- New 8-hydroxyquinoline derivatives highlight the potential of this class for treatment of fungal infections
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The oral administration of clioquinol - a potent 8-hydroxyquinoline antimicrobial drug - was forbidden due to suspicion of it being the cause of SMON (subacute myelo-optic-neuropathy) in Japan. However, this adverse effect was only observed in Japan, desp
- Joaquim, Angélica Rocha,Reginatto, Paula,Lopes, Marcela Silva,Bazana, Luana Candice Genz,Gionbelli, Mariana Pies,de Cesare, Maycon Antonio,Kaminski, Taís Fernanda Andrzejewski,Teixeira, Mário Lettieri,Abegg, Maxwel Adriano,Fuentefria, Alexandre Meneghello,de Andrade, Saulo Fernandes
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p. 18158 - 18170
(2021/10/12)
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- Tumor cellular proteasome inhibition and growth suppression by 8-hydroxyquinoline and clioquinol requires their capabilities to bind copper and transport copper into cells
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We have previously reported that when mixed with copper, 8-hydroxyquinoline (8-OHQ) and its analog clioquinol (CQ) inhibited the proteasomal activity and proliferation in cultured human cancer cells. CQ treatment of high-copper-containing human tumor xenografts also caused cancer suppression, associated with proteasome inhibition in vivo. However, the nature of the copper dependence of these events has not been elucidated experimentally. In the current study, using chemical probe molecules that mimic the structures of 8-OHQ and CQ, but have no copper-binding capability, we dissected the complex cellular processes elicited by 8-OHQ-Cu and CQ-Cu mixtures and revealed that copper binding to 8-OHQ or CQ is required for transportation of the copper complex into human breast cancer cells and the consequent proteasome-inhibitory, growth-suppressive, and apoptosis-inducing activities. In contrast, the non-copper-binding analogs of 8-OHQ or CQ blocked the very first step-copper binding-in this chain of events mediated by 8-OHQ-Cu or CQ-Cu.
- Zhai, Shumei,Yang, Lei,Cui, Qiuzhi Cindy,Sun, Ying,Dou, Q. Ping,Yan, Bing
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experimental part
p. 259 - 269
(2011/12/16)
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- Synthesis of ortho-alkoxy-aryl carboxamides via alladium-catalyzed aminocarbonylation
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Various aryl carboxamides with alkoxy substituents at the ortho-position, applicable as direct intermediates toward novel ligands, were synthesised via aminocarbonylation of aryl-iodides (2-iodoanisole, 5-chloro-7-iodo-8-methoxy- quinoline, and 5-chloro-7-iodo-8-benzyloxy-quinoline) in the presence of in situ generated palladium(0) catalysts. Simple primary and secondary amines as well as aminoacid esters were used as N-nucleophiles. The optimization of the reaction conditions allowed the preferential formation of carboxamides or ketocarboxamides by simple or double carbon monoxide insertion, respectively. A strong dependence of the chemoselectivity on carbon monoxide pressure was observed. Copyright Taylor & Francis Group, LLC.
- Takacs, Attila,Abreu, Artur R.,Peixoto, Andreia F.,Pereira, Mariette,Kollar, Laszlo
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body text
p. 1534 - 1548
(2009/10/17)
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- MASS SPECTROMETRY OF 8-HYDROXYQUINOLINE DERIVATIVES
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In contrast to the fragmentation of the corresponding alkyl aryl ethers, characteristic + and + fragments were observed in the fragmentation of 5-nitro(halo)-substituted 8-alkoxyquinolines.It was found by means of deuterium labeling that a hydrogen atom is split out primarily from the alkoxy group.It was demonstrated that an + fragment was from the + ion, which has a three-ring structure and quaternary nitrogen atom.The formation of an + fragment is characteristic for the fragmentation of 5(7)-nitro(halo)-substituted 8-hydroxyquinolines.The interrelationship between the intensities of the +, +, and + ion peaks and the protonation constants (pKa) of the investigated compounds is discussed.
- Ermakov, A. I.,Voronin, V. G.,Sorokin, A. A.,Epshtein, N. I.,Muravskaya, I. D.,et al.
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p. 637 - 642
(2007/10/02)
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