Photocontrolled micellar aggregation of amphiphilic DNA-azobenzene conjugates

Gu, Renpeng; Lamas, Joseph; Rastogi, Shiva K.; Li, Xiaopeng; Brittain, William J.; Zauscher, Stefan

doi:10.1016/j.colsurfb.2015.07.010

Cited by 12 publications

(12 citation statements)

References 51 publications

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“…Gu, Brittain and co-workers have developed a DNA-azobenzene conjugate which can be used for photoregulated micelle formation. 175 The azobenzene end-caps aggregate in the trans configuration, while the cis conjugates are more hydrophilic. Upon irradiation with UV light to form the cis isomers, no complete micelle disassociation was observed.…”

Section: End-capping Of Oligonucleotides With Molecular Photoswitchesmentioning

confidence: 99%

Recent developments in reversible photoregulation of oligonucleotide structure and function

2017

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There is a growing interest in the photoregulation of biological functions, due to the high level of spatiotemporal precision achievable with light. Additionally, light is non-invasive and waste-free. In particular, the photoregulation of oligonucleotide structure and function is a rapidly developing study field with relevance to biological, physical and material sciences. Molecular photoswitches have been incorporated in oligonucleotides for 20 years, and the field has currently grown beyond fundamental studies on photochemistry of the switches and DNA duplex stability, and is moving towards applications in chemical biology, nanotechnology and material science. Moreover, the currently emerging field of photopharmacology indicates the relevance of photocontrol in future medicine. In recent years, a large number of publications has appeared on photoregulation of DNA and RNA structure and function. New strategies are evaluated and novel, exciting applications are shown. In this comprehensive review, the key strategies for photoswitch inclusion in oligonucleotides are presented and illustrated with recent examples. Additionally the applications that have emerged in recent years are discussed, including gene regulation, drug delivery and materials design. Finally, we identify the challenges that the field currently faces and look forward to future applications.

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Section: End-capping Of Oligonucleotides With Molecular Photoswitchesmentioning

confidence: 99%

Recent developments in reversible photoregulation of oligonucleotide structure and function

2017

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“…Second, the charged polymers, i.e., polyelectrolytes, could endow the system with additional features, such as pH- or temperature-dependence, rendering the material excellent dual sensitivity. Finally, the electrostatically driven complex formation of the azo surfactants with different biomacromolecules can be used to actuate by light their secondary and tertiary structures and therefore the biological activity. − …”

Section: Introductionmentioning

confidence: 99%

Photosensitive Cationic Azobenzene Surfactants: Thermodynamics of Hydration and the Complex Formation with Poly(methacrylic acid)

Montagna

Guskova

2017

Langmuir

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In this computational work, we investigate the photosensitive cationic surfactants with the trimethylammonium or polyamine hydrophilic head and the azobenzene-containing hydrophobic tail. The azobenzene-based molecules are known to undergo a reversible trans-cis-trans isomerization reaction when subjected to UV-visible light irradiation. Combining the density functional theory and the all-atom molecular dynamics simulations, the structural and the hydration properties of the trans- and the cis-isomers and their interaction with the oppositely charged poly(methacrylic acid) in aqueous solution are investigated. We establish and quantify the correlations of the molecular structure and the isomerization state of the surfactants and their hydrophilicity/hydrophobicity and the self-assembling altered by light. For this reason, we compare the hydration free energies of the trans- and the cis-isomers. Moreover, the investigations of the interaction strength between the azobenzene molecules and the polyanion provide additional elucidations of the recent experimental and theoretical studies on the light triggered reversible deformation behavior of the microgels and the polymer brushes loaded with azobenzene surfactants.

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“…Many such applications have been reported, for example, the formation of light-responsive micelles studied by atomic force microscopy 23 and scanning electron microscope 24 techniques, light-switchable vesicles, 25 and block copolymer vesicles dissociated and reformed by light. 26 Azobenzene amphiphiles have also been used in the targeted disruption of giant unimolecular vesicles 27 or for thermo-and phototriggered aqueous microgels, 28 erasable multilayer thin films, 29 aggregation and disaggregation of DNA conjugates, 30 and photoresponsive nanostructures for drug delivery. 31 In this work, we investigate the properties and photoresponse of azobenzene-based reverse micelles in chloroform using 1 H NMR and absorption spectroscopy.…”

Section: ■ Introductionmentioning

confidence: 99%

Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations

Filipová¹,

Kohagen

Štacko³

et al. 2017

Langmuir

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We designed and studied the structure, dynamics, and photochemistry of photoswitchable reverse micelles (RMs) composed of azobenzene-containing ammonium amphiphile 1 and water in chloroform at room and subzero temperatures by NMR spectroscopy and molecular dynamics simulations. The NMR and diffusion coefficient analyses showed that micelles containing either the E or Z configuration of 1 are stable at room temperature. Depending on the water-to-surfactant molar ratio, the size of the RMs remains unchanged or is slightly reduced because of the partial loss of water from the micellar cores upon extensive E → Z or Z → E photoisomerization of the azobenzene group in 1. Upon freezing at 253 or 233 K, E-1 RMs partially precipitate from the solution but are redissolved upon warming whereas Z-1 RMs remain fully dissolved at all temperatures. Light-induced isomerization of 1 at low temperatures does not lead to the disintegration of RMs remaining in the solution; however, its scope is influenced by a precipitation process. To obtain a deeper molecular view of RMs, their structure was characterized by MD simulations. It is shown that RMs allow for amphiphile isomerization without causing any immediate significant structural changes in the micelles.

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Photocontrolled micellar aggregation of amphiphilic DNA-azobenzene conjugates

Cited by 12 publications

References 51 publications

Recent developments in reversible photoregulation of oligonucleotide structure and function

Recent developments in reversible photoregulation of oligonucleotide structure and function

Photosensitive Cationic Azobenzene Surfactants: Thermodynamics of Hydration and the Complex Formation with Poly(methacrylic acid)

Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations

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