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1 article(s) from Yang, Wang-Yong

Fine-tuning alkyne cycloadditions: Insights into photochemistry responsible for the double-strand DNA cleavage via structural perturbations in diaryl alkyne conjugates

Wang-Yong Yang,
Samantha A. Marrone,
Nalisha Minors,
Diego A. R. Zorio and
Igor V. Alabugin

Beilstein J. Org. Chem. 2011, 7, 813–823, doi:10.3762/bjoc.7.93

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Graphical Abstract

Figure 1: Structure of C-lysine conjugates.

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Figure 2: Alternative pathways of enediyne photoreactivity: photo-Bergman cyclization (left), C1–C5 cyclizati...

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Figure 3: Summary of possible mechanistic alternatives for the observed DNA cleavage by monoacetylene conjuga...

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Scheme 1: Proposed mechanism of photocycloaddition of acetylene with 1,4-CHD.

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Figure 4: p-, m-, and o-amidyl acetylenes and respective lysine conjugates.

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Scheme 2: Synthesis of amido-substituted monoacetylenes and lysine conjugates. Reagents and conditions: a. Pd...

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Scheme 3: Photochemical reactions of TFP-substituted aryl alkynes with selected π-systems. In short, the reac...

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Scheme 4: Photocycloaddition of amido acetylenes with 1,4-CHD.

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Scheme 5: Possible mechanism for photochemical hydration of diaryl acetylene moiety catalyzed by the ortho-am...

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Figure 5: Stern–Volmer plots of three regioisomers, 3 (blue diamond), 4 (red square), and 5 (green triangle),...

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Figure 6: Absorption spectra of three isomers, 3, 4, 5, and Ph-TFP in acetonitrile (10 μM).

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Figure 7: Quantified DNA cleavage data for 1 (a), 6 (b) and 7 (c). Blue: Form I (supercoiled) DNA; red: Form ...

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Figure 8: Effect of hydroxyl radical/singlet oxygen scavengers (20 mM) on the efficiency of DNA cleavage at p...

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Figure 9: Cell proliferation assay using A375 cells (human melanoma) and compound 1 (green square), 6 (red up...

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Published 16 Jun 2011

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