Chalconoid metal chelates: spectral, biological and catalytic applications

Johnson, J.R.T; Yardily, A.

doi:10.1080/00958972.2019.1669022

Cited by 20 publications

(15 citation statements)

References 98 publications

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“…11 The heterodiene molecular functionalities form stable complexes with the transition and non-transition elements. 12 In recent years, there have been outstanding developments in several areas of pharmaceutical science. The wide range of biological activities associated with chalcone based complexes has been explored their therapeutic potentials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Patil¹,

Zangade

2021

JSCS

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A series of binary metal complexes [halo, hydroxyl and methoxy sub-stituted bis (2-(E) acryloyl)naphthalen-1-yl)oxy)Cu(II) and Zn(II) (C1-C10)] of Cu2+ and Zn2+ ions derived from bi-coordinated hydroxylated 1,3-diaryl-2- -propene-1-ones were synthesized. The newly synthesized metal complexes were structurally determined by FT-IR, 1H NMR, 13CNMR, ESR spectral, XRD and TGA analysis. The FT-IR and ESR studies demonstrated that interactions between metal ions with ligands occur through carbonyl oxygen and deprotonated hydroxyl oxygen and corresponds to square-planar geometry for all complexes. In-vitro the metal complexes were screened and evaluated for their antimicrobial and cytotoxic activity. The complexes C1 and C4 showed the significant antimicrobial activity while the remaining complexes were showed the moderately antimicrobial activity against the tested pathogens. The complexes were evaluated for cytotoxic activity against the organism Artemia salina. The complexes C2, C3, C4 and C5 were showed the LC50 values as 630.45, 969.99, 921.94 and 918.41 ?M mL-1 respectively. Further complexes were evaluated for anticancer activity against liver cancer cell line (Hep G2) in comparison with 5-fluorouracil standard. The complex C5 showed the significant IC50 value 58.94 ?g mL-1. Therefore the present study is useful to develop the new class of antimicrobial and anticancer agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Patil¹,

Zangade

2021

JSCS

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“…The partial conversion of α,β-unsaturated ketones to enolic form upon metal influence is well documented. 42 Interestingly, cesium ion significantly enhances the fluorescence intensity for the emission band at 470 nm in conjunction with the emergence of the emission band at 430 nm for the derivative 3k (Figure 5B). The latter suggests that the cesium metal is interacting with the oxygen of the methoxy moiety (Figure 5C), which suppressed its donor character, leading to an increase and recovery of the LE state emission band intensity (at 426−436 nm) compared to the CT-state emission band (at 476 nm).…”

Section: ■ Results and Discussionmentioning

confidence: 87%

Photo-Induced Partially Aromatized Intramolecular Charge Transfer

Romero

Piro

et al. 2021

J. Phys. Chem. B

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Diverse models of intramolecular charge transfer (ICT) have been proposed for interpreting the origin of the charge-transfer (CT) state in donor–acceptor (D–A) dyes. However, a large variety of fused-heterocyclic dyes containing a pseudo-aromatic ring in the rigid structure have shown to be incompatible with them. To approximate a solution within the ICT concept, we reported a novel ICT model called partially aromatized intramolecular charge transfer (PAICT). PAICT involves the generation of a CT state from an ICT that occurred within a pre-excited D–A fused-heterocyclic structure possessing a pseudo-aromatic or unstable aromatic ring as the acceptor moiety. The model was proposed from the multiple-emissive mesomeric D–A N 1 -aryl-2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1H)-one, whose excited mesomeric states, which are defined by the aromatic and pseudo-aromatic forms of the pyrindin-4(1H)-one ring, led to a common partial aromatized CT state upon excitation via PAICT. The latter was supported through theoretical calculations on the excited mesomeric states, one-dimensional (1D) and two-dimensional (2D) excitation–emission measurements in different solvents, and the detection of three excited states by lifetime measurements upon 370 nm excitation. The existence of mesomerism was supposed from: (i) two overlapping bands at 370–390 (or 400–420 nm) in UV–vis spectra, (ii) the direct interaction between the pyridinic nitrogen of one molecule and the carbonylic oxygen of the other found in the solid state and, (iii) the detection of three excited states by lifetime measurements. The PAICT opens new perspectives for interpreting the charge-transfer phenomenon in fused-heterocyclic dyes, in particular, those containing a pseudo-aromatic or unstable aromatic ring as an acceptor moiety.

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“…Moreover, both chalcones and Schiff bases are known for their ability to form complexes with metal cations, especially divalent cations of transition metals [ 30 , 31 ]. The complexation of one of the systems, either Schiff base or chalcone, may significantly impact the interactions between Schiff base-functionalized materials and chalcones.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, both molecular and fragmentation signals in the FAPA-MS spectra of the chalcones released from material-chalcone complexes even reached 4 × 10 5 , which, in comparison to the pre-performed calibration curves, indicate an effective chalcones binding on the materials (the intensities correspond to the chalcones' concentration of ∼1 × 10 −5 M). Moreover, both chalcones and Schiff bases are known for their ability to form complexes with metal cations, especially divalent cations of transition metals [30,31]. The complexation of one of the systems, either Schiff base or chalcone, may significantly impact the interactions between Schiff base-functionalized materials and chalcones.…”

Section: Adsorption Of the Chalcones On The Schiff Base-modified Materialsmentioning

confidence: 99%

Mass Spectrometric Investigation of Organo-Functionalized Magnetic Nanoparticles Binding Properties toward Chalcones

et al. 2021

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Chalcones are naturally occurring compounds exhibiting multiple biological functions related to their structure. The investigation of complexes formed by chalcones, namely 2′,4′-dihydroxy-2-methoxychalcone (DH-2-MC) and 2′,4′-dihydroxy-3-methoxychalcone (DH-3-MC), with organo-functionalized Fe3O4 magnetic nanoparticles using mass spectrometric techniques is reported. The magnetic nanoparticles were obtained by the silanization of Fe3O4 particles with 3-aminopropyltrimethosysilane, which were subsequently reacted with 3-hydroxybenzaldehyde (3-HBA) or 2-pyridinecarboxaldehyde (2-PCA), resulting in the formation of Schiff base derivatives. The formation of their complexes with chalcones was studied using electrospray (ESI) and flowing atmosphere-pressure afterglow (FAPA) mass spectrometric (MS) ionization techniques. The functional nanoparticles which were synthesized using 3-hydroxybenzaldehyde displayed higher affinity towards examined chalcones than their counterparts obtained using 2-pyridinecarboxaldehyde, which has been proved by both ESI and FAPA techniques. For the examined chalcones, two calibration curves were obtained using the ESI-MS method, which allowed for the quantitative analysis of the performed adsorption processes. The presence of Cu(II) ions in the system significantly hindered the formation of material–chalcone complexes, which was proved by the ESI and FAPA techniques. These results indicate that both mass spectrometric techniques used in our study possess a large potential for the investigation of the binding properties of various functional nanoparticles.

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Chalconoid metal chelates: spectral, biological and catalytic applications

Cited by 20 publications

References 98 publications

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Photo-Induced Partially Aromatized Intramolecular Charge Transfer

Mass Spectrometric Investigation of Organo-Functionalized Magnetic Nanoparticles Binding Properties toward Chalcones

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