Photochemically controlled ion permeability of liposomal membranes containing amphiphilic azobenzene

Sato, Tomoo; Kijima, Masato; Shiga, Yoshihiro.; Yonezawa, Yoshiro

doi:10.1021/la00058a059

Cited by 44 publications

(48 citation statements)

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“…A similar observation was made for the permeability of K + from phospholipid liposomes containing an azobenzene derivative, where, after turning off the light causing trans-cis isomerization, the K + release from the liposomes continued at the same rate as before. 10 We showed above that it was possible to restore the trans form rapidly by illumination at 450 nm. With this in mind, we examined the possibility of stopping payload release by restoring the trans isomers.…”

Section: Resultsmentioning

confidence: 92%

“…10,16,37 The free volume accessible to AzoC 10 N + when inserted in bilayers is expected to be considerably more limited than that of the form solubilized in organic solution. It was previously reported that the mobility of the chromophore is crucial for efficient isomerization.…”

Section: Resultsmentioning

confidence: 99%

“…The azobenzene group is a functional group that can undergo reversible trans-cis isomerization under irradiation of UV or visible light. [9][10][11] Thermodynamically, the trans isomer is favored because of the minimized steric hindrance. Because of the greater stability of the trans form, there is thermal relaxation of the system from the cis to the trans isomer; this relaxation process is generally much slower than the photoconversion from one isomer to the other.…”

Section: Introductionmentioning

confidence: 99%

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Nonphospholipid Fluid Liposomes with Switchable Photocontrolled Release

et al. 2014

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We created novel nonphospholipid photosensitive liposomes from a mixture of a monoacylated azobenzene amphiphile (AzoC10N(+)) and cholesterol sulfate (Schol). This system belongs to the family of sterol-enriched nonphospholipid liposomes that were shown to form stable large unilamellar vesicles (LUVs) with enhanced impermeability. Fluid bilayers were successfully prepared from AzoC10N(+)/Schol (25/75 molar ratio) mixtures, and LUVs could be derived at room temperature using standard extrusion methods. The isomerization process of the bilayer-inserted AzoC10N(+) was characterized. Leakage from these liposomes could be induced by the photoconversion of AzoC10N(+) from its trans form to its cis form. This photocontrolled release from fluid liposomes contrasts with the case of phospholipid-based azo-containing liposomes, which are generally required to be in the gel phase to be photosensitive. It is proposed that the very high degree of conformational order of the monoalkylated amphiphile and the tight packing of the hydrophobic core of the AzoC10N(+)/Schol liposomes make them responsive to the presence of the bulky cis azo isomer. Interestingly, the liposome impermeability could be fully restored by the photoisomerization of the cis form back to the trans form, providing a sharp on-and-off control of payload release. In addition, these nonphospholipid liposomes display a very limited passive release. Therefore, it is shown that AzoC10N(+)/Schol LUVs can be used as nanocontainers, whose content can be released by light in a controlled and switchable manner.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Nonphospholipid Fluid Liposomes with Switchable Photocontrolled Release

et al. 2014

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“…In those molecules, often based on azobenzenes, isomerization occurs when their spatial orientation switches from the trans to cis state. When incorporated into liposomal membranes, for example, this transition is associated with bilayer disruption followed by cargo release . Azobenzenes have two phenyl rings which are interconnected by two nitrogen atoms paired by a double bond.…”

Section: Mechanisms Of Light‐triggered Release From Liposomesmentioning

confidence: 99%

Mechanisms of light‐induced liposome permeabilization

Miranda

Lovell

2016

Bioengineering & Transla Med

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Liposomes have been widely studied for drug delivery applications. The inclusion of photoactive molecules into liposomes opens the possibility of light-controlled cargo release to enhance drug biodistribution or bioavailability at target sites. Membrane permeabilization induced by light can be an effective strategy for enhancing cargo delivery with spatial and temporal control, which holds potential for chemophototherapy approaches. Several diverse mechanisms have been reported including light-induced oxidation, photocrosslinking, photoisomerization, photocleavage and photothermal release. Here, we review selected recent reports of light-triggered cargo release from liposomes.

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“…The interface and surface chemistry of liposomes can be manipulated to deliver the encapsulated molecules in vivo in a temporally and spatially controlled manner [17][18][19][20][21][22]. Such controlled release technologies allow treatment strategies when there are short but therapeutically crucial, temporal windows, such as those observed spanning minutes to hours.…”

Section: Introductionmentioning

confidence: 99%

Dual Propionibacterium acnes therapy using skin penetration-enhanced liposomes loaded with a photosensitizer and an antibiotic

Park

2015

J. Porphyrins Phthalocyanines

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Various antibiotics and photosensitizers are used for Propionibacterium acnes therapy. However, the success rate of therapy is limited because of antibiotic resistance, side-effects of photodynamic therapy using photosensitizer and the low skin-penetration efficiency of antibiotics and photosensitizers. In this study, to enhance the skin penetration efficiency, maintain their photodynamic activity and induce dual antibacterial therapeutic effects, we prepare erythromycin and branched polyethyleneimin-hematoporphyrin (bPEI-HPP) conjugates were loaded into liposomes (cationic photosensitizer-erythromycin loaded liposomes, CP-L (bPEI-HPP 10 mg; CP-L 1 and 20 mg; CP-L 2)). The tissue penetration efficiency of CP-Ls was determined by the Franz cell diffusion system and fluorescence microscopy. The penetration efficiency of CP-Ls is greater than that of bPEI-HPP, unloaded cationic photosensitizer and free HPP because CP-Ls comprised phospholipids that are similar to the cell membrane lipid composition. For in vitro antibacterial effects, Propionibacterium acnes (P. acnes) were used. The loss of viability rate of P. acnes by CP-L 2 (95%) from the colony forming unit (CFU) assay, was 2.4-fold higher than erythromycin-loaded liposomes (39%) and 1.9-fold higher than bPEI-HPPloaded liposomes (50%). Therefore, we suggest that polycationic photosensitizer and antibiotic-loaded liposomes have potential applications in clinical photodynamic anti-bacterial therapy. † These authors contributed equally to the work J. Porphyrins Phthalocyanines Downloaded from www.worldscientific.com by EMORY UNIVERSITY on 07/30/15. For personal use only.

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Photochemically controlled ion permeability of liposomal membranes containing amphiphilic azobenzene

Cited by 44 publications

References 0 publications

Nonphospholipid Fluid Liposomes with Switchable Photocontrolled Release

Nonphospholipid Fluid Liposomes with Switchable Photocontrolled Release

Mechanisms of light‐induced liposome permeabilization

Dual Propionibacterium acnes therapy using skin penetration-enhanced liposomes loaded with a photosensitizer and an antibiotic

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