scholarly journals Fine-Tuning of Molecular Structures to Generate Carbohydrate Based Super Gelators and Their Applications for Drug Delivery and Dye Absorption

Gels ◽  
2021 ◽  
Vol 7 (3) ◽  
pp. 134
Author(s):  
Jonathan Bietsch ◽  
Mary Olson ◽  
Guijun Wang
Keyword(s):  
Drug Delivery ◽  
Aqueous Solutions ◽  
Organic Solvents ◽  
Self Assembly ◽  
Variable Temperature ◽  
Molecular Structures ◽  
Fine Tuning ◽  
Assembly Mechanism ◽  
Amide Derivatives ◽  
Structural Connection

Carbohydrate-based low molecular weight gelators (LMWGs) exhibit many desirable properties making them useful in various fields including applications as drug delivery carriers. In order to further understand the structural connection to gelation properties, especially the influence of halide substitutions, we have designed and synthesized a series of para-chlorobenzylidene acetal protected D-glucosamine amide derivatives. Fifteen different amides were synthesized, and their self-assembling properties were assessed in multiple organic solvents, as well as mixtures of organic solvents with water. All derivatives were found to be gelators for at least one solvent and majority formed gels in multiple solvents at concentrations lower than 2 wt%. A few derivatives rendered remarkably stable gels in aqueous solutions at concentrations below 0.1 wt%. The benzamide 13 formed gels in water and in EtOH/H2O (v/v 1:2) at 0.36 mg/mL. The gels were characterized using optical microscopy and atomic force microscopy, and the self-assembly mechanism was probed using variable temperature 1H-NMR spectroscopy. Gel extrusion studies using H2O/DMSO gels successfully printed lines of gels on glass slides, which retained viscoelasticity based on rheology. Gels formed by the benzamide 13 were used for encapsulation and the controlled release of chloramphenicol and naproxen, as well as for dye removal for toluidine blue aqueous solutions.

scholarly journals Self-Assembly Mechanism of a Peptide-Based Drug Delivery Vehicle

ACS Omega ◽  
2018 ◽  
Vol 3 (3) ◽  
pp. 3143-3155 ◽  
Author(s):  
Gopal Pandit ◽  
Karabi Roy ◽  
Umang Agarwal ◽  
Sunanda Chatterjee
Keyword(s):  
Drug Delivery ◽  
Self Assembly ◽  
Delivery Vehicle ◽  
Drug Delivery Vehicle ◽  
Assembly Mechanism

Norbornene-Functionalised Chitosan Hydrogels and Microgels via an Unprecedented Photo-Initiated Self-Assembly for Potential Biomedical Applications

2020 ◽  
Author(s):  
Sarah michel ◽  
Alice Kilner ◽  
Jean-Charles Eloi ◽  
Sarah E rogers ◽  
Wuge H. Briscoe ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Self Assembly ◽  
Biomedical Applications ◽  
Hydrophobic Interactions ◽  
Gelation Mechanism ◽  
Swelling Behaviour ◽  
Assembly Mechanism ◽  
Significant Toxicity ◽  
Chitosan Hydrogels

<p><br></p><p> Access to biocompatible self-assembled gels and microgels is of great interests for a variety of biological applications from tissue engineering to drug delivery. Here, the facile synthesis of supramolecular hydrogels of norbornene (nb)-functionalised chitosan (CS-nb) via UV-triggered self-assembly in the presence of Irgacure 2959 (IRG) is reported. The <i>in vitro </i>stable hydrogels are injectable and showed pH-responsive swelling behaviour, while their structure and mechanical properties could be tuned by tailoring the stereochemistry of the norbornene derivative (e.g. <i>endo</i>- or -<i>exo</i>). Interestingly, unlike other nb-type hydrogels, the gels possess nanopores within their structure, which might lead to potential drug delivery applications. A gelation mechanism was proposed based on hydrophobic interactions following the combination of IRG on norbornene, as supported by 1H NMR. This self-assembly mechanism was used to access microgels of size 100-150 nm which could be further functionalised and showed no significant toxicity to human dermofibroblast cells. </p>

scholarly journals Nanostructures and Self-Assembly of Organogels via Benzimidazole/Benzothiazole Imide Derivatives with Different Alkyl Substituent Chains

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Xihai Shen ◽  
Tifeng Jiao ◽  
Qingrui Zhang ◽  
Haiying Guo ◽  
Yaopeng Lv ◽  
...  
Keyword(s):  
Organic Solvents ◽  
Self Assembly ◽  
Bond Formation ◽  
Alkyl Substituent ◽  
Soft Materials ◽  
Molecular Structures ◽  
Spectral Studies ◽  
Hydrophobic Force ◽  
Alkyl Chains ◽  
Gelation Behavior

New benzimidazole/benzothiazole imide derivatives with different alkyl substituent chains were designed and synthesized. Their gelation behaviors in 22 solvents were tested as novel low-molecular-mass organic gelators. The test showed that the alkyl substituent chains and headgroups of benzimidazole/benzothiazole residues in gelators played a crucial role in the gelation behavior of all compounds in various organic solvents. More alkyl chains in molecular skeletons in present gelators are favorable for the gelation of organic solvents. SEM and AFM observations revealed that the gelator molecules self-assemble into different aggregates from wrinkle, lamella and belt to dot with change of solvents. Spectral studies indicated that there existed different H-bond formation between imide groups and hydrophobic force of alkyl substituent chains in molecular skeletons. The present work may give some insights into design and character of new organogelators and soft materials with special molecular structures.

scholarly journals Norbornene-Functionalised Chitosan Hydrogels and Microgels via an Unprecedented Photo-Initiated Self-Assembly for Potential Biomedical Applications

2020 ◽  
Author(s):  
Sarah michel ◽  
Alice Kilner ◽  
Jean-Charles Eloi ◽  
Sarah E rogers ◽  
Wuge H. Briscoe ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Self Assembly ◽  
Biomedical Applications ◽  
Hydrophobic Interactions ◽  
Gelation Mechanism ◽  
Swelling Behaviour ◽  
Assembly Mechanism ◽  
Significant Toxicity ◽  
Chitosan Hydrogels

<p><br></p><p> Access to biocompatible self-assembled gels and microgels is of great interests for a variety of biological applications from tissue engineering to drug delivery. Here, the facile synthesis of supramolecular hydrogels of norbornene (nb)-functionalised chitosan (CS-nb) via UV-triggered self-assembly in the presence of Irgacure 2959 (IRG) is reported. The <i>in vitro </i>stable hydrogels are injectable and showed pH-responsive swelling behaviour, while their structure and mechanical properties could be tuned by tailoring the stereochemistry of the norbornene derivative (e.g. <i>endo</i>- or -<i>exo</i>). Interestingly, unlike other nb-type hydrogels, the gels possess nanopores within their structure, which might lead to potential drug delivery applications. A gelation mechanism was proposed based on hydrophobic interactions following the combination of IRG on norbornene, as supported by 1H NMR. This self-assembly mechanism was used to access microgels of size 100-150 nm which could be further functionalised and showed no significant toxicity to human dermofibroblast cells. </p>

scholarly journals Structure Effect of Diacid/Triacid on Self-Assembly of Binary Organogels Based on Glutamic Acid Amino Derivative

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Jinming Dai ◽  
Wei Hong ◽  
Youbo Di
Keyword(s):  
Citric Acid ◽  
Glutamic Acid ◽  
Organic Solvents ◽  
Self Assembly ◽  
Sebacic Acid ◽  
Amino Derivative ◽  
Molecular Structures ◽  
Diethyl Ester ◽  
Spectral Studies ◽  
Morphological Studies

The gelation behaviors of binary organogels composed of N-(4-aminobenzoyl)-L-glutamic acid diethyl ester with sebacic acid and citric acid in various organic solvents were designed and investigated. Their gelation behaviors in 20 solvents were tested as new binary organic gelators. It showed that the molecular structures and organic solvents have played a crucial role in the gelation behavior of all gelator mixtures. More carboxyl groups in molecular skeletons in the present mixture gelators are unfavorable for the gelation of organic solvents. The mixture containing sebacic acid can form 5 kinds of organogels, while another mixture containing citric acid can only form 3 kinds of organogels in different solvents. Morphological studies revealed that the gelator molecules self-assemble into different aggregates from wrinkle and belt to fiber with change of solvents. Spectral studies indicated that there existed different H-bond formations and hydrophobic forces, depending on solvents and molecular structures. The as-prepared nanomaterials have wide perspectives in nanoscience and functional textile materials with special microstructures.

scholarly journals Supramolecular gel formation regulated by water content in organic solvents: self-assembly mechanism and biomedical applications

RSC Advances ◽  
2021 ◽  
Vol 11 (19) ◽  
pp. 11519-11528
Author(s):  
Lieqiang Liao ◽  
Xinjian Jia ◽  
Haoxiang Lou ◽  
Jinlian Zhong ◽  
Huijin Liu ◽  
...  
Keyword(s):  
Drug Release ◽  
Water Content ◽  
Organic Solvents ◽  
Self Assembly ◽  
Biomedical Applications ◽  
Gel Formation ◽  
Cell Cultivation ◽  
Supramolecular Gel ◽  
Assembly Mechanism ◽  
Crystal Transition

Supramolecular hydrogels with solution–gel–crystal transition, pH- and thermo-reversible characteristics were constructed via a solvent-mediated strategy and applied to cell cultivation and controllable drug release.

scholarly journals New Insights on the Self-Assembly of Bio-sourced Block Copolymer MH-b-PS in Aqueous Solutions: Nanocorals, Cubosomes & Nanocubes

2021 ◽  
Author(s):  
Yomen Atassi ◽  
Redouane Borsali
Keyword(s):  
Aqueous Solution ◽  
Block Copolymer ◽  
Aqueous Solutions ◽  
Self Assembly ◽  
Room Temperature ◽  
Linear Structure ◽  
The Self ◽  
Fine Tuning ◽  
Experimental Parameters ◽  
First Time

Polymer self-assembly in solution still constitutes a simple methodology for the preparation of elegant yet sophisticated nanomaterials. This work aims at presenting how the fine tuning of the experimental parameters of the nanoprecipitation process can lead to a variety of novel morphologies ranging from nanocorals through cubosomes to nanocubes. A carbohydrate dibloc copolymer with a simple and linear structure MH1.2k-b-PS2.3 has been used as a model to illustrate the formation of these new self-assemblies. This is the first time that nanocube morphology has been generated using this type of bio-sourced co-polymer in aqueous solution and at room temperature.

scholarly journals Reconfiguring confined magnetic colloids with tunable fluid transport behavior

2020 ◽  
Author(s):  
Zhizhi Sheng ◽  
Mengchuang Zhang ◽  
Jing Liu ◽  
Paolo Malgaretti ◽  
Jianyu Li ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Drug Delivery ◽  
Self Assembly ◽  
Fluid Transport ◽  
Materials Science ◽  
Colloidal Suspension ◽  
Fine Tuning ◽  
Collective Dynamics ◽  
Theoretical Investigations ◽  
Magnetic Colloids

Abstract Collective dynamics of confined colloids is crucial in diverse scenarios such as self-assembly and phase behavior in materials science, microrobot swarms for drug delivery, and microfluidic control. Yet, fine-tuning the dynamics of colloids in microscale confined spaces is still a formidable task due to the complexity of the dynamics of colloidal suspension and to the lack of methodology to probe colloids in confinement. Here, we show that the collective dynamics of confined magnetic colloids can be finely tuned by external magnetic fields. In particular, the mechanical properties of the confined colloidal suspension can be probed in real-time and this strategy can be also used to tune microscale fluid transport. Our experimental and theoretical investigations reveal that the collective configuration characterized by the colloidal entropy is controlled by the colloidal concentration, confining ratio, and external field strength and direction. Indeed, our results show that mechanical properties of the colloidal suspension as well as the transport of the solvent in microfluidic devices can be controlled upon tuning the entropy of the colloidal suspension. Our approach opens new avenues for the design and applications of drug delivery, microfluidic logic, dynamic fluid control, chemical reaction, and beyond.

Synthetic meroterpenoids based on terpene alcohols: synthesis, self-assembly, and membranotropic properties

2020 ◽  
Vol 63 (7) ◽  
pp. 11-18
Author(s):  
Alan A. Akhmedov ◽  
◽  
Dmitriy N. Shurpik ◽  
Zainab R. Latypova ◽  
Rustem R. Gamirov ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Aqueous Solutions ◽  
Self Assembly ◽  
Lipid Membrane ◽  
Bilayer Membrane ◽  
Water Soluble ◽  
Polar Component ◽  
Terpene Alcohols ◽  
Archaeal Lipids ◽  
Pharmacologically Active

Currently, targeted drug delivery is of great interest in the field of medicine. The study of compounds capable of permeating cell membranes is a major problem in this area. The synthesis of pharmacologically active compounds includes the formation of structures with various combinations of pharmacophore fragments and properties. Amphiphilic compounds tend to exhibit membranotropic activity. From this point of view, the modification of natural products, especially terpenoids, is of particular interest. Terpenoid structures are used as membrane anchors in the development of modulators for membrane-integrated proteins or structures for creating nanocontainers. In this paper we synthesized a number of water-soluble amphiphilic meroterpenoids containing a charged pyridinium fragment on the basis of acyclic terpene alcohols. Residue of terpene alcohols – geraniol (monoterpenol), farnesol (sesquiterpenol), and phytol (diterpenol) – were used as the hydrophobic part of the amphiphilic structure. Linear acyclic alcohols are commercially available reagents and have a structure similar to that of polyprenols in archaeal lipids, which made it possible to obtain synthetic lipid-like meroterpenoids capable of self-assembly in aqueous solutions. The charged pyridinium fragment, which is included in numerous natural compounds, was of interest as a polar component. This meroterpenoids are synthetic analogs of archaeal lipids. It was shown that the studied meroterpenoids form nanosized aggregates in aqueous solutions by the method of dynamic light scattering and the Doppler microelectrophoresis method. Turbidimetric titration on model dipalmitoylphosphatidylcholine vesicles revealed that the synthesized compounds are embedded into the bilayer membrane without destroying it. Self-assembled aggregates of synthesized compounds in water can find application for drug delivery – in the creation of nanocontainers containing membrane anchors capable of interacting with the outer surface of the cell (lipid membrane).

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