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Recent Developments in Texaphyrin Chemistry and Drug Discovery
Preihs, Christian,Arambula, Jonathan F.,Magda, Darren,Jeong, Heeyeong,Yoo, Dongwon,Cheon, Jinwoo,Siddik, Zahid H.,Sessler, Jonathan L. American Chemical Society 2013 Inorganic chemistry Vol.52 No.21
<P>Texaphyrins are pentaaza expanded porphyrins with the ability to form stable complexes with a variety of metal cations, particularly those of the lanthanide series. In biological milieus, texaphyrins act as redox mediators and mediate the production of reactive oxygen species (ROS). In this review, newer studies involving texaphyrin complexes targeting several different applications in anticancer therapy are described. In particular, the preparation of bismuth and lead texaphyrin complexes as potential α-core emitters for radiotherapy is detailed, as are gadolinium texaphyrin functionalized magnetic nanoparticles with features that make them of interest as dual-mode magnetic resonance imaging contrast agents and as constructs with anticancer activity mediated through ROS-induced sensitization and concurrent hyperthermia. Also discussed are gadolinium texaphyrin complexes as possible carrier systems for the targeted delivery of platinum payloads.</P><P>Texaphyrins are pentaaza expanded porphyrins with the ability to form stable complexes with a variety of metal cations, particularly those of the lanthanide series. In biological milieus, texaphyrins act as redox mediators and mediate the production of reactive oxygen species. In this review, newer studies involving texaphyrin complexes targeting several different applications in anticancer therapy are described.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/inocaj/2013/inocaj.2013.52.issue-21/ic400226g/production/images/medium/ic-2013-00226g_0016.gif'></P>
Bismuth– and lead–texaphyrin complexes: towards potential α-core emitters for radiotherapy
Preihs, Christian,Arambula, Jonathan F.,Lynch, Vincent M.,Siddik, Zahid H.,Sessler, Jonathan L. The Royal Society of Chemistry 2010 Chemical communications Vol.46 No.42
<P>Lead(<SMALL>II</SMALL>)–texaphyrins and the first discrete binuclear μ–oxo bismuth(<SMALL>III</SMALL>)–texaphyrin are reported. The latter was characterized <I>via</I>single crystal X-ray diffraction analysis. Cell proliferation assays using the A2780 ovarian cancer cell line were used to determine the cytotoxicity of the complexes.</P> <P>Graphic Abstract</P><P>Bismuth(<SMALL>III</SMALL>)– and lead(<SMALL>II</SMALL>)–texaphyrins have been synthesized with Bi(<SMALL>III</SMALL>) residing in a unique binuclear μ–oxo coordination sphere. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c0cc03528a'> </P>
Double‐Effector Nanoparticles: A Synergistic Approach to Apoptotic Hyperthermia
Yoo, Dongwon,Jeong, Heeyeong,Preihs, Christian,Choi, Jin‐,sil,Shin, Tae‐,Hyun,Sessler, Jonathan L.,Cheon, Jinwoo WILEY‐VCH Verlag 2012 Angewandte Chemie Vol.124 No.50
<P><B>Hoch effiziente</B> apoptotische Hyperthermie ergeben magnetische Nanopartikel, die in einer Doppelfunktion sowohl reaktive Sauerstoffspezies (ROS) als auch Wärme erzeugen. Durch die ROS werden Krebszellen verwundbarer für die anschließende Wärmebehandlung: 100 mm<SUP>3</SUP> große implantierte Tumore in Mäusen werden nach 30 min Hyperthermiebehandlung bei 43 °C binnen 8 Tagen vollständig eliminiert.</P>
Ishida, Masatoshi,Kim, Soo-Jin,Preihs, Christian,Ohkubo, Kei,Lim, Jong Min,Lee, Byung Sun,Park, Jung Su,Lynch, Vincent M.,Roznyatovskiy, Vladimir V.,Sarma, Tridib,Panda, Pradeepta K.,Lee, Chang-Hee,Fu Nature Publishing Group 2013 Nature chemistry Vol.5 No.1
Proton-coupled electron transfer (PCET) processes are among the most important phenomena that control a variety of chemical and biological transformations. Although extensively studied in a variety of natural systems and discrete metal complexes, PCET mechanisms are less well codified in the case of purely organic compounds. Here we report that a planar 棺,棺??phenylene-bridged hexaphyrin (1.0.1.0.1.0), a 24 ?-electron antiaromatic species termed rosarin, displays unique redox reactivity on protonation. Specifically, treatment with acid (for example, HI) yields a 26 ?-electron aromatic triprotonated monocationic species that is produced spontaneously via an intermediate??but stable??25 ?-electron non-aromatic triprotonated monoradical dication. This latter species is also produced on treatment of the original 24 ?-electron antiaromatic starting material with HCl or HBr. The stepwise nature of the proton-coupled reduction observed in the planar rosarin stands in marked contrast to that seen for non-annulated rosarins and other ostensibly antiaromatic expanded porphyrinoids.
Formation of Ground State Triplet Diradicals from Annulated Rosarin Derivatives by Triprotonation
Fukuzumi, Shunichi,Ohkubo, Kei,Ishida, Masatoshi,Preihs, Christian,Chen, Bo,Borden, Weston Thatcher,Kim, Dongho,Sessler, Jonathan L. American Chemical Society 2015 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.137 No.31
<P>Annulated rosarins, β,β′-bridged hexaphyrin(1.0.1.0.1.0) derivatives <B>1</B>–<B>3</B>, are formally 24 π-electron antiaromatic species. At low temperature, rosarins <B>2</B> and <B>3</B> are readily triprotonated in the presence of trifluoroacetic acid in dichloromethane to produce ground state triplet diradicals, as inferred from electron paramagnetic resonance (EPR) spectral studies. From an analysis of the fine structure in the EPR spectrum of triprotonated rosarin <B>H</B><SUB><B>3</B></SUB><B>3</B><SUP><B>3+</B></SUP>, a distance of 3.6 Å between the two unpaired electrons was estimated. The temperature dependence of the singlet–triplet equilibrium was determined by means of an EPR titration. Support for these experimental findings came from calculations carried out at the (U)B3LYP/6-31G* level, which served to predict a very low-lying triplet state for the triprotonated form of a simplified model system <B>1</B>.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2015/jacsat.2015.137.issue-31/jacs.5b05309/production/images/medium/ja-2015-05309k_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja5b05309'>ACS Electronic Supporting Info</A></P>