17323-81-8Relevant articles and documents
Comparison Study of the Site-Effect on Regioisomeric Pyridyl-Pyrene Conjugates: Synthesis, Structures, and Photophysical Properties
Lu, Qing,Kole, Goutam Kumar,Friedrich, Alexandra,Müller-Buschbaum, Klaus,Liu, Zhiqiang,Yu, Xiaoqiang,Marder, Todd B.
, p. 4256 - 4266 (2020/03/23)
To investigate the "site effect" of pyridyl substituents on a pyrene core, four regioisomeric monopyridyl-pyrene (1-4) and five regioisomeric dipyridyl-pyrene (5-9) conjugates were synthesized and characterized and their structures confirmed by single-crystal X-ray diffraction. The photophysical properties and related frontier orbital features of these compounds have been studied both experimentally and theoretically and demonstrate the dependence of the properties of the compounds on the position of substitution of the pyridyl moieties connecting to the pyrene core. It was found that the absorption spectra of 2- A nd 4-substituted pyrene derivatives display similar and weak influence on the S2 a? S0 excitations, whereas they are quite different from those of 1-substituted isomers. The emission spectra of 1- A nd 4-substituted pyrenes are quite similar, whereas those of 2-substituted isomers display the largest bathochromic shift. The 1,6-disubstituted compound 5 exhibits a near-unity emission quantum yield in solution, which is nearly three times higher than those of other regioisomeric dipyridyl-pyrenes. In addition, the tetrasubstituted 1,6-dipyridyl-3,8-di-n-butyl-pyrene (10) exhibits the highest solid-state quantum yield of 0.24 among all of the 10 pyridyl-pyrenes prepared in this study.
Recognition of double-stranded DNA using energetically activated duplexes with interstrand zippers of 1-, 2- or 4-pyrenyl-functionalized O2′-alkylated RNA monomers
Karmakar, Saswata,Madsen, Andreas S.,Guenther, Dale C.,Gibbons, Bradley C.,Hrdlicka, Patrick J.
supporting information, p. 7758 - 7773 (2015/01/09)
Despite advances with triplex-forming oligonucleotides, peptide nucleic acids, polyamides and-more recently-engineered proteins, there remains an urgent need for synthetic ligands that enable specific recognition of double-stranded (ds) DNA to accelerate studies aiming at detecting, regulating and modifying genes. Invaders, i.e., energetically activated DNA duplexes with interstrand zipper arrangements of intercalator-functionalized nucleotides, are emerging as an attractive approach toward this goal. Here, we characterize and compare Invaders based on 1-, 2- and 4-pyrenyl-functionalized O2′-alkylated uridine monomers X-Z by means of thermal denaturation experiments, optical spectroscopy, force-field simulations and recognition experiments using DNA hairpins as model targets. We demonstrate that Invaders with +1 interstrand zippers of X or Y monomers efficiently recognize mixed-sequence DNA hairpins with single nucleotide fidelity. Intercalator-mediated unwinding and activation of the double-stranded probe, coupled with extraordinary stabilization of probe-target duplexes (ΔTm/modification up to +14.0 °C), provides the driving force for dsDNA recognition. In contrast, Z-modified Invaders show much lower dsDNA recognition efficiency. Thus, even very conservative changes in the chemical makeup of the intercalator-functionalized nucleotides used to activate Invader duplexes, affects dsDNA-recognition efficiency of the probes, which highlights the importance of systematic structure-property studies. The insight from this study will guide future design of Invaders for applications in molecular biology and nucleic acid diagnostics.
Derivatised molecules for mass spectrometry
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Page 64, (2008/06/13)
Compounds of formula (IIa): are provided where:X is a group capable of being cleaved from the α-carbon atom to form an ion of formula (I')C is a carbon atom bearing a single positive charge or a single negative charge; The invention further provides compounds of formula (IIb): where:X is a counter-ion to C. The compounds of formula (IIa) and (IIb) may form ions of formula (I') by either cleaving the C-X bond between X and the α-carbon atoms in the case of the compounds of formula (IIa) or dissociating X in the case of compounds of formula (IIb).
