- Viologen embedded polyaromatic hydrocarbons (VPAH2+): Synthesis, computational, photophysical, and electrochemical characterizations of 3,8-diazaphenanthrenyl viologens
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Several new dicationic viologen sensitizers are synthesized and characterized both photo- and electro-chemically. Benzo-annulation of methyl viologen increases its fluorescence lifetime by a factor of 6.6. Similar lifetime increases were observed for methylated derivatives, that have the added advantage of enhanced solubilities. These electron transfer sensitizers can oxidize organic substrates with oxidation potentials of approximately 2.4 eV and lower.
- Bakupog, Thomas,Clennan, Edward L.,Zhang, Xiaoping
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Read Online
- Anticancer Agent with Inexplicable Potency in Extreme Hypoxia: Characterizing a Light-Triggered Ruthenium Ubertoxin
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Tumor hypoxia renders treatments ineffective that are directly (e.g., radiotherapy and photodynamic therapy) or indirectly (e.g., chemotherapy) dependent on tumor oxygenation. This study introduces a ruthenium compound as a light-responsive anticancer agent that is water-soluble, has minimal dark cytotoxicity, is active at concentrations as low as 170 pM in ～18.5% O2normoxia and near 10 nM in 1% O2hypoxia, and exhibits phototherapeutic indices as large as >500,000 in normoxia and >5,800 in 1% O2hypoxia using broadband visible and monochromatic blue light treatments. These are the largest values reported to date for any compound class. We highlight the response in four different cell lines to improve rigor and reproducibility in the identification of promising clinical candidates.
- Barrett, Patrick C.,Cameron, Colin G.,Cole, Houston D.,Hodges, Rachel O.,Lifshits, Liubov M.,Mcfarland, Sherri A.,Ramasamy, Elamparuthi,Roque, John A.,Shi, Ge
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supporting information
(2021/12/17)
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- Sequential multiple-target chemosensor: Co2+, Cu2+, PPi, and HSˉ discrimination by a bis(half-salamo)-type probe
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A bis(half-salamo)-type chemosensor LPBHS based on phenanthroline, which can identify multiple targets continuously, was synthesized. The chemosensor LPBHS utilizes the N3O cavities to combine with metal cations, and further identify the anions after the complexes have been formed. The chemosensor LPBHS has an O-phenanthroline unit with excellent luminescence, so that the strong fluorescence of the chemosensor LPBHS can be observed under 365 nm UV light. The quenching of luminescence occurs after the introduction of Cu2+ and Co2+ into the chemosensor LPBHS, which can be identified in natural light by observing the change in color of the solution with the naked eye. The LPBHS-Cu2+ complex further recognizes HSˉ and PPi (pyrophosphoric acid), and strong luminescence are also observed under UV light after the addition of HSˉ and PPi to LPBHS-Cu2+. HSˉ and PPi can also be identified by the change in color of the solution under natural light with the naked eye. Using the strong fluorescence emission of LPBHS, a test strip was developed to detect Cu2+ and Co2+ rapidly, and the quenching of fluorescence was clearly observed under UV light. HSˉ and PPi can be further identified by the phenomenon of fluorescence recovery after Cu2+ detection on the test strip.
- Bian, Ruo-Nan,Dong, Wen-Kui,Li, Li-Li,Li, Mei,Liu, Guo-Hua
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- METHOD OF PRODUCING PHENANTHRILINE AND DERIVATIVE THEREOF
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An application of the present invention provides a method of producing ortho-aminoarenecarbaldehyde, ortho-aminoarenecarbaldehyde produced therefrom, and a method for producing phenanthroline and derivatives thereof which can be utilized in the field of OLED and diagnostic reagents using the same. The application comprises: a first step of producing a compound of formula 2 by oxidizing a compound of formula 1 with NaIO_4; and a second step of producing a compound of formula 3 by reducing the compound of formula 2 with nascent hydrogen generated by acid and metal.COPYRIGHT KIPO 2020
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Paragraph 0107; 0113-0117
(2020/05/20)
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- Preparation of a New Friedl?nder Synthon, 2,3-Diaminobenzene-1,4-dicarbaldehyde, and Its Application towards Synthesis of 1,10-Phenanthrolines and Related Cyclophane
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A new Friedl?nder synthon, 2,3-diaminobenzene-1,4-dicarbaldehyde, was prepared from p-xylene in 4 steps, of which the Friedl?nder reaction with acetaldehyde and acetone in a Schulenk bottle afforded 1,10-phenathroline and neocuprine in 44% and 82% yield, respectively. The scope of the Friedl?nder reactions of 2,3-diaminobenzene-1,4-dicarbaldehyde, including the synthesis of hexaazacyclic cyclophane with 1,10-phenanthroline and pyridine units, was described.
- Lu, Yang,Jahng, Yurngdong
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p. 221 - 225
(2019/02/03)
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- Phototoxicity of strained Ru(II) complexes: Is it the metal complex or the dissociating ligand?
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A photochemically dissociating ligand in Ru(bpy)2(dmphen)Cl2 [bpy = 2,2′-bipyridine; dmphen = 2,9-dimethyl-1,10-phenanthroline] was found to be more cytotoxic on the ML-2 Acute Myeloid Leukemia cell line than Ru(bpy)2(H2O)22+ and prototypical cisplatin. Our findings illustrate the potential potency of diimine ligands in photoactivatable Ru(ii) complexes.
- Azar, Daniel F.,Audi, Hassib,Farhat, Stephanie,El-Sibai, Mirvat,Abi-Habib, Ralph J.,Khnayzer, Rony S.
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supporting information
p. 11529 - 11532
(2017/09/18)
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- APPLICATION OF 2,9-DI-SEC-BUTYL-1,10-PHENANTHROLINE AS A GLIOBLASTOMA TUMOR CHEMOTHERAPY
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A method of inhibiting cancer cell growth is provided. In some versions, the method includes exposing lung cancer cells or glioma cells to 2,9-di-sec-butyl-1,10-phenanthroline (SBP) or derivatives of SBP in an amount effective to inhibit glioma cell growth. Also, a method of treating a lung cancer or a glioma tumor in a subject in need of such treatment is provided. The method includes administering SBP or derivatives of SBP to the subject in an amount effective to treat the lung cancer or glioma tumor. For either method, the method can further include exposing or administering pseudo five coordinate gold(III) complexes of SBP derivatives.
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Paragraph 0123; 0124
(2015/05/13)
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- Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach
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The synthesis of 8-aminoquinolines and 1,10-phenanthrolines with substituents in α of the nitrogen has been performed through an inverse-demanding aza-Diels-Alder (Povarov reaction) in the fluoroalcohols TFE or HFIP. This path involves simple starting materials: 1,2-phenylenediamines, enol ethers and aldehydes.
- De, Kavita,Legros, Julien,Crousse, Benoit,Chandrasekaran, Srinivasan,Bonnet-Delpon, Daniele
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supporting information; experimental part
p. 347 - 350
(2011/02/26)
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- A new approach to the 1,10-phenanthroline core
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A protocol for the synthesis of substituted 1,10-phenanthrolines is reported. The phenanthroline scaffold has been obtained constructing the central cycle starting from two pyridine rings. The method is hinged upon the intramolecular coupling of cis-1,2-di(2-bromo-3-pyridyl)ethenes that are in turn obtained from the Wittig reaction of 2-bromonicotinaldehydes with phosphonium salts prepared from 2-bromo-3-(bromomethyl)pyridines. Yields up to 75% have been obtained.
- Chelucci, Giorgio,Addis, Daniele,Baldino, Salvatore
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p. 3359 - 3362
(2008/02/12)
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- Zinc(II) complexes and methods related thereto
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Zinc(II) complexes and methods relating thereto are disclosed. The zinc(II) complexes comprise a zinc(II) ion complexed by a multi-dentate ligand. Methods of this invention include the use of the zinc(II) complexes as anti-viral agents and/or as anti-inflammatory agents. Methods of this invention also include inhibition of viral infection, as well as inhibiting transmission of sexually transmitted diseases. Exemplary zinc(II) complexes include zinc(II):neocuproine (2:1) and zinc(II):bathocuproine disulfonic acid (2:1).
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- Synthesis of New Azonia-Helicenes with a Quaternary Nitrogen at the Inner Helix Skeleton
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The 16c-azoniahelicene salts, in which a carbon atom at the inner helix skeleton of helicene is replaced by a quaternary nitrogen atom, have been synthesized by photo-induced intramolecular quaternization of 2-benzoquinolines in acetonitrile.
- Arai, Sadao,Ishikura, Masanori,Sato, Kiyoshi,Yamagishi, Takamichi
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p. 1081 - 1084
(2007/10/02)
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- Synthesis and antimycoplasmal activity of 2,2'-bipyridyl analogues. Part III. 1,10-Phenanthrolines and 2,2'-bipyridyls
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The synthesis and antimycoplasmal activity in the presence of copper of a series of 1,10-phenanthrolines and 2,2'-bipyridyls are presented. It is shown that the unsubstituted parent compounds have the lowest activity. Introduction of substituents in one or both of the orthopositions raises the activity, alkyl groups having the most pronounced activity enhancing effect. Generally 1,10-phenanthrolines are 2-4 times more active than corresponding 2,2'-bipyridyls.
- Pijper,Van der Goot,Timmerman,Nauta Th.
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p. 399 - 404
(2007/10/02)
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- Process for the preparation of 4-nitrodiphenylamines
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The invention relates to a process for the preparation of 4-nitrodiphenylamines by the reaction of halogenonitrobenzenes with primary aromatic amines in the presence of copper or a copper compound, a neutralizing agent and a cyclic diaza compound.
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