Photo-responsive liposomes composed of spiropyran-containing triazole-phosphatidylcholine: investigation of merocyanine-stacking effects on liposome–fiber assembly-transition

Zhang, Dawei; Shah, Parag K.; Culver, Heidi R.; David, Sabrina N.; Stansbury, Jeffrey W.; Yin, Xiaobo; Bowman, Christopher N.

doi:10.1039/c8sm02181c

Cited by 20 publications

(15 citation statements)

References 48 publications

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“…The cerasome dispersion was loaded into a quartz capillary and was allowed 1 week to precipitate. In 1-D WAXS (Figure a), a sharp fundamental diffraction peak (first order diffraction) at Q = 0.148 Å –1 (4.2 nm) confirms the lamellar structure formed by stacking of the bilayer membranes. − There are also second and third harmonics at Q = 0.295 Å –1 and 0.439 Å –1 , which indicate well-defined stacking of bilayer membranes. The two broad peaks over the whole Q vector range are attributed to diffraction from the amorphous SiO 2 structure.…”

Section: Resultsmentioning

confidence: 88%

Hybrid Cerasomes Composed of Phosphatidylcholines and Silica Networks for the Construction of Vesicular Materials with Functionalized Shells

Zhang

Culver

Bowman

2019

ACS Appl. Nano Mater.

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A phosphatidylcholine-based cerasome (PC-cerasome) was prepared by a combination of a copper-catalyzed azide alkyne cyclo-addition (CuAAC) reaction and a sol–gel condensation process. In a 2 wt % urea aqueous solution, azide precursors containing a triethoxysilane group (TEOS) were coupled with an alkyne lysolipid (AL) through a CuAAC reaction to generate triethoxysilane triazole-phosphatidylcholine (TEOSTPC) molecules. TEOSTPC self-assembled into liposomes immediately after formation. Incubation of the liposomes at 50 °C led to a gradual hydrolysis and decomposition of urea, which caused a mildly basic condition. Simultaneously, a base-catalyzed sol–gel condensation of TEOS groups occurred and drove formation of a silica network in the bilayer membranes of the TEOSTPC-liposomes, resulting in cerasomes with an organic/inorganic hybrid shell composed of PC and an SO2 network. Because of the presence of the SO2 network in the bilayer membrane, the cerasomes exhibited good structural stability in the aqueous phase and maintained the vesicular structure even when dispersed in water-miscible organic solvents. Coexistence of the bilayer membrane and SiO2 was verified, which is indicative of an intramembrane sol–gel condensation. The formation process of an SiO2 network in the bilayer membrane was verified using spiropyran-containing triazole-phosphatidylcholine (SPTPC) as a molecular probe. The SPTPC was embedded in TEOSTPC-liposomes, and subsequent sol–gel condensation anchored the SPTPCs in the SiO2 network. During sol–gel condensation, SP isomerized to merocyanine (MC), indicating that the polarity of the microenvironment in the bilayer membrane increased due to formation of the SiO2 network. Moreover, the rigidity of the SiO2 network prohibited MC-to-SP recovery, resulting in a cerasome with a MC-functionalized shell. Based on the structural stability of the PC-cerasome and the convenient preparation method combining CuAAC and sol–gel condensation, we anticipate that these PC-cerasomes will find broad utility in the construction of vesicular materials with functionalized shells.

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Section: Resultsmentioning

confidence: 88%

Hybrid Cerasomes Composed of Phosphatidylcholines and Silica Networks for the Construction of Vesicular Materials with Functionalized Shells

Zhang

Culver

Bowman

2019

ACS Appl. Nano Mater.

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“…For example, light irradiation has been exploited for both in situ assembly of liposomes and subsequent triggering of content release. Here, Zhang and co-workers utilized CuAAC to drive the in situ assembly through the coupling of alkynyl-PC analogue 15 and azido-lipid 28 containing a photocleavable o -nitrobenzyl moiety. , Following assembly, light irradiation was used to decompose the resulting phospholipid into a new product that permeabilizes the membrane. This approach was extended when Konetski and co-workers exploited photocleavage to induce pinocytosis-like behavior upon irradiation .…”

Section: Combined Liposome Demolition and Rebuildingmentioning

confidence: 99%

Demolish and Rebuild: Controlling Lipid Self-Assembly toward Triggered Release and Artificial Cells

et al. 2021

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The ability to modulate the structures of lipid membranes, predicated on our nuanced understanding of the properties that drive and alter lipid self-assembly, has opened up many exciting biological applications. In this Perspective, we focus on two endeavors in which the same principles are invoked to achieve completely opposite results. On one hand, controlled liposome decomposition enables triggered release of encapsulated cargo through the development of synthetic lipid switches that perturb lipid packing in the presence of disease-associated stimuli. In particular, recent approaches have utilized artificial lipid switches designed to undergo major conformational changes in response to a range of target conditions. On the other end of the spectrum, the ability to drive the in situ formation of lipid bilayer membranes from soluble precursors is an important component in the establishment of artificial cells. This work has culminated in chemoenzymatic strategies that enable lipid manufacturing from simple components. Herein, we describe recent advancements in these two unique undertakings that are linked by their reliance on common principles of lipid self-assembly.

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“…Cancer microenvironmental cues (such as pH gradient and reactive oxygen species [ROS] stress) [ 70 , 71 ] and stimuli (such as thermal energy, magnetism, and light) have been employed to design triggered-release liposomes [ 72 , 73 , 74 ] ( Figure 2 A). Liposomes designed to release their cargo in the intracellular cancer environment often have pH-sensitive polymers incorporated into their structure, as this enables the encapsulated drug to be released when the liposome reaches the acidic microenvironment [ 75 ].…”

Section: Current Lipid-based Nanoplatformsmentioning

confidence: 99%

“…Alternatively, thermosensitive or photo-sensitive polymers can be included in the liposomal structure to enable controlled drug release in response to a temperature change or light of a specific wavelength [ 74 , 78 ]. Thermosensitive liposomes are often composed of 1,2-dipalmitoyl-sn-glycerol-3-phosphocholine (DPPC), which can facilitate cargo release when the microenvironment approaches its phase-transition temperature [ 79 ].…”

Section: Current Lipid-based Nanoplatformsmentioning

confidence: 99%

Lipid-Based Drug Delivery Nanoplatforms for Colorectal Cancer Therapy

Yang

Merlin

2020

Nanomaterials

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Colorectal cancer (CRC) is a prevalent disease worldwide, and patients at late stages of CRC often suffer from a high mortality rate after surgery. Adjuvant chemotherapeutics (ACs) have been extensively developed to improve the survival rate of such patients, but conventionally formulated ACs inevitably distribute toxic chemotherapeutic drugs to healthy organs and thus often trigger severe side effects. CRC cells may also develop drug resistance following repeat dosing of conventional ACs, limiting their effectiveness. Given these limitations, researchers have sought to use targeted drug delivery systems (DDSs), specifically the nanotechnology-based DDSs, to deliver the ACs. As lipid-based nanoplatforms have shown the potential to improve the efficacy and safety of various cytotoxic drugs (such as paclitaxel and vincristine) in the clinical treatment of gastric cancer and leukemia, the preclinical progress of lipid-based nanoplatforms has attracted increasing interest. The lipid-based nanoplatforms might be the most promising DDSs to succeed in entering a clinical trial for CRC treatment. This review will briefly examine the history of preclinical research on lipid-based nanoplatforms, summarize the current progress, and discuss the challenges and prospects of using such approaches in the treatment of CRC.

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Photo-responsive liposomes composed of spiropyran-containing triazole-phosphatidylcholine: investigation of merocyanine-stacking effects on liposome–fiber assembly-transition

Abstract: Assembly-transition study of photo-responsive liposomes composed of spiropyran-containing triazole-phosphatidylcholine (SPTPC).

Cited by 20 publications

References 48 publications

Hybrid Cerasomes Composed of Phosphatidylcholines and Silica Networks for the Construction of Vesicular Materials with Functionalized Shells

Hybrid Cerasomes Composed of Phosphatidylcholines and Silica Networks for the Construction of Vesicular Materials with Functionalized Shells

Demolish and Rebuild: Controlling Lipid Self-Assembly toward Triggered Release and Artificial Cells

Lipid-Based Drug Delivery Nanoplatforms for Colorectal Cancer Therapy

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