Curcumin-benzodioxaborole chelates

Balaban, Alexandrù T.; Párkányi, Cyril; Ghiviriga, Ion; Aaron, Jean‐Jacques; Zajickova, Zuzana; Martínez, Omar R.

doi:10.3998/ark.5550190.0009.d01

Cited by 13 publications

(3 citation statements)

References 24 publications

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“…Their optical properties and those of their metal complexes have been investigated extensively. With boric acid, curcumin, the main curcuminoid, has long been known to form a highly colored dicurcuminatoboronium salt, the so-called rosocyanine, that has been used for the colorimetric determination of boron . Despite that work, the fluorescence emission properties and excited-state behavior of difluoroboron complexes of natural and abiotic curcuminoids have far less been investigated.…”

Section: Introductionmentioning

confidence: 98%

“…With boric acid, curcumin, the main curcuminoid, has long been known to form a highly colored dicurcuminatoboronium salt, the so-called rosocyanine, that has been used for the colorimetric determination of boron. 23 Despite that work, the fluorescence emission properties and excited-state behavior of difluoroboron complexes of natural and abiotic curcuminoids have far less been investigated. Recently, Moore and co-workers reported the application of the BF 2 complex of 1,5-bis(N,N-dimethylaminostyryl)acacH as an amyloid-β plaque-specific fluorescent probe providing a promising near-infrared fluorescent dye for in vivo biological studies.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and Photophysical Properties of Difluoroboron Complexes of Curcuminoid Derivatives Bearing Different Terminal Aromatic Units and a meso-Aryl Ring

2013

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The synthesis of nine curcuminoids and their difluoroboron complexes is described, with seven of them containing a meso-phenyl ring. Dynamic (19)F NMR confirmed the fact that rotation of that meso-aryl fragment is restricted in the latter systems at room temperature and become allowed at higher temperature (>45 °C). The molecular structure of a meso-substituted derivative in the solid state showed that the phenyl ring lies in a highly twisted plane with respect to the mean curcuminoid plane. The photophysical properties of the nine compounds were investigated in solvents of different polarity. Meso-substitution with a phenyl ring has little influence on fluorescence emission properties in solution, radiative and nonradiative kinetic constants being similar for meso- and nonsubstituted compounds, which is in contrast to the case of BODIPY derivatives. However, introduction of an electron donor p-methoxy group at the meso-phenyl ring leads to small perturbation of the curcuminoid π-system fluorescence emission. We also report the influence of the meso-phenyl group on the emission properties of the aggregated solids.

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Section: Introductionmentioning

confidence: 98%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Photophysical Properties of Difluoroboron Complexes of Curcuminoid Derivatives Bearing Different Terminal Aromatic Units and a meso-Aryl Ring

2013

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“…The curcumin complexes structure were elucidated using infrared, electronic spectra, 1 H-NMR, SEM, and TEM. The molar conductance Cur metal complexes solutions of 1 x 10 -3 mol/cm 3 in DMSO, Λm, were 32, 27, 28 and 33 Ω −1 mol −1 cm −1 for Mg(II), Ca(II), Cu(II) and Se(IV), respectively, which is very low, proving the absence of chloride ions inside or outside chelation sphere confirming non-electrolytic nature, while for Cr(III) curcumin Λm = 45 Ω −1 mol −1 cm −1 relatively high compared to other curcumin complexes, confirming that chloride ions are inside complexation sphere [26,27] and this was confirmed by AgNO3 test.…”

Section: Microanalytical and Conductance Studiesmentioning

confidence: 90%

Antioxidant novel activities of curcumin complexes with Mg(II), Ca(II), Cu(II), Cr(III) and Se(IV) metal ions: synthesis and spectral studies

M. El-Megharbel,

H. Qahl,

Althobaiti

et al. 2024

Bull. Chem. Soc. Eth.

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Curcumin (Cur) metal complexes of Mg(II), Ca(II), Cu(II), Cr(III), and Se(IV) were prepared and characterized using elemental analysis, molar conductance, IR, UV-spectra, 1H NMR, SEM, TEM, and X-ray diffraction. The very low values of molar conductance confirm that Cl- ions are absent inside or outside the chelation sphere confirming their non-electrolytic nature, while for Cr(III) Cur is high compared to other curcumin complexes, confirming that Cl- ions are inside the complexation sphere. Based on IR and electronic spectra, the Cur C=O group in enol form chelated to Mg(II), Ca(II), Cu(II), Cr(III), and tetravalent metal (Se). The surface morphology of the curcumin chelates showed an increase in particle size and irregular grains shaped with an elongated morphology. Transmission electron microscopy revealed that the Cur chelates have spherical black spots like shape with a particle size of 72.21-88.75 nm, 34.89-57.33 nm, and 80.71-100 nm for Cu(II), Zn(II), and Se(IV) Cur respectively. X–ray powder diffraction patterns for Cu(II) Cur complexes showed particle size within 70-90 nm; the antioxidant activities of Cur and its metal complexes were assessed. Results showed that the Cur complexes with Cr, Mg, Ca, Cu, or Se showed potent antioxidant activities. Further studies could evaluate the potency of these complexes to elevate the antioxidant defense system and enhance body functions against degenerative diseases, such as aging, Alzheimer's disease, and viral diseases. KEY WORDS: Curcumin, Mg/Cur, Cu/Cur, Se/Cur, Electronic spectra, Antioxidant, Oxidative stress Bull. Chem. Soc. Ethiop. 2024, 38(2), 347-363. DOI: https://dx.doi.org/10.4314/bcse.v38i2.6

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Three‐Membered Carbocycles

2010

Name Reactions for Carbocyclic Ring Formations

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Curcumin-benzodioxaborole chelates

Abstract: The reaction of substituted benzodioxaboroles with curcumin affords crystalline chelates, whose large dipole moments as well as electronic absorption and NMR spectra were studied.

Cited by 13 publications

References 24 publications

Synthesis and Photophysical Properties of Difluoroboron Complexes of Curcuminoid Derivatives Bearing Different Terminal Aromatic Units and a meso-Aryl Ring

Synthesis and Photophysical Properties of Difluoroboron Complexes of Curcuminoid Derivatives Bearing Different Terminal Aromatic Units and a meso-Aryl Ring

Antioxidant novel activities of curcumin complexes with Mg(II), Ca(II), Cu(II), Cr(III) and Se(IV) metal ions: synthesis and spectral studies

Three‐Membered Carbocycles

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