density lipoprotein (LDL) oxidation, 8) AAPH-induced linoleic oxidation. 9) Lastly, the protective effects of curcumin on oxidative injury have been demonstrated in vivo in several animal diseases models. [10][11][12] Free radicals are normally formed by the physiological processes of the cell. For example superoxide anion radical (O 2 −· ) is produced during the mitochondrial respiratory chain reaction and the nitric oxide radical (NO) is generated by the activation of nitric oxide synthase. In some circumstances, the overproduction of those radicals, as well as the formation of toxic radicals such as the hydroxyl radical (HO · ) leads to the damage of biological molecules, thus resulting in many ...

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Section: Resultsmentioning

confidence: 99%

Electron Paramagnetic Resonance Study of the Free Radical Scavenging Capacity of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Morales

Sirijaroonwong

Yamanont

et al. 2015

Biological & Pharmaceutical Bulletin

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“…The medical activity of curcumin has been known since ancient times. The beneficial effects can be attributed to the curcumin antioxidant activity, which involves radical and peroxide scavenging as well as metal chelating effect [21][22][23][24][25][26]; in addition, curcumin shows anti-proliferative [27], antiapoptotic [28] and anti-angiogenetic [29] properties.…”

Section: Introductionmentioning

confidence: 99%

Direct chemical grafted curcumin on halloysite nanotubes as dual-responsive prodrug for pharmacological applications

Massaro

Amorati

Cavallaro

et al. 2016

Colloids and Surfaces B: Biointerfaces

150

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“…1) is present or when it is fully in keto form [7][8][9] with the resulting properties depending on the latter. The strong chelating ability of diketones has been widely investigated towards a great number of metal ions; therefore, curcumin could be of great importance in the chelating treatment of metal intoxication and overload [10]. The formation of various metal complexes with curcumin has been investigated [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…The strong chelating ability of diketones has been widely investigated towards a great number of metal ions; therefore, curcumin could be of great importance in the chelating treatment of metal intoxication and overload [10]. The formation of various metal complexes with curcumin has been investigated [10][11][12]. The stoichiometries of curcumin with some metal ions were also reported [10,12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of some Ternary Metal Complexes of Curcumin with 1,10-phenanthroline and their Anticancer Applications

et al. 2014

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Some ternary complexes of curcumin have been synthesized by the reaction of M(II) nitrate with curcumin as primary ligand and 1,10-phenanthroline (phen) as supporting ligand in water/ethanol solution under a nitrogen atmosphere. The composition of the complexes has been characterized by elemental analysis, molar conductivity, thermogravimetric analysis, IR, UV-vis spectroscopy. The results reveal that curcumin ligand coordinates with M(II) in bidentate mode after deprotonation. The supporting ligand (phen) uses its two N atoms in coordination with metal ions in bidentate mode. The general formula of the complexes is [M(Cur)(phen)]NO 3 (M = Ni(II), Co(II), Cu(II) and Z(II)). The results of antibacterial activity indicated that the complexes have good antibacterial ability for the testing bacterium than that of curcumin. Furthermore, the [M(Cur)(phen)]NO 3 complexes were evaluated for its in vitro anticancer activity against hepatocellular carcinoma.

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Curcuminoids as potential new iron-chelating agents: spectroscopic, polarographic and potentiometric study on their Fe(III) complexing ability

Cited by 180 publications

References 25 publications

Electron Paramagnetic Resonance Study of the Free Radical Scavenging Capacity of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Electron Paramagnetic Resonance Study of the Free Radical Scavenging Capacity of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Direct chemical grafted curcumin on halloysite nanotubes as dual-responsive prodrug for pharmacological applications

Synthesis and Characterization of some Ternary Metal Complexes of Curcumin with 1,10-phenanthroline and their Anticancer Applications

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