Creation of Functional Giant Vesicles through Approaches of Synthetic Chemistry

The promising aspects of iron in synthetic chemistry are being explored for three-four decades as a green and eco-friendly alternative to late transition metals. This present review unveils these rich iron-chemistry towards different transformations.

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pH-Tolerant giant vesicles composed of cationic lipids with imine linkages and oleic acids

RSC Advances ◽

10.1039/d0ra06822e ◽

2020 ◽

Vol 10 (56) ◽

pp. 34247-34253

Author(s):

Daichi Sawada ◽

Ayana Hirono ◽

Kouichi Asakura ◽

Taisuke Banno

Keyword(s):

Oleic Acid ◽

Cationic Lipids ◽

Giant Vesicles ◽

Acidic Conditions

Giant vesicles composed of cationic lipids having an imine linkage and oleic acid were stable at strong acidic conditions.

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Giant Vesicles Produced with Phosphatidylcholines (PCs) and Phosphatidylethanolamines (PEs) by Water-in-Oil Inverted Emulsions

Life ◽

10.3390/life11030223 ◽

2021 ◽

Vol 11 (3) ◽

pp. 223

Author(s):

Boying Xu ◽

Jinquan Ding ◽

Jian Xu ◽

Tetsuya Yomo

Keyword(s):

Encapsulation Efficiency ◽

Analytical Study ◽

Giant Vesicles ◽

Imaging Flow Cytometry ◽

Artificial Cell ◽

Transfer Method ◽

Long Term Preservation ◽

Natural Cell ◽

Cell Construction

(1) Background: giant vesicles (GVs) are widely employed as models for studying physicochemical properties of bio-membranes and artificial cell construction due to their similarities to natural cell membranes. Considering the critical roles of GVs, various methods have been developed to prepare them. Notably, the water-in-oil (w/o) inverted emulsion-transfer method is reported to be the most promising, owning to the relatively higher productivity and better encapsulation efficiency of biomolecules. Previously, we successfully established an improved approach to acquire detailed information of 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC)-derived GVs with imaging flow cytometry (IFC); (2) Methods: we prepared GVs with different lipid compositions, including phosphatidylcholines (PCs), phosphatidylethanolamines (PEs), and PC/PE mixtures by w/o inverted emulsion methods. We comprehensively compared the yield, purity, size, and encapsulation efficiency of the resulting vesicles; (3) Results: the relatively higher productivities of GVs could be obtained from POPC, 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dilauroyl-sn-glycero-3-phosphoethanolamine (DLPE), DOPC: DLPE (7:3), and POPC: DLPE (6:4) pools. Furthermore, we also demonstrate that these GVs are stable during long term preservation in 4 °C. (4) Conclusions: our results will be useful for the analytical study of GVs and GV-based applications.

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Spontaneous Formation of Giant Phospholipid Vesicles

Zeitschrift für Naturforschung C ◽

10.1515/znc-1988-11-1222 ◽

1988 ◽

Vol 43 (11-12) ◽

pp. 938-947 ◽

Cited By ~ 2

Author(s):

Rolf-M. Servuss

Keyword(s):

Aqueous Solution ◽

Light Microscopy ◽

Fluid Phase ◽

Significant Part ◽

Phospholipid Vesicles ◽

Electrostatic Repulsion ◽

Giant Vesicles ◽

Spontaneous Formation

The spontaneous formation of giant (diameter > 10 μm) vesicles from a number of phospholipids in excess aqueous solution has been studied by light-microscopy. Electrically neutral as well as charged phospholipids swell to form giant vesicles only if the lipids are in the fluid phase. This shows that electrostatic repulsion alone cannot explain the spontaneous formation of giant vesicles. The results confirm the suggestion that steric forces between extended membranes play a significant part in this process.

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Oxidative cyclo-rearrangement of helicenes into chiral nanographenes

Nature Communications ◽

10.1038/s41467-021-22992-6 ◽

2021 ◽

Vol 12 (1) ◽

Author(s):

Chengshuo Shen ◽

Guoli Zhang ◽

Yongle Ding ◽

Na Yang ◽

Fuwei Gan ◽

...

Keyword(s):

Functional Materials ◽

Optical Devices ◽

Oxidative Cyclization ◽

Synthetic Chemistry ◽

Aromatic Rings ◽

Cyclization Reactions ◽

Rearrangement Reaction ◽

Skeletal Reconstruction ◽

Gradual Release

AbstractNanographenes are emerging as a distinctive class of functional materials for electronic and optical devices. It is of remarkable significance to enrich the precise synthetic chemistry for these molecules. Herein, we develop a facile strategy to recompose helicenes into chiral nanographenes through a unique oxidative cyclo-rearrangement reaction. Helicenes with 7~9 ortho-fused aromatic rings are firstly oxidized and cyclized, and subsequently rearranged into nanographenes with an unsymmetrical helicoid shape through sequential 1,2-migrations. Such skeletal reconstruction is virtually driven by the gradual release of the strain of the highly distorted helicene skeleton. Importantly, the chirality of the helicene precursor can be integrally inherited by the resulting nanographene. Thus, a series of chiral nanographenes are prepared from a variety of carbohelicenes and heterohelicenes. Moreover, such cyclo-rearrangement reaction can be sequentially or simultaneously associated with conventional oxidative cyclization reactions to ulteriorly enrich the geometry diversity of nanographenes, aiming at innovative properties.

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Photochemically induced cyclic morphological dynamics via degradation of autonomously produced, self-assembled polymer vesicles

Communications Chemistry ◽

10.1038/s42004-021-00464-8 ◽

2021 ◽

Vol 4 (1) ◽

Author(s):

Chenyu Lin ◽

Sai Krishna Katla ◽

Juan Pérez-Mercader

Keyword(s):

Morphological Evolution ◽

Chemical Degradation ◽

Chemical Mechanism ◽

Giant Vesicles ◽

Water Influx ◽

Physico Chemical ◽

Osmotic Water ◽

Periodic Growth ◽

Oxygen Conditions ◽

Self Assembled

AbstractAutonomous and out-of-equilibrium vesicles synthesised from small molecules in a homogeneous aqueous medium are an emerging class of dynamically self-assembled systems with considerable potential for engineering natural life mimics. Here we report on the physico-chemical mechanism behind a dynamic morphological evolution process through which self-assembled polymeric structures autonomously booted from a homogeneous mixture, evolve from micelles to giant vesicles accompanied by periodic growth and implosion cycles when exposed to oxygen under light irradiation. The system however formed nano-objects or gelation under poor oxygen conditions or when heated. We determined the cause to be photoinduced chemical degradation within hydrated polymer cores inducing osmotic water influx and the subsequent morphological dynamics. The process also led to an increase in the population of polymeric objects through system self-replication. This study offers a new path toward the design of chemically self-assembled systems and their potential application in autonomous material artificial simulation of living systems.

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Balancing skeleton and functional groups in total syntheses of complex natural products: a case study of tigliane, daphnane and ingenane diterpenoids

Natural Product Reports ◽

10.1039/d0np00086h ◽

2021 ◽

Author(s):

Zhi Liu ◽

Zhengwei Ding† ◽

Kai Chen ◽

Ming Xu ◽

Tao Yu ◽

...

Keyword(s):

Natural Products ◽

Functional Groups ◽

Synthetic Chemistry ◽

Total Syntheses ◽

Strategic Balance

The fruitful advancement in synthetic chemistry of the title families of complex diterpenes has stimulated and enjoyed strategic balance between building the skeletons and installing the functional groups.

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