47895-81-8Relevant academic research and scientific papers
A long-lived cuprous bis-phenanthroline complex for the photodynamic therapy of cancer
Al Hageh, Cynthia,Al Assaad, Majd,El Masri, Zeinab,Samaan, Nawar,El-Sibai, Mirvat,Khalil, Christian,Khnayzer, Rony S.
, p. 4959 - 4967 (2018)
Copper is an earth-abundant and a biologically essential metal that offers a promising alternative to noble metals in photochemistry and photobiology. In this work, a series of sterically encumbered Cu(i) bis-phenanthroline complexes were investigated for their use in photochemotherapy (PCT). It was found that Cu(dsbtmp)2+ [dsbtmp = 2,9-disec-butyl-3,4,7,8-tetramethyl-1,10-phenanthroline] (compound 3), which possessed the longest excited state lifetime, exhibited significant in vitro photocytotoxicity on A375 (human malignant melanoma) and A549 (human lung carcinoma) cell lines. Fluorescence imaging demonstrated the significant uptake and localization of compound 3 in a perinuclear fashion. A comet assay indicated the induction of DNA damage in the dark. The DNA breaks were significantly amplified upon photoactivation. The light-induced enhancement of cytotoxicity was associated with the formation of reactive oxygen species (ROS), a known intermediate in photodynamic therapy (PDT). This successful demonstration of photocytotoxicity using long-lived cuprous phenanthroline paves the way to exploit this class of photosensitizers for PDT applications.
A general copper-based photoredox catalyst for organic synthesis: Scope, application in natural product synthesis and mechanistic insights
Deldaele, Christopher,Michelet, Bastien,Baguia, Hajar,Kajouj, Sofia,Romero, Eugenie,Moucheron, Cecile,Evano, Gwilherm
, p. 621 - 629 (2018/10/04)
Organic transformations can broadly be classified into four categories including cationic, anionic, pericyclic and radical reactions. While the last category has been known for decades to provide remarkably efficient synthetic pathways, it has long been hampered by the need for toxic reagents, which considerably limited its impact on chemical synthesis. This situation has come to an end with the introduction of new concepts for the generation of radical species, photoredox catalysis – which simply relies on the use of a catalyst that can be activated upon visible light irradiation – certainly being the most efficient one. The state-of-the-art catalysts mostly rely on the use of ruthenium and iridium complexes and organic dyes, which still considerably limits their broad implementation in chemical processes: alternative readily available catalysts based on inexpensive, environmentally benign base metals are therefore strongly needed. Furthermore, expanding the toolbox of methods based on photoredox catalysis will facilitate the discovery of new light-mediated transformations. This article details the use of a simple copper complex which, upon activation with blue light, can initiate a broad range of radical reactions.
Steric vs electronic effects and solvent coordination in the electrochemistry of phenanthroline-based copper complexes
Magni, Mirko,Colombo, Alessia,Dragonetti, Claudia,Mussini, Patrizia
, p. 324 - 330 (2014/11/12)
The present exhaustive electrochemical study proposes a rationalization of the redox properties of 1,10-phenanthroline-based copper complexes as a function of i) ligand molecular structure, evidencing the competition between electronic and steric effects of alkyl/aryl substituents, and ii) nature of working medium in terms of both solvent and supporting electrolyte anion. Occupancy of the 2 and 9 positions of the phenanthroline is a powerful tool to modulate the oxidation potentials of this family of complexes in a wide potential range. Solvent molecules play a key role in the metal-centred oxidative electron transfer process (unlike the optical electron transition), acting as ancillary ligands that allow the transition between tetrahedral four-coordinated Cu(I) state to tetragonal five-coordinated Cu(II). Actually clear evidences of the entry of one solvent molecule in the inner coordination sphere of the complexes are proved by the Kolthoff and Lingane method. Proof of ionic couple formation is also found.
Electron self-exchange, oxidation, and reduction reactions of bis(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)copper(II/I) and bis(6,6′-dimethyl-2,2′-bipyridine)copper(II/I) couples in acetonitrile: Gated et for the reduction, oxidation, and self-exchan
Koshino, Nobuyoshi,Kuchiyama, Yoshio,Funahashi, Shigenobu,Takagi, Hideo D.
, p. 1498 - 1507 (2007/10/03)
The electron self-exchange rate constant for the Cu(dmbp)22+/+ couple (dmbp = 6,6′-dimethyl-2,2′-bipyridine) was measured in acetonitrile by the NMR method (kex = 5.5 × 103 kg mol-1 s-1, ΔH
Photodriven Electron and Energy Transfer from Copper Phenanthroline Excited States
Ruthkosky, Mark,Castellano, Felix N.,Meyer, Gerald J.
, p. 6406 - 6412 (2008/10/09)
Electron and energy transfer from copper 1,10-phenanthroline excited states is observed at room temperature in organic solvents. The copper phenanthroline excited states are metal-to-ligand charge-transfer in nature and have lifetimes of ～70-250 ns in dic
