Metal Chelates of Curcuminoids

Krishnankutty, K.; Venugopalan, P.

doi:10.1080/00945719809349407

Cited by 48 publications

(33 citation statements)

References 10 publications

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“…The 1 H NMR spectra of all the compounds (Table 1) displayed a one proton singlet in the low field at ∼16 ppm and another singlet at δ ≈ 5.9-6.9 ppm assignable respectively to the strong intramolecularly hydrogen bonded enolic and methine protons respectively. 7,15 The compound 1a shows another singlet at δ ≈ 10.04 ppm due to the phenolic group. The trans oriented alkenyl protons can be identified from the position of their signals (δ ≈ 7.9 ppm) and from their observed J values (J ≈ 16 Hz).…”

Section: Structural Characterization Of the 17-diaryl-16-heptadienementioning

confidence: 98%

“…Additional bands appear at ∼475 and ∼420 cm −1 assignable to ν(M-O) vibrations. 7 The band due to trans −CH CH-remains as such in the complex at ∼970 cm −1 .…”

Section: Structural Characterization Of the 17-diaryl-16-heptadienementioning

confidence: 99%

“…1). 7 It has been reported that metal complexation of these α,β-unsaturated 1,3-diketones leads to dramatic changes in their biochemical activities, 8 -11 including antitumour activity. As a part of our studies 7,12 on chemical and biochemical properties of synthetic analogues of active *Correspondence to: K. Krishnankutty, Department of Chemistry, University of Calicut, Kerala 673635, India.…”

Section: Introductionmentioning

confidence: 99%

“…7 It has been reported that metal complexation of these α,β-unsaturated 1,3-diketones leads to dramatic changes in their biochemical activities, 8 -11 including antitumour activity. As a part of our studies 7,12 on chemical and biochemical properties of synthetic analogues of active *Correspondence to: K. Krishnankutty, Department of Chemistry, University of Calicut, Kerala 673635, India. E-mail: john vd@rediffmail.com chemical compounds of such indigenous valuable green medicines and their metal complexes, the present study reports the synthesis, structural characterization, and cytotoxic and antitumour activities of four new curcuminoid analogues, 1a-d, and their copper(II) complexes.…”

Section: Introductionmentioning

confidence: 99%

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Antitumour activity of synthetic curcuminoid analogues (1,7-diaryl-1,6-heptadiene-3,5-diones) and their copper complexes

John¹,

Krishnankutty²

2006

Appl. Organometal. Chem.

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Four new curcuminoid analogues, 1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 1a; 1,7-di(2-furyl)-1,6-heptadiene-3,5-dione, 1b; 1,7-di(2-naphthyl)-1,6-heptadiene-3,5-dione, 1c; 1,7-bis(2-chlorophenyl)-1,6-heptadiene-3,5-dione, 1d; and their copper(II) complexes of ML 2 stoichiometry were synthesized and characterized by UV, IR, 1 H NMR, ESR and mass spectral data. The compounds were investigated for their possible cytotoxic and antitumour activities. It was found that copper chelates are remarkably active compared with free curcuminoid analogues. All the compounds were found to be cytotoxic towards Ehrlich ascites carcinoma cells and cultured L929 (lung fibroblast cells). In the case of culture studies, concentrations needed for 50% cell death were around 5 µg/ml for copper complexes and 10 µg/ml for curcuminoid analogues. Copper complex of 1a with hydroxyl group in the phenyl ring was found to be most active towards L929cells (1 µg/ml produced 43.3 ± 1.3% cell death). Compound 1b, which possesses a furyl ring system, was found to show least activity towards increase in life span of tumour-bearing mice (increase in life span 39.31%). Copper chelates of all curcuminoid analogues showed a significant reduction (p < 0.001) of solid tumour volume in mice.

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Section: Structural Characterization Of the 17-diaryl-16-heptadienementioning

confidence: 98%

“…Additional bands appear at ∼475 and ∼420 cm −1 assignable to ν(M-O) vibrations. 7 The band due to trans −CH CH-remains as such in the complex at ∼970 cm −1 .…”

Section: Structural Characterization Of the 17-diaryl-16-heptadienementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Antitumour activity of synthetic curcuminoid analogues (1,7-diaryl-1,6-heptadiene-3,5-diones) and their copper complexes

John¹,

Krishnankutty²

2006

Appl. Organometal. Chem.

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“…The [Au(curcumin) 2 Cl] was a five coordinate gold complex [13], which had anti-arthritic properties and assessed in an adjuvant-induced rat poly arthritis model. The [Cu(curcumin) 2 ] complexes [14] were most cytotoxic in cultured L929 cells and showed significant reduction in solid tumor volume in as cites tumor bearing mice. In addition, vanadyl, gallium and indium complexes of curcumin [15] have reported for medicinal applications.…”

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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Antimicrobial activity of cotton fabrics treated with curcumin

Reddy

Han

Zhao

et al. 2012

J of Applied Polymer Sci

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Curcumin, a yellow pigment known to have various biological activities, was applied onto cotton as an antimicrobial agent. Curcumin could provide both color and antimicrobial activity to cotton and can be dyed using a batch or continuous process. However, curcumin and cotton have low affinity and therefore the ability of curcumin to impart durable antimicrobial activity on cotton needs to be studied. In this research, the ability of curcumin dyed onto cotton fabrics to inhibit the growth of Escherichia coli and Staphylococcus aureus was studied. Relationships that can predict the rate of inhibition based on the curcumin concentration or shade depth (K/S values) were developed without the need for an antimicrobial test. Durability of antimicrobial activity to laundering and to light was also studied. Curcumin was more effective in inhibiting S. aureus than E. coli. The reduction of bacteria and durability of antimicrobial activity of curcumin to laundering was inferior on cotton fabrics compared with wool.

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Metal Chelates of Curcuminoids

Cited by 48 publications

References 10 publications

Antitumour activity of synthetic curcuminoid analogues (1,7-diaryl-1,6-heptadiene-3,5-diones) and their copper complexes

Antitumour activity of synthetic curcuminoid analogues (1,7-diaryl-1,6-heptadiene-3,5-diones) and their copper complexes

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

Antimicrobial activity of cotton fabrics treated with curcumin

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