- In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization
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Photoswitchable oligonucleotides can determine specific biological outcomes by light-induced conformational changes. In particular, artificial probes activated by visible-light irradiation are highly desired in biological applications. Here, we report two novel types of visible-light photoswitchable peptide nucleic acids (PNAs) based on the molecular transducers: hemithioindigo and tetra-ortho-fluoroazobenzene. Our study reveals that the tetra-ortho-fluoroazobenzene–PNA conjugates have promising properties (fast reversible isomerization, exceptional thermal stability, high isomer conversions and sensitivity to visible-light irradiation) as reversible modulators to control oligonucleotide hybridization in biological contexts. Furthermore, we verified that this switchable modification delivers a slightly different hybridization behavior in the PNA. Thus, both melting experiments and strand-displacement assays showed that in all the cases the trans-isomer is the one with superior binding affinities. Alternative versions, inspired by our first compounds here reported, may find applications in different fields such as chemical biology, nanotechnology and materials science.
- Zhang, Lei,Linden, Greta,Vázquez, Olalla
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supporting information
p. 2500 - 2508
(2019/12/11)
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- SUBSTITUTED DIHYDROINDENE-4-CARBOXAMIDES AND ANALOGS THEREOF, AND METHODS USING SAME
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The present invention includes novel substituted bicyclic compounds, and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) infections in a patient. In certain embodiments, the compounds and compositions of the invention are capsid inhibitors. (Formula I)
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- An unexpected triethylsilane-triggered rearrangement of thioaurones to thioflavonols under SPPS conditions
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Thioaurones are converted to a mixture of thiaindenes and thioflavonols when exposed to reaction conditions employed in SPPS, that is, treatment with trifluoroacetic acid in the presence of triethylsilane.
- Varedian, Miranda,Langer, Vratislav,Bergquist, Jonas,Gogoll, Adolf
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supporting information; experimental part
p. 6033 - 6035
(2009/04/11)
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- Chemistry and folding of photomodulable peptides - Stilbene and thioaurone-type candidates for conformational switches
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Optimized synthetic strategies for the preparation of photoswitchable molecular scaffolds based on stilbene or on thioaurone chromophores and their conformationally directing properties, as studied by computations and by NMR spectroscopy, are addressed. For the stilbene peptidomimetics 1, 2 and 3, the length of connecting linkers between the chromophore and the peptide strands was varied, resulting in photochromic dipeptidomimetics with various flexibility. Building blocks of higher rigidity, based on para-substituted thioaurone (4 and 6) and meta-substituted thioaurone chromophores (5 and 7) are shown to have a stronger conformationally directing effect. Design, synthesis, theoretical and experimental conformational analyses are presented.
- Erdelyi, Mate,Varedian, Miranda,Skoeld, Christian,Niklasson, Ida B.,Nurbo, Johanna,Persson, Asa,Bergquist, Jonas,Gogoll, Adolf
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experimental part
p. 4356 - 4373
(2009/02/07)
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- Photochromism of Hemithioindigo Derivatives. I. Preparation and Photochromic Properties in Organic Solvents
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Thirteen hemithioindigo (HT) derivatives bearing alkyl chains are newly synthesized and their photochromism and emission properties are investigated.The Z/E photoisomerisms of these compounds in organic solvents are essentially in agreeement with data reported by Mostoslavskii and Izmail'skii (J.Gen.Chem.USSR, Engl Transl.), 31, 21 (1961), and subsequent papers).At 77 K both the E and Z isomers of HT chromophore emit fluoresscences of comparable intensities, whereas at room temperature very weak fluorescence is observed only from the Z isomer.Examination of repeatable numbers of Z/E photoisomerization reveals that the HT chromophore possesses remarkable inherent photofatigue resistance.
- Yamaguchi, Takeo,Seki, Takahiro,Tamaki, Takashi,Ichimura, Kunihiro
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p. 649 - 656
(2007/10/02)
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