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Synthesis and In Vitro Antitumor Activity of Two Mixed-Ligand Oxovanadium(IV) Complexes of Schiff Base and Phenanthroline.

Zhang Y, Wang X, Fang W, Cai X, Chu F, Liao X, Lu J - Bioinorg Chem Appl (2013)

Bottom Line: Two oxovanadium(IV) complexes of [VO(msatsc)(phen)], (1) (msatsc = methoxylsalicylaldehyde thiosemicarbazone, phen = phenanthroline) and its novel derivative [VO (4-chlorosatsc)(phen)], (2) (4-chlorosatsc = 4-chlorosalicylaldehyde thiosemicarbazone), have been synthesized and characterized by elemental analysis, IR, ES-MS, (1)H NMR, and magnetic susceptibility measurements.Both 1 and 2 decreased significantly the ΔΨm, causing the depolarization of the mitochondrial membrane.Complex 2 showed greater antitumor efficiency than that of complex 1.

View Article: PubMed Central - PubMed

Affiliation: Department of Biology, School of Basic Courses, Guangdong Pharmaceutical University, Guangzhou, Guangdong 510006, China.

ABSTRACT
Two oxovanadium(IV) complexes of [VO(msatsc)(phen)], (1) (msatsc = methoxylsalicylaldehyde thiosemicarbazone, phen = phenanthroline) and its novel derivative [VO (4-chlorosatsc)(phen)], (2) (4-chlorosatsc = 4-chlorosalicylaldehyde thiosemicarbazone), have been synthesized and characterized by elemental analysis, IR, ES-MS, (1)H NMR, and magnetic susceptibility measurements. Their antitumor effects on BEL-7402, HUH-7, and HepG2 cells were studied by MTT assay. The antitumor biological mechanism of these two complexes was studied in BEL-7402 cells by cell cycle analysis, Hoechst 33342 staining, Annexin V-FITC/PI assay, and detection of mitochondrial membrane potential (ΔΨm). The results showed that the growth of cancer cells was inhibited significantly, and complexes 1 and 2 mainly caused in BEL-7402 cells G0/G1 cell cycle arrest and induced apoptosis. Both 1 and 2 decreased significantly the ΔΨm, causing the depolarization of the mitochondrial membrane. Complex 2 showed greater antitumor efficiency than that of complex 1.

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Absorption spectra of VO(msatsc)(phen) (A) and its ligand salsem (B) in (a) and VO(4-cholrobrsatsc)(phen) (C) and its ligand 4-cholrobrsatsc (D) in (b), respectively.
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fig1: Absorption spectra of VO(msatsc)(phen) (A) and its ligand salsem (B) in (a) and VO(4-cholrobrsatsc)(phen) (C) and its ligand 4-cholrobrsatsc (D) in (b), respectively.

Mentions: The electronic spectra of the two complexes and their ligands were shown in Figure 1. The complexes show an intense band at ca. 265 nm assignable to π-π* transitions of aromatic rings of phenanthroline [18–20, 28]. A medium band is observed near 400 nm, which is attributed to a ligand-to-metal charge-transfer transition (LMCT) as a charge transfer from a p-orbital on the lone-pair of ligands oxygen atoms to the empty d-orbital of the vanadium atom [27, 29]. The remaining bands appearing in the UV-region (320–350 nm) are assignable to the intraligand transitions of the Schiff base [18, 26–28]. Complexes of oxovanadium(IV) with coordination numbers 5 and 6 are usually square pyramidal/trigonal bipyramidal and distorted octahedral, respectively [19, 21, 29]. From the above obtained spectral data, it indicates that the Schiff bases bonded through the phenolate oxygen, imine nitrogen, and thiolate sulfur atoms leaving the thiomethyl as the pendant group. This implies that complexes 1 and 2 bear the central V (IV) atom in a square-pyramidal geometry [18, 29, 30].


Synthesis and In Vitro Antitumor Activity of Two Mixed-Ligand Oxovanadium(IV) Complexes of Schiff Base and Phenanthroline.

Zhang Y, Wang X, Fang W, Cai X, Chu F, Liao X, Lu J - Bioinorg Chem Appl (2013)

Absorption spectra of VO(msatsc)(phen) (A) and its ligand salsem (B) in (a) and VO(4-cholrobrsatsc)(phen) (C) and its ligand 4-cholrobrsatsc (D) in (b), respectively.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3569890&req=5

fig1: Absorption spectra of VO(msatsc)(phen) (A) and its ligand salsem (B) in (a) and VO(4-cholrobrsatsc)(phen) (C) and its ligand 4-cholrobrsatsc (D) in (b), respectively.
Mentions: The electronic spectra of the two complexes and their ligands were shown in Figure 1. The complexes show an intense band at ca. 265 nm assignable to π-π* transitions of aromatic rings of phenanthroline [18–20, 28]. A medium band is observed near 400 nm, which is attributed to a ligand-to-metal charge-transfer transition (LMCT) as a charge transfer from a p-orbital on the lone-pair of ligands oxygen atoms to the empty d-orbital of the vanadium atom [27, 29]. The remaining bands appearing in the UV-region (320–350 nm) are assignable to the intraligand transitions of the Schiff base [18, 26–28]. Complexes of oxovanadium(IV) with coordination numbers 5 and 6 are usually square pyramidal/trigonal bipyramidal and distorted octahedral, respectively [19, 21, 29]. From the above obtained spectral data, it indicates that the Schiff bases bonded through the phenolate oxygen, imine nitrogen, and thiolate sulfur atoms leaving the thiomethyl as the pendant group. This implies that complexes 1 and 2 bear the central V (IV) atom in a square-pyramidal geometry [18, 29, 30].

Bottom Line: Two oxovanadium(IV) complexes of [VO(msatsc)(phen)], (1) (msatsc = methoxylsalicylaldehyde thiosemicarbazone, phen = phenanthroline) and its novel derivative [VO (4-chlorosatsc)(phen)], (2) (4-chlorosatsc = 4-chlorosalicylaldehyde thiosemicarbazone), have been synthesized and characterized by elemental analysis, IR, ES-MS, (1)H NMR, and magnetic susceptibility measurements.Both 1 and 2 decreased significantly the ΔΨm, causing the depolarization of the mitochondrial membrane.Complex 2 showed greater antitumor efficiency than that of complex 1.

View Article: PubMed Central - PubMed

Affiliation: Department of Biology, School of Basic Courses, Guangdong Pharmaceutical University, Guangzhou, Guangdong 510006, China.

ABSTRACT
Two oxovanadium(IV) complexes of [VO(msatsc)(phen)], (1) (msatsc = methoxylsalicylaldehyde thiosemicarbazone, phen = phenanthroline) and its novel derivative [VO (4-chlorosatsc)(phen)], (2) (4-chlorosatsc = 4-chlorosalicylaldehyde thiosemicarbazone), have been synthesized and characterized by elemental analysis, IR, ES-MS, (1)H NMR, and magnetic susceptibility measurements. Their antitumor effects on BEL-7402, HUH-7, and HepG2 cells were studied by MTT assay. The antitumor biological mechanism of these two complexes was studied in BEL-7402 cells by cell cycle analysis, Hoechst 33342 staining, Annexin V-FITC/PI assay, and detection of mitochondrial membrane potential (ΔΨm). The results showed that the growth of cancer cells was inhibited significantly, and complexes 1 and 2 mainly caused in BEL-7402 cells G0/G1 cell cycle arrest and induced apoptosis. Both 1 and 2 decreased significantly the ΔΨm, causing the depolarization of the mitochondrial membrane. Complex 2 showed greater antitumor efficiency than that of complex 1.

No MeSH data available.


Related in: MedlinePlus