Novel heteroleptic complexes of titanium(IV) derived from 2-hydroxyacetophenone: synthesis, characterization, antibacterial and molecular docking studies

Samuel, Blassan; Tummalapalli, Kiran; Giri, Prasanth Vuppalapati; Pathak, Madhvesh

doi:10.1007/s00044-013-0660-y

Cited by 6 publications

(5 citation statements)

References 26 publications

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“…Oxime groups are presented as excellent chemical modifiers with a wide versatility of coordination modes going from mono- κN, κO to di-hapto κ 2 N,O, either with side on or bridging coordination, depending on the nature of the ligand and the metal centre [49–51,62]. Some titanium oximato compounds have shown interesting antibacterial properties [60,61], however, their anticarcinogenic effects have not been reported before.…”

Section: Introductionmentioning

confidence: 99%

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

Cueva-Alique

Muñoz-Moreno

Benabdelouahab

et al. 2016

Journal of Inorganic Biochemistry

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The synthesis and characterization of new enantiopure cyclopentadienyl titanium oximato compounds (S,R)-[(η5-C5H5)Ti{κ2NO,(R)NH·HCl}Cl2] (R = Ph (phenyl) 1a·HCl, Bn (benzyl) 1b·HCl, 2-pic (2-picolyl) 1c·HCl), (S,R)-[(η5-C5H5)TiCl2{κ2NO,(Ph)NH}] (1a) and (S,R)-[(η5-C5H5)2TiCl{κ2NO,(R)NH}] (R = Ph 2a, Bn 2b, 2-pic 2c), along with studies on their behaviour in D2O at different pD values are reported. The structure of previously described ammonium-oxime (2S,5R)-{NOH,(Bn)NH·HCl} (b·HCl) and novel titanium derivative 1a have been determined by single crystal X-ray crystallography. The effect of the compounds on cytotoxicity, cell adhesion and migration of the androgen-independent prostate cancer PC-3 cells has been assessed. Compounds 2b and 2c are more cytotoxic than additive doses of titanocene dichloride and free oxime proligand, probing the synergistic effect of these novel compounds. The cytotoxicity of 2b and 2c has been further evaluated against human renal Caki-1, colon DLD-1 and triple negative breast MDA-MB-231 cancer cell lines. The activity found for 2c on PC-3 and Caki-1 is higher than that of highly active Titanocene Y (bis-[(p-methoxybenzyl)cyclopentadienyl]titanium(IV) dichloride), while showing selectivity against renal cancer when compared to a non-tumorigenic human renal (HEK-293T) cell line. Compounds 2b and especially 2c are apoptotic in Caki-1 cancer cell lines. Cell adhesion and wound-healing assays confirmed that derivatives 1c·HCl, 2b and 2c affect the adhesion and migration patterns of the PC-3 cell line. Interactions of the novel compounds with plasmid (pBR322) DNA have also been studied, showing that the oximato Ti(IV) derivatives have a weak or no interaction with DNA at physiological pH.

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Section: Introductionmentioning

confidence: 99%

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

Cueva-Alique

Muñoz-Moreno

Benabdelouahab

et al. 2016

Journal of Inorganic Biochemistry

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“…Being excessively hygroscopic in nature, obtaining nano-crystallites of ZrO 2 from zirconium alkoxides using the well-established sol-gel technology requires considerable attention and care because precipitation dominates over gelation [9]. Therefore, the moisture sensitivity of zirconium alkoxides could be retarded by substituting hydrolysable alkoxy groups with chelating ligands as modifiers [8,10,11]. Thus, the controlled hydrolysis of modified zirconium derivatives results in fine and uniform nano-sized zirconia via sol-gel synthetic route.…”

Section: Introductionmentioning

confidence: 97%

Synthesis, spectral characterization and crystal structure of a new precursor [(CH3COCHCOCH3)2Zr{C6H4(N=CHC6H4O)2}] for nano-zirconia: an investigation on the wettability of polyvinylidene fluoride–nano-zirconia composite material

Giri

Prasad

Tummalapalli

et al. 2015

J Sol-Gel Sci Technol

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A new octa-coordinated metallo-organic complex of zirconium (IV) [(CH 3 COCHCOCH 3 ) 2 Zr{C 6 H 4 (N=CHC 6 H 4 O) 2 }] was synthesized quantitatively by treating Zr(OPr i ) 4 ÁPr i OH with CH 3 COCH 2 COCH 3 and tetradentate Schiff's base ligand (L) [where L = {C 6 H 4 (N=CHC 6 H 4 OH) 2 }] in 1:2:1 stoichiometry in anhydrous refluxing toluene. The yellow solid complex was characterized by elemental analysis, FTIR, UV-visible, fluorescence and NMR ( 1 H and 13 C) spectra as well as by single-crystal XRD. The complex was processed to obtain nano-structured zirconia (ZrO 2 ) by sol-gel technique, and oxide ceramic was subjected to powder XRD, TEM and EDX analyses. Further, the same zirconia was employed in preparing superhydrophobic PVDF-nano-ZrO 2 composite coatings by spray coating method, and the effect of nano-oxide ceramic on the wettability of PVDF-nano-ZrO 2 composite coatings was studied systematically. The composite material was also characterized by FTIR and powder XRD.Electronic supplementary material The online version of this article (

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“…The synthesis of water-soluble titanium complexes is attracting considerable attention due to their potential in several fields; for example, such complexes can be designed to be nontoxic and environmentally safe precursors of titanium oxide and other inorganic materials containing titanium . Moreover, titanium complexes have been the subject of interest because in some cases they show antitumor activity or have a strong antibacterial effect . In both instances the stability of the complexes in water solution is a central issue.…”

Section: Introductionmentioning

confidence: 99%

“…1 Moreover, titanium complexes have been the subject of interest because in some cases they show antitumor activity 2 or have a strong antibacterial effect. 3 In both instances the stability of the complexes in water solution is a central issue.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The chelidamate anion can bond the metal in a way similar to that for the dipicolinate group, but it incorporates an OH moiety that could enhance the solubility in water of the corresponding metal derivatives. Moreover, chelidamic acid can adopt two tautomeric (Scheme 1) forms resulting from intra-or intermolecular proton transfer that can affect the coordination properties of the ligand on account of the sp 3 character of the N in the keto form that can change the planarity of the ONO coordinating moiety. 6 In addition, this multidentate ligand can be useful for the assembly of MOFs 7 as well as in the area of medicinal chemistry.…”

Section: ■ Introductionmentioning

confidence: 99%

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Experimental and Theoretical Studies on the Reactivity of Titanium Chelidamate Complexes: the Significant Role of the Hydroxide Pyridine Moiety

et al. 2018

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The reaction of [TiCp 2 Cl 2 ] with dipotassium chelidamate yields the carboxylate derivative [TiCp 2 {(OOC) 2 PyOH}] (2), which is sparsely soluble in water at neutral pH but soluble in basic medium. [TiCp*Cl 3 ] reacts with chelidamic acid in the presence of NEt 3 to yield the dimetallic derivative [TiCp*{(OOC) 2 PyOH}] 2 O (5). The reaction of [TiCp*Cl 3 ] with potassium chelidamate renders the hydroxide compound [TiCp*(OH){(OOC) 2 PyOH}] (6). Compound 6 evolves in DMSO solution to give the trimetallic derivative [TiCp*(DMSO){(OOC) 2 PyO}] 3 (7). Complex 6 reacts with NaOH to render the heterometallic complex [TiCp*-{(OOC) 2 PyONa(OH 2 ) 3 }] 2 (O) ( 8). The structures of complexes 7 and 8b were determined by X-ray diffraction studies. The electrostatic potential surfaces, Mulliken population analysis, and frontier molecular orbitals were determined for complex 6, allowing us to infer its reactivity.

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Novel heteroleptic complexes of titanium(IV) derived from 2-hydroxyacetophenone: synthesis, characterization, antibacterial and molecular docking studies

Cited by 6 publications

References 26 publications

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

Synthesis, spectral characterization and crystal structure of a new precursor [(CH3COCHCOCH3)2Zr{C6H4(N=CHC6H4O)2}] for nano-zirconia: an investigation on the wettability of polyvinylidene fluoride–nano-zirconia composite material

Experimental and Theoretical Studies on the Reactivity of Titanium Chelidamate Complexes: the Significant Role of the Hydroxide Pyridine Moiety

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