19535-47-8Relevant articles and documents
Three thymine/adenine binding modes of the ruthenium complex Λ-[Ru(TAP)2(dppz)]2+ to the G-quadruplex forming sequence d(TAGGGTT) shown by X-ray crystallography
McQuaid, Kane,Hall, James P.,Baumgaertner, Lena,Cardin, David J.,Cardin, Christine J.
, p. 9116 - 9119 (2019)
Λ-[Ru(TAP)2(dppz)]2+ was crystallised with the G-quadruplex-forming heptamer d(TAGGGTT). Surprisingly, even though there are four unique binding sites, the complex is not in contact with any G-quartet surface. Two complexes stabilise cavities formed from terminal T·A and T·T mismatched pairs. A third shows kinking by a TAP ligand between T·T linkages, while the fourth shows sandwiching of a dppz ligand between a T·A/T·A quadruplex and a T·T mismatch, stabilised by an additional T·A base pair stacking interaction on a TAP surface. Overall, the structure shows an unexpected affinity for thymine, and suggests models for G-quadruplex loop binding.
Mitochondria specific highly cytoselective iridium(iii)-Cp* dipyridophenazine (dppz) complexes as cancer cell imaging agents
Roy, Nilmadhab,Sen, Utsav,Ray Chaudhuri, Shreya,Muthukumar, Venkatesan,Moharana, Prithvi,Paira, Priyankar,Bose, Bipasha,Gauthaman, Ashna,Moorthy, Anbalagan
, p. 2268 - 2283 (2021)
Cancer is the most incurable pernicious disease to date after cardiovascular disease with an immeasurable rate of mortality. However, effective cancer medication and therapy are still castles in the sky to researchers. Therefore, in search of an appropriate strategy to annihilate cancer, we have designed a set of Ir(iii)-Cp* dipyridophenazine complexes as luminescent anticancer agents combining the cancer inhibiting potency of the planar dipyridophenazine (dppz) moiety through DNA interaction and mitochondrial dysfunction with the wonderful photoluminescence ability and target specificity of iridium metal. Hence, with the synergy of these dual aspects in the same system, we have aspired to emphasize the theranostic approach of cancer treatment in the present study by preparing effective, aqueous-soluble, mitochondria-targeting, highly cytoselective, luminescent, cancer cell-permeable scaffolds, enabling diagnosis as well as the healing of cancer cells in the body. Here, the presence of the cyclopentadienyl (Cp*) moiety in association with the fluorine group has boosted the lipophilic character of the complexes. Also, the cytotoxicity screening of the prepared Cp*Ir(iii)-dipyridophenazine complexes (IrL1-IrL7) against colorectal adenocarcinoma cells (Caco-2) and human epitheloid cervix carcinoma cells (HeLa) clearly identified them as potential anticancer agents and imaging studies unveiled their superb cellular imaging properties. Among them, the complex [(η5-Cp*)IrCl(11-fluorodipyrido[3,2-a:2′,3′-c]phenazine)] (IrL6) achieved the best cytoselectivity. However, the superiority of the anticancer potency of [(η5-Cp*)IrCl(benzo[i]dipyrido[3,2-a:2′,3′-c]phenazine)] (IrL3) was also corroborated by its activity against the most aggressive colorectal carcinoma cell line (HT-29), whereas (η5-Cp*)IrCl(11-(trifluoromethyl)dipyrido[3,2-a:2′,3′-c]phenazine (IrL5) came into the limelight as the best theranostic agent as it showed remarkable cytoselectivity as well as significant cellular imaging properties, endowing it with the highest quantum yield value among all the complexes.
Crystalline ruthenium polypyridine nanoparticles: A targeted treatment of bacterial infection with multifunctional antibacterial, adhesion and surface-anchoring photosensitizer properties
Yin, Chenyang,Wang, Zekun,Ding, Xiaoyuan,Chen, Xiaoqing,Wang, Jingyuan,Yang, Endong,Wang, Weiyun,Martin, Lisandra L.,Sun, Dongdong
, p. 3808 - 3825 (2021)
Photodynamic antibacterial therapy employs nanocomposites as an alternative to traditional antibiotics for the treatment of bacterial infections. However, many of these antibacterial materials are less effective towards bacteria than traditional drugs, either due to poor specificity or antibacterial activity. This can result in needless and excessive drug use in treatments. This paper describes a multifunctional drug delivery nanoparticle (MDD-NP), Sph-Ru-MMT@PZ, based on the nanostructured-form of [Ru(bpy)2dppz] (PF6)2 (Sph-Ru), which has adhesive properties towards its microbial targets as well as surface-anchoring photosensitizer effects. The design and construction of MDD-NP is based on the adhesive properties of the outer layers of montmorillonite (MMT), which allows Sph-Ru-MMT@PZ to successfully reach its bacterial target; the outer layer of the E. coli. In addition, under 670 nm red irradiation therapy (R-IT), the surface-anchoring properties use the photosensitizer phthalocyanine zinc (PZ) to destroy the bacteria by producing reactive oxygen species (ROS) which causes cell lysis of E. coli. More importantly, Sph-Ru-MMT@PZ has no fluorescence response to live E. coli with intact cell membranes but selectively stained and demonstrated fluorescence during membrane damage of early-stage cells as well as exposure of nuclear materials at late-stage of cell lysis. Sph-Ru-MMT@PZ showed beneficial and synergistic anti-infective effects in vivo by inhibiting the E. coli infection-induced inflammatory response and eventually promoting wound healing in mice. This new strategy for high precision antibacterial therapy towards specific targets, provides an exciting opportunity for the application of multifunctional nanocomposites towards microbial infections.
Synthesis, structures, DNA-binding, cytotoxicity and molecular docking of CuBr(PPh3)(diimine)
Abdellattif, Magda H.,Alzahrani, Khaled A.,Arshad, Muhammed N.,Asiri, Abdullah M.,Babgi, Bandar A.,Du, Jun,Humphrey, Mark G.,Hussien, Mostafa A.,Mashat, Khlood H.
, (2020)
The copper(I) coordination compounds of general formula [CuBr(PPh3)(N^N)] (N^N = 2,2′-bipyridine (1), 1,10-phenanthroline (2), 4,4′-dimethyl-2,2′-bipyridine (3), 4,4′-dimethoxy-2,2′-bipyridine (4), 3-(2-pyridyl)-4,5-diphenyl-1,2,4-triazine (5),
Ru(ii) photosensitizers competent for hypoxic cancersviagreen light activation
Ballester, Francisco J.,Bautista, Delia,Ortega, Enrique,Ruiz, José,Santana, M. Dolores
, p. 10301 - 10304 (2020)
A family of five heteroleptic complexes [Ru(C^N)(N^N)2][PF6] (HC^N = methyl 1-butyl-2-arylbenzimidazolecarboxylate; N^N = polypyridine) has been synthesized to act as biologically-compatible green light photosensitizers (PSs) with phototherapeutic indexes (PIs) up to higher than 700 under hypoxia (2% O2) in HeLa cancer cells under short time of irradiation.
Ni(II) curcumin complexes for cellular imaging and photo-triggered in vitro anticancer activity
Banaspati, Atrayee,Raza, Md Kausar,Goswami, Tridib K.
, (2020)
Nickel(II) complexes [Ni(cur)(L)2](OAc) (1-3) where L is N,N-donor heterocyclic bases namely 1,10-phenanthroline (phen in 1), dipyrido[3,2-d:2′,3′-f]quinoxaline (dpq in 2), dipyrido[3,2-a:2′,3′-c]phenazine (dppz in 3) and Hcur is curcumin were
Synthesis, characterization, photophysical and oxygen-sensing properties of a copper(I) complex
Zhou, Chuanqi,Wang, Qingshuang
, p. 605 - 611 (2010)
In this paper, we report the synthesis, crystal structure, photophysical properties, and electronic nature of a phosphorescent Cu(I) complex of [Cu(TBT)(POP)]BF4, where TBT and POP stand for 4, 5, 9, 14-tetraaza-benzo[b]-triphenylene and bis(2-(diphenylphosphanyl)phenyl) ether, respectively. [Cu(TBT)(POP)]BF4 renders a red phosphorescence peaking at 622 nm, with a long excited-state lifetime of 13.2 μs. Density functional calculation reveals that the emission comes from a triplet metal-to- ligandcharge-transfer excited state. We electrospun composite nanofibers of [Cu(TBT)(POP)]BF4 and polystyrene, hoping to explore the possibility of replacing precious-metal-based oxygen sensors with cheap Cu-based ones. The finally obtained samples with average diameter of ～700 nm exhibit a maximum sensitivity of 5.8 toward molecular oxygen with short response/recovery time (5/13 s) due to the large surface-area-to-volume ratio of nanofibrous membranes. No photobleaching is detected in these samples. All these results suggest that phosphorescent Cu(I) complexes doped nanofibrous membranes are promising candidates for low-cost and quick-response oxygen-sensing materials. Springer Science+Business Media B.V. 2010.
A gadolinium(III) complex based dual-modal probe for MRI and fluorescence sensing of fluoride ions in aqueous medium and: In vivo
Wang, Yue,Song, Renfeng,Guo, Ke,Meng, Qingtao,Zhang, Run,Kong, Xiangfeng,Zhang, Zhiqiang
, p. 17616 - 17623 (2016)
A novel Gd(iii) complex, Gd(TTA)3-DPPZ, was designed and assembled as a dual-modal probe for the simultaneous fluorescence and magnetic resonance imaging (MRI) detection of fluoride ions in aqueous media and in vivo. In this system, the Gd(iii) center is not only serving as a MRI signal output unit, but also as a binding site for fluoride ions. When appropriate equivalents of fluoride ions were added into the solution of Gd(TTA)3-DPPZ, the replacement of the coordination water led to a decrease of the longitudinal relaxivity (r1) as well as distinct spectroscopic changes, by which MRI/fluorescence dual-modal fluoride ion sensing was achieved. In the presence of fluoride ions, a 2-fold fluorescence emission enhancement of Gd(TTA)3-DPPZ, and a notable decrease of the UV-vis absorption spectrum were observed. The fluorescence detection limit for fluoride ions was established at 70 nM. Gd(TTA)3-DPPZ also exhibits about 75% decrease of the longitudinal relaxivity (r1) upon addition of fluoride ions in aqueous medium. The appropriate blood circulation time of Gd(TTA)3-DPPZ allows its potential application in MRI in vivo. The results demonstrated that Gd(TTA)3-DPPZ could serve as a potential MRI/fluorescence bimodal imaging agent for the specific and high-sensitive sensing of fluoride ions in vivo.
Minor groove intercalation of Δ-[Ru(Me2phen)2dppz]2+ to the hexanucleotide d(GTCGAC)2
Greguric, Antun,Greguric, Ivan D.,Hambley, Trevor W.,Aldrich-Wright, Janice R.,Collins, J. Grant
, p. 849 - 855 (2002)
The metal complex Δ-[Ru(Me2phen)2dppz]2+ (Me2phen = 2,9-dimethyl-1,10-phenanthroline; dppz = dipyrido-[3,2-a:2′,3′-c]phenazine) has been synthesised and its binding to the hexanucleotide d(GTCGAC)2 studied by 1H NMR spectroscopy. The crystal structure of rac-[Ru(Me2phen)2dppz](PF6)2 ·2H2O has been determined. Addition of Δ-[Ru(Me2phen)2dppz]2+ to d(GTCGAC)2 induced significant broadening of the Me2phen and dppz resonances and large upfield shifts of the dppz resonances, consistent with the metal complex binding through intercalation of the dppz ligand. Also indicative of intercalation are the observed upfield shifts of the T2 and G4 imino protons and the 173°C increase in the melting temperature of the hexanucleotide upon addition of the metal complex. NOE cross-peaks from the Me2phen protons were only observed to hexanucleotide minor groove H1′ and H4′/H5′/H5″ protons in NOESY spectra of the hexanucleotide with added metal complex. In addition, NOEs were also observed between the H13/14 protons of the dppz ligand and the hexanucleotide major groove T2methyl and sugar H2′/H2″ protons. From the combined NMR data it is concluded that the dppz-based ruthenium(II) complex Δ-[Ru(Me2phen)2dppz]2+ intercalates from the minor groove of the hexanucleotide mini-duplex d(GTCGAC)2.
Studies on synthesis, characterization, and G-quadruplex binding of Ru(II) complexes containing two dppz ligands
Sun, Jing,An, Yan,Zhang, Li,Chen, Huo-Yan,Han, Yan,Wang, Yu-Jia,Mao, Zong-Wan,Ji, Liang-Nian
, p. 149 - 154 (2011)
In this work, the interaction between the guanine-rich single-strand oligomer AG3(T2AG3)3 quadruplex and two Ru(II) complexes, [Ru(L1)(dppz)2](PF6) 4 (1) and [Ru(L2)(dppz)2](PF6) 4 (2) (L1 = 5,5′-di(1-(trimethylammonio)methyl)-2, 2′-dipyridyl cation, L2 = 5,5′-di(1-(triethylammonio) methyl)-2,2′-dipyridyl cation, dppz = dipyrido[3,2-a:2′,3′-c] phenazine), has been studied by UV-Visible, fluorescence, DNA melting, and circular dichroism in K+ buffer. The two complexes after binding to G-quadruplex have shown different DNA stability and fluorescence enhancement. The results show that both complexes can induce the stabilization of quadruplex DNA. ΔTm values of complexes 1 and 2 at [Ru]/[DNA] ratio of 1:1 were 9.4 and 7.0, respectively. Binding stoichiometry along with the quadruplex was investigated through a luminescence-based Job plot. The major inflection points for complexes 1 and 2 were 0.49 and 0.46, respectively. The data were consistent with the binding mode at a [quadruplex]/[complex] ratio of 1:1. In addition, the conformation of G-quadruplex was not changed by the complexes at the high ionic strength of K+ buffer.
Synthesis, characterization and luminescence property of ternary rare earth complexes with azatriphenylenes as highly efficient sensitizers
Sun, Hui-Juan,Fu, Xiao-Tao,Chu, Hai-Bin,Du, Yan,Lin, Xue-Mei,Li, Xin,Zhao, Yong-Liang
, p. 243 - 249 (2011)
A series of novel ternary rare earth complexes showing attractive luminescence properties were prepared with both neutral and anion ligands. Three azatriphenylene neutral ligands, 1,10-phenanthroline (phen), dipyrido [3,2-a: 2′,3′-c] quinoxaline (dpq) and dipyrido [3,2-a: 2′,3′-c] phenazine (dppz) were investigated systematically as sensitizers in the ternary rare earth complexes. Benzoate ions (BA-) and phenoxyacetate ions (POA-) were chosen as anion ligands. The compositions of these complexes were characterized by elemental analysis, rare earth coordination titration, molar conductivity measurement, IR spectroscopy, UV-vis absorption spectroscopy, 1H NMR spectroscopy and TGA-DTA. The luminescence spectra, luminescence decay time and quantum efficiency of the complexes were also studied. The very strong luminescence intensities and rather long luminescence lifetimes (typically > 1.0 ms) were achieved for both Eu 3+ and Tb3+ ternary complexes with phen and dpq as neutral ligands. Moreover, high quantum efficiencies (40-60%) were also obtained for Eu3+ ternary complexes with phen and dpq as neutral ligands.
Hydrothermal syntheses of some derivatives of tetraazatriphenylene
Che, Guangbo,Li, Wenlian,Kong, Zhiguo,Su, Zisheng,Chu, Bei,Li, Bin,Zhang, Zhiqiang,Hu, Zhizhi,Chi, Haijun
, p. 2519 - 2524 (2006)
Some derivatives of tetraazatriphenylene can be synthesized readily by a hydrothermal synthetic method. Compared with the traditional technique, this method is effective and simple process, and much high yields of products with higher purity can be harvested. Copyright Taylor & Francis Group, LLC.
Constructing triplet trap in Eu(III) complexes and corresponding application for halogen fluorescent optical sensing
Zhao, Yuqing
, (2020/03/05)
In this paper, a series of Eu(III) complexes was designed using 2-thenoyltrifluoroacetone (TTA) as the first ligand, and phenanthroline derivatives as the second ligand. Their molecular structure was analyzed via their single crystals. Detailed photophysical analysis on these Eu(III) complexes suggested that ligand TTA was the major energy transfer antenna for emissive Eu(III). The phenanthroline-derived ligands showed low triplet levels (T1), leading to a reverse energy transfer (triplet trap) from Eu(III) 5D0 to T1 of diamine ligands. This procedure actually compromised emission performance of these Eu(III) complexes. It was found that halogen anions, especially fluorine ion, interacted with these diamine ligands, which heightened triplet level of these diamine ligands. With the elimination of such triplet trap in these Eu(III) complexes, their Eu(III) emission was greatly improved, showing emission turn-on effect. Detailed sensing performance was discussed carefully. Eu(TTA)3Phen showed a down-bending working curve following a two-site model Stern-Volmer equation. Eu(TTA)3DPPZ and Eu(TTA)3DPOX showed linear working curves with good selectivity. In addition to its emission turn-on sensing, Eu(TTA)3DPOX still showed ratiometric sensing. Detailed sensing mechanism was discussed and confirmed.
