57436-95-0Relevant academic research and scientific papers
Quaternarized pdppz: Synthesis, DNA-binding and biological studies of a novel dppz derivative that causes cellular death upon light irradiation
Elmes, Robert B. P.,Erby, Marialuisa,Cloonan, Suzanne M.,Quinn, Susan J.,Williams, D. Clive,Gunnlaugsson, Thorfinnur
, p. 686 - 688 (2011)
The quaternarized pdppz derivative 1 was shown to bind strongly to DNA with concomitant changes in its ground and excited state photophysical properties. Furthermore, the compound also showed rapid cellular uptake, and induced apoptosis upon light irradiation in various cancer cell lines after 24 hours of incubation. The Royal Society of Chemistry 2011.
Detailed Biological Profiling of a Photoactivated and Apoptosis Inducing pdppz Ruthenium(II) Polypyridyl Complex in Cancer Cells
Cloonan, Suzanne M.,Elmes, Robert B. P.,Erby, Marialuisa,Bright, Sandra A.,Poynton, Fergus E.,Nolan, Derek E.,Quinn, Susan J.,Gunnlaugsson, Thorfinnur,Williams, D. Clive
, p. 4494 - 4505 (2015)
Ruthenium polypyridyl complexes show great promise as new photodynamic therapy (PDT) agents. However, a lack of detailed understanding of their mode of action in cells poses a challenge to their development. We have designed a new Ru(II) PDT candidate that efficiently enters cells by incorporation of the lipophilic aromatic pdppz ([2,3-h]dipyrido[3,2-a:2′,3′-c]phenazine) ligand and exhibits photoactivity through incorporation of 1,4,5,8-tetraazaphenanthrene ancillary ligands. Its photoreactivity toward biomolecules was studied in vitro, where light activation caused DNA cleavage. Cellular internalization occurred via an energy dependent mechanism. Confocal and transmission electron microscopy revealed that the complex localizes in various organelles, including the mitochondria. The complex is nontoxic in the dark, with cellular clearance within 96 h; however, upon visible light activation it induces caspase-dependent and reactive-oxygen-species-dependent apoptosis, with low micromolar IC50 values. This investigation greatly increases our understanding of such systems in cellulo, aiding development and realization of their application in cancer therapy.
Photochemistry of Heteroleptic 1,4,5,8-Tetraazaphenanthrene- And Bi-1,2,3-triazolyl-Containing Ruthenium(II) Complexes
Ashton, Gage P.,Boota, Rayhaan Z.,Elliott, Paul I. P.,Hardman, Samantha J. O.,Rice, Craig R.,Scattergood, Paul A.
, p. 15768 - 15781 (2021/10/26)
Diimine metal complexes have significant relevance in the development of photodynamic therapy (PDT) and photoactivated chemotherapy (PACT) applications. In particular, complexes of the TAP ligand (1,4,5,8-tetraazaphenanthrene) are known to lead to photoinduced oxidation of DNA, while TAP- and triazole-based complexes are also known to undergo photochemical ligand release processes relevant to PACT. The photophysical and photochemical properties of heteroleptic complexes [Ru(TAP)n(btz)3-n]2+ (btz = 1,1′-dibenzyl-4,4′-bi-1,2,3-triazolyl, n = 1 (1), 2 (2)) have been explored. Upon irradiation in acetonitrile, 1 displays analogous photochemistry to that previously observed for [Ru(bpy)(btz)2]2+ (bpy = 2,2′-bipyridyl) and generates trans-[Ru(TAP)(btz)(NCMe)2]2+ (5), which has been crystallographically characterized, with the observation of the ligand-loss intermediate trans-[Ru(TAP)(κ2-btz)(κ1-btz)(NCMe)]2+ (4). Complex 2 displays more complicated photochemical behavior with not only preferential photorelease of btz to form cis-[Ru(TAP)2(NCMe)2]2+ (6) but also competitive photorelease of TAP to form 5. Free TAP is then taken up by 6 to form [Ru(TAP)3]2+ (3) with the proportion of 5 and 3 observed to progressively increase during prolonged photolysis. Data suggest a complex set of reversible photochemical ligand scrambling processes in which 2 and 3 are interconverted. Computational DFT calculations have enabled optimization of geometries of the pro-trans 3MCcis states with repelled btz or TAP ligands crucial for the formation of 5 from 1 and 2, respectively, lending weight to recent evidence that such 3MCcis states play an important mechanistic role in the rich photoreactivity of Ru(II) diimine complexes.
Furazan ring opening upon treatment of benzofurazan with ethanolamine to yield quinoxalines
Samsonov
experimental part, p. 2510 - 2512 (2009/02/05)
Heating of benzofurazans with ethanolamine in the presence of catalytic amount of p-toluenesulfonic acid leads to quinoxalines.
