scholarly journals Diarylethene-modified nucleotides for switching optical properties in DNA

2012 ◽  
Vol 8 ◽  
pp. 905-914 ◽  
Author(s):  
Sebastian Barrois ◽  
Hans-Achim Wagenknecht
Keyword(s):  
Optical Properties ◽  
Nucleic Acid ◽  
Modified Nucleotides ◽  
Photochromic Properties ◽  
Photochromic Compounds ◽  
Acid Absorption ◽  
Base Modification ◽  
Dna Base ◽  
Phosphoramidite Chemistry ◽  
The Way

Diarylethenes were attached to the 5-position of 2’-deoxyuridine in order to yield three different photochromic nucleosides. All nucleosides were characterized with respect to their absorption and photochromic properties. Based on these results, the most promising photochromic DNA base modification was incorporated into representative oligonucleotides by using automated phosphoramidite chemistry. The switching of optical properties in DNA can be achieved selectively at 310 nm (forward) and 450 nm (backward); both wavelengths are outside the normal nucleic acid absorption range. Moreover, this nucleoside was proven to be photochemically stable and allows switching back and forth several times. These results open the way for the use of diarylethenes as photochromic compounds in DNA-based architectures.

NEW ACIDO- AND PHOTOSWITCHABLE CHROMOPHORES FOR SECOND-ORDER NONLINEAR OPTICS

2004 ◽  
Vol 13 (03n04) ◽  
pp. 423-426 ◽  
Author(s):  
L. SANGUINET ◽  
S. AHMED ◽  
J. L. POZZO ◽  
V. RODRIGUEZ ◽  
F. ADAMIETZ
Keyword(s):  
Optical Properties ◽  
Nonlinear Optics ◽  
Nonlinear Optical ◽  
Rayleigh Scattering ◽  
Second Order ◽  
Nonlinear Optical Properties ◽  
Photochromic Compounds ◽  
The Way

New acidochromic and photochromic compounds with nonlinear optical properties have been designed and synthesized. The hyperpolarizabilities of the zwitterionic colored forms have been quantified with polarized hyper-Rayleigh scattering experiments. The static value of oxazolidino-indoline 2 is found to be as high as Disperse Red One. This opens the way to novel multi-addressable NLO-systems.

scholarly journals Synthesis and optical properties of pyrrolidinyl peptide nucleic acid carrying a clicked Nile red label

2014 ◽  
Vol 10 ◽  
pp. 2166-2174 ◽  
Author(s):  
Nattawut Yotapan ◽  
Chayan Charoenpakdee ◽  
Pawinee Wathanathavorn ◽  
Boonsong Ditmangklo ◽  
Hans-Achim Wagenknecht ◽  
...  
Keyword(s):  
Optical Properties ◽  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Nile Red ◽  
Fluorescent Label ◽  
Dna Duplexes ◽  
Enhanced Fluorescence ◽  
Structure And Dynamics ◽  
Close Proximity ◽  
Base Insertion

DNA or its analogues with an environment-sensitive fluorescent label are potentially useful as a probe for studying the structure and dynamics of nucleic acids. In this work, pyrrolidinyl peptide nucleic acid (acpcPNA) was labeled at its backbone with Nile red, a solvatochromic benzophenoxazine dye, by means of click chemistry. The optical properties of the Nile red-labeled acpcPNA were investigated by UV–vis and fluorescence spectroscopy in the absence and in the presence of DNA. In contrast to the usual quenching observed in Nile red-labeled DNA, the hybridization with DNA resulted in blue shifting and an enhanced fluorescence regardless of the neighboring bases. More pronounced blue shifts and fluorescence enhancements were observed when the DNA target carried a base insertion in close proximity to the Nile red label. The results indicate that the Nile red label is located in a more hydrophobic environment in acpcPNA–DNA duplexes than in the single-stranded acpcPNA. The different fluorescence properties of the acpcPNA hybrids of complementary DNA and DNA carrying a base insertion are suggestive of different interactions between the Nile red label and the duplexes.

Research on Photochromic Compounds with Efficient Synthesis and Photochromic Properties of 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-methyl-5-(4-pentylphenyl)-3-thienyl] perfluorocyclopentene

2014 ◽  
Vol 1003 ◽  
pp. 39-42
Author(s):  
Jun Jie Song ◽  
Gang Liu
Keyword(s):  
Fluorescence Intensity ◽  
Uv Light ◽  
Pmma Film ◽  
Efficient Synthesis ◽  
Photochromic Properties ◽  
Photochromic Compounds

A novel isomeric photochromic diarylethene, 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-methyl-5-(4-pentylphenyl)-3-thienyl] perfluorocyclopentene, was designed and synthesized. Its fluorescent and photochromic properties were also studied in detail. The compound exhibited excellent photochromism, changing from colorless to bule after irradiation with UV light both in solution and in PMMA film. In addition, the fluorescence intensity of the photochromic diarylethene 1a declined remarkably, when irradiation with UV light.

OLIGONUCLEOTIDE DNA AND RNA AS DIRECT CAPPING LIGAND FOR NANOCRYSTALS: AN EMERGING METHOD FOR BIOLOGICAL DIAGNOSTICS AND THERAPEUTICS

NANO ◽  
2009 ◽  
Vol 04 (04) ◽  
pp. 189-199 ◽  
Author(s):  
BENJAMIN A. BAKER ◽  
JONG HYUN CHOI
Keyword(s):  
Optical Properties ◽  
Nucleic Acid ◽  
Surface Passivation ◽  
Target Recognition ◽  
Biological Imaging ◽  
Functional Potential ◽  
Dna And Rna ◽  
Hydrophilic Nature ◽  
Synthesis Properties ◽  
Direct Capping

Various types of nanocrystals have extensively demonstrated significant advantages in magnetic, chemical, catalytic, and particularly optical properties. Still, some limitations prevent these properties from being utilized for improved biological imaging, therapeutics or micro/nano-optoelectronics. A recently emerging, facile approach employing oligonucleotide DNA or RNA for direct surface passivation of nanocrystals is showing promise to bridge the gap between functional potential and realization. Oligonucleotide capping can provide hydrophilic nature, target recognition capabilities, and enhanced cellular uptake for nanocrystals, with a simplified synthesis capable of both templating and functionalizing. We overview synthesis, properties, and applications of nucleic acid templated nanocrystals and contrast these with nanocrystals synthesized by more classical capping methods. Finally, we highlight areas of research in oligonucleotide templated nanocrystals that have been largely unexplored to date, where further investigations can provide many new insights.

scholarly journals Hydroxyl radical mediated DNA base modification by manmade mineral fibres.

1989 ◽  
Vol 46 (7) ◽  
pp. 435-438
Author(s):  
P Leanderson ◽  
P Soderkvist ◽  
C Tagesson
Keyword(s):  
Hydroxyl Radical ◽  
Base Modification ◽  
Dna Base
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