Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane

Benedini LA, Alejandra Sequeira M, Laura Fanani M, Maggio B, Dodero VI (2016)
JOURNAL OF PHYSICAL CHEMISTRY B 120(17): 4053-4063.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
We report the synthesis and characterization of a simple nonionic azoamphiphile, C(12)OazoE(3)OH, which behaves as an optically controlled molecule alone and in a biomembrane environment. First, Langmuir monolayer and Brewster angle microscopy (BAM) experiments showed that pure C(12)OazoE(3)OH enriched in the (E) isomer was able to form solidlike mesophase even at low surface pressure associated with supramolecular organization of the azobenzene derivative at the interface. On the other hand, pure C(12)OazoE(3)OH enriched in the (Z) isomer formed a less solidlike monolayer due to the bent geometry around the azobenzene moiety. Second, C(12)OazoE(3)OH is well-mixed in a biological membrane model, Lipoid s75 (up to 20%mol), and photoisomerization among the lipids proceeded smoothly depending on light conditions. It is proposed that the cross-sectional area of the hydroxyl triethylenglycol head of C(12)OazoE(3)OH inhibits azobenzenes H-aggregation in the model membrane; thus, the tails conformation change due to photoisomerization is transferred efficiently to the lipid membrane. We showed that the lipid membrane effectively senses the azobenzene geometrical change photomodulating some properties, like compressibility modulus, transition temperature, and morphology. In addition, photomodulation proceeds with a color change from yellow to orange, providing the possibility to externally monitor the system. Finally, Gibbs monolayers showed that C(12)OazoE(3)OH is able to penetrate the highly packing biomembrane model; thus, C(12)OazoE(3)OH might be used as photoswitchable molecular probe in real systems.
Erscheinungsjahr
Zeitschriftentitel
JOURNAL OF PHYSICAL CHEMISTRY B
Band
120
Zeitschriftennummer
17
Seite
4053-4063
ISSN
PUB-ID

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Benedini LA, Alejandra Sequeira M, Laura Fanani M, Maggio B, Dodero VI. Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane. JOURNAL OF PHYSICAL CHEMISTRY B. 2016;120(17):4053-4063.
Benedini, L. A., Alejandra Sequeira, M., Laura Fanani, M., Maggio, B., & Dodero, V. I. (2016). Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane. JOURNAL OF PHYSICAL CHEMISTRY B, 120(17), 4053-4063. doi:10.1021/acs.jpcb.6b00303
Benedini, L. A., Alejandra Sequeira, M., Laura Fanani, M., Maggio, B., and Dodero, V. I. (2016). Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane. JOURNAL OF PHYSICAL CHEMISTRY B 120, 4053-4063.
Benedini, L.A., et al., 2016. Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane. JOURNAL OF PHYSICAL CHEMISTRY B, 120(17), p 4053-4063.
L.A. Benedini, et al., “Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane”, JOURNAL OF PHYSICAL CHEMISTRY B, vol. 120, 2016, pp. 4053-4063.
Benedini, L.A., Alejandra Sequeira, M., Laura Fanani, M., Maggio, B., Dodero, V.I.: Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane. JOURNAL OF PHYSICAL CHEMISTRY B. 120, 4053-4063 (2016).
Benedini, Luciano A., Alejandra Sequeira, M., Laura Fanani, Maria, Maggio, Bruno, and Dodero, Veronica Isabel. “Development of a Nonionic Azobenzene Amphiphile for Remote Photocontrol of a Model Biomembrane”. JOURNAL OF PHYSICAL CHEMISTRY B 120.17 (2016): 4053-4063.

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Photo-switching of a non-ionic azobenzene amphiphile in Langmuir and Langmuir-Blodgett films.
Piosik E, Kotkowiak M, Korbecka I, Galewski Z, Martyński T., Phys Chem Chem Phys 19(34), 2017
PMID: 28825748

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