Liponucleoside thin films: The special behaviour of guanosine

Čoga, Lucija; Ilc, Tina; Devetak, Miha; Masiero, Stefano; Gramigna, Lucia; Spada, Gian Piero; Drevenšek‐Olenik, Irena

doi:10.1016/j.colsurfb.2012.10.019

Cited by 4 publications

(3 citation statements)

References 26 publications

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“…Such hysteresis appears in Langmuir films of lipophilic nucleoside derivatives of various nucleobases and was investigated in more detail in our previous work. 82 …”

Section: Experimental Resultsmentioning

confidence: 99%

Reversible Photoisomerization in Thin Surface Films from Azo-Functionalized Guanosine Derivatives

et al. 2021

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Two novel azo-functionalized guanosine derivatives were synthesized, and their photoisomerization process was investigated in molecular monolayers at the air–water interface and in the Langmuir–Blodgett (LB) films on solid substrates. Measurements of surface pressure vs area isotherms, surface potential measurements, UV–visible (vis) absorption spectroscopy, Brewster angle microscopy (BAM), and atomic force microscopy (AFM) were performed. Despite not having a typical amphiphilic molecular structure, the derivatives formed stable films on the water surface. They could also undergo repeated photoisomerization in all of the investigated thin-film configurations. The observations suggest that in the films at the air–water interface, the molecules first exhibit a conformational change, and then they reorient to an energetically more favored orientation. In the LB films transferred onto solid substrates, the isomerization process occurs on a similar time scale as in solution. However, the isomerization efficiency is about an order of magnitude lower than that in solution. Our results show that DNA nucleobases functionalized with azobenzene moieties are suitable candidates for the fabrication of photoactive two-dimensional (2D) materials that can provide all beneficial functionalities of DNA-based compounds.

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“…Such hysteresis appears in Langmuir films of lipophilic nucleoside derivatives of various nucleobases and was investigated in more detail in our previous work. 82 …”

Section: Experimental Resultsmentioning

confidence: 99%

Reversible Photoisomerization in Thin Surface Films from Azo-Functionalized Guanosine Derivatives

et al. 2021

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“…In our previous works, we have already reported that amphiphilic guanosine derivatives behave very differently from derivatives of other nucleobases. 51 It was speculated that in guanosine films guanosine molecules may form so-called Hoogsteen base pairs that are interlinked by two instead of three hydrogen bonds present in the G–C pair. 61 While in the present work the isotherms of GAzo-G mixed films were also found to exhibit quite a unique behavior, the irradiation-induced changes in those films were found to be the same as those in films with noncomplementary nucleobases (GAzo-A and GAzo-T).…”

Section: Discussionmentioning

confidence: 99%

“…The synthesis and surface pressure vs area isotherms of Langmuir films of the latter compounds are described in our previous works. 51,52…”

Section: Methodsmentioning

confidence: 99%

Photoisomerizable Guanosine Derivative as a Probe for DNA Base-Pairing in Langmuir Monolayers

2019

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Mixtures of azo-functionalized amphiphilic derivatives of guanosine and of amphiphilic derivatives of other DNA nucleobases were deposited at an air–water interface and repeatedly irradiated with light of 340 and 440 nm wavelengths. The consequent switching between cis and trans configurations of the azobenzene moiety caused changes in the surface pressure of the film, which were analyzed using a model based on the two-dimensional Van der Waals equation of state. For mixed films of guanosine and cytidine derivatives, the analysis revealed a significant modification of the strength of intermolecular interaction caused by the optical irradiation, while no such modifications were identified in mixed films involving other nucleobases. The difference is attributed to light-induced breaking of the hydrogen bonding that is established only between specific nucleobases. The results demonstrate that photosensitive nucleoside derivatives can be used as an efficient probe for base-pairing in Langmuir monolayers.

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Molecular recognition of a lipophilic guanosine derivative in Langmuir films at the air-water interface

Čoga

Spindler

Masiero

et al. 2017

Biochimica et Biophysica Acta (BBA) - General Subjects

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Liponucleoside thin films: The special behaviour of guanosine

Cited by 4 publications

References 26 publications

Reversible Photoisomerization in Thin Surface Films from Azo-Functionalized Guanosine Derivatives

Reversible Photoisomerization in Thin Surface Films from Azo-Functionalized Guanosine Derivatives

Photoisomerizable Guanosine Derivative as a Probe for DNA Base-Pairing in Langmuir Monolayers

Molecular recognition of a lipophilic guanosine derivative in Langmuir films at the air-water interface

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