pH‐Switchable Helicity of DNA‐Templated Assemblies

Janssen, Pim G. A.; Ruiz‐Carretero, Amparo; González‐Rodríguez, David; Meijer, E. W.; Schenning, Albertus P. H. J.

doi:10.1002/ange.200903507

Cited by 29 publications

(14 citation statements)

References 61 publications

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“…The λ max of NDI-L-Glu ( 1 ) is red-shifted from 380 nm at pH 7.0 to 385 for 1 + H + at pH 3.0, while blue-shifted absorption was observed to 372 nm for pH 9.0 (Fig. 2a ) 43 . Typically, when the pH values of solution were changed from 3.0 to 9.0, a decrease in absorption intensity along with blue-shift absorption and the appearance of shoulder at 425 nm were observed.…”

Section: Resultsmentioning

confidence: 90%

Dynamic multistimuli-responsive reversible chiral transformation in supramolecular helices

Goskulwad

Kobaisi

et al. 2018

Sci Rep

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The design of new chiral chromophores that allow tunable assembly of higher order helical structures by using natural stimuli offers promising avenue in understanding various biological processes. In particular, access to dynamic multistimuli-responsive systems can provide real-time monitoring of chiral transformation in chemical and biological systems. We report on the synthesis of naphthalenediimide appended L-glutamate (NDI-L-Glu) that self-assembles into chiral supramolecular structures under physiological conditions. Specifically, NDI-L-Glu shows a mixture of left- and right-handed helices under physiological conditions, and any deviation from the ambient biochemical environment has a remarkable influence on the chirality of these structures. For instance, acidic environments shift the helicity to left-handedness while the alkaline conditions reversed the helical structures to right-handedness, thereby mimicking the molecular virulence mechanism of tobacco mosaic virus (TMV). The chirality of these supramolecular assemblies can also be controllably tuned by using temperature as an external stimulus, allowing reversible flip of helicity.

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Section: Resultsmentioning

confidence: 90%

Dynamic multistimuli-responsive reversible chiral transformation in supramolecular helices

Goskulwad

Kobaisi

et al. 2018

Sci Rep

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“…Typical designs of helical assemblies consist of optically active monomers, which bias the handedness during the (supramolecular) polymerization process [8][9][10][11][12][13][14][15][16][17][18][19] . In this respect, helicity induction in racemic or achiral assemblies constructed from achiral monomers through non-covalent interactions with the chiral guest molecules is an alternative, synthetic strategy [20][21][22][23][24][25][26] . This host-guest design for helical motifs not only provides new opportunities to investigate mechanistic details of supramolecular chirality, but also offers practical chirotechnological applications.…”

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confidence: 99%

A dynamic supramolecular polymer with stimuli-responsive handedness for in situ probing of enzymatic ATP hydrolysis

et al. 2014

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Design of artificial systems, which can respond to fluctuations in concentration of adenosine phosphates (APs), can be useful in understanding various biological processes. Helical assemblies of chromophores, which dynamically respond to such changes, can provide realtime chiroptical readout of various chemical transformations. Towards this concept, here we present a supramolecular helix of achiral chromophores, which shows chiral APs responsive tunable handedness along with dynamically switchable helicity. This system, composing of naphthalenediimides with phosphate recognition unit, shows opposite handedness on binding with ATP compared with ADP or AMP, which is comprehensively analysed with molecular dynamic simulations. Such differential signalling along with stimuli-dependent fast stereomutations have been capitalized to probe the reaction kinetics of enzymatic ATP hydrolysis. Detailed chiroptical analyses provide mechanistic insights into the enzymatic hydrolysis and various intermediate steps. Thus, a unique dynamic helical assembly to monitor the real-time reaction processes via its stimuli-responsive chiroptical signalling is conceptualized.

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“…The final assembly is driven by hydrogen bonding and π ‐stacking of the nucleolipids with the DNA strand as well as by microphase separation 57. Similar assemblies can also be achieved with nucleobases functionalized with polyethylene oxide,58–61 as shown in Figure 4(b).…”

Section: Nucleic Acid–lipid and ‐Polymer Assemblymentioning

confidence: 82%

Long‐range assembly of DNA into nanofibers and highly ordered networks

Carneiro

Avakyan

Sleiman

2013

WIREs Nanomed Nanobiotechnol

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Long-range assembly of DNA currently comprises both top-down and bottom-up methods. The top-down techniques consist of physical alignment of DNA and lithographic patterning to organize DNA on surfaces. The bottom-up approaches include lipid-and polymer-DNA co-assembly, the self-assembly of DNA amphiphiles, and the remarkably specific and versatile methods of DNA nanotechnology. DNA-based materials possess unprecedented molecular control and may offer innovative solutions in the fields of nanotechnology, sensing, nanomedicine, as well as optical and electronic devices. To realize the potential of these materials, a number of hurdles must be addressed. Bridging the gap between top-down fabrication and bottom-up assembly is of critical importance to the successful development of functional DNA-based technology. A profound understanding of both regimes is necessary to achieve this goal.

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pH‐Switchable Helicity of DNA‐Templated Assemblies

Cited by 29 publications

References 61 publications

Dynamic multistimuli-responsive reversible chiral transformation in supramolecular helices

Dynamic multistimuli-responsive reversible chiral transformation in supramolecular helices

A dynamic supramolecular polymer with stimuli-responsive handedness for in situ probing of enzymatic ATP hydrolysis

Long‐range assembly of DNA into nanofibers and highly ordered networks

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