A family of mixed-ligand oxidovanadium(<scp>v</scp>) complexes with aroylhydrazone ligands: a combined experimental and computational study on the electronic effects of para substituents of hydrazone ligands on the electronic properties, DNA binding and nuclease activities

Patra, Debashis; Biswas, Nirmalendu; Kumari, Bhavini; Das, Prolay; Sepay, Nayim; Chatterjee, Shamba; Drew, Michael G. B.; Ghosh, Tapas

doi:10.1039/c5ra17844d

Cited by 26 publications

(9 citation statements)

References 116 publications

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“…New bands which are not present in the ligand appeared in the ranges 503–514.62 cm −1 and 619–623 cm −1 in 1–6 attributed to v (M‐N) and v (M‐O) vibrations, respectively. 1 and 2 show two bands at 852.53 and 996.27cm −1 corresponding to V=O stretching vibrations …”

Section: Resultssupporting

confidence: 83%

Three pairs of enantiomers bearing mitochondria‐targeted TPP⁺ groups as potential anti‐cancer agents

Liu

Song

et al. 2019

Applied Organom Chemis

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Six complexes with chiral Schiff-base ligands containing TPP + groups, [VOL R,R / S,S ](ClO 4 ) 2 (1 for RR, 2 for SS), [NiL R,R/S,S ](ClO 4 ) 2 ·C 2 H 5 OH (3 for RR, 4 for SS) and [CuL R,R/S,S ](ClO 4 ) 2 ·CHCl 3 ·CH 3 CH 2 OH (5 for RR, 6 for SS) (L R,R/S,S = N,N′-Bis{5-[(triphenylphosphonium)-methyl]salicylidine}-(1R,2R/1S,2S)-diphenylethane-1,2-diamine, were synthesized to serve as mitochondrion-targeting anticancer drugs. The introduction of TPP + group(s) might markedly influence the properties of complexes. Compounds 3 and 5 were structurally characterized by X-ray crystallography. Complexes 1-6 could be moderate intercalating agents to CT-DNA which is determined by several spectroscopy methods. DNA cleavage experiments revealed that all compounds could promote oxidative cleavage of pBR322 plasmid DNA in the presence of H 2 O 2 . MTT assay indicated 1-6 exhibited effective cytotoxicity on A549 and MCF-7 cell lines. Notably, the IC 50 values of 5 (1.24 ± 0.33 μM) or 6 (1.47 ± 0.52 μM) were approximately 9-11 fold lower than that of cisplatin (IC 50 = 13.56 ± 0.88 μM) on A549 cells. 5 and 6 were picked for further study, which indicated that the cytotoxicity seems to result from multiple mechanisms of action, including effectively suppress the growth and proliferation of A549 cells, generation of reactive oxygen species, dissipation of mitochondrial membrane potential, cell cycle perturbation and apoptosis induction. Compounds 1-6 could highly accumulate in the mitochondria by means of ICP-MS assay. This study demonstrates that 1-6 with mitochondrion-targeting function could be efficient anticancer drugs.

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Section: Resultssupporting

confidence: 83%

Three pairs of enantiomers bearing mitochondria‐targeted TPP⁺ groups as potential anti‐cancer agents

Liu

Song

et al. 2019

Applied Organom Chemis

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“…In the title compound, there are two crystallographically independent molecules in the asymmetric unit, which have very similar conformations. Compared with those of closely related structure, such a structural feature is uncommon [15]. The bond lengths and angles are in the expected ranges which fit with those of related compounds in literature [11][12][13][14][15][16][17].…”

Section: Commentsupporting

confidence: 79%

“…In recent years, Schiff bases as one of the important synthetic intermediates have attracted more and more attention due to the wide applications in the fields of coordination chemistry, biochemistry, pharmacy, nanotechnology, and photochemistry [3][4][5][6][7][8][9][10]. From the structural point of view, o-hydroxy Schiff bases are attractive because of their intramolecular H-bond, and thus have been extensively investigated and reported [11][12][13][14][15][16][17]. In addition, the heteroatoms (such as N, F, Cl, Br, S) can act as hydrogen bonding acceptors for bioactive molecules in order to exhibit higher biological activity [18,19].…”

Section: Commentmentioning

confidence: 99%

The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C₁₅H₁₂ClFN₂O₂

Yan

Zhong

Zhang

2019

Zeitschrift Für Kristallographie - New Crystal Structures

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C15H 12 ClFN 2 O 2 , monoclinic, P21/c (no. 14), a = 13.9210(13) Å, b = 13.2329(15) Å, c = 18.7191(19) Å, β = 126.250(2)°, V = 2780.9(5) Å 3 , Z = 8, Rgt(F) = 0.0499, wR ref (F 2 ) = 0.1420, T = 293(2) K. CCDC no.: 1958013The asymmetric unit of the molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

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“…There are also two other potential donor sites in the coordinated hydrazone ligand viz., oxygen of amide carbonyl C7O1 and oxygen of lactone carbonyl C22O5 which are not coordinated in both 2 and 3 due to their non‐planarity with the three donor sites (Figure ). In both the complexes metal‐oxygen (M‐O) bond lengths are: M‐O3 pyrone < M‐O2 amido probably due to the order of O→M π‐bonding . The CIF files have been deposited with CCDC No.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structural characterization and biological evaluation of mononuclear transition metal complexes of zwitterionic dehydroacetic acidN‐aroylhydrazone ligand

Kendur

Chimmalagi

Patil

et al. 2018

Applied Organom Chemis

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Synthesis and characterization of mononuclear transition metal complexes viz., Co(II), Ni(II), Cu(II) and Zn(II) with a newly designed ligand, (E)-2-benzamido-N'- (1-(2-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl) ethylidene) benzohydrazide (H 2 L) are reported. Molecular structures of H 2 L, Ni(II) and Cu(II) complexes were determined by single-crystal X-ray diffraction studies. The structures were stabilized by various intra/inter-molecular H-bonding, C-H···π and π···π stacking interactions. H 2 L exists in zwitterionic form and acts in a monoanionic manner. Ligand/metal ratio was 2:1 for cobalt, nickel and zinc, whereas 1:1 for the copper complex. Co(II), Ni(II) and Zn(II) complexes display distorted octahedral geometry, while the Cu(II) complex shows distorted square pyramidal geometry around the metal ion. Hirshfeld surface analysis and 2D fingerprint plots revealed that H 2 L and its complexes were supported mainly by H⋯H, O⋯H and C⋯H intermolecular interactions. The synthesized compounds were screened for in vitro anti-inflammatory activity by gelatin zymography and the activity was comparable with tetracycline. Their cleavage behavior towards calf thymus DNA has been studied using agarose gel electrophoresis method. H 2 L and Cu(II) complex were selected by National Cancer Institute (NCI) for in vitro single dose testing in the full NCI 60 cell lines panel assay. Finally, molecular docking simulation effectively proves the binding of all the synthesized compounds at cyclooxygenase-2 (COX-2) active sites. KEYWORDS(E)-2-amino-N'-(1-(2-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)ethylidene) benzohydrazide, antiinflammatory and anticancer activity, molecular docking, single crystal X-ray diffraction study, transition metal complexes

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A family of mixed-ligand oxidovanadium(v) complexes with aroylhydrazone ligands: a combined experimental and computational study on the electronic effects of para substituents of hydrazone ligands on the electronic properties, DNA binding and nuclease activities

Abstract: Substituents at 5-position in the acetophenone ring of the hydrazone ligands in a family of mixed-ligand oxidovanadium(v) complexes show marked influence on the electronic properties, DNA binding ability and nuclease activity.

Cited by 26 publications

References 116 publications

Three pairs of enantiomers bearing mitochondria‐targeted TPP⁺ groups as potential anti‐cancer agents

Three pairs of enantiomers bearing mitochondria‐targeted TPP⁺ groups as potential anti‐cancer agents

The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C₁₅H₁₂ClFN₂O₂

Synthesis, structural characterization and biological evaluation of mononuclear transition metal complexes of zwitterionic dehydroacetic acidN‐aroylhydrazone ligand

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A family of mixed-ligand oxidovanadium(v) complexes with aroylhydrazone ligands: a combined experimental and computational study on the electronic effects of para substituents of hydrazone ligands on the electronic properties, DNA binding and nuclease activities

Abstract: Substituents at 5-position in the acetophenone ring of the hydrazone ligands in a family of mixed-ligand oxidovanadium(v) complexes show marked influence on the electronic properties, DNA binding ability and nuclease activity.

Cited by 26 publications

References 116 publications

Three pairs of enantiomers bearing mitochondria‐targeted TPP+ groups as potential anti‐cancer agents

Three pairs of enantiomers bearing mitochondria‐targeted TPP+ groups as potential anti‐cancer agents

The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2

Synthesis, structural characterization and biological evaluation of mononuclear transition metal complexes of zwitterionic dehydroacetic acidN‐aroylhydrazone ligand

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Three pairs of enantiomers bearing mitochondria‐targeted TPP⁺ groups as potential anti‐cancer agents

Three pairs of enantiomers bearing mitochondria‐targeted TPP⁺ groups as potential anti‐cancer agents

The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C₁₅H₁₂ClFN₂O₂