scholarly journals Redox-sensitive reversible self-assembly of amino acid–naphthalene diimide conjugates

2017 ◽  
Vol 7 (6) ◽  
pp. 20160099 ◽  
Author(s):  
Wathsala Liyanage ◽  
Paul W. Rubeo ◽  
Bradley L. Nilsson
Keyword(s):  
Amino Acid ◽  
Self Assembly ◽  
Functional Materials ◽  
Supramolecular Materials ◽  
Responsive Materials ◽  
Naphthalene Diimide ◽  
Reducing Conditions ◽  
Aqueous Solvent ◽  
Stimulus Responsive ◽  
Fibril Aggregates

Peptide and low molecular weight amino acid-based materials that self-assemble in response to environmental triggers are highly desirable candidates in forming functional materials with tunable biophysical properties. In this paper, we explore redox-sensitive self-assembly of cationic phenylalanine derivatives conjugated to naphthalene diimide (NDI). Self-assembly of the cationic Phe-NDI conjugates into nanofibrils was induced in aqueous solvent at high ionic strength. Under reducing conditions, these self-assembled Phe-NDI conjugate fibrils underwent a morphological change to non-fibril aggregates. Upon reoxidation, the initially observed fibrils were reformed. The study herein provides an interesting strategy to effect reversible switching of the structure of supramolecular materials that can be applied to the development of sophisticated stimulus-responsive materials.

Unique Functional Materials Derived from β-Amino Acid Oligomers

2017 ◽  
Vol 70 (2) ◽  
pp. 126 ◽  
Author(s):  
Mark P. Del Borgo ◽  
Ketav Kulkarni ◽  
Marie-Isabel Aguilar
Keyword(s):  
Amino Acid ◽  
Drug Design ◽  
Self Assembly ◽  
Functional Materials ◽  
Bioactive Molecules ◽  
Peptide Drug ◽  
New Materials ◽  
Amino Acid Oligomers

The unique structures formed by β-amino acid oligomers, or β-peptide foldamers, have been studied for almost two decades, which has led to the discovery of several distinctive structures and bioactive molecules. Recently, this area of research has expanded from conventional peptide drug design to the formation of assemblies and nanomaterials by peptide self-assembly. The unique structures formed by β-peptides give rise to a set of new materials with altered properties that differ from conventional peptide-based materials; such new materials may be useful in several bio- and nanomaterial applications.

Assembly of amino acid containing naphthalene diimide-based molecules: the role of intervening amide groups in self-assembly, gelation, optical and semiconducting properties

Soft Matter ◽  
2019 ◽  
Vol 15 (14) ◽  
pp. 3018-3026 ◽  
Author(s):  
Nibedita Nandi ◽  
Kousik Gayen ◽  
Arindam Banerjee
Keyword(s):  
Amino Acid ◽  
Self Assembly ◽  
Naphthalene Diimide ◽  
Semiconducting Properties

Two isomeric amino-acid containing naphthalene diimide based molecules differ in their respective assembly and the intervening amide groups plays an important role in gelation, optical and semiconducting nature of these molecules.

Amino Acid Functional Polymers: Biomimetic Polymer Design Enabling Catalysis, Chiral Materials, and Drug Delivery

2016 ◽  
Vol 69 (7) ◽  
pp. 705 ◽  
Author(s):  
Emma R. L. Brisson ◽  
Zeyun Xiao ◽  
Luke A. Connal
Keyword(s):  
Drug Delivery ◽  
Amino Acids ◽  
Amino Acid ◽  
Self Assembly ◽  
Building Blocks ◽  
Functional Polymers ◽  
Responsive Materials ◽  
Biomimetic Polymer ◽  
Tunable Optical Properties ◽  
Natural Building

Amino acids are the natural building blocks for the world around us. Highly functional, these small molecules have unique catalytic properties, chirality, and biocompatibility. Imparting these properties to surfaces and other macromolecules is highly sought after and represents a fast-growing field. Polymers functionalized with amino acids in the side chains have tunable optical properties, pH responsiveness, biocompatibility, structure and self-assembly properties. Herein, we review the synthesis of amino acid functional polymers, discuss manipulation of available strategies to achieve the desired responsive materials, and summarize some exciting applications in catalysis, chiral particles, and drug delivery.

Rational Design of Multiple-Stimulus-Responsive Materials via Supramolecular Self-Assembly

2015 ◽  
Vol 119 (28) ◽  
pp. 16349-16357 ◽  
Author(s):  
Yanjun Gong ◽  
Tiliu Jiao ◽  
Qiongzheng Hu ◽  
Ni Cheng ◽  
Wenwen Xu ◽  
...  
Keyword(s):  
Self Assembly ◽  
Rational Design ◽  
Responsive Materials ◽  
Multiple Stimulus ◽  
Stimulus Responsive

scholarly journals Characterizing and controlling nanoscale self-assembly of suckerin-12

2020 ◽  
Author(s):  
Jasmine M. Hershewe ◽  
William D. Wiseman ◽  
James E. Kath ◽  
Chelsea C. Buck ◽  
Maneesh K. Gupta ◽  
...  
Keyword(s):  
Amino Acid ◽  
Self Assembly ◽  
Protein Concentration ◽  
Functional Materials ◽  
Structural Proteins ◽  
Size Distributions ◽  
Naturally Occurring ◽  
Canonical Amino Acid ◽  
Supramolecular Networks ◽  
Fine Tune

AbstractStructural proteins such as the “suckerins” present promising avenues for fabricating functional materials. Suckerins are a family of naturally occurring block copolymer-type proteins that comprise the sucker ring teeth of cephalopods and are known to self-assemble into supramolecular networks of nanoconfined β-sheets. Here, we report characterization and controllable, nanoscale self-assembly of suckerin-12 (S12). We characterize impacts of salt, pH, and protein concentration on S12 solubility, secondary structure, and self-assembly. In doing so, we identify conditions for fabricating ~100 nm nanoassemblies (NAs) with narrow size distributions. Finally, by installing a non-canonical amino acid (ncAA) into S12, we demonstrate the assembly of NAs that are covalently conjugated with a hydrophobic fluorophore, and the ability to change self-assembly and β-sheet content by PEGylation. This work presents new insights into the biochemistry of suckerin-12 and demonstrates how ncAAs can be used to expedite and fine-tune the design of protein materials.

scholarly journals Self-Assembly of Aromatic Amino Acid Enantiomers into Supramolecular Materials of High Rigidity

ACS Nano ◽  
2020 ◽  
Vol 14 (2) ◽  
pp. 1694-1706 ◽  
Author(s):  
Santu Bera ◽  
Bin Xue ◽  
Pavel Rehak ◽  
Guy Jacoby ◽  
Wei Ji ◽  
...  
Keyword(s):  
Amino Acid ◽  
Self Assembly ◽  
Aromatic Amino Acid ◽  
Supramolecular Materials ◽  
Amino Acid Enantiomers ◽  
High Rigidity

scholarly journals Self-assembly of amino acids toward functional biomaterials

2021 ◽  
Vol 12 ◽  
pp. 1140-1150
Author(s):  
Huan Ren ◽  
Lifang Wu ◽  
Lina Tan ◽  
Yanni Bao ◽  
Yuchen Ma ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Self Assembly ◽  
Functional Materials ◽  
Building Blocks ◽  
The Self ◽  
Self Assembled ◽  
Functional Biomaterials ◽  
Proteins And Peptides

Biomolecules, such as proteins and peptides, can be self-assembled. They are widely distributed, easy to obtain, and biocompatible. However, the self-assembly of proteins and peptides has disadvantages, such as difficulty in obtaining high quantities of materials, high cost, polydispersity, and purification limitations. The difficulties in using proteins and peptides as functional materials make it more complicate to arrange assembled nanostructures at both microscopic and macroscopic scales. Amino acids, as the smallest constituent of proteins and the smallest constituent in the bottom-up approach, are the smallest building blocks that can be self-assembled. The self-assembly of single amino acids has the advantages of low synthesis cost, simple modeling, excellent biocompatibility and biodegradability in vivo. In addition, amino acids can be assembled with other components to meet multiple scientific needs. However, using these simple building blocks to design attractive materials remains a challenge due to the simplicity of the amino acids. Most of the review articles about self-assembly focus on large molecules, such as peptides and proteins. The preparation of complicated materials by self-assembly of amino acids has not yet been evaluated. Therefore, it is of great significance to systematically summarize the literature of amino acid self-assembly. This article reviews the recent advances in amino acid self-assembly regarding amino acid self-assembly, functional amino acid self-assembly, amino acid coordination self-assembly, and amino acid regulatory functional molecule self-assembly.

Single Amino Acid Based Self-Assemblies of Cysteine and Methionine

2018 ◽  
Author(s):  
Nidhi Gour ◽  
Bharti Koshti ◽  
Chandra Kanth P. ◽  
Dhruvi Shah ◽  
Vivek Shinh Kshatriya ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Self Assembly ◽  
Aromatic Amino Acids ◽  
Neutral Condition ◽  
Single Amino Acid ◽  
Binding Assays ◽  
Human Neuroblastoma ◽  
Cytotoxicity Assays ◽  
First Time

We report for the very first time self-assembly of Cysteine and Methionine to discrenible strucutres under neutral condition. To get insights into the structure formation, thioflavin T and Congo red binding assays were done which revealed that aggregates may not have amyloid like characteristics. The nature of interactions which lead to such self-assemblies was purported by coincubating assemblies in urea and mercaptoethanol. Further interaction of aggregates with short amyloidogenic dipeptide diphenylalanine (FF) was assessed. While cysteine aggregates completely disrupted FF fibres, methionine albeit triggered fibrillation. The cytotoxicity assays of cysteine and methionine structures were performed on Human Neuroblastoma IMR-32 cells which suggested that aggregates are not cytotoxic in nature and thus, may not have amyloid like etiology. The results presented in the manuscript are striking, since to the best of our knowledge,this is the first report which demonstrates that even non-aromatic amino acids (cysteine and methionine) can undergo spontaneous self-assembly to form ordered aggregates.

Self-assembling behaviour of a modified aromatic amino acid in competitive medium

Soft Matter ◽  
2020 ◽  
Vol 16 (28) ◽  
pp. 6599-6607 ◽  
Author(s):  
Pijush Singh ◽  
Souvik Misra ◽  
Nayim Sepay ◽  
Sanjoy Mondal ◽  
Debes Ray ◽  
...  
Keyword(s):  
Amino Acid ◽  
Self Assembly ◽  
Aromatic Amino Acid ◽  
Photophysical Properties ◽  
Solvent Mixture ◽  
The Self ◽  
Solvent Ratio ◽  
Self Assembling

The self-assembly and photophysical properties of 4-nitrophenylalanine (4NP) are changed with the alteration of solvent and final self-assembly state of 4NP in competitive solvent mixture and are dictated by the solvent ratio.

scholarly journals Diketopiperazine Gels: New Horizons from the Self-Assembly of Cyclic Dipeptides

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3376
Author(s):  
Marco Scarel ◽  
Silvia Marchesan
Keyword(s):  
Drug Discovery ◽  
Enzymatic Hydrolysis ◽  
Self Assembly ◽  
Biological Activities ◽  
Functional Materials ◽  
The Self ◽  
Cyclic Dipeptides ◽  
New Horizons ◽  
Concise Review

Cyclodipeptides (CDPs) or 2,5-diketopiperazines (DKPs) can exert a variety of biological activities and display pronounced resistance against enzymatic hydrolysis as well as a propensity towards self-assembly into gels, relative to the linear-dipeptide counterparts. They have attracted great interest in a variety of fields spanning from functional materials to drug discovery. This concise review will analyze the latest advancements in their synthesis, self-assembly into gels, and their more innovative applications.

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