<i>cis</i>‐On/<i>trans</i>‐Off of DNA Hybridization with Alkylthio‐azobenzene on L‐Threoninol Responding to Visible Light

Asanuma, Hiroyuki; Ishikawa, Teruchika; Yamano, Yuuhei; Murayama, Keiji; Liang, Xingguo

doi:10.1002/cptc.201900060

Cited by 15 publications

(20 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…17C). 13 More recently, several modications have been made to improve the modest photoisomerization efficiency of D-tAzo (e.g., 30% of cis-isomer at 37 C with irradiation with 365 nm (ref. 134)) or L-tAzo.…”

Section: Azobenzenementioning

confidence: 99%

“…The destabilization effect of the cis-Azo was observed by various research groups and for several different azobenzene nucleoside surrogates. 5,13,131,133,136 In general, the T m differences between the cisand trans-forms of AzoB modications in DNA duplexes are $1-5 C. 130,131,136 The impact of AzoB on the thermal stability of the DNA also depends on the stereochemical environment of the group. For instance, the trans-form of D-tAzoB is more stable than that of L-tAzoB because D-threoninol prefers a clockwise winding, as does the DNA double helix.…”

Section: Azobenzenementioning

confidence: 99%

“…In some reversible reactions, the forward or reverse reactions are promoted by distinct wavelengths of light, offering a unique advantage. 13,14 Dr Amirrasoul Tavakoli received his Bachelor's degree in Chemistry and Master's degree in Nanotechnology from the University of Tehran (Tehran, IRAN). He obtained his PhD degree in Biochemistry under the supervision of Prof. Jung-Hyun Min from Baylor University (Texas, USA) on light-induced modulation of DNA recognition by the Rad4/XPC damage sensor protein using photoreactive DNA.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Photochemical modifications for DNA/RNA oligonucleotides

Tavakoli

Min

2022

RSC Adv.

View full text Add to dashboard Cite

show abstract

Section: Azobenzenementioning

confidence: 99%

Section: Azobenzenementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Photochemical modifications for DNA/RNA oligonucleotides

Tavakoli

Min

2022

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…The use of azobenzenes as molecular photoswitches for biological applications can be traced back to the pioneering work of Yamana et al., who employed azobenzene as a photoisomerizable linker to connect two oligonucleotide segments . Following this pioneering work, Asanuma, Komiyama, and co‐workers reported the control of DNA or RNA hybridization and gene expression by using azobenzene as a molecular photoswitch . The utility of azobenzenes for photoregulating the conformation and function of peptides and proteins, photocontrolling ion channels, and photorestoring human vision have also been reported .…”

Section: Introductionmentioning

confidence: 99%

Sulfonated Pyrene as a Photoregulator for Single‐Stranded DNA Looping

Miyamoto

Tojo

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

Controlling the conformationa nd functiono fb iomolecules through photoregulators holds great promise as a spatiotemporally controllable tool for disease control.I na ddition, introducing photoregulators into biomoleculesh as also found applicationsi nc onstructings martn anomaterials. In spite of the astonishing advances that have been made in the past few years, realizing highly controllable and efficient regulation over the conformation and functiono fb iomolecules under physiological conditionsi ss till challenging. Herein,s ulfonated pyrene SPy was synthesized and used as ap hotoregulator to control the looping of single-stranded DNAs (ssDNAs) in aqueous solution.Due to its water solubility, SPy merits use in the study of biomolecules in aqueous solution.T he looping of the doubly SPy-modified ssDNAs is stimulated by irradiation and regulated by SPy.P hotoionization generatest he radicalc ation of SPy (SPyC + ). The association of SPyC + + with its neutralc ounterpart, SPy,g ives rise to the dimer radicalc ation of SPy (SPy 2 C + + ). During the association process, the stabilization energy released to form SPy 2 C + + provides ad riving force for the looping of ssDNAs. Conversely,t he formed loop conformationsw ere trapped by the formation of SPy 2 C + + ,a nd this allowed the looping dynamics to be investigated. The results reported herein suggest potential of SPy as ap hotoregulator for controlling the conformationa nd function of biomolecules under physiological conditions.[a] J.[a] Immediately formed SPy 2 C + + component. P static = DOD t = 10 ns /DOD max .

show abstract

“…During the last years, the pioneering structural studies of reversible photoregulation of DNA/RNA duplex stability of Asanuma and Komiyama [16–17] have become functional ones, affecting DNA/RNA cleavage [18–20], transcription [21–23], and translation [24–25]. Except a handful of current examples [22,24,26], most of these photoresponsive oligonucleotides are canonical ones where the classical azobenzene is the prominently used photoswitch; although spiropyrans [27], stilbenes [28], diarylethanes [29] and overcrowded alkenes [30] have also been employed. In vivo application demands the development of a new generation of artificial agents to target DNA/RNA-associated processes.…”

Section: Introductionmentioning

confidence: 99%

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

Zhang¹,

Linden²,

Vázquez³

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Photoswitchable oligonucleotides can determine specific biological outcomes by light-induced conformational changes. In particular, artificial probes activated by visible-light irradiation are highly desired in biological applications. Here, we report two novel types of visible-light photoswitchable peptide nucleic acids (PNAs) based on the molecular transducers: hemithioindigo and tetra-ortho-fluoroazobenzene. Our study reveals that the tetra-ortho-fluoroazobenzene–PNA conjugates have promising properties (fast reversible isomerization, exceptional thermal stability, high isomer conversions and sensitivity to visible-light irradiation) as reversible modulators to control oligonucleotide hybridization in biological contexts. Furthermore, we verified that this switchable modification delivers a slightly different hybridization behavior in the PNA. Thus, both melting experiments and strand-displacement assays showed that in all the cases the trans-isomer is the one with superior binding affinities. Alternative versions, inspired by our first compounds here reported, may find applications in different fields such as chemical biology, nanotechnology and materials science.

show abstract

cis‐On/trans‐Off of DNA Hybridization with Alkylthio‐azobenzene on L‐Threoninol Responding to Visible Light

Abstract: This is the author manuscript accepted for publication and has undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record.

Cited by 15 publications

References 35 publications

Photochemical modifications for DNA/RNA oligonucleotides

Photochemical modifications for DNA/RNA oligonucleotides

Sulfonated Pyrene as a Photoregulator for Single‐Stranded DNA Looping

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

Contact Info

Product

Resources

About