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Synthesis, Characterization, and Anticancer Activity of New Metal Complexes Derived from 2-Hydroxy-3-(hydroxyimino)-4-oxopentan-2-ylidene)benzohydrazide.

El-Tabl AS, Mohamed Abd El-Waheed M, Wahba MA, Abd El-Halim Abou El-Fadl N - Bioinorg Chem Appl (2015)

Bottom Line: The ESR spectra of the solid copper(II) complexes are characteristic to d(9) configuration and have an axial symmetry type of a d(x (2)-y (2)) ground state.The g values confirmed the tetragonal octahedral geometry with a considerably ionic or covalent environment.The cytotoxic activity of the ligand and its metal complexes showed potent cytotoxicity effect against growth of human liver cancer HepG2 cell lines compared to the clinically used Sorafenib (Nexavar).

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Faculty of Science, Menoufia University, P.O. Box 5744, Shibin Al Kawm, Egypt.

ABSTRACT
Novel metal(II) complexes derived from 2-hydroxy-N'-((Z)-3-(hydroxyimino)-4-oxopentan-2-ylidene)benzohydrazide ligand (H2L) were synthesized and characterized by elemental and thermal analyses (DTA and TGA), IR, UV-VIS, (1)H-NMR, ESR and mass spectroscopy, magnetic susceptibilities, and conductivities measurements. The complexes adopt distorted octahedral geometry. The ESR spectra of the solid copper(II) complexes are characteristic to d(9) configuration and have an axial symmetry type of a d(x (2)-y (2)) ground state. The g values confirmed the tetragonal octahedral geometry with a considerably ionic or covalent environment. The cytotoxic activity of the ligand and its metal complexes showed potent cytotoxicity effect against growth of human liver cancer HepG2 cell lines compared to the clinically used Sorafenib (Nexavar).

No MeSH data available.


Related in: MedlinePlus

IC50 values of the ligand H2L (1) and its metal complexes (2), (3), (4), and (9) against human liver HepG2 cancer cell.
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fig3: IC50 values of the ligand H2L (1) and its metal complexes (2), (3), (4), and (9) against human liver HepG2 cancer cell.

Mentions: The cytotoxic activity of the oxime hydrazone ligand H2L (1) and its metal complexes (2), (3), (4), and (9) was evaluated against human liver HepG2 cancer cell, (HepG2 cell line) within 0.1–100 μg/L concentration range. The IC50 values were calculated for each compound and results are presented in Figure 3 and Table 6. As shown, most complexes displayed significantly cytotoxic activities compared to Sorafenib (Nexavar) standard drug. It seems that changing the anion, coordination sites, and the nature of the metal ion has effect on the biological behavior. Cytotoxicity activity of the complexes may be attributed to the central metal atom which was explained by Tweedy's chelation theory [55, 56]. Cytotoxicity results indicated that all tested complexes (IC50 = 2.24–6.49 μM) (except complex (9) with IC50 = 36.80 μM) demonstrated potent cytotoxicity against HepG2 cancer cells. Copper complex (4) showed the highest cytotoxicity effect with IC50 value of 2.24 μM, followed by complex (3) with IC50 value 2.67 μM and then complex (2) with IC50 value 6.49 μM. It was observed also that all complexes are more active than the free ligand. This indicated enhancing of the antitumor activity upon coordination. The enhancement of cytotoxic activity may be assigned to that the positive charge of the metal increased the acidity of coordinated ligand that bears protons, leading to stronger hydrogen bonds which enhanced the biological activity [57, 58]. It seems that changing the anion, coordination sites, and the nature of the metal ion has a pronounced effect on the biological behavior by altering the binding ability of DNA [59, 60]. Gaetke and Chow had reported that metal has been suggested to facilitate oxidative tissue injury through a free-radical mediated pathway analogous to the Fenton reaction [61].


Synthesis, Characterization, and Anticancer Activity of New Metal Complexes Derived from 2-Hydroxy-3-(hydroxyimino)-4-oxopentan-2-ylidene)benzohydrazide.

El-Tabl AS, Mohamed Abd El-Waheed M, Wahba MA, Abd El-Halim Abou El-Fadl N - Bioinorg Chem Appl (2015)

IC50 values of the ligand H2L (1) and its metal complexes (2), (3), (4), and (9) against human liver HepG2 cancer cell.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4496588&req=5

fig3: IC50 values of the ligand H2L (1) and its metal complexes (2), (3), (4), and (9) against human liver HepG2 cancer cell.
Mentions: The cytotoxic activity of the oxime hydrazone ligand H2L (1) and its metal complexes (2), (3), (4), and (9) was evaluated against human liver HepG2 cancer cell, (HepG2 cell line) within 0.1–100 μg/L concentration range. The IC50 values were calculated for each compound and results are presented in Figure 3 and Table 6. As shown, most complexes displayed significantly cytotoxic activities compared to Sorafenib (Nexavar) standard drug. It seems that changing the anion, coordination sites, and the nature of the metal ion has effect on the biological behavior. Cytotoxicity activity of the complexes may be attributed to the central metal atom which was explained by Tweedy's chelation theory [55, 56]. Cytotoxicity results indicated that all tested complexes (IC50 = 2.24–6.49 μM) (except complex (9) with IC50 = 36.80 μM) demonstrated potent cytotoxicity against HepG2 cancer cells. Copper complex (4) showed the highest cytotoxicity effect with IC50 value of 2.24 μM, followed by complex (3) with IC50 value 2.67 μM and then complex (2) with IC50 value 6.49 μM. It was observed also that all complexes are more active than the free ligand. This indicated enhancing of the antitumor activity upon coordination. The enhancement of cytotoxic activity may be assigned to that the positive charge of the metal increased the acidity of coordinated ligand that bears protons, leading to stronger hydrogen bonds which enhanced the biological activity [57, 58]. It seems that changing the anion, coordination sites, and the nature of the metal ion has a pronounced effect on the biological behavior by altering the binding ability of DNA [59, 60]. Gaetke and Chow had reported that metal has been suggested to facilitate oxidative tissue injury through a free-radical mediated pathway analogous to the Fenton reaction [61].

Bottom Line: The ESR spectra of the solid copper(II) complexes are characteristic to d(9) configuration and have an axial symmetry type of a d(x (2)-y (2)) ground state.The g values confirmed the tetragonal octahedral geometry with a considerably ionic or covalent environment.The cytotoxic activity of the ligand and its metal complexes showed potent cytotoxicity effect against growth of human liver cancer HepG2 cell lines compared to the clinically used Sorafenib (Nexavar).

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Faculty of Science, Menoufia University, P.O. Box 5744, Shibin Al Kawm, Egypt.

ABSTRACT
Novel metal(II) complexes derived from 2-hydroxy-N'-((Z)-3-(hydroxyimino)-4-oxopentan-2-ylidene)benzohydrazide ligand (H2L) were synthesized and characterized by elemental and thermal analyses (DTA and TGA), IR, UV-VIS, (1)H-NMR, ESR and mass spectroscopy, magnetic susceptibilities, and conductivities measurements. The complexes adopt distorted octahedral geometry. The ESR spectra of the solid copper(II) complexes are characteristic to d(9) configuration and have an axial symmetry type of a d(x (2)-y (2)) ground state. The g values confirmed the tetragonal octahedral geometry with a considerably ionic or covalent environment. The cytotoxic activity of the ligand and its metal complexes showed potent cytotoxicity effect against growth of human liver cancer HepG2 cell lines compared to the clinically used Sorafenib (Nexavar).

No MeSH data available.


Related in: MedlinePlus