Characterization of the Photophysical Behavior of DFHBI Derivatives: Fluorogenic Molecules that Illuminate the Spinach RNA Aptamer

The Journal of Physical Chemistry. B
Kalyan SantraJacob W Petrich

Abstract

( Z)-5-(3,5-Difluoro-4-hydroxybenzylidene)-2,3-dimethyl-3,5-dihydro-4 H-imidazol-4-one (DFHBI) and its analogues are fluorogenic molecules that bind the Spinach aptamer (a small RNA molecule), which was selected for imaging RNA. They are extremely weakly fluorescent in liquid solvents. It had been hypothesized that photoisomerization is a very efficient nonradiative process of deactivation. We show, consistent with the results of other studies, that if the isomerization is impeded, the fluorescence signal is enhanced significantly. In addition, we provide a thorough characterization of the photophysical behavior of DFHBI and its derivatives, notably that of ( Z)-5-(3,5-difluoro-4-hydroxybenzylidene)-2-methyl-3-((perfluorophenyl)methyl)-3,5-dihydro-4 H-imidazol-4-one (PFP-DFHBI) in various solvent environments. Solvent-dependent studies were performed with various mixtures of solvents. The results suggest that hydrogen bonding or strong interactions of the solvents with the phenolic-OH group change the absorption band near 420-460 nm and the nature of emission near 430 and 500 nm through various degrees of stabilization and the transformation between the neutral and the anionic species at both ground and excited states. These ob...Continue Reading

References

Feb 23, 1995·Nature·R HeimR Y Tsien
Feb 11, 1994·Science·M ChalfieD C Prasher
Oct 23, 1996·Biochemical and Biophysical Research Communications·G ZhangS R Kain
Nov 26, 1996·Proceedings of the National Academy of Sciences of the United States of America·H NiwaF I Tsuji
Apr 5, 2003·Science·David J Stephens, Victoria J Allan
Apr 5, 2003·Science·Jennifer Lippincott-Schwartz, George H Patterson
Nov 13, 2003·Current Opinion in Plant Biology·David Ehrhardt
Apr 11, 2007·Proceedings of the National Academy of Sciences of the United States of America·J Nathan HendersonS James Remington
Mar 15, 2008·Organic Letters·Tudor P ConstantinBruce A Armitage
Aug 2, 2008·The Journal of Physical Chemistry. B·Valerio VolianiFabio Beltram
Sep 23, 2009·Chemical Society Reviews·Stephen R Meech
Sep 18, 2010·The Journal of Physical Chemistry. B·Saikat BanerjeeBiman Bagchi
Jul 30, 2011·Science·Jeremy S PaigeSamie R Jaffrey
Aug 25, 2011·Accounts of Chemical Research·Laren M TolbertKyril M Solntsev
Oct 20, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Moustafa El-ArabyAsharf A Abdel-Rahman
May 22, 2013·Chemical Communications : Chem Comm·Mikhail S BaranovIlia V Yampolsky
Nov 30, 2013·Journal of the American Chemical Society·Kyu Young HanTaekjip Ha
Jan 8, 2014·Journal of the American Chemical Society·Wenjiao SongSamie R Jaffrey
Feb 15, 2014·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Andrew Z Wang, Omid C Farokhzad
Jun 24, 2014·Nature Chemical Biology·Hao HuangJoseph A Piccirilli
Jul 16, 2014·Nature Structural & Molecular Biology·Katherine Deigan WarnerAdrian R Ferré-D'Amaré
Aug 8, 2014·ACS Chemical Biology·Elena V DolgosheinaPeter J Unrau
Oct 23, 2014·Journal of the American Chemical Society·Grigory S FilonovSamie R Jaffrey
Dec 9, 2014·RNA Biology·Martyna O UrbanekWlodzimierz J Krzyzosiak
Mar 18, 2015·European Journal of Medicinal Chemistry·Fadi M AwadallahHanan H Georgey
Jun 23, 2015·Annual Review of Biophysics·Mingxu You, Samie R Jaffrey
Jun 29, 2015·Current Opinion in Chemical Biology·Christopher L WalkerKyril M Solntsev
Aug 16, 2012·The Journal of Physical Chemistry Letters·Kiri AddisonStephen R Meech
Dec 29, 2015·Methods : a Companion to Methods in Enzymology·Muslum IlguMarit Nilsen-Hamilton
Feb 19, 2016·Chemical Communications : Chem Comm·Teru KatoMasumi Hyuga
Jul 26, 2016·Frontiers in Chemistry·Jonathan Ouellet
Aug 23, 2016·Nature Chemical Biology·Andrew K LewisJonathan N Sachs
Oct 22, 2016·European Journal of Medicinal Chemistry·Ryota SaitoToshiya Komatsu
May 12, 2017·Current Opinion in Biotechnology·Steven PauffGlenn A Burley
Jul 12, 2017·Frontiers in Microbiology·Lieke A van Gijtenbeek, Jan Kok
Nov 12, 2015·Methods and Applications in Fluorescence·Ludovic Jullien, Arnaud Gautier
Jan 4, 2018·International Journal of Molecular Sciences·Farah BouheddaMichael Ryckelynck

❮ Previous
Next ❯

Citations

Apr 3, 2021·Organic Chemistry Frontiers : an International Journal of Organic Chemistry·Katarina L Keel, Jetze Tepe
Nov 10, 2020·Advances in Colloid and Interface Science·Jia KongZhimin He

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Ewa KrystkowiakAndrzej Maciejewski
© 2022 Meta ULC. All rights reserved