Heteroleptic complexes of cocaine/TMEDA with some f block metals: Synthesis, DFT studies, spectral, thermal, cytotoxicity and antimetastatic properties

Zaki, Nadia G.; Mahmoud, Walaa H.; Kerdawy, Ahmed M. El; Abdallah, Abanoub Mosaad

doi:10.1016/j.saa.2019.117938

Cited by 16 publications

(12 citation statements)

References 55 publications

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“…The MTT assay is based on the production of a bluish-purple formazan reduction product of 3-[4,5 dimethylthiazol-2-yl]-2,5 diphenyltetrazolium bromide (MTT) by mitochondrial reductase enzyme in living cells. 26 Stock solutions of MET (positive control) and the optimized HA-MPS in DMSO were individually diluted into serial dilutions (0.39, 1.56, 6.25, 25 and 100 μg/mL). A 96-well plate (1.2–1.8 ×10 4 cells/well) was used.…”

Section: Methodsmentioning

confidence: 99%

Hyaluronic Acid Conjugated Metformin-Phospholipid Sonocomplex: A Biphasic Complexation Approach to Correct Hypoxic Tumour Microenvironment

Farag¹,

Malak²,

Yehia³

et al. 2021

IJN

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Purpose Development of hyaluronic acid conjugated metformin-phospholipid sonocomplexes (HA-MPS), a biphasic complexation product compiled for enhancing both the lipophilicity and targeting potential of Metformin (MET) to CD44 receptors on pancreatic cancer. Methods MET was chemically conjugated to hyaluronic acid (HA) via amide coupling reaction. Then, the HA conjugated MET was physically conjugated to Lipoid™S100 via ultrasound irradiation. A combined D-optimal design was implemented to statistically optimize formulation variables. The HA-MPS were characterized through solubility studies, partition coefficient, drug content uniformity, particle size and zeta potential. The optimized HA-MPS was tested via proton nuclear magnetic resonance, infrared spectroscopy to elucidate the nature of physicochemical interactions in the complex which was further scrutinized on molecular level via molecular docking and dynamic simulation. Results The solubility and partition studies showed a lipophilicity enhancement up to 67 folds as they adopted inverted micelles configuration based on the packing parameter hypothesis. The optimized HA-MPS showed 11.5 folds lower IC 50 , extra 25% reduction in oxygen consumption rate, better reduction in hypoxia-inducible factor and reactive oxygen species in MiaPaCa-2 cells. Conclusion These results proved better internalization of MET which was reflected by abolishing hypoxic tumour microenvironment, a mainstay toward a normoxic and less resistant pancreatic cancer.

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Section: Methodsmentioning

confidence: 99%

Hyaluronic Acid Conjugated Metformin-Phospholipid Sonocomplex: A Biphasic Complexation Approach to Correct Hypoxic Tumour Microenvironment

Farag¹,

Malak²,

Yehia³

et al. 2021

IJN

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“…The charges on the metal atoms were +0.5574, +0.3913, –0.0738, +0.2277, +0.1750, +0.2377, +0.5797, and +0.6934 e for Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes, respectively, which were reduced from the formal charge +3 (for Cr(III) and Fe(III) ions) or +2 (for Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) ions) as a result of accepting electron density from the donating atoms of the ligands. [ 41 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structural characterization, density functional theory calculations, and antimicrobial, anticancer, and antimetastatic properties of nanosized heteroleptic complexes of cocaine/TMEDA with d‐block metal ions

Abdallah

Zaki

Mahmoud

et al. 2021

Applied Organom Chemis

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In the field of transition metal chemistry, the development of transition metal‐based drugs for the treatment of diseases such as cancer or microbial infections with minimization of adverse effects and drug resistance constitutes an active area of research. Herein, eight novel nanosized heteroleptic complexes of cocaine/TMEDA with the formula [M(COC)(TMEDA)Cly(OH2)z]nCl·xH2O (M = Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II); COC = cocaine; TMEDA = N,N,N′,N′‐tetramethylethylenediamine, y = 1–2; z = 0–1; n = 0–1; and x = 0–2) were synthesized and structurally characterized via elemental analysis, molar conductivity, mass spectrometry, and spectroscopic and microscopic techniques. The thermal properties and kinetic thermodynamic parameters of the synthesized complexes were also studied. The geometry and electronic structures were investigated via density functional theory (DFT) calculations. The antiproliferative activity of the complexes on HepG‐2 and MCF‐7 cancer cell lines was quantified via MTT assay. The Fe(III) and Cd(II) complexes exhibited promising cytotoxic activities against the HepG‐2 and MCF‐7 cancer cell lines, respectively, with minimum effect on HFB4 human normal cells. Further molecular mechanistic studies were performed on the Cd(II) complex to inspect its influence on different cancer pathophysiology‐related processes in the MCF‐7 cell line including metastasis, apoptosis, and cellular oxidative stress and on the cellular levels of the human tumor suppressor nuclear proteins p21 and p27. The results revealed that the Cd(II) complex is a promising anticancer agent that acts through several molecular mechanisms with minimum effect on the normal cells and with additional antimetastatic properties. Furthermore, the antibacterial and antifungal activities of the prepared complexes were investigated.

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“…The bands in range of 501-515 cm −l were attributed to stretching vibration of ν(M-N). [49][50][51][52] It can be assumed that the 1,2,4-triazole Schiff base ligand prepared was treated as a neutral bidentate ligand coordinated to the metal ions through the thiol sulfur atom and the azomethine nitrogen atom.…”

Section: Atommentioning

confidence: 99%

Synthesis, characterization, antimicrobial, and MOE evaluation of nano 1,2,4‐triazole‐based Schiff base ligand with some d‐block metal ions

Mahmoud

Abbas

Mohamed

2021

Applied Organom Chemis

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Three new metal complexes of 4-(benzylideneamino)-5-phenyl-4H-1,-2,4-triazole-3-thiol ligand (L) and three transition metal ions: Fe (III), Cu (II), and Zn (II) were synthesized and characterized. The ligand derived from 4-amino-5-phenyl-1,2,4-triazole-3-thiol and benzaldehyde was synthesized in a 1:1 molar ratio. All the chelates were characterized by elemental analysis, conductivity measurements, thermal analysis, FT-IR, and 1 H-NMR spectroscopy.The IR spectrum revealed that the Schiff base ligand coordinated in a neutral bidentate manner with the metal ions through the azomethine N and thiol S. The thiol group coordinated to the metal ions without proton displacement as confirmed from the 1 H NMR spectra. The conductivity data showed the electrolytic nature of the Fe (III) and Cu (II) complexes while the Zn (II) complex was nonelectrolyte. All metal complexes had octahedral structure as depicted by spectral and elemental analyses. The complexes start decomposition at 35 C, and they decomposed in four to five steps. The scanning electron microscope (SEM) analysis confirmed the presence of metal complexes in nanostructure. The 1,2,4-triazole Schiff base ligand (L) and its transition metal complexes have been screened for their antibacterial (Gram [+] bacteria): Bacillis subtilis and Staphylococcus aureus, (Gram [−] bacteria): Escherichia coli and Pseudomonas aeruginosa and two fungi: Candida albicans and Aspergillus flavus by agar diffusion method. The two metal complexes were subjected to molecular docking study against crystal structure of Aspergillus fumigatus (PDB ID: 6NE0) and crystal structure of Mycobacterium tuberculosis (PDB ID: 5UHF). The mode of binding between the A. fumigatus (PDB ID: 6NE0) and Mycobacterium tuberculosis strains and the complexes was discussed. K E Y W O R D S 1,2,4-triazole, Candida albicans, diffusion method, MOE, thermal analysis Three metal chelates of new Schiff base were prepared and characterized.

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Heteroleptic complexes of cocaine/TMEDA with some f block metals: Synthesis, DFT studies, spectral, thermal, cytotoxicity and antimetastatic properties

Cited by 16 publications

References 55 publications

Hyaluronic Acid Conjugated Metformin-Phospholipid Sonocomplex: A Biphasic Complexation Approach to Correct Hypoxic Tumour Microenvironment

Hyaluronic Acid Conjugated Metformin-Phospholipid Sonocomplex: A Biphasic Complexation Approach to Correct Hypoxic Tumour Microenvironment

Synthesis, structural characterization, density functional theory calculations, and antimicrobial, anticancer, and antimetastatic properties of nanosized heteroleptic complexes of cocaine/TMEDA with d‐block metal ions

Synthesis, characterization, antimicrobial, and MOE evaluation of nano 1,2,4‐triazole‐based Schiff base ligand with some d‐block metal ions

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