14049-94-6

Upstream product

• 5144-89-8 1,10-phenanthroline hydrate 
• 7646-85-7 zinc(II) chloride 
• 66-71-7 1,10-Phenanthroline 
• 7647-01-0 hydrogenchloride 
• 5970-45-6 zinc(II) acetate dihydrate 

Downstream Products

• 66-71-7 1,10-Phenanthroline 

Relevant academic research and scientific papers

Evaluation of insulin‐like activity of novel zinc metal–organics toward adipogenesis signaling

Diabetes mellitus is a debilitating disease, plaguing a significant number of people around the globe. Attempts to develop new drugs on well‐defined atoxic metalloforms, which are capable of influencing fundamental cellular processes overcoming insulin resistance, has triggered an upsurge in molecular research linked to zinc metallodrugs. To that end, meticulous efforts were launched toward the design and synthesis of materials with insulin mimetic potential. Henceforth, trigonelline and N‐(2‐hydroxyethyl)‐iminodiacetic acid (HEIDAH2) were selected as organic substrates seeking binding to zinc (Zn(II)), with new crystalline compounds characterized by elemental analysis, FT‐IR, X‐rays, thermogravimetry (TGA), luminescence, NMR, and ESI‐MS spectrometry. Physicochemical characterization was followed by in vitro biochemical experiments, in which three out of the five zinc compounds emerged as atoxic, exhibiting bio‐activity profiles reflecting enhanced adipogenic potential. Concurrently, well‐defined qualitative–quantitative experiments provided links to genetic loci responsible for the observed effects, thereby unraveling their key involvement in signaling pathways in adipocyte tissue and insulin mimetic behavior. The collective results (a) signify the quintessential role of molecular studies in unearthing unknown facets of pathophysiological events in diabetes mellitus II, (b) reflect the close associations of properly configured molecular zincoforms to well‐defined biological profiles, and (c) set the stage for further physicochemical‐based development of efficient zinc antidiabetic metallodrugs.

Improving the bioactivity of Zn(ii)-curcumin based complexes

New Zn(ii)-curcumin based heteroleptic complexes (1-5) have been synthesized and fully characterized, with the aim to improve the bioactivity of the precursor derivative [(bpy-9)Zn(curc)Cl] (A), a potentially intercalating antitumor agent recently reported. Some structural changes have been made starting from the reference complex A, in order to introduce new functionalities, such as electrostatic and/or covalent interactions. In particular, keeping the same N,N chelating ligand, namely bpy-9, two completely different Zn(ii) species have been obtained: a tetracoordinated Zn(ii) cation with tetrafluoroborate as counterion (1) and a dimeric neutral complex in which the sulfate anion acts as a bridging group through two Zn(ii) centres (2). Moreover, by changing the N,N chelating unit, [(Ln)Zn(curc)Cl] complexes (3-5), in which the Zn(ii) ion shows the same pentacoordination seen in the precursor complex A, have been obtained. The antitumour activity of all new Zn(ii) complexes was tested in vitro against the human neuroblastoma cell line SH-SY5Y in a biohybrid membrane system and the results indicate that all species exhibit strong cytotoxic activity. In particular the ionic tetrafluoroborate Zn(ii) complex, 1, and the neutral phenanthroline based Zn(ii) derivative, 4, show the strongest growth inhibition, being even more effective than the model complex A. Both complexes have a dose-dependent anti-proliferative effect on cells as demonstrated by the decrease of viability and the increase of Annexin V and PI-positive cells with the increase of their concentration. Cells treated with complexes 1 and 4 undergo apoptosis that involves the activation of JNK, caspase 3 and MMP changes. Finally, complex 1 is more effective in the induction of caspase-3 activation demonstrating its ability to trigger the execution-phase of cell apoptosis. The Royal Society of Chemistry 2013.

Norfloxacin Zn(II)-based complexes: Acid base ionization constant determination, DNA and albumin binding properties and the biological effect against Trypanosoma cruzi

Zn(II) complexes with norfloxacin (NOR) in the absence or in the presence of 1,10-phenanthroline (phen) were obtained and characterized. In both complexes, the ligand NOR was coordinated through a keto and a carboxyl oxygen. Tetrahedral and octahedral geometries were proposed for [ZnCl 2(NOR)]·H2O (1) and [ZnCl2(NOR)(phen)] ·2H2O (2), respectively. Since the biological activity of the chemicals depends on the pH value, pH titrations of the Zn(II) complexes were performed. UV spectroscopic studies of the interaction of the complexes with calf-thymus DNA (CT DNA) have suggested that they can bind to CT DNA with moderate affinity in an intercalative mode. The interactions between the Zn(II) complexes and bovine serum albumin (BSA) were investigated by steady-state and time-resolved fluorescence spectroscopy at pH 7.4. The experimental data showed static quenching of BSA fluorescence, indicating that both complexes bind to BSA. A modified Stern-Volmer plot for the quenching by complex 2 demonstrated preferential binding near one of the two tryptophan residues of BSA. The binding constants obtained (K b ) showed that BSA had a two orders of magnitude higher affinity for complex 2 than for 1. The results also showed that the affinity of both complexes for BSA was much higher than for DNA. This preferential interaction with protein sites could be important to their biological mechanisms of action. The analysis in vitro of the Zn(II) complexes and corresponding ligand were assayed against Trypanosoma cruzi, the causative agent of Chagas disease and the data showed that complex 2 was the most active against bloodstream trypomastigotes.

1,10-Phenanthroline-dithiolate mixed ligand transition metal complexes. Synthesis, characterization and EPR spectroscopy

A series of new N2S2 mixed ligand transition metal complexes, where N2 is phenanthroline and S2 is 1,2-dithiooxalate (dto) or 1,2-dithiosquarate (dtsq), has been synthesized and characterized. IR spectra reveal that the 1,2-dithiolate ligands are coordinated via the sulfur atoms forming a N2S2 coordination sphere. The copper(II) complex [Cu(phen)(dto)] was studied by EPR spectroscopy as a diamagnetically diluted powder. The diamagnetic dilution resulted from doping of the copper complex into the isostructural host lattice of the nickel complex [Ni(phen)(dto)]. The electronic situation in the frontier orbitals of the copper complex calculated from the experimental data is compared to the results of EHT and DFT calculations. Furthermore, one side product, chlorobis(1,10-phenanthroline)copper(I) ethanol solvate hydrate [(phen)2CuCl]·C2H5OH·H2O, was formed by a reduction process and characterized by X-ray diffraction. In the crystal packing one-dimensional columns of dimers are formed, stabilized by significant π-π interactions.

An effective non-chromatographic method for the purification of phenanthrolines and related ligands

1,10-Phenanthrolines are widely employed as ligands, but their use on a large scale is constrained by their difficult purification, which usually requires lengthy chromatographic separations. Herein, we describe a purification strategy that takes advantage of the high stability and low solubility of phenanthroline complexes to separate them from the by products of their synthesis. The formation of ZnCl2 complexes was employed, from which the free ligand can be recovered by reaction with aqueous NH3 in a biphasic CH2Cl2/H2O system. The same strategy was also successfully employed to purify related quinolino-guanidine ligands, demonstrating that the procedure is of general applicability.

Modulating the structure and photochromic performance of hybrid metal chlorides with nonphotochromic 1,10-phenanthroline and its derivative

Hybrid photochromic materias (HPMs), especially crystalline HPMs (CHPMs), have been widely investigated due to their feasibility in maintaining the advantages of each constituent and genearating captivating photomodulated functionality. Metal-organic complexes (MOCs), as promising candidates for fabricating CHPMs, have attracted the interest of researchers. The molecular predesign of ligands plays a crucial role in yielding MOC-based CHPMs with tunable photochromic functionality. Hitherto, a great majority of CHPMs are driven by photosensitive ligands. However, the complicated synthesis and high cost of photosensitive ligands obviously prevent the macro-synthesis and future application of these CHPMs. Thus, it is indispensable to explore novel branches of CHPMs. Herein, we report a series of photochromic solid materials bearing modulated photochromic properties by hybridizing metal chlorides with a nonphotosensitive coplanar dipyridine unit 1,10-phenanthroline (phen) and its derivative 5-chloro-1,10-phenanthroline (5-Cl-phen). The resulting hybrids, [ZnCl2(phen)] (1), [CdCl2(phen)] (2), [PbCl2(phen)] (3), [ZnCl(H2O)(5-Cl-phen)2]Cl·2H2O (4), [Cd2Cl4(5-Cl-phen)2] (5) and [Pb2Cl4(5-Cl-phen)2] (6), exhibit distinct structures from the isolated molecular complexes (1and4) to the hybrid chain (2,3,5and6) because of the distinct coordination mode of central metal ions and chloride ions. After photo-irradiation with a Xe-lamp, all complexes, as expected, exhibited apparent color change because of the photoinduced electron transfer (ET) between coordinated chloride ions (Cl?) as electron donors (EDs) and the coordinated coplanar phen and 5-Cl-phen species as electron acceptors (EAs). More importantly, the photochromic performance of the title complexes could be modulated by phen and 5-Cl-phen. This study provides a general and facile way for modulating the structure and photochromic performance of hybrid metal chlorides with phen or phen-based derivatives under the synergy of crystalline engineering strategy and ET mechanism.

Structures of 1: 1 Mononuclear Adducts of Zinc(ii) Halides, ZnX2 (X = Cl, Br, I) and of New Hydrates of 1: 1 Adducts of Zinc(ii) Nitrate and Sulfate with Aromatic N, N -Bidentate Base Derivatives of Pyridine (bpy, phen)

Single crystal X-ray structure determinations have been executed for several title compounds of the mononuclear form [LMX2], namely [(bpy)ZnX2], X = Cl, Br; [(phen)ZnX2], X = Cl, Br, I (bpy = 2,2-bipyridine; phen = 1,10-phenanthroline). Also reported are

Magnesium, calcium, and zinc phenanthrolinate peroxodisulfates: Crystal structure of the complex [Mg(Phen)2(H2O) 2]S2O8·2Phen

The reactions of MCl2·nH2O (M = Mg, Ca, Zn; n = 0-6) with Phen·H2O (Phen = C12H8N 2) and (NH2)S2O8 gave peroxodisulfates Mg(Phen)2S2O8·4H 2O, Ca(Phen)3S2O8·2H 2O, and Zn(Phen)2S2O8·2H 2O. According to IR spectra, the metal coordination sphere is formed by phenanthroline and water molecules. In the zinc compound, the S 2O8 group may also be coordinated to the central atom. The solubilities in water at 20°C (g in 100 g water) are 0.15, 0.17, and 0.04 for the magnesium, calcium and zinc compounds, respectively. The compounds are stable under ambient conditions. The oxidation of phenanthroline by the S 2O82- ion takes place on heating above 120°C. The complex [Mg(Phen)2(H2O)2]S 2O8·2Phen (I) was studied by X-ray diffraction. The crystals are monoclinic, a = 16.840(4) A?, b = 22.377(3) A?, c = 13.806(2) A?, β = 123.39(2)°, V = 4343(1) A?3, Z = 4, space group C2/c, R = 0.039 for 2292 reflections with I > 2σ(I). The crystal of I is built of octahedral [Mg(Phen)2(H 2O)2]2+ cations (C2 symmetry), outer-sphere persulfate S2O82- anions, and outersphere phenanthroline molecules. The average Mg-O and Mg-N bond lengths in the complex are 2.021(3) and 2.202(3) A?, respectively. The structural units are linked by O(H2O)?O(S2O8) and O(H2O)?N (noncoordinated Phen) hydrogen bonds to form an aggregate with the composition {Mg(Phen)2(H2O) 2S2O8·2Phen}.