Coordination polymer of zinc based on chiral non-racemic trans-N,N′-bis-(2-hydroxy-1-naphthalidehydene)-(1R,2R)-cyclohexa-nediamine: Synthesis, crystal structure, novel coordinational models and anticancer activity

Bi, Shuangyu; Wang, Aidong; Bi, Caifeng; Yu, Fan; Xiao, Yan; Liu, Shanbin; Wang, Qiang

doi:10.1016/j.inoche.2011.10.016

Cited by 13 publications

(5 citation statements)

References 23 publications

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“…This work explores the effect of a bridging diamine having a defined stereochemistry on the aggregation properties of some Zn II Schiff-base complexes. Actually, the Schiff-bases derived from the (1 R ,2 R )-(−)- or (1 S ,2 S )-(+)- trans -1,2-diaminocyclohexane establish a preorganized helical scaffold for the metal complexation. , It is therefore expected that this can play a crucial role on the structural and aggregation properties of these complexes. Indeed, present chiral complexes in solution are characterized by a number of unusual features.…”

Section: Discussionmentioning

confidence: 99%

Supramolecular Aggregates of Defined Stereochemical Scaffolds: Aggregation/Deaggregation in Schiff-Base Zinc(II) Complexes Derived from Enantiopure trans-1,2-Diaminocyclohexane

et al. 2016

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This contribution explores, through detailed H NMR, DOSY NMR, optical absorption, and circular dichroism spectroscopic studies, the aggregation properties in solution of noncoordinating solvents of some new Zn Schiff-base complexes, (R)-1, (S)-1, and (R)-2, derived from the chiral trans-1,2-diaminocyclohexane. It is found that chloroform solutions of 1 are characterized by the presence of three species, the predominance of which consists of large oligomeric aggregates. For chloroform solutions of 1, upon heating or standing, all species are irreversibly converted into a dimer, 1C, which is very stable and hardly disaggregable. Analysis of H NMR, UV/vis, and CD spectroscopic data and chemical evidence allow proposing a double helicate ZnL structure with a tetrahedral coordination around the Zn ions for 1C, as a consequence of the defined stereochemistry of the trans-1,2-diaminocyclohexane chelate bridge. This represents a different, uncommon aggregation mode in Zn complexes of tetradentate Schiff-bases.

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Section: Discussionmentioning

confidence: 99%

Supramolecular Aggregates of Defined Stereochemical Scaffolds: Aggregation/Deaggregation in Schiff-Base Zinc(II) Complexes Derived from Enantiopure trans-1,2-Diaminocyclohexane

et al. 2016

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“…xanthine oxidase inhibitors (Amin et al, 2010 (Friscic et al, 1998), (C 28 H 26 N 2 O 2 ) (Bi et al, 2012) and (C 28 H 20 N 2 O 2 -CHCL 3 ) (Popović et al, 2001) crystallized in the orthorhombic space groups Pbca, Pbcn, P2 1 2 1 2 1 , and P2 1 2 1 2 1 , respectively. The hydrogen atom in the title compound is located on the nitrogen atom (Fig.1).…”

Section: S1 Results and Discussionmentioning

confidence: 99%

“…For ultrasonic synthesis of similar compounds, see: Rayati & Abdolalian (2013); Khan et al (2014); Kanagarajan et al (2011). For related crystal structures, see: Ouari et al (2010Ouari et al ( , 2015b; Popović et al (2001); Friscic et al (1998); Bi et al (2012); Temel et al (2010). For their applications, see: Kö se et al (2015); Grivani et al (2013); Amin et al (2010); Panneerselvam et al (2009); Nasr et al (2009); Nejo et al (2009); Taha et al (2012 Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 1,1′-{(dodecane-1,12-diyl)bis[(azaniumylylidene)methanylylidene]}bis(naphthalen-2-olate)

et al. 2015

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“…The effect of stereochemistry on biological activity is of great importance in medicinal chemistry, as many of the biological targets are chiral [30,31]. The anticancer properties of chiral metal derivatives have been largely studied [32][33][34][35][36][37][38][39][40][41][42][43][44][45][46], but the role of the stereochemistry in the biological activity of non-platinum based compounds has been less investigated [22,[47][48][49][50][51][52][53][54][55][56][57][58][59][60][61]. Effect of the absolute configuration on the anticancer efficiency of titanium compounds was firstly explored by Tshuva in 2010 [50].…”

Section: Introductionmentioning

confidence: 99%

Study of the anticancer properties of optically active titanocene oximato compounds

Cueva-Alique

Sierra

Pérez‐Redondo

et al. 2019

Journal of Organometallic Chemistry

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New water soluble and optically active cyclopentadienyl titanium derivatives [(η 5-C 5 H 5) 2 Ti{(1R,4S)-ĸON,(R)NH}Cl] (R = Bn (Benzyl) 1a', 2-pic (2-picolylamine) 1b') have been synthesized. The novel compounds along with those previously described [(η 5-C 5 H 5) 2 Ti{(1S,4R)-ĸON,(R)NH}Cl] (R = Bn 1a, 2-pic 1b) were evaluated by polarimetry, ultraviolet and circular dichroism spectroscopy. The structure of 1b was determined by single crystal X-ray crystallography and showed a unique terminal monohapto Ti-O disposition of the oximato ligand. All enantiomers have been tested against several cancer cell lines in vitro: prostate PC-3 and DU-145, lung A-549, pancreas MiaPaca-2, colorectal HCT-116, leukemia Jurkat and cervical HeLa. In addition, 1a, 1b and 1b' were tested against non-tumorigenic prostate RWPE-1 cell line. After 24 h of incubation, 1b and 1b' were moderately active against Jurkat and A-549 cells. The anti-proliferative effect of titanium compounds on prostate PC-3, DU-145 and RWPE-1 cell lines was also assessed after 72 h of drug exposure. The cytotoxic profile of the enantiomers was similar, exception made for the PC-3 cells, with S,R-isomers exhibiting cytotoxicities 2 to 3 times higher than R,S-compounds. Under these conditions, derivative 1b showed calculated IC 50 values better than those of Tacke´s Titanocene-Y (bis-[(p-methoxybenzyl)cyclopentadienyl]titanium(IV) dichloride) on both the prostate PC-3 and DU-145 cells. 1a and 1b cytotoxic behaviour shows certain selectiveness, with activities 2-4 times lower on normal prostate RWPE-1 than on cancer PC-3 cells. Furthermore, 1b produces higher cytotoxicity on prostate PC-3, DU-145 and RWPE-1 cells than the additive dose of titanocene dichloride and pro-ligand b•HCl. Additionally, compound-DNA interactions have been investigated by equilibrium dialysis, Fluorescence Resonance Energy Transfer (FRET) melting assays and viscometric titrations, which suggest that these metal complexes and/or their hydrolysis products bind DNA either in the minor groove or externally. Highlights (85 characters) • Synthesis of novel enantiopure titanocene amino-oximato compounds is reported. • The X-ray crystal structure of one of the compounds shows a unique monohapto Ti-ON coordination. • One enantiomer shows IC 50 values lower than Titanocene-Y on both PC-3 and DU-145 cells. • One enantiomer is more active than additive doses of Ti(η 5-C 5 H 5)Cl 2 and oxime pro-ligand.

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Coordination polymer of zinc based on chiral non-racemic trans-N,N′-bis-(2-hydroxy-1-naphthalidehydene)-(1R,2R)-cyclohexa-nediamine: Synthesis, crystal structure, novel coordinational models and anticancer activity

Cited by 13 publications

References 23 publications

Supramolecular Aggregates of Defined Stereochemical Scaffolds: Aggregation/Deaggregation in Schiff-Base Zinc(II) Complexes Derived from Enantiopure trans-1,2-Diaminocyclohexane

Supramolecular Aggregates of Defined Stereochemical Scaffolds: Aggregation/Deaggregation in Schiff-Base Zinc(II) Complexes Derived from Enantiopure trans-1,2-Diaminocyclohexane

Crystal structure of 1,1′-{(dodecane-1,12-diyl)bis[(azaniumylylidene)methanylylidene]}bis(naphthalen-2-olate)

Study of the anticancer properties of optically active titanocene oximato compounds

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