Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells

An, Peng; Yu, Zhipeng; Lin, Qing

doi:10.1039/c3cc45752d

Cited by 93 publications

(105 citation statements)

References 33 publications

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“…In addition, microscopes are not typically equipped with UV lasers, preventing the wider use of photoclick chemistry in biological systems. To overcome these limitations, a 405 nm laser-activatable terthiophene-tetrazole was designed (structure 3 in Figure 1) [9]. The oligothiophene was used because it readily accommodates the isosteric tetrazole ring in its chain without disruption of the extended π conjugation system.…”

Section: Tuning Photoactivation Wavelengthmentioning

confidence: 99%

Photoclick chemistry: a fluorogenic light-triggered in vivo ligation reaction

Ramil

Lin

2014

Current Opinion in Chemical Biology

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The ability to use chemical reactivity to monitor and control biomolecular processes with a spatial and temporal precision motivated the development of light-triggered in vivo chemistries. To this end, the photoinduced tetrazole-alkene cycloaddition, also termed “photoclick chemistry” offers a very rapid chemical ligation platform for the manipulation of biomolecules and matrices in vivo. Here we outline the recent developments in the optimization of this chemistry, ranging from the search for substrates that offer two-photon photoactivatability, superior reaction kinetics, and/or genetic encodability, to the study of the reaction mechanism. The applications of the photoclick chemistry in protein labeling in vitro and in vivo as well as in preparing “smart” hydrogels for 3D cell culture are highlighted.

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Section: Tuning Photoactivation Wavelengthmentioning

confidence: 99%

Photoclick chemistry: a fluorogenic light-triggered in vivo ligation reaction

Ramil

Lin

2014

Current Opinion in Chemical Biology

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122

100

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“…The hydrazones (23) can be synthesized easily from the aliphatic or aromatic aldehydes (21) and the diazonium salts from the corresponding amines with NaNO 2 under acidic conditions. The second method has been used to prepare the thiophene conjugated tetrazoles (29) which exhibit longer photoactivation wavelength [26][27][28].…”

Section: Synthesis Of Tetrazolesmentioning

confidence: 99%

Photo-Triggered Click Chemistry for Biological Applications

Herner¹,

Qi²

2015

Cycloadditions in Bioorthogonal Chemistry

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In the last decade and a half, numerous bioorthogonal reactions have been developed with a goal to study biological processes in their native environment, i.e., in living cells and animals. Among them, the photo-triggered reactions offer several unique advantages including operational simplicity with the use of light rather than toxic metal catalysts and ligands, and exceptional spatiotemporal control through the application of an appropriate light source with pre-selected wavelength, light intensity and exposure time. While the photoinduced reactions have been studied extensively in materials research, e.g., on macromolecular surface, the adaptation of these reactions for chemical biology applications is still in its infancy. In this chapter, we review the recent efforts in the discovery and optimization the photo-triggered bioorthogonal reactions, with a focus on those that have shown broad utility in biological systems. We discuss in each cases the chemical and mechanistic background, the kinetics of the reactions and the biological applicability together with the limiting factors.

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“…can be achieved by expanding the aromatic systems included into the core structure of the photo active moiety, as well as the introduction of further substituents. 182,[204][205][206][207] However, the reactivity of the photo sensitive molecule towards desired moieties can potentially be affected by the resulting changes in the molecules' structure. 205,206 In addition, large absorption coefficients do not imply efficient photo activation.…”

Section: Azirine Photoligationmentioning

confidence: 99%

“…182,[204][205][206][207] However, the reactivity of the photo sensitive molecule towards desired moieties can potentially be affected by the resulting changes in the molecules' structure. 205,206 In addition, large absorption coefficients do not imply efficient photo activation. 208 The photophysical properties of the modified chromophore are decisive for the success of the photoreaction.…”

Section: Azirine Photoligationmentioning

confidence: 99%

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From UV to NIR light, photo-triggered 1,3 dipolar cycloadditions as a modern ligation method in solution and on surface

Lederhose¹

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angefertigt.Ich erkläre hiermit, dass ich die vorliegende Arbeit im Rahmen der Betreuung durch Prof. tracking. In addition, the trigger wavelength of the pyrene functionalized tetrazole was extended deep into the NIR range via the combination of the NITEC with upconversion nanoparticles (UCNPs). Assisted by the UCNPs, photoinduced ligation of both, small and macromolecules was obtained with irradiation at 974 nm. Full conversion and rapid formation of the desired pyrazoline cycloadducts were observed. In addition, a block copolymer featuring the biological relevant biotin moiety was prepared via NITEC at 974 nm, demonstrating the suitability of the approach for applications in the field of biology. Biotin was found to retain bioactivity after being exposed to the NITEC reaction conditions. The efficient penetration ability of the NIR irradiation applied was verified by 'through tissue' conjugation experiments. After the NITEC reaction was demonstrated to be a powerful ligation tool in solution, the concept was employed for the modification of surfaces in a λ-orthogonal approach. The selective ability of the pyrene tetrazole and an UV-active diaryl tetrazole to undergo independent NITEC reactions at 410 -420 nm, and 320 nm respectively, was demonstrated in solution. Importantly, the UV-active tetrazole remains unreacted if exposed to visible light, even for prolonged irradiation times. Subsequently, a surface grafted with pyrene functional tetrazole and UV-active tetrazole was prepared and utilized for formation of advanced patterned surfaces.

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Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells

Cited by 93 publications

References 33 publications

Photoclick chemistry: a fluorogenic light-triggered in vivo ligation reaction

Photoclick chemistry: a fluorogenic light-triggered in vivo ligation reaction

Photo-Triggered Click Chemistry for Biological Applications

From UV to NIR light, photo-triggered 1,3 dipolar cycloadditions as a modern ligation method in solution and on surface

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