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Institute for Advanced Studies in Basic Sciences (IASBS)

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Department of Chemistry
Elham Safaei  
Associate Professor
Room: chemistry Building 200
Tel: 33153200
Fax: 33153232
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1- Safaei, E., Hajikhan Mirzaei, L., karimi, B., Wojtczak, A., Cotic, P., Lee, Y. I., "TEMPO-mediated aerobic oxidation of alcohols using copper(II) complex of bis(phenol) di-amine ligand as biomimetic model for Galactose oxidase enzyme", Polyhedron, 106, 153-162, (2016).

Mononuclear copper complexes of four-dentate N2O2 bis(phenol) diamine ligands (H2LNEX X: C and OB in which C and OB are chloro and tert-butyl-methoxy substituents on phenol groups) have been synthesized and characterized by IR, UV–Vis, single crystal X-ray diffraction, magnetic susceptibility studies and cyclic voltammetry techniques. The CuLNEX complexes show the square pyramid geometry of the coordination sphere with the copper centers surrounded by two nitrogen and oxygen atoms from the coordinating ligand and an axially bound water molecule. The effective magnetic moments of 1.7 and 1.8 BM confirm a monomer complex with copper(II) center. Electrochemical oxidation of these complexes yielded the corresponding Cu(II)-phenoxyl radical species. In addition, CuLNEX complexes, have shown efficient catalytic activities for TEMPO-mediated oxidation of a set of alcohols to the corresponding aldehydes in the presence of molecular oxygen as oxidant at room temperature.
2- Hassani , L., Fazeli , Z., Safaei, E., Rastegar , H., Akbari, M., "A spectroscopic investigation of the interaction between c-MYC DNA and tetrapyridinoporphyrazinatozinc(II)", Journal of Biological Physics, 40, 275-283 , (2014).

The c-MYC gene plays an important role in the regulation of cell proliferation and growth and it is overexpressed in a wide variety of human cancers. Around 90% of c-MYC transcription is controlled by the nuclease-hypersensitive element III1 (NHE III1), whose 27-nt purine-rich strand has the ability to form a G-quadruplex structure under physiological conditions. Therefore, c-MYC DNA is an attractive target for drug design, especially for cancer chemotherapy. Here, the interaction of water-soluble tetrapyridinoporphyrazinatozinc(II) with 27-nt G-rich strand (G/c-MYC), its equimolar mixture with the complementary sequence (GC/c-MYC) and related C-rich oligonucleotide (C/c-MYC) is investigated. Circular dichroism (CD) measurements of the G-rich 27-mer oligonucleotide in 150 mM KCl, pH 7 demonstrate a spectral signature consistent with parallel G-quadruplex DNA. Furthermore, the CD spectrum of the GC rich oligonucleotide shows characteristics of both duplex and quadruplex structures. Absorption spectroscopy implies that the complex binding of G/c-MYC and GC/c-MYC is a two-step process; in the first step, a very small red shift and hypochromicity and in the second step, a large red shift and hyperchromicity are observed in the Q band. Emission spectra of zinc porphyrazine are quenched upon addition of three types of DNA. According to the results of spectroscopy, it can be concluded the dominant binding mode is probably, outside binding and end stacking.
3- Hassani, L., Hakimian, F., Safaei, E., "Spectroscopic investigation on the interaction of copper porphyrazines and phthalocyanine with human telomeric G-quadruplex DNA", Biophys. Chem, 187, 7-13, (2014).

The G-quadruplex DNA is a novel target for anticancer drug discovery and many scientific groups are investigating interaction of small molecules with G-quadruplex DNA to discover therapeutic agents for cancer. Here, interaction of a phthalocyanine (Cu(PcTs)) and two tetrapyridinoporphyrazines ([Cu(2,3-tmtppa)]4+ and [Cu(3,4-tmtppa)]4+) with Na+ and K+ forms of human telomeric G-quadruplex DNA has been investigated by spectroscopic techniques. The results indicated that interaction of the cationic porphyrazines is remarkably stronger than the anionic phthalocyanine and they presumably bind to the G-quadruplex DNA through end-stacking. Fluorescent intercalator displacement assay implied the displacement ability of the complexes with thiazole orange. In addition, circular dichroism spectra of both quadruplex forms converge to the Na+ isoform after binding to the porphyrazines. In conclusion, the porphyrazines as the complexes that bind to the G-quadruplex DNA, could be suitable candidates for further investigations about inhibition of telomerase enzyme.
4- Sheykhi, H., Safaei, E., "A proline-based aminophenol ligand: Synthesis, iron complexation, magnetic, electronic and redox investigation", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy , 118, 915-920, (2014).

A new proline-based aminophenol ligand was synthesized by a convenient procedure. The ligand was characterized by 1H NMR, 13C NMR and IR spectroscopies, elemental analysis and optical activity measurements. Mononuclear iron(III) complex (FeLPro) of this ligand was synthesized and characterized by IR, UV–vis, ESI-MS, magnetic susceptibility studies and cyclic voltammetry techniques. The equilibrium formation constant of FeLPro and the pure UV–vis spectral profile of the complex was determined by multivariate hard modeling method. The molecular structure of FeLPro determined by ESI-MS consist of two aminophenolate ligands. The variation of magnetic susceptibility with temperature indicates paramagnetic iron(III) in the monomeric complex. FeLPro complex undergo metal-centered reduction, and ligand-centered oxidation.
5- Hassani , L., Hakimian, F., Safaei, E., Fazeli, Z., "Antibacterial effect of cationic porphyrazines and anionic phthalocyanine and their interaction with plasmid DNA", J. Mol. Struct, 1052, 221-227, (2013).

Resistance to antibiotics is a public health issue and identification of new antibacterial agents is one of the most important goals of pharmacological research. Among the novel developed antibacterial agents, porphyrin complexes and their derivatives are ideal candidates for use in medical applications. Phthalocyanines differ from porphyrins by having nitrogen atoms link the individual pyrrol units. The aza analogues of the phthalocyanines (azaPcs) such as tetramethylmetalloporphyrazines are heterocyclic Pc analogues. In this investigation, interaction of an anionic phthalocyanine (Cu(PcTs)) and two cationic tetrapyridinoporphyrazines including [Cu(2,3-tmtppa)]4+ and [Cu(3,4-tmtppa)]4+ complexes with plasmid DNA was studied using spectroscopic and gel electrophoresis methods. In addition, antibacterial effect of the complexes against Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria was investigated using dilution test method. The results indicated that both porphyrazines have significant antibacterial properties, but Cu(PcTs) has weak antibacterial effect. Compairing the binding of the phthalocyanine and the porphyrazines to DNA demonstrated that the interaction of cationic porphyrazines is stronger than the anionic phthalocyanine remarkably. The extent of hypochromicity and red shift of absorption spectra indicated preferential intercalation of the two porphyrazine into the base pairs of DNA helix. Gel electrophoresis result implied Cu(2,3-tmtppa) and Cu(3,4-tmtppa) are able to perform cleavage of the plasmid DNA. Consequently, DNA binding and cleavage might be one of the antibacterial mechanisms of the complexes.
1- Safaei, E., Dolatyari, V., Karimi, B., "Synthesis and Characterization of Mn(II) and Pd(II) Complexes of Bis(picolyl amine) and Bis(phenol) amine Ligands Supported on Ordered Mesoporous Silica (SBA-15)", 17th Iranian Inorganic Chemistry Conference, Azarbaijan Shahid Madani University, Tabriz, Iran, (2015).

In coordination chemistry, various ligands are used to modulate the electronicand steric properties of the metal ion and consequently the reactivity of metal species.1 As homogeneous catalysts are mostly often difficult to separate forreuse after reactions, the immobilization of a homogeneous catalyst onto a solid surface is one of the major challenges in catalysis chemistry. By loading these complexes onto mesoporous materials, one can achieve fixed homogeneous catalysts, which facilitates the separation and reuse of valuable catalysts, able to reduce both environmental pollutions and material costs. Covalent bond grafting is one of the most important strategies which have been developed for loading of such molecular catalysts.2,3 In our work, new Mn(II) complex of bis(phenol) amine ligand and Pd(II) complex of bis(picolyl amine) ligand supported on functionalized SBA-15 were synthesized. The precursor and supported complexes were characterized by different techniques such as: FT-IR, TGA, SEM, TEM, EDX, XRD, ICP, CHN and porosimetry. All results confirmed the successful anchoring of complexes onto the functionalized SBA-15 by covalent bonding.
2- Hassani , L., Fazeli , Z., Safaei , E., Hakimian, F., "comparative study on the interaction of water soluble zinc porphyrazine with G and C-rich strands and the complete c-MYC silencer element ", 1st Tabriz International Life Science Conference and 12th Iran Biophysical Chemistry Conference, 241-241, (2013).
3- Safaei , E., "A spectroscopic studty on the interaction of a water soluble tetra-methyl metallo-porphyrazine to calf thymus DNA ", 1nd International Conference of Chemistry and it,s applications, Doha, Qatar , (2013).
4- Balaghi, S. E., Safaei, E., "Highly Efficient and Aerial Alcohol Oxidation by a Chloro Bridged Cu(II)-Cu(II) Complex of an Aminophenol Ligand", 14th Iranian Inorganic Chemistry Conference, Sharif University of Technology , 1-1, (2012).

Many biological reactions are controlled by metalloenzymes containing one or more metal atoms and their coordinated ligands such as histidine and tyrosine holding them.Copper is one of these metal ions which serves as cofactor in many fundamental reactions mediated by copper enzymes. Galactose oxidase (GOase) best characterized member of radical-copper oxidase family has the ability to catalyze the oxidation of a wide range of primary alcohols to aldehydes. Hemocyanines and tyrosinases are type III multi-copper proteins which their active sites contain binuclear copper complexes. As well as galactose oxidase, these two enzymes are responsible for catalyzing some biological process associated with redox reactions. Significant efforts have also been made to provide multinuclear copper complexes containing chloro, hydroxo and oxo bridged complexes as models for active sites of multi-copper enzymes and their effective role in catalytic enzymatic reactions such as oxidation of alcohols to aldehydes. Although there are some reports about chloro bridged binuclear copper complexes as structural models for catechol oxidase, however according to our best knowledge there is not any report of these complexes as oxidase functional models. In this work, we describe a highly efficient, selective and eco-friendly oxidation of alcohols to aldehydes with air or oxygen as oxidant and [LAphCuCl]2 copper complex of a newly synthsized [N-O]-donor aminophenol ligand (HLAph, 2,4-di-tert-butyl-6-(pyridine-2-ylmethylamino)phenol) as catalyst.
5- Balaghi, S. E., Safaei, E., "Synthesis, Molecular and Electronic Structures of a Six-Coordinate Cobalt Complex with an Oxazoline Ligand", 14th Iranian Inorganic Chemistry Conference, Sharif University of Technology , 1-1, (2012).

Metalloenzymes often feature redox-active ligands. These ligands are very interesting due to their easily redox processes by one or more electrons, and affecting the reactivity and selectivity of metal ions in the active site of enzymes. Often these ligands transform into ligand radicals upon binding to transition metals. Metal complexes exhibiting intra-molecular electron transfer between a metal center and a redox-active ligand have attracted much attention in coordination chemistry due to their switchable magnetic and optical properties in molecular electronic devices and catalytic systems. In this work the geometric and electronic structure of a redox-active cobalt complex ([Co(LBAIQ)2]; HLBAIQ = (E)-2,4-di-tert-butyl-6-((2-(5,7-di-tert-butylbenzo[d]oxazol-2-yl) phenyl) imino) cyclohexa-2,4-dienone) with an oxazoline-based o-aminophenol ligand has been investigated. X-ray crystallography analysis revealed an octahedral monomer complex in which cobalt(II) ion has been surrounded by two LBSQ. Based on the X-ray analysis the complex consists of a Co(II) centre and two semiquinone radical ligands. Frozen solution EPR a single isotropic signal at g = 1.995. The g-value is however lower than the free electron value and thus this seems to indicate some interaction between Co(II) center and two LBSQ ligands. Electrochemical redox reaction of cobalt complex show a quasi-reversible oxidation peak related to cobalt(III)/cobalt(II) redox process.
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