- Naphthotriazole derivatives: Synthesis and fluorescence properties
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Eight fluorescent compounds containing a naphthotriazole moiety substituted at position 2 by a (vinylsulfonyl)aryl group or its precursors, containing either a hydroxyl or sulphonic acid groups or N-methylglycine, were prepared and characterized. The products were recovered in moderate yield after column chromatography or recrystallization and identified using 1H and 13C NMR; double resonance, heteronuclear multiple quantum coherence and heteronuclear multiple bond correlation experiments were carried out for complete assignment of proton and carbon signals. Absorption and emission spectra were obtained, in acetonitrile and fluorescence quantum yield determined. All compounds offer promise as fluorescent probes owing to their high fluorescence quantum yield.
- Oliveira-Campos, Ana M.F.,Rodrigues, Lígia M.,Esteves, Ana P.,Silva, Marília E.,Sivasubramanian, Aravind,Hrdina, Radim,Soares, Gra?a M.B.,Pinto, Tiago A.D.,Machalicky, Oldrich
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experimental part
p. 188 - 193
(2010/08/20)
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- CBI DERIVATIVES SUBJECT TO REDUCTIVE ACTIVATION
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A unique class of N-acyl O-amino phenol prodrugs of CBI-TMI and CBI-indole2 were synthesized and shown to be prodrugs, subject to reductive activation by nucleophilic cleavage of a weak N-O bond, effectively releasing the free drug in functional cellular assays for cytotoxic activity approaching or matching the activity of the free drug, yet remain essentially stable to ex vivo DNA alkylation conditions. Most impressively, assessment of the in vivo antitumor activity of a representative O- (acylamino) prodrug, 8, indicate that they approach the potency and exceed the efficacy of the free drug itself (CBI-indole2), indicating that the inactive prodrugs not only effectively release the free drug in vivo, but that they offer additional advantages related to a controlled or targeted release in vivo.
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- A unique class of duocarmycin and CC-1065 analogues subject to reductive activation
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N-Acyl O-amino phenol derivatives of CBI-TMI and CBI-indole2 are reported as prototypical members of a new class of reductively activated prodrugs of the duocarmycin and CC-1065 class of antitumor agents. The expectation being that hypoxic tumor environments, with their higher reducing capacity, carry an intrinsic higher concentration of "reducing" nucleophiles (e.g., thiols) capable of activating such derivatives (tunable N-O bond cleavage) and increasing their sensitivity to the prodrug treatment. Preliminary studies indicate the prodrugs effectively release the free drug in functional cellular assays for cytotoxic activity approaching or matching the activity of the free drug, yet remain essentially stable and unreactive to in vitro DNA alkylation conditions (1/2 = 3 h). Characterization of a representative O-(acylamino) prodrug in vivo indicates that they approach the potency and exceed the efficacy of the free drug itself (CBI-indole2), indicating that not only is the free drug effectively released from the inactive prodrug but also that they offer additional advantages related to a controlled or targeted release in vivo.
- Jin, Wei,Trzupek, John D.,Rayl, Thomas J.,Broward, Melinda A.,Vielhauer, George A.,Weir, Scott J.,Hwang, Inkyu,Boger, Dale L.
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p. 15391 - 15397
(2008/09/18)
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- ANTHRACENE DERIVATIVES OF BENZOQUINOLINE. SYNTHESIS, SPECTRA, AND LUMINESCENCE
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By condensation of 9-anthracene with methyl ketones under conditions of acid catalysis, 1-R-3-(9-anthryl)benzoquinolines have been obtained.The byproducts of the reaction have been identified: 1-R-3-(9-anthryl)-2-propen-1-ones and N--2-naphthylamines.The spectral and luminescence properties of these compounds have been examined critically.
- Koslov, N. S.,Shmanai, G. S.,Gladchenko, L. F.
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p. 1268 - 1272
(2007/10/02)
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