171565-44-9

Upstream product

• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 645-49-8 cis-stilben 
• 1657-53-0 cis-4-methoxystilbene 
• 100-51-6 benzyl alcohol 
• 168646-54-6 1,10-o-phenanthroline-5,6-diamine 
• 66-71-7 1,10-Phenanthroline 

Downstream Products

• 1208231-48-4 [(dpephos)(2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline)copper(I)]BF₄ 
• 1192310-65-8 [Mn(2-phenylimidazo[4,5-f]1,10-phenanthroline)(1,4-naphthalenedicarboxylic acid(-2H))]*H₂O 
• 926310-93-2 [Mn(2-phenylimidazo[4,5-f]1,10-phenanthroline)(benzene-1,3-dicarboxylic acid(-2H))] 

Relevant academic research and scientific papers

Computational and spectroscopic studies of the imidazole-fused phenanthroline derivatives containing phenyl, naphthyl, and anthryl groups

Three N,N-bidentate ligands, 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline (1), 2-(2-naphyl)-1H-imidazo[4,5-f]phenanthroline (2), and 2-(2-anthryl)-1H-imidazo[4,5-f]phenanthroline (3) have been synthesized and characterized. Effects of aryl subsistiuents (phenyl, naphthyl, and anthryl) on the photophysical properties of these ligands in solution have been studied. Ligand 1 exhibit the main absorption band at 283 nm with the shoulder bands at 300-350 nm and these bands are assigned as the typical π→π(imPhen) state (imPhen = 1H-imidazo[4,5-f][1,10]phenanthroline). A similar absorption spectrum was also observed in the case of 2, in which the charge transfer (CT) state should be considered. 3 shows the slightly different absorption properties compared to that of 1 and 2. The highest-lying absorption band at 257 nm is assigned as a mixed π→π(imPhen)/π→π(Anth) (Anth = anthracene) state. Additionally, the characteristic absorption band of anthryl group with three vibronic bands at 352, 367, and 386 nm also observed in the visible region range from 340 to 400 nm. 1 shows the typical ligand-centered 1π→πemission, while 2 and 3 emit from the mixed 1π→π/CT states. Density functional theory (DFT) and time-dependent density functional theory (TDDFT) were employed to rationalize the photophysical properties of these ligands studied. The theoretical data confirm the assignment of the experimental absorption spectra and the nature of the emitting states.

Degenerate four-wave mixing determination of third-order optical nonlinearities of three mixed ligand nickel(II) complexes

Three mixed ligand nickel(II) complexes were synthesized and characterized by UV-visible, IR, MS and elemental analysis. Their off-resonant third-order nonlinear optical properties were measured using femtosecond laser and degenerate four-wave mixing technique. The third-order nonlinear optical susceptibilities χ(3) were 3.20-3.51 × 10-13 esu. The nonlinear refractive indexes n2 were 5.89-6.45 × 10-12 esu. The second-order hyperpolarizabilities γ of the molecules were 3.20-3.50 × 10-31 esu. The response times were 55-81 fs. The results show that these complexes have potential nonlinear optical applications.

Synthesis and Characterization of Ru(II) Complexes with π-Expansive Imidazophen Ligands for the Photokilling of Human Melanoma Cells

Ru(II) complexes were synthesized with π-expanding (phenyl, fluorenyl, phenanthrenyl, naphthalen-1-yl, naphthalene-2-yl, anthryl and pyrenyl groups) attached at a 1H-imidazo[4,5-f][1,10]phenanthroline ligand and 4,4′-dimethyl-2,2′-bipyridine (4,4′-dmb) coligands. These Ru(II) complexes were characterized by 1D and 2D NMR, and mass spectroscopy, and studied for visible light and dark toxicity to human malignant melanoma SK-MEL-28 cells. In the SK-MEL-28 cells, the Ru(II) complexes are highly phototoxic (EC50?=?0.2–0.5?μm) and have low dark toxicity (EC50?=?58–230?μm). The highest phototherapeutic index (PI) of the series was found with the Ru(II) complex bearing the 2-(pyren-1-yl)-1H-imidazo[4,5-f][1,10]phenanthroline ligand. This high PI is in part attributed to the π-rich character added by the pyrenyl group, and a possible low-lying and longer-lived 3IL state due to equilibration with the 3MLCT state. While this pyrenyl Ru(II) complex possessed a relatively high quantum yield for singlet oxygen formation (Φ??=?0.84), contributions from type-I processes (oxygen radicals and radical ions) are competitive with the type-II (1O2) process based on effects of added sodium azide and solvent deuteration.

Synthesis, characterization, and DNA binding of complexes [Pt(bpy)(pip)]2+ and [Pt(bpy)(hpip)]2+

Two new platinum(II) complexes, [Pt(bpy)(pip)](NO3)2 (1) and [Pt(bpy)(hpip)](NO3)2·2H2O (2) (bpy is 2,2′-bypyridine; pip is 2-phenylimidazo[4,5-f][1,10] phenanthroline; hpip is 2-(2-hydroxyphenyl) imidazo[4,5-f][1,10]phenanthroline), have been synthesized and fully characterized by CHN analysis, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, 1H-NMR spectroscopy, IR spectroscopy (attenuated total reflection), and UV-vis spectroscopy. The DNA-binding behaviors of both complexes have been studied by spectroscopic methods and viscosity measurements, and their ability to inhibit DNA transcription was measured. The results indicate that both complexes show some degree of binding to DNA in an intercalative mode, resulting in intrinsic binding constants of (2.88 ± 0.4) × 104 and (5.38 ± 0.8) × 104 for 1 and 2, respectively. The comparatively observed difference in the DNA-binding affinities of the two complexes can be reasonably explained by the presence of intramolecular hydrogen bonding between the ortho phenolic group and the nitrogen atom of the imidazole ring. The extended coplanarity of the hpip ligand due to intramolecular hydrogen bonding may lead to an enhancement of the DNA-binding affinity of the hpip complex. In addition, the complexes can promote photocleavage of pUC19 DNA on irradiation as revealed by the spectroscopic and viscometric measurements, with 2 promoting cleavage of pUC19 DNA at lower concentration. Moreover, increasing concentrations of both complexes inhibited DNA transcription, and as expected 2 was shown to be a better antitumor agent than 1.

Platinum phenanthroimidazole complexes as G-quadruplex DNA selective binders

Complexes that bind and stabilize G-quadruplex DNA structures are of significant interest due to their potential to inhibit telomerase and halt tumor cell proliferation. We here report the synthesis of the first PtII G-quadruplex selective molecules, containing π-extended phenanthroimidazole ligands. Binding studies of these complexes with duplex and quadruplex d(T 4G4T4)4 DNA were performed. Intercalation to duplex DNA was established through UV/Vis titration, CD spectroscopy, and thermal denaturation studies. Significantly stronger binding affinity of these phenanthroimidazole PtII complexes to G-quadruplex DNA was observed by UV/Vis spectroscopy and competitive equilibrium dialysis studies. Observed binding constants to quadruplex DNA were nearly two orders of magnitude greater than for duplex DNA. Circular dichroism studies show that an increase in π-surface leads to a significant increase in the thermal stability of the PtII/quadruplex DNA complex. The match in the π-surface of these phenanthroimidazole PtII complexes with quadruplex DNA was further substantiated by molecular modeling studies. Numerous favorable π-stacking interactions with the large aromatic surface of the intermolecular G-quadruplex, and unforeseen hydrogen bonds between the ancillary ethylenediamine ligands and the quadruplex phosphate backbone are predicted. Thus, both biological and computational studies suggest that coupling the square-planar geometry of PtII with π-extended ligands results in a simple and modular method to create effective G-quadruplex selective binders, which can be readily optimized for use in telomerase-based antitumor therapy.

A ruthenium(II) complex capable of inducing and stabilizing bcl-2 G-quadruplex formation as a potential cancer inhibitor

Two ruthenium(II) complexes (Ru-complexes) were synthesized and characterized in this study. The selectivity and ability of the complexes to interact with bcl-2 DNA were investigated here. It turned out that [Ru(ip) 3](ClO4)2·2H2O (complex 1, ip = 1H-iminazole [4,5-f][1,10] phenanthroline) could induce and stabilize the formations of G-quadruplexes more effectively than [Ru(pip)3] (ClO4)2·2H2O (complex 2, pip = 2-phenylimidazo-[4,5-f][1,10]phenanthroline) did. Considering the important role of the Ru-complex ligand in inducing and stabilizing the formations of G-quadruplex in our previous studies, we speculate that the overlarge ligand of complex 2 may block its binding affinity for G-quadruplexes. Complex 1 also induced cell apoptosis in in vitro assays. In general, this study provided potentially important information for further development of the Ru-complexes as good inducers and stabilizers of bcl-2 G-quadruplex DNA for cancer treatment.

A Rhodium(III) Complex as an Inhibitor of Neural Precursor Cell Expressed, Developmentally Down-Regulated 8-Activating Enzyme with in Vivo Activity against Inflammatory Bowel Disease

We report herein the identification of the rhodium(III) complex [Rh(phq)2(MOPIP)]+ (1) as a potent and selective ATP-competitive neural precursor cell expressed, developmentally down-regulated 8 (NEDD8)-activating enzyme (NAE) inhibitor. Structure-activity relationship analysis indicated that the overall organometallic design of complex 1 was important for anti-inflammatory activity. Complex 1 showed promising anti-inflammatory activity in vivo for the potential treatment of inflammatory bowel disease.

Microwave-assisted synthesis of phenanthroimidazole derivatives as stabilizer of c-myc G-quadruplex DNA

c-myc G-quadruplex DNA, which plays a central role in tumor progression and resistance, has been extensively investigated as potential target of antitumor drugs. In this paper, a series of phenanthroimidazole derives have been synthesized under irradiation of microwave in yields of 51-80%. The antitumor activity of these compounds against various tumor cells has been evaluated, and the results show that these compounds exhibit great inhibition to MDA-MB-231, MCF-7 and Hela cells, especially 5 inhibit the growth of MDA-MB-231 cells with IC50 about 3.6 μM. The further studies show that 5 can bind and stabilize c-myc G4 DNA in π-π stacking mode, which confirmed by the hypochromise in the electronic spectra of 5 with the increasing of c-myc G4 DNA. When dealt with 5, the strength of CD signal attributed to c-myc G4 DNA is decreased and the FRET melting point of c-myc G4 DNA is increased. Moreover, the molecule docking calculation was conducted to show that 5 suitably stack onto the 5′ G-quartet surface, and parallels to the surfaces of the G5 and G-quartet consisting of G7, G11, G16, and G20. As a result, the replication of c-myc oligomers is blocked by 5. In a word, this type of phenanthroimidazole derives can act as potential inhibitor against breast cancer cells by binding and stabilizing c-myc G4 DNA through π-π stacking.

Synthesis of polypyridyl ruthenium complexes with 2-(1-aryl)-1H-imidazo[4,5-f]-1,10-phenanthroline ligand and its application for luminescent oxygen sensing

Polypyridyl ruthenium (Ru) complexes 1-3 were prepared. Their photophysical properties were investigated by UV-Vis absorption and luminescence emission spectra. The luminescent lifetimes of these Ruthenium complex were prolonged by more than 5 folds (τ = 2. 50 μs for complex 3) when compared with the parent Ru complex 1 (τ = 0. 45 μs). We propose that the extended luminescent lifetime of complex 3 is due to the equilibrium between 3MLCT state and the pyrene localized 3π-π* triplet state (3IL). The luminescent O2-sensing property of the complexes in solution and the IMPEK-C polymer film were studied, and the O2 sensing was quantified with the two-site model. The oxygen-sensing property of the Ru complexes can be improved by 104-fold with extension of the luminescent lifetimes. For example, the quenching constant KSV was improved from 0. 0023 Torr-1 of 1 to 0. 2393 Torr-1 for 3. Our results demonstrated a versatile approach for the preparation of Ru (II) polypyridine complexes with extended luminescent lifetimes as functional materials, for example, for luminescent oxygen-sensing applications.

Copper(I) complexes of phenanthrolineimidazole ligands: Structures, photophysical properties, and quantum chemical studies

Three copper(I) complexes, [Cu(PimP)(POP)]PF6 (1), [Cu(NimP)(POP)]PF6 (2), and [Cu(AimP)(POP)]PF6 (3) (PimP = 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline, NimP = 2-(2-naphthyl-1H-imidazo[4,5-f]phenanthroline, AimP = 2-(9-anthryl)-1H-imidazo[4,5-f]phenanthroline, POP = bis[2-diphenylphosphino]-phenyl)ether) have been synthesized and characterized. Investigations into the effects of the varying substituents on the structural, absorption, and emission characteristics of the corresponding complexes are presented. Complexes 1 and 2 exhibit similar photophysical properties with the weaker lowest lying MLCT absorption at λ > 400 nm and the phosphorescence 3MLCT/3LLCT emission in the range of 570-590 nm, whereas complex 3 shows different absorption and emission properties, in which the LLCT absorption band is overlapped with the structured absorption bands belonging to the characteristic peaks of the anthracene moiety, and the emitting excited state is described as the 3LLCT character. Density functional theory and time-dependent density functional theory calculations were employed to rationalize the photophysical properties of the complexes.