Themed collection Nucleic acids: new life, new materials
Nucleic acids: new life, new materials
Guest editors introduce this web collection highlighting recent achievements in nucleic acids research and applications in emerging areas. Featuring articles published in ChemComm, OBC and RSC Advances, the collection is dedicated to the memory of Professor Har Gobind Khorana (1922–2011) and Dr Daniel McGillivray Brown (1923–2012), acknowledging their legacy to the nucleic acids community.
Org. Biomol. Chem., 2013,11, 2058-2059
https://doi.org/10.1039/C3OB90017G
The bacterial second messenger c-di-GMP: probing interactions with protein and RNA binding partners using cyclic dinucleotide analogs
We report an overview of c-di-GMP signaling in bacteria, the RNA and protein effectors that bind this second messenger, and recent advances in targeting these binding partners with synthetic dinucleotide analogs.
Org. Biomol. Chem., 2012,10, 9113-9129
https://doi.org/10.1039/C2OB26724A
Tuning and assembling metal nanostructures with DNA
Here, we highlight the strategies for the synthesis and tuning of a variety of metal nanostructures and nanoassemblies with oligonucleotides and their applications.
Chem. Commun., 2013,49, 2597-2609
https://doi.org/10.1039/C2CC37536B
Expansion of the aptamer library from a “natural soup” to an “unnatural soup”
Extension of aptamer selection from natural components to from unnatural components realizes the creation of new functional molecules.
Chem. Commun., 2013,49, 1786-1795
https://doi.org/10.1039/C2CC36348H
Nucleic acid aptamers: an emerging frontier in cancer therapy
The development and application of nucleic acid aptamers for targeted cancer therapy and cancer biomarker identification were reviewed.
Chem. Commun., 2012,48, 10472-10480
https://doi.org/10.1039/C2CC35042D
The number of amino acids in a genetic code
In this review, we introduce our recently-developed simplified genetic code in order to discuss why the genetic code likely evolved from a simpler form encoding fewer than 20 amino acids.
RSC Adv., 2013,3, 12512-12517
https://doi.org/10.1039/C3RA40609A
DNA glycoclusters and DNA-based carbohydrate microarrays: From design to applications
This article covers glycoclusters prepared by DNA automated synthesis and click chemistry to their interactions with lectins studied with a DNA-based microarray
RSC Adv., 2012,2, 12043-12068
https://doi.org/10.1039/C2RA21550K
A simple pyrene “click”-type modification of DNA affects solubilisation and photoluminescence of single-walled carbon nanotubes
Pyrene chromophores attached to the 2′-position of short oligonucleotides affect the solubilisation of as-prepared single walled carbon nanotube solids when sonicated in an aqueous buffer solution.
RSC Adv., 2013,3, 6331-6333
https://doi.org/10.1039/C3RA00163F
Synthesis and enzymatic incorporation of norbornene-modified nucleoside triphosphates for Diels–Alder bioconjugation
The synthesis and incorporation of norbornene-modified nucleoside triphosphates for an efficient multiple labelling of DNA by inverse-electron-demand Diels–Alder reaction is described.
RSC Adv., 2013,3, 4181-4183
https://doi.org/10.1039/C3RA40373D
Transfer of a protein pattern from self-assembled DNA origami to a functionalized substrate
A pattern formed by self-assembly of 20 streptavidins in a V-shape on DNA origami was transferred to a biotin modified self-assembled monolayer.
Chem. Commun., 2013,49, 1927-1929
https://doi.org/10.1039/C3CC37408D
DNA nanostructure serum stability: greater than the sum of its parts
A combination of end-modifications and 3D topology is shown to stabilize DNA triangular prisms in fetal bovine serum up to 62 hours.
Chem. Commun., 2013,49, 1172-1174
https://doi.org/10.1039/C2CC37556G
Oligo switches: photoresponsive oligonucleotide conjugates by solid-supported click chemistry
Site-specific incorporation of photoswitches with tuneable thermal stability.
RSC Adv., 2013,3, 1652-1655
https://doi.org/10.1039/C2RA22815G
A G-quadruplex-selective luminescent switch-on probe for the detection of sub-nanomolar human neutrophil elastase
A novel G-quadruplex-selective luminescent iridium(III) complex has been employed as a sensitive and selective switch-on probe for the detection of sub-nanomolar human neutrophil elastase in homogenous solution.
RSC Adv., 2013,3, 1656-1659
https://doi.org/10.1039/C2RA21996D
Structural stabilization of DNA-templated nanostructures : crosslinking with 2,5-bis(2-thienyl)pyrrole monomers
Ordered 2,5-bis(2-thienyl)pyrrole (SNS) zipper arrays are formed by hybridization of complementary DNA oligomers each containing covalently bound SNS monomers.
Org. Biomol. Chem., 2013,11, 35-40
https://doi.org/10.1039/C2OB26716K
Hydrogen-bonding controlled rigidity of an isoindoline-derived nitroxide spin label for nucleic acids
Two new nitroxide-modified nucleosides, OxU and ImU, were synthesized and incorporated into DNA. ImU has lower mobility in duplex DNA due to an intramolecular hydrogen bond.
Chem. Commun., 2013,49, 999-1001
https://doi.org/10.1039/C2CC36389E
A luminescent G-quadruplex switch-on probe for the highly selective and tunable detection of cysteine and glutathione
A G-quadruplex-selective luminescent iridium(III) switch-on probe has been developed for the detection of cysteine (Cys) in aqueous solution.
Chem. Commun., 2013,49, 771-773
https://doi.org/10.1039/C2CC37710A
An invasive DNA approach toward a general method for portable quantification of metal ions using a personal glucose meter
A general method has been developed using personal glucose meters to quantify different metal ions through an invasive DNA approach.
Chem. Commun., 2013,49, 585-587
https://doi.org/10.1039/C2CC37156A
Polyelectrolyte-assisted transconformation of a stem-loop DNA
A cationic comb-type copolymer triggered rapid dimerization of a self-complementary stem-loop DNA. Reversible transformation was driven by successive addition of the copolymer and polyanion.
Chem. Commun., 2013,49, 475-477
https://doi.org/10.1039/C2CC37139A
A clocked finite state machine built from DNA
A finite state machine built from DNA with transitions between states triggered by a clock signal.
Chem. Commun., 2013,49, 237-239
https://doi.org/10.1039/C2CC37227D
RNA-templated molecule release induced protein expression in bacterial cells
RNA templated molecular releasing reaction is applied to the protein expression in bacterial cells.
Chem. Commun., 2013,49, 270-272
https://doi.org/10.1039/C2CC37826D
Construction of ratiometric fluorescent sensors by ribonucleopeptides
RNA aptamers to biologically active small ligands, such as tetracycline, dopamine, and streptomycin, are converted to modular fluorescent sensors that are amenable for ratiometric detection of the ligand.
Org. Biomol. Chem., 2012,10, 8767-8769
https://doi.org/10.1039/C2OB26722E
DNA cohesion through bubble–bubble recognition
This communication reports a novel intermolecular interaction for structural DNA nanotechnology.
Chem. Commun., 2012,48, 12216-12218
https://doi.org/10.1039/C2CC37106E
A ferrocene nucleic acid oligomer as an organometallic structural mimic of DNA
A synthetic and organometallic nucleic acid analogue can be prepared by replacing repeating dinucleotide units in DNA with ferrocene units.
Chem. Commun., 2012,48, 12165-12167
https://doi.org/10.1039/C2CC36428J
Synthesis and hybridization properties of oligonucleotides modified with 5-(1-aryl-1,2,3-triazol-4-yl)-2′-deoxyuridines
Oligonucleotides modified with consecutive incorporations of 5-(1-aryl-1,2,3-triazol-4-yl)-2′-deoxyuridine monomers display strong thermal affinity and binding specificity toward RNA targets, due to the formation of chromophore arrays in the major groove.
Org. Biomol. Chem., 2012,10, 8575-8578
https://doi.org/10.1039/C2OB26717A
Synthesis of biotin labelled cap analogue – incorporable into mRNA transcripts and promoting cap-dependent translation
We report a biotin-labeled dinucleotide cap analogue that can be incorporated into transcripts to produce 5′-capped and biotinylated mRNAs which retain their biological functionality and may be employed for biotin-(strept)avidin technologies.
Org. Biomol. Chem., 2012,10, 8570-8574
https://doi.org/10.1039/C2OB26060C
In vitro selection of a photo-responsive peptide aptamer using ribosome display
A photoresponsive peptide aptamer was selected using ribosome display from a random sequence library of peptides carrying azobenzene residues.
Chem. Commun., 2012,48, 11871-11873
https://doi.org/10.1039/C2CC36618E
Reduction of metal ions by boranephosphonate DNA
Reduction of metal ions by boranephosphonate DNA via a novel reaction pathway producing nanoparticles and phosphate diesters or triesters is described.
Org. Biomol. Chem., 2012,10, 9130-9133
https://doi.org/10.1039/C2OB26661J
Mercury–thymine interaction with a chair type G-quadruplex architecture
The T–Hg–T bond was utilized to cross-link two lateral loops of chair-type G-quadruplex DNA (G4-DNA) structures.
Chem. Commun., 2012,48, 11464-11466
https://doi.org/10.1039/C2CC36481F
Modulation of the current signatures of DNA abasic site adducts in the α-hemolysin ion channel
The size, shape and rigidity of the amine adduct influence the electrical current through the nanopore providing characteristic signatures.
Chem. Commun., 2012,48, 11410-11412
https://doi.org/10.1039/C2CC36366F
Clear-cut observation of PNA invasion using nanomechanical DNA origami devices
Invasive binding event of PNA into DNA duplex was clearly observed both by atomic force microscope (AFM) imaging and electrophoretic mobility shift assay (EMSA) with the aid of nanomechanical DNA origami devices as ‘single-molecule’ visual probes.
Chem. Commun., 2012,48, 11361-11363
https://doi.org/10.1039/C2CC36358E
Visualization of the intracellular location and stability of DNA origami with a label-free fluorescent probe
Visualization of the intracellular distribution and stability of DNA origami was achieved with a label-free fluorescent cyanine molecule.
Chem. Commun., 2012,48, 11301-11303
https://doi.org/10.1039/C2CC36185J
Synthesis of oligodeoxyribonucleotides containing a conformationally-locked anti analogue of O6-methyl-2′-deoxyguanosine and their recognition by MGMT and Atl1
DNA containing the locked anti O6-alkylguanine analogue (right) is not repaired by MGMT, suggesting why O6-alkylguanines some are poor MGMT substrates.
Chem. Commun., 2012,48, 11214-11216
https://doi.org/10.1039/C2CC36252J
Fast and efficient DNA crosslinking and multiple orthogonal labelling by copper-free click chemistry
Oligonucleotides containing cyclooctyne-labelled thymidines have been used to efficiently crosslink DNA strands and to orthogonally label fluorescent genetic probes.
Chem. Commun., 2012,48, 11184-11186
https://doi.org/10.1039/C2CC35084J
A DNA based five-state switch with programmed reversibility
A programmable DNA switch based on a molecular beacon including strategically positioned FRET pairs allows the specific addressing of five discrete states with variable fluorescence readout; the structure and switching of the beacon strongly depends on the type of fluorophores used.
Chem. Commun., 2012,48, 11088-11090
https://doi.org/10.1039/C2CC35799B
Excess electron transfer dynamics in DNA hairpins conjugated with N,N-dimethylaminopyrene as a photosensitizing electron donor
It is revealed that the excess electron hopping rate between T's in DNA hairpins is faster than that of the hole.
Chem. Commun., 2012,48, 11008-11010
https://doi.org/10.1039/C2CC36054C
A modified guanosine phosphoramidite for click functionalization of RNA on the sugar edge
The effect of 5′-labeling on RNAi activity has been explored, by comparing a guanine sugar edge label to 5′-phosphate labeled siRNA.
Chem. Commun., 2012,48, 11014-11016
https://doi.org/10.1039/C2CC34015A
Site-specific functionalization of RNA molecules by an unnatural base pair transcription system via click chemistry
A site-specific labeling method for large RNA molecules, by combining the unnatural base pair transcription system and the post-transcriptional modification using click chemistry, has been developed.
Chem. Commun., 2012,48, 10835-10837
https://doi.org/10.1039/C2CC36293G
Screening mutant libraries of T7 RNA polymerase for candidates with increased acceptance of 2′-modified nucleotides
A high-throughput screening assay based on fluorescence readout was used to screen mutant libraries of T7 RNA polymerase to identify a mutant with increased acceptance of 2′-methylseleno-2′-deoxyuridine 5′-triphosphate.
Chem. Commun., 2012,48, 9870-9872
https://doi.org/10.1039/C2CC35028A
pH-induced morphology-shifting of DNA-b-poly(propylene oxide) assemblies
A designed DNA-b-PPO copolymer can undergo in situ transition between diblock and triblock, and alter assembly morphologies accordingly upon pH changes.
Chem. Commun., 2012,48, 9753-9755
https://doi.org/10.1039/C2CC33708H
Dehydration from conserved stem regions is fundamental for ligand -dependent conformational transition of the adenine-specific riboswitch
Dehydration during conformational transition of the add-A riboswitch in response to a binding of ligand.
Chem. Commun., 2012,48, 9684-9686
https://doi.org/10.1039/C2CC34506D
Triplex-directed covalent cross-linking of a DNA nanostructure
Triplex DNA recognition is utilized to direct inter-strand cross-linking reactions at precise locations within a pre-assembled DNA nanostructure.
Chem. Commun., 2012,48, 9592-9594
https://doi.org/10.1039/C2CC35407A
Hybridization and reaction-based fluorogenic nucleic acid probes
We developed fluorogenic probes, which are photoactivated in the presence of specific nucleic acid templates with the release of fluorescent dyes.
Chem. Commun., 2012,48, 9664-9666
https://doi.org/10.1039/C2CC33827K
A highly selective G-quadruplex-based luminescent switch-on probe for the detection of gene deletion
A G-quadruplex-based switch-on luminescence assay has been developed for the detection of gene deletion using a cyclometallated iridium(III) complex as a G-quadruplex-selective probe.
Chem. Commun., 2012,48, 9462-9464
https://doi.org/10.1039/C2CC32253F
Interstrand disulfide crosslinking of DNA bases supports a double nucleotide unpairing mechanism for flap endonucleases
Reversible disulfide crosslinks between thionucleosides in DNA substrates demonstrate double nucleotide unpairing is required for structure-sensing nuclease specificity.
Chem. Commun., 2012,48, 8895-8897
https://doi.org/10.1039/C2CC33400C
Efficient synthesis of 2′-C-α-aminomethyl-2′-deoxynucleosides
A convergent synthesis is developed to give efficiently all four 2′-C-α-aminomethyl-2′-deoxynucleosides 15a–d (U, C, A, G) in 38%, 42%, 12%, 12–42% yield, respectively.
Chem. Commun., 2012,48, 8754-8756
https://doi.org/10.1039/C2CC34556K
Interactions of non-polar and “Click-able” nucleotides in the confines of a DNA polymerase active site
Modified nucleotides play a paramount role in many cutting-edge biomolecular techniques.
Chem. Commun., 2012,48, 8320-8322
https://doi.org/10.1039/C2CC34181F
Templated chemistry for monitoring damage and repair directly in duplex DNA
Designed DNA bases and fluorogenic templated chemistry have been used to detect enzymatic removal of damaged bases in double-stranded DNA.
Chem. Commun., 2012,48, 8069-8071
https://doi.org/10.1039/C2CC34060G
Fully automated sequential solid phase approach towards viral RNA-nucleopeptides
Preparation of ribonucleoprotein fragments of unprecedented complexity comprising solid-phase peptide and reverse RNA synthesis on a single solid support.
Chem. Commun., 2012,48, 8093-8095
https://doi.org/10.1039/C2CC33477A
Synthetic mammalian riboswitches based on guanine aptazyme
Guanine-responsive allosteric ribozymes were designed and used to control mammalian gene expression via two mechanisms.
Chem. Commun., 2012,48, 7215-7217
https://doi.org/10.1039/C2CC33140C
Folding super-sized DNA origami with scaffold strands from long-range PCR
A 26 kilobase ssDNA obtained from long-range PCR amplification was folded into a super-sized DNA origami nanostructure with 792 staple strands.
Chem. Commun., 2012,48, 6405-6407
https://doi.org/10.1039/C2CC32204H
Interstrand interactions on DNA duplexes modified by TTF units at the 3′ or 5′-ends
Short DNA duplexes carrying TTF units at the same termini exhibit a high increase in melting temperature.
RSC Adv., 2012,2, 4069-4071
https://doi.org/10.1039/C2RA20477K
Double-headed nucleotides in DNA-zipper structures; base–base interactions and UV-induced cross-coupling in the minor groove
Double-headed nucleotides are used to organize additional nucleobases in the minor groove of the DNA duplex. By UV, cross-linking between two thymines is obtained.
RSC Adv., 2013,3, 10696-10706
https://doi.org/10.1039/C3RA40857D
Ligand assembly and chirality transfer guided by DNA modified with enantiomerically pure [2.2]paracyclophanes
Enantiomerically pure (Rp)- and (Sp)-4-azido[2.2]paracyclophane was incorporated into DNA using copper-catalysed azide–alkyne cycloaddition. UV-vis and CD data indicate that the transfer of chirality from paracylophane-DNA to the perylene is dependent on the arrangement of the chiral paracyclophanes in the preformed duplex.
RSC Adv., 2013,3, 9373-9380
https://doi.org/10.1039/C3RA41841C
Accurate prediction of 1H chemical shifts in interstrand cross-linked DNA
Proton chemical shifts in modified DNA oligonucleotides are accurately predicted using DFT-NMR calculations during MD simulations in a (QM/)MM framework.
RSC Adv., 2013,3, 3925-3938
https://doi.org/10.1039/C3RA22408B
Antisense oligonucleotide mediated knockdown of HOXC13 affects cell growth and induces apoptosis in tumor cells and over expression of HOXC13 induces 3D-colony formation
HOXC13 is a homeobox containing gene that plays crucial roles in hair development and origin of replication. Herein, we investigated the biochemical functions of HOXC13 and explored its potential roles in tumor cell viability.
RSC Adv., 2013,3, 3260-3269
https://doi.org/10.1039/C2RA22006G
DNA origami templated self-assembly of discrete length single wall carbon nanotubes
A convenient, versatile method to organize discrete length single-walled carbon nanotubes (SWNT) into complex geometries using 2D DNA origami structures is developed here.
Org. Biomol. Chem., 2013,11, 596-598
https://doi.org/10.1039/C2OB26942B
Design of synthetic oligoribonucleotide-based agonists of Toll-like receptor 3 and their immune response profiles in vitro and in vivo
Double-stranded synthetic oligoribonucleotides (dsORNs) of 50-mer length show potent TLR3 activation in vitro and in vivo in mice and non-human primates.
Org. Biomol. Chem., 2013,11, 1049-1058
https://doi.org/10.1039/C2OB26946E
2,6-Bis(functionalized) purines as metal-ion-binding surrogate nucleobases that enhance hybridization with unmodified 2′-O-methyl oligoribonucleotides
Terminal Cu2+-mediated base pairs dramatically stabilize short oligonucleotide duplexes, without compromising sequence-selectivity.
Org. Biomol. Chem., 2013,11, 991-1000
https://doi.org/10.1039/C2OB26885J
Thermal stabilisation of RNA·RNA duplexes and G-quadruplexes by phosphorothiolate linkages
Phosphorothiolate linkages are now shown to stabilise RNA·RNA duplexes and G-quadruplex structures.
Org. Biomol. Chem., 2013,11, 966-974
https://doi.org/10.1039/C2OB26940F
Synthesis of nucleosides and dNTPs bearing oligopyridine ligands linked through an octadiyne tether, their incorporation into DNA and complexation with transition metal cations
Nucleotides bearing terpyridine ligands attached via a flexible octadiynyl tether were prepared and enzymatically incorporated into DNA where formation of intra-strand complexes with Fe2+ and Ni2+ was observed.
Org. Biomol. Chem., 2013,11, 78-89
https://doi.org/10.1039/C2OB26881G
Synthesis and structural studies of S-type/N-type-locked/frozen nucleoside analogues and their incorporation in RNA-selective, nuclease resistant 2′–5′ linked oligonucleotides
Locking/freezing the sugar conformation in the S-type geometry in 2′–5′ DNA would improve the strength of RNA binding through entropic advantage.
Org. Biomol. Chem., 2013,11, 746-757
https://doi.org/10.1039/C2OB26762D
Light up G-quadruplex DNA with a [2.2.2]heptamethinecyanine dye
It is shown that a [2.2.2]heptamethinecyanine dye binds selectively to quadruplex DNA. The association with the nucleic acid leads to a significant increase of the emission intensity of the otherwise weakly fluorescent dye, thus enabling the fluorimetric detection of quadruplex DNA.
Org. Biomol. Chem., 2013,11, 480-487
https://doi.org/10.1039/C2OB26779A
A nucleic acid probe labeled with desmethyl thiazole orange: a new type of hybridization-sensitive fluorescent oligonucleotide for live-cell RNA imaging
A nucleoside with desmethyl thiazole orange dyes has been developed for live-cell RNA imaging.
Org. Biomol. Chem., 2013,11, 362-371
https://doi.org/10.1039/C2OB26707A
Synthesis and duplex-forming ability of oligonucleotides containing 4′-carboxythymidine analogs
Oligonucleotides containing 4′-carboxythymidine had an increased binding affinity to RNA complements compared to a natural oligonucleotide.
Org. Biomol. Chem., 2012,10, 9639-9649
https://doi.org/10.1039/C2OB26712H
Concise and efficient syntheses of preQ1 base, Q base, and (ent)-Q base
Short and high-yielding syntheses based on cheap and readily available starting compounds for the nucleobases preQ1 base, Q base, and (ent)-Q base are described. For the latter two bases, preQ1 served as a central synthon.
Org. Biomol. Chem., 2012,10, 8660-8668
https://doi.org/10.1039/C2OB26387D
Capping of oligonucleotides with “clickable” m3G-CAPs
Methodology and synthesis of different m3G-CAP constructs equipped with an azide handle and their attachment by “click reaction” with an activated triple bond partner allows efficient formation of oligonucleotide m3G-CAP conjugates.
RSC Adv., 2012,2, 12949-12962
https://doi.org/10.1039/C2RA22345G
Two-photon excitation of the fluorescent nucleobase analogues 2-AP and tC
Two-photon excitation of fluorescent nucleobase analogues is a promising approach to the sensitive detection and imaging of nucleic acids.
RSC Adv., 2012,2, 11397-11403
https://doi.org/10.1039/C2RA21881J
Easy introduction of maleimides at different positions of oligonucleotide chains for conjugation purposes
New derivatives incorporating protected maleimides allow easy access to oligonucleotides with a maleimide linked to either the 3′-end or to internal positions, from which a variety of conjugates can be prepared.
Org. Biomol. Chem., 2012,10, 8478-8483
https://doi.org/10.1039/C2OB26514A
Quick regulation of mRNA functions by a few seconds of photoirradiation
By the use of oligodeoxyribonucleotides containing 3-cyanovinylcarbazole nucleoside (CNVK) as antisense oligonucleotides, quick and selective photo-regulation of the mRNA functions was achieved.
Org. Biomol. Chem., 2012,10, 7820-7825
https://doi.org/10.1039/C2OB25883H
Synthesis and properties of novel L-isonucleoside modified oligonucleotides and siRNAs
A novel isonucleoside 5 containing a 5′-CH2 extended chain at the sugar moiety was synthesized. In siRNA, passenger strand modified with isonucleoside (5a/b) at 3′ or 5′ terminal can retain the silencing activity and minimize the passenger strand specific off-target effect.
Org. Biomol. Chem., 2012,10, 7566-7577
https://doi.org/10.1039/C2OB26219C
About this collection
This joint ChemComm-OBC-RSC Advances web-based themed issue highlights recent achievements in nucleic acids research and applications in emerging areas. Some of the work presented in this virtual collection is also dedicated to the memory of Professor Har Gobind Khorana (1922 - 2011) and Dr Daniel McGillivray Brown (1923 - 2012) acknowledging their legacy to the nucleic acids community.
The guest editors for this issue are:
Mike Gait (Medical Research Council, Laboratory of Molecular Biology, Cambridge, UK)
Makoto Komiyama (University of Tsukuba, Japan)
David Liu (Harvard University, USA)
Jason Micklefield (University of Manchester, UK)
Ned Seeman (New York University, USA)
Oliver Seitz (Humboldt-Universität zu Berlin, Germany)
Articles in this web themed issue will be added below as soon as possible after they are published. Please return to this page frequently to see the collection grow.