Literature DB >> 29064490

Fluorescent nucleobases as tools for studying DNA and RNA.

Wang Xu1, Ke Min Chan1, Eric T Kool1.   

Abstract

Understanding the diversity of dynamic structures and functions of DNA and Rn class="Chemical">NA in biology requires tools that can selectively and intimately probe these biomolecules. Synthetic fluorescent nucleobases that can be incorporated into nucleic acids alongside their natural counterparts have emerged as a powerful class of molecular reporters of location and environment. They are enabling new basic insights into DNA and RNA, and are facilitating a broad range of new technologies with chemical, biological and biomedical applications. In this Review, we will present a brief history of the development of fluorescent nucleobases and explore their utility as tools for addressing questions in biophysics, biochemistry and biology of nucleic acids. We provide chemical insights into the two main classes of these compounds: canonical and non-canonical nucleobases. A point-by-point discussion of the advantages and disadvantages of both types of fluorescent nucleobases is made, along with a perspective into the future challenges and outlook for this burgeoning field.

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Year:  2017        PMID: 29064490      PMCID: PMC5819341          DOI: 10.1038/nchem.2859

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  113 in total

1.  A porphyrin C-nucleoside incorporated into DNA.

Authors:  Hugo Morales-Rojas; Eric T Kool
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

2.  2-Pyrenyl-DNA: synthesis, pairing, and fluorescence properties.

Authors:  Filip Wojciechowski; Jory Lietard; Christian J Leumann
Journal:  Org Lett       Date:  2012-10-01       Impact factor: 6.005

3.  Natural versus artificial creation of base pairs in DNA: origin of nucleobases from the perspectives of unnatural base pair studies.

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Journal:  Acc Chem Res       Date:  2012-01-20       Impact factor: 22.384

4.  Switching on the fluorescence of 2-aminopurine by site-selective microhydration.

Authors:  Simon Lobsiger; Susan Blaser; Rajeev K Sinha; Hans-Martin Frey; Samuel Leutwyler
Journal:  Nat Chem       Date:  2014-10-19       Impact factor: 24.427

5.  4-amino-1H-benzo[g]quinazoline-2-one: a fluorescent analog of cytosine to probe protonation sites in triplex forming oligonucleotides.

Authors:  F Godde; J J Toulmé; S Moreau
Journal:  Nucleic Acids Res       Date:  2000-08-01       Impact factor: 16.971

6.  Fluorescence properties of pteridine nucleoside analogs as monomers and incorporated into oligonucleotides.

Authors:  M E Hawkins; W Pfleiderer; F M Balis; D Porter; J R Knutson
Journal:  Anal Biochem       Date:  1997-01-01       Impact factor: 3.365

Review 7.  Fluorescent pteridine nucleoside analogs: a window on DNA interactions.

Authors:  M E Hawkins
Journal:  Cell Biochem Biophys       Date:  2001       Impact factor: 2.194

8.  Base-modified DNA labeled by [Ru(bpy)(3)](2+) and [Os(bpy)(3)](2+) complexes: construction by polymerase incorporation of modified nucleoside triphosphates, electrochemical and luminescent properties, and applications.

Authors:  Milan Vrábel; Petra Horáková; Hana Pivonková; Lubica Kalachova; Hana Cernocká; Hana Cahová; Radek Pohl; Peter Sebest; Ludek Havran; Michal Hocek; Miroslav Fojta
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

9.  Fluorescence emission properties of 8-azapurines and their nucleosides, and application to the kinetics of the reverse synthetic reaction of purine nucleoside phosphorylase.

Authors:  J Wierzchowski; B Wielgus-Kutrowska; D Shugar
Journal:  Biochim Biophys Acta       Date:  1996-05-21

10.  Electronic Band Structure and Sub-band-gap Absorption of Nitrogen Hyperdoped Silicon.

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Journal:  Sci Rep       Date:  2015-05-27       Impact factor: 4.379

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  41 in total

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Authors:  Zhiwei Wen; Paloma R Tuttle; A Hasan Howlader; Anna Vasilyeva; Laura Gonzalez; Antonija Tangar; Ruipeng Lei; Eduardo E Laverde; Yuan Liu; Jaroslava Miksovska; Stanislaw F Wnuk
Journal:  J Org Chem       Date:  2019-03-06       Impact factor: 4.354

Review 2.  Approaches for measuring the dynamics of RNA-protein interactions.

Authors:  Donny D Licatalosi; Xuan Ye; Eckhard Jankowsky
Journal:  Wiley Interdiscip Rev RNA       Date:  2019-08-20       Impact factor: 9.957

3.  Nano-plasmonics and electronics co-integration in CMOS enabling a pill-sized multiplexed fluorescence microarray system.

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Journal:  Biomed Opt Express       Date:  2018-10-26       Impact factor: 3.732

4.  Emissive Synthetic Cofactors: Enzymatic Interconversions of tz A Analogues of ATP, NAD+ , NADH, NADP+ , and NADPH.

Authors:  François Hallé; Andrea Fin; Alexander R Rovira; Yitzhak Tor
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-21       Impact factor: 15.336

5.  4-Cyanoindole-2'-deoxyribonucleoside (4CIN): A Universal Fluorescent Nucleoside Analogue.

Authors:  Kellan T Passow; Daniel A Harki
Journal:  Org Lett       Date:  2018-07-10       Impact factor: 6.005

6.  Single-Molecule Detection of a Fluorescent Nucleobase Analogue via Multiphoton Excitation.

Authors:  David Nobis; Rachel S Fisher; Mats Simmermacher; Patrycja A Hopkins; Yitzhak Tor; Anita C Jones; Steven W Magennis
Journal:  J Phys Chem Lett       Date:  2019-08-16       Impact factor: 6.475

7.  Stacking-induced fluorescence increase reveals allosteric interactions through DNA.

Authors:  Michael J Morten; Sergio G Lopez; I Emilie Steinmark; Aidan Rafferty; Steven W Magennis
Journal:  Nucleic Acids Res       Date:  2018-11-30       Impact factor: 16.971

8.  What Makes Thienoguanosine an Outstanding Fluorescent DNA Probe?

Authors:  Jagannath Kuchlyan; Lara Martinez-Fernandez; Mattia Mori; Krishna Gavvala; Stefano Ciaco; Christian Boudier; Ludovic Richert; Pascal Didier; Yitzhak Tor; Roberto Improta; Yves Mély
Journal:  J Am Chem Soc       Date:  2020-09-23       Impact factor: 15.419

9.  Nucleic Acid Conformation Influences Postsynthetic Suzuki-Miyaura Labeling of Oligonucleotides.

Authors:  Manisha B Walunj; Seergazhi G Srivatsan
Journal:  Bioconjug Chem       Date:  2020-10-22       Impact factor: 4.774

10.  Bioorthogonal chemistry-based RNA labeling technologies: evolution and current state.

Authors:  Jerrin Thomas George; Seergazhi G Srivatsan
Journal:  Chem Commun (Camb)       Date:  2020-10-07       Impact factor: 6.222

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