376362-92-4Relevant articles and documents
Selectivity of Terpyridine Platinum Anticancer Drugs for G-quadruplex DNA
Morel, Elodie,Beauvineau, Claire,Naud-Martin, Delphine,Landras-Guetta, Corinne,Verga, Daniela,Ghosh, Deepanjan,Achelle, Sylvain,Mahuteau-Betzer, Florence,Bombard, Sophie,Teulade-Fichou, Marie-Paule
, (2019)
Guanine-rich DNA can form four-stranded structures called G-quadruplexes (G4s) that can regulate many biological processes. Metal complexes have shown high affinity and selectivity toward the quadruplex structure. Here, we report the comparison of a panel of platinum (II) complexes for quadruplex DNA selective recognition by exploring the aromatic core around terpyridine derivatives. Their affinity and selectivity towards G4 structures of various topologies have been evaluated by FRET-melting (Fluorescence Resonance Energy Transfert-melting) and Fluorescent Intercalator Displacement (FID) assays, the latter performed by using three different fluorescent probes (Thiazole Orange (TO), TO-PRO-3, and PhenDV). Their ability to bind covalently to the c-myc G4 structure in vitro and their cytotoxicity potential in two ovarian cancerous cell lines were established. Our results show that the aromatic surface of the metallic ligands governs, in vitro, their affinity, their selectivity for the G4 over the duplex structures, and platination efficiency. However, the structural modifications do not allow significant discrimination among the different G4 topologies. Moreover, all compounds were tested on ovarian cancer cell lines and normal cell lines and were all able to overcome cisplatin resistance highlighting their interest as new anticancer drugs.
A Designed TEMPO-derivate Catalyst with Switchable Signals of EPR and Photoluminescence: Application in the Mechanism of Alcohol Oxidation
Yin, Lu,Zhang, Jiaxiang,Yao, Jia,Li, Haoran
, p. 3513 - 3519 (2018)
Construction the in situ, real-time monitoring methodology for chemical changes, especially in the mechanism of oxidation, has long been regarded as a significant and challenging concern. Herein, we designed and synthesized a TEMPO-mediated alkynylplatinum(II) terpyridine complex with switchable activity in photoluminescence and EPR (Electron Paramagnetic Resonance) spectra. This complex of alkynylplatinum(II) terpyridine-TEMPO [(2, 2,6,6-tetramethylpiperidin-1-yl)oxyl] is paramagnetic, while the in situ formed alkynylplatinum(II) terpyridine-TEMPOH is diamagnetic, so that concentration changes of TEMPO/ TEMPOH species were obtained successfully by photoluminescence and EPR spectra in an operando way. As a model example, we investigated the mechanism of alcohol oxidation mediated by TEMPO/ bis(acetoxy)iodo]benzene (BAIB). It was found that, with the consumption of co-oxidant (BAIB), the concentration and conformation of catalyst (TEMPO) were changed gradually, and the vital role of catalyst and co-oxidant in the benzyl alcohol oxidation was clearly showed by photoluminescence and EPR spectroscopies. On the basis of these observations, we suggested an effective methodology to study the mechanism of chemical reaction, which is promising for further practical applications in analytical or environmental issues.
Luminescent Pt(2,6-bis(: N -methylbenzimidazol-2-yl)pyridine)X+: A comparison with the spectroscopic and electrochemical properties of Pt(tpy)X+(X = Cl, CCPh, Ph, or CH3)
Connick, William B.,Grove, Levi J.,Shingade, Vikas M.
supporting information, p. 9651 - 9661 (2020/07/30)
A series of platinum(ii) pincer complexes of the formula Pt(mbzimpy)X+, 1(a-d), (mbzimpy = 2,6-bis(N-methylbenzimidazol-2-yl)pyridine; X = Cl; (a), CCPh; (b), Ph; (c), or CH3; (d), CCPh = phenylacetylide, and Ph = Phenyl) have been synthesized and characterized. Electronic absorption and emission, as well as electrochemical properties of these compounds, have been investigated. Pt(tpy)X+ analogs (tpy = 2,2′;6′2′′-terpyridine), 2(a-d), have also been investigated and compared. Electrochemistry shows that 1 and 2 analogs undergo two chemically reversible one-electron reduction processes that are shifted cathodically along the a b c d series. Notably, these reductions occur at slightly higher negative potentials in the case of 1. The absorption spectra of 1 and 2 in acetonitrile exhibit ligand-centered (1LC) transitions (? ≈ 104 M-1 cm-1) in the UV region and metal-to-ligand-charge transfer (1MLCT) transitions (? ≈ 103 M-1 cm-1) in the visible region. The corresponding visible bands of 1b and 2b have been assigned to 1(LLCT/MLCT) mixed state (LLCT: ligand-to-ligand-charge transfer). The preceding 1LC and 1MLCT transitions of 1 occur at lower energies than that of 2. These 1LC transitions have distinctly been blue-shifted along a c d in 2, but occur at nearly identical energies in 1. Conversely, 1MLCT transitions are red-shifted along a c d in both the analogs. The 77 K glassy solutions of 1 and 2 exhibit an intense vibronically-structured emission band at λmax(0-0) in the 470-560 nm range. This band is red-shifted along b a ≤ c d in 1 and along a ≤ d ≈ c ? b in 2. The main character of these emissions is assigned to 3LLCT emissive state in 1b and 2b, whereas to 3LC in the rest of the compounds. Relative stabilization of these spin-forbidden emissive states is discussed by invoking configuration mixing with the higher-lying 3MLCT state.
Synthesis, luminescence, electrochemistry, and ion-binding studies of platinum(II) terpyridyl acetylide complexes
Yam, Vivian Wing-Wah,Tang, Rowena Pui-Ling,Wong, Keith Man-Chung,Cheung, Kung-Kai
, p. 4476 - 4482 (2008/10/08)
A series of platinum(II) terpyridyl acetylide complexes, [Pt(trpy)(C≡CR)]PF6 (R = C6H5, C6H4Cl-4, C6H4CH3-4, C6H4OCH3-4, C6H4NO2-4, benzo-15-crown-5, C6H3-(OCH3)2-3,4), have been synthesized and characterized. Their luminescence and electrochemical behaviors have been studied. The ion-binding properties of [Pt(trpy)(C≡C-benzo-15-crown-5)]PF6 and the X-ray crystal structure of [Pt(trpy)(C≡CC6H5)]PF6 are also reported.
