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Synthesis of N-Tetradecyl-1,10-phenathrolinium-Based New Salts for Biological Applications.

ABSTRACT: New organic salts were synthesized by quaternizing 1,10-phenanthroline using 1-bromotetradecane. The first step yielded an organic salt of formula [C26H37N2]Br. Anion exchange reaction using Li[(CF3SO2)2N] resulted in a more stable salt of formula [C26H37N2][(CF3SO2)2N]. The organic salts were investigated by spectrometry (1H, 13C, 19F NMR, X-ray photoelectron spectroscopy (XPS), UV-Vis, and matrix-assisted laser desorption/ionization mass spectroscopy (MALDI MS), CHNSBr elemental analysis, and thermal analysis (TGA and DSC). The thermal characterization showed the melting and decomposition points of [C26H37N2][(CF3SO2)2N] to be 48°C and 290°C, respectively, which indicates it is an ionic liquid with large liquidus range. The biological activities of the salts were investigated against two Gram-positive (Staphylococcus aureus and Streptococcus pyogenes) and two Gram-negative (Escherichia coli and Klebsiella pneumoniae) bacteria, and they are found to be active against all of them. They were compared with [Cu(1,10-phenanthroline)2Cl]Cl. They are found more active against the Gram-negative bacteria. The salts demonstrated minimum inhibitory concentration as low as 50?µg/L. These results suggest the synthesized salts can be considered as a better alternative to certain transition metal complex drugs. This minimizes the concern of introducing metal ions into the organism.

PROVIDER: S-EPMC6079542 | BioStudies |

REPOSITORIES: biostudies

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Three phenanthroline-metal complexes with topologically similar but geometrically different conformations.

Project description:The structures of three related complexes of general formula M(pds)(nab)2 [pds is the peroxodi-sulfate anion and nab is an nitro-gen-containing aromatic base], viz. bis(2,9-dimethyl-1,10-phenanthroline-?2N,N')(peroxodi-sulfato-?2O,O')cadmium, [Cd(S2O8)(C14H12N2)2], (V), bis-(3,4,7,8-tetra-methy-1,10-phenanthroline-?2N,N')(peroxodi-sulfato-?2O,O')zinc, [Zn(S2O8)(C16H16N2)2], (VI), and bis-(3,4,7,8-tetra-methy-1,10-phenanthroline-?2N,N')(peroxodi-sulfato-?2O,O')cadmium, [Cd(S2O8)(C16H16N2)2], (VII), present the same topological coordination, with three chelating ligands in an MN4O2 polyhedron. The main difference resides in the fact that the first two complexes are bis-ected by a crystallographic twofold axis, thus providing a symmetrical environment to the cation, while in the third one this symmetry is disrupted into a clearly unsymmetrical disposition, probably by way of an unusually strong intra-molecular C-H?O hydrogen bond. The situation is compared with similar inter-actions in the literature. The structure of (V) is based on a redetermination in the correct space group C2/c of the structure originally described in the Cc space group [Harvey et al. (2001). Aust. J. Chem.54, 307-311; Marsh (2004 ?). Acta Cryst. B60, 252-253].

2016-01-01 | S-EPMC5095838 | BioStudies

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2017-01-01 | S-EPMC5423883 | BioStudies

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Project description:A new complex salt of composition [Co(phen)(3)](3)(V(4)O(12))(2)Cl·27H(2)O (phen = 1,10-phenanthroline and [V(4)O(12)](4-) = tetrameric dodecaoxotetravanadate ion) was synthesized by reacting appropriate salts in aqueous medium. The complex salt has been characterized by elemental analyses, thermogravimetric analysis (TGA), cyclic voltammetry (CV), FT-IR and UV/Vis spectroscopies, solubility product and conductance measurements. Single crystal X-ray structure determination revealed ionic structure consisting of three complex cations, [Co(phen)(3)](3+), two [V(4)O(12)](4-) anions, one chloride and twenty seven lattice waters. Detailed structural and spectroscopic analyses of [Co(phen)(3)](3)(V(4)O(12))(2)Cl·27H(2)O show that the large anion is stabilized by the large cationic metal complex as there is preferred shape compatibility that leads to a large number of lattice stabilizing non-covalent interactions.

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Characteristics of a copper-dependent cross-linking reaction between two forms of cytochrome P-450 in rabbit-liver microsomal membranes.

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1980-01-01 | S-EPMC1162512 | BioStudies

Effects of the Bidentate Ligand on the Photophysical Properties, Cellular Uptake, and (Photo)cytotoxicity of Glycoconjugates Based on the [Ru(tpy)(NN)(L)]2+ Scaffold.

Project description:Ruthenium polypyridyl complexes have received widespread attention as potential chemotherapeutics in photodynamic therapy (PDT) and in photochemotherapy (PACT). Here, we investigate a series of sixteen ruthenium polypyridyl complexes with general formula [Ru(tpy)(N-N)(L)]+/2+ (tpy=2,2':6',2''-terpyridine, N-N=bpy (2,2'-bipyridine), phen (1,10-phenanthroline), dpq (pyrazino[2,3-f][1,10]phenanthroline), dppz (dipyrido[3,2-a:2',3'-c]phenazine, dppn (benzo[i]dipyrido[3,2-a:2',3'-c]phenazine), pmip (2-(4-methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline), pymi ((E)-N-phenyl-1-(pyridin-2-yl)methanimine), or azpy (2-(phenylazo)pyridine), L=Cl- or 2-(2-(2-(methylthio)ethoxy)ethoxy)ethyl-?-d-glucopyranoside) and their potential for either PDT or PACT. We demonstrate that although increased lipophilicity is generally related to increased uptake of these complexes, it does not necessarily lead to increased (photo)cytotoxicity. However, the non-toxic complexes are excellent candidates as PACT carriers.

2018-01-01 | S-EPMC5838788 | BioStudies

Necroptosis-inducing rhenium(V) oxo complexes.

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| S-EPMC4702498 | BioStudies

9-(2-Pyridylmeth-oxy)-1,10-phenanthrolin-1-ium perchlorate methanol solvate.

Project description:In the title organic salt, C(18)H(14)N(3)O(+)·ClO(4) (-)·CH(4)O, there is a ?-? stacking inter-action between neighbouring 1,10-phenanthroline rings and the relevant distances are 3.5453?(18)?Å for the centroid-centroid distance and 3.354?Å for the perpendicular distance. There is also a relatively close contact between a C-H bond and a symmetry-related pyridine ring. There are classical N-H?O and O-H?N hydrogen bonds and non-classical C-H?O hydrogen bonds involving the cation, methanol solvent mol-ecule and perchlorate anion.

| S-EPMC2962027 | BioStudies

Tris(N-{bis-[meth-yl(phen-yl)amino]-phosphor-yl}benzene-sulfonamidato-?2O,O')(1,10-phenanthroline-?2N,N')lanthanum(III).

Project description:The asymmetric unit of [La(C20H21N3O3PS)3(C12H8N2)] is created by one LaIII ion, three deprotonated N-{bis-[meth-yl(phen-yl)amino]-phosphor-yl}benzene-sulfonamidate (L-) ligands and one 1,10-phenanthroline (Phen) mol-ecule. Each LaIII ion is eight-coordinated (6O+2N) by three phosphoryl O atoms, three sulfonyl O atoms of three L- ligands and two N atoms of the chelating Phen ligand, leading to the formation of six- and five-membered metallacycles, respectively. The lanthanum coordination polyhedron has a bicapped trigonal-prismatic geometry. 'Sandwich-like' intra-molecular ?-? stacking inter-actions are observed between the 1,10-phenanthroline ligand and two benzene rings of two different L- ligands. The phenyl rings of L- that are not involved in the stacking inter-actions show minor positional disorder. Mol-ecules form layers parallel to the (010) plane due to weak C-H?O inter-molecular hydrogen bonds. Unidentified highly disordered solvate mol-ecules that occupy ca 400?Å3 large voids have been omitted from the refinement model.

| S-EPMC5499295 | BioStudies

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