Photo-responsive oligonucleotides carrying azobenzene in the side-chains

Asanuma, Hiroyuki; Ito, Takanori; Komiyama, Makoto

doi:10.1016/s0040-4039(98)02022-x

Cited by 58 publications

(52 citation statements)

References 8 publications

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“…These spectral changes are characteristics of pure azobenzene (Zimmerman et al, 1958), and indicate that azobenzene moieties of the scaffold DNA takes the transform when irradiated with visible light, corresponding to the energy gap of the n-p Ã (S0-S1) transition, and the cis-form when irradiated with UV light, corresponding to that of the p-p Ã (S0-S2) transition. This is consistent with the report of Asanuma et al (1998) who characterized a modified oligonucleotide carrying a single azobenzene side chain. The 260-nm peak of the scaffold DNA mostly represents absorption of the oligonucleotide.…”

Section: Resultssupporting

confidence: 93%

“…To switch or regulate the activities of those nanobiotechnological devices, non-invasive methods to assemble and disassemble specific nanoscale components are needed. In that regard, it is noteworthy that Asanuma et al demonstrated reversible photocontrol of duplex formation of oligonucleotides that depends on reversible, light-induced isomerization of azobenzene moieties introduced in the side chain of an oligonucleotide (Asanuma et al, 1998(Asanuma et al, , 1999(Asanuma et al, , 2005Liang et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

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Photoregulated assembly/disassembly of DNA‐templated protein arrays using modified oligonucleotide carrying azobenzene side chains

Hachikubo¹,

Iwai²,

Uyeda³

2010

Biotech & Bioengineering

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DNA-templated self-assembly of nanomaterials provides great potential for applications including biosensors, nanoelectronics, and programmable and autonomous molecular machines. To switch or regulate the activities of those nanobiotechnological devices, non-invasive methods to assemble and disassemble specific nanoscale components are needed. Here, we describe photocontrol of assembly of DNA-templated protein arrays in solution, by using photo-controlled duplex formation of oligonucleotides carrying azobenzene. As a proof of concept prototype, we designed a one-dimensional protein array system that consists of a scaffold of DNA and two kinds of anchor DNA that were conjugated with fluorescent proteins (CFP and YFP, respectively). The scaffold DNA was modified to carry multiple azobenzene side chains so that the hybridization involving the scaffold DNA is regulated by photoirradiation through conformational changes of the azobenzene moieties. Melting temperatures of duplex made of the modified DNA scaffold and an anchor oligonucleotide were shifted significantly and reversibly by UV and visible photoirradiation (difference of T(m) was 34.8 degrees C in 150 mM potassium acetate). Measurements of Förster resonance energy transfer between CFP and YFP showed that the assembly of the protein array system was also changed by photoirradiation. Such non-invasive and reversible method to control assembly/disassembly of multiple, specific proteins in a DNA-templated protein array system would provide many functions for nanobiotechnological devices such as on/off switches and the ability to change the configuration reversibly.

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Section: Resultssupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Photoregulated assembly/disassembly of DNA‐templated protein arrays using modified oligonucleotide carrying azobenzene side chains

Hachikubo¹,

Iwai²,

Uyeda³

2010

Biotech & Bioengineering

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“…[2] The acyl group of acylzirconocene chloride reacted as a formal ªunmaskedº acyl anion. [3] In particular, the regioselectivity of the reaction can be controlled by modifying the palladium catalyst system. For example, in the reaction of nonanoylzirconocene chloride (1) (5 mol %) as catalyst in toluene gave the 1,2-addition product 2, whereas the use of 10 mol % [Pd(OAc) 2 ]/BF 3´O Et 2 in THF/ diethyl ether gave the 1,4-addition product 3 (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

“…[3,4] The two diastereomers 1 a and 1 b, based on the chirality of the the NMR spectra of the bis-MTPA derivatives showed no difference between the stereoisomers. [8] The 2 H NMR spectrum of a statistical mixture of the three stereoisomers R,R/S,S and R,S is shown in Figure 3.…”

mentioning

confidence: 99%

Photoregulation of the Formation and Dissociation of a DNA Duplex by Using thecis-trans Isomerization of Azobenzene

Asanuma¹,

Ito²,

Yoshida³

et al. 1999

Angew. Chem. Int. Ed.

Self Cite

282

204

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The duplex-forming activity of an oligonucleotide has been photoregulated by making use of the isomerization of an azobenzene moiety in the side chain. When the azobenzene moiety is isomerized from the trans form to the cis form upon photoirradiation, the melting temperature of the duplex between the oligonucleotide and its complementary counterpart is significantly lowered, and the duplex is largely dissociated into two single-stranded oligonucleotides (shown schematically).

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“…Examples of biomolecular systems into which azobenzene has been incorporated for photo-regulation are peptides [1][2][3] , enzymes [4][5][6][7] , oligonucleotides 8,9 and ion channels 10,11 . Methods for incorporating azobenzene chromophores into biomolecules include solid-phase peptide or oligonucleotide synthesis 7,12 , nonsense suppression via azobenzenecharged suppressor tRNAs 4 , and both non-selective 13 and targeted chemical modification of protein side chains 14 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3,3′-bis(sulfonato)-4,4′-bis(chloroacetamido)azobenzene and cysteine cross-linking for photo-control of protein conformation and activity

2007

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Photo-responsive oligonucleotides carrying azobenzene in the side-chains

Cited by 58 publications

References 8 publications

Photoregulated assembly/disassembly of DNA‐templated protein arrays using modified oligonucleotide carrying azobenzene side chains

Photoregulated assembly/disassembly of DNA‐templated protein arrays using modified oligonucleotide carrying azobenzene side chains

Photoregulation of the Formation and Dissociation of a DNA Duplex by Using thecis-trans Isomerization of Azobenzene

Synthesis of 3,3′-bis(sulfonato)-4,4′-bis(chloroacetamido)azobenzene and cysteine cross-linking for photo-control of protein conformation and activity

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