Single‐Layered Chiral Nanosheets with Dual Chiral Void Spaces for Highly Efficient Enantiomer Absorption

Feng, Xiaopeng; Shen, Bowen; Sun, Bo; Kim, Jehan; Liu, Xin; Lee, Myongsoo

doi:10.1002/ange.202003807

Cited by 9 publications

(3 citation statements)

References 45 publications

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“…The tetra-branched dendrimer was synthesized in a stepwise manner, initially by the etherification of 3-chloro-2-chloromethyl-1-propene with linear tri-ethylene glycol monomethyl ether, followed by hydroboration to obtain a di-branched chain. The resulting hydroxy-terminated di-branched chain was subjected to repeated reactions to obtain a tetra-branched dendrimer, esterified with 13cRA to yield 13cRA-D [26][27][28][29]. The obtained product was characterized by 1 H-NMR and was in full agreement with the expected chemical structure.…”

Section: Chemical Synthesis Of 13cra-dmentioning

confidence: 76%

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Dendrimer-conjugated isotretinoin for controlled transdermal drug delivery

Zhao,

Zhou,

et al. 2023

J Nanobiotechnol

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Background In the present study, we aimed to develop a novel isotretinoin delivery model for treating skin diseases, revealing its potential advantages in drug delivery and targeted therapy. Using a self-assembly strategy, we grafted a dendrimer, based on a well-defined branched structure for nanomedical devices, with a well-defined nanoarchitecture, yielding spherical, highly homogeneous molecules with multiple surface functionalities. Accordingly, a self-assembled dendrimer-conjugated system was developed to achieve the transdermal delivery of isotretinoin (13cRA-D). Results Herein, 13cRA-D showed remarkable controlled release, characterized by slow release in normal tissues but accelerated release in tissues with low pH, such as sites of inflammation. These release characteristics could abrogate the nonteratogenic side effects of isotretinoin and allow efficient skin permeation. Moreover, 13cRA-D exhibited high therapeutic efficacy in acne models. Based on in vitro and in vivo experimental results, 13cRA-D afforded better skin penetration than isotretinoin and allowed lesion targeting. Additionally, 13cRA-D induced minimal skin irritation. Conclusion Our findings suggest that 13cRA-D is a safe and effective isotretinoin formulation for treating patients with skin disorders. Graphical Abstract

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Section: Chemical Synthesis Of 13cra-dmentioning

confidence: 76%

“…Imiquimod cream was purchased from Sichuan Mingxin Pharmaceutical (Chengdu, China). The hydrophilic oligoether dendrimer was synthesized as reported previously [26][27][28][29].…”

Section: Materials and Reagentsmentioning

confidence: 99%

Dendrimer-conjugated isotretinoin for controlled transdermal drug delivery

Zhao,

Zhou,

et al. 2023

J Nanobiotechnol

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“…Considering the parallel arrangements of the helical fibers, the void spaces formed between the 2D fiber arrangements are chiral, which discriminate one enantiomer from racemic mixture solution. Recently, we reported the formation of chiral 2D sheet structures with dual chiral void spaces by self‐assembly of rectangular‐shaped coplanar aromatic amphiphiles [24] . The chirality of the sheets is induced by a slipped‐cofacial stack of rectangular‐shaped coplanar aromatic segments with a preferred direction in clusters that are arranged laterally with up and down in‐plane packing, resulting in dual chiral void spaces.…”

Section: Introductionmentioning

confidence: 99%

Spontaneous Chirality Induction in the Assembly of a Single Layer 2D Network with Switchable Pores

et al. 2023

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Although two-dimensional (2D) chiral sheet structures are attractive because of their unique chemical and physical properties, single layer 2D chiral network structures with switchable pore interior remain elusive. Here we report spontaneous chirality induction in a single layer 2D network structure formed from the self-assembly of tetrapod azobenzene molecules. The chirality induction arises from multiple sublayers slipped in a preferred direction in which the sublayer consists of unidentical molecular arrangements in the in-plane a and b directions, breaking both the plane of symmetry and inversion symmetry. The protruded azobenzene units in the pore interior can be selectively isomerized upon UV irradiation, resulting in a reversible deformation of the chiral pores while maintaining the 2D frameworks. The chiral network can thus selectively entrap one enantiomer from a racemic solution with near perfect enantioselectivity, and then release it upon UV irradiation.

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Handedness Inversion of Chiral 3‐Aminophenol Formaldehyde Resin Nanotubes Mediated by Metal Coordination

et al. 2021

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Precise adjustment of microstructure and handedness of chiral nanomaterials is important to regulate their properties and performance. Herein, helical 3‐aminophenol formaldehyde resin (APF) nanotubes and corresponding carbonaceous nanotubes with controllable handedness and optical activity were obtained via an external metal ion‐mediated supramolecular co‐templating method in an enantiomerically pure template system, in which an appropriate amount of Mn2+ (Co2+ or Ni2+) with moderate coordination abilities can reverse the spatial arrangement of the phenylglycine‐based amphiphilic template molecules through metal coordination. Different stacking modes of coordination complexes in disparate metal ion systems lead to diverse helical senses (diameter and pitch) of the obtained helical APF. In addition, this coordination mode of metal intervention can be applied to other amine‐based helical polymer synthesis systems, which paves the way for the design of high‐quality chiral nanomaterials with satisfactory physical parameters and properties.

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Single‐Layered Chiral Nanosheets with Dual Chiral Void Spaces for Highly Efficient Enantiomer Absorption

Cited by 9 publications

References 45 publications

Dendrimer-conjugated isotretinoin for controlled transdermal drug delivery

Dendrimer-conjugated isotretinoin for controlled transdermal drug delivery

Spontaneous Chirality Induction in the Assembly of a Single Layer 2D Network with Switchable Pores

Handedness Inversion of Chiral 3‐Aminophenol Formaldehyde Resin Nanotubes Mediated by Metal Coordination

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