Self-assembly of supramolecular chemoenzymatic poly-L-phenylalanine

Published on Mar 9, 2021in Polymer Chemistry5.342
· DOI :10.1039/D0PY01659D
Alejandra Romero , Alejandra Romero-Montero3
Estimated H-index: 3
+ 2 AuthorsMiquel Gimeno18
Estimated H-index: 18
Source
Abstract
The self-assembly behavior of chemoenzymatic high molecular weight (ca. 30 000 Da) poly-L-phenylalanine (ePLP) and the nano-morphologies thereof are investigated. Interestingly, this supramolecular ePLP changes from a non-ordered secondary structure when solubilized in water to an α-helix with the addition of only 1 vol% HFIP co-solvent, and at a relatively low concentration (0.5 mg mL−1). The results also indicate a temperature-dependent structural stabilization, wherein the self-assembly process is mainly governed by hydrogen bonding. The analyses evidence self-assembly under controlled conditions to obtain nanotubes with an average diameter of 0.21 ± 0.04 μm, and above 100 μm length. Microbeam synchrotron radiation infrared (SRIR) spectroscopy demonstrates parallel orientations of the amide moieties in the α-helical structure, which is extraordinary for this long chain ePLP. The achievement of these highly homogeneous nanotubes is relevant since previous reports only demonstrated this arrangement for end-capped F-moc-containing short oligophenylalanines. In the same way, the conductivity behaviors of the nanotubular structure remained unchanged in the range of 273–313 K demonstrating its stability from hydrogen bonds, and also, direct dielectric measurements reveal a high orientation and stabilization by intra- and intermolecular hydrogen bonds in the nanotubes. These characteristics allow drug delivery assays with tetracycline-loaded nanotubes and further applications are envisaged.
📖 Papers frequently viewed together
32 Citations
55 Citations
References56
Newest
#1Zheng Lian (Chinese People's Public Security University)H-Index: 1
#2Tianjiao Ji (Boston Children's Hospital)H-Index: 1
Last. Tianjiao Ji (Boston Children's Hospital)H-Index: 1
view all 2 authors...
Peptide is one of the most important functional motifs to construct smart drug delivery systems (DDSs). Functional peptides can be conjugated with drugs or carriers via covalent bonds, or assembled to DDSs via supramolecular forces, which enables the DDSs obtain desired functions such as targeting and/or environmental responsiveness. In this mini review, we first introduce types of functional peptides that are commonly used for constructing DDSs, and we highlight representative strategies on des...
5 CitationsSource
#1Evangelos Georgilis (CNRS: Centre national de la recherche scientifique)H-Index: 5
#2Mona Abdelghani (TU/e: Eindhoven University of Technology)H-Index: 3
Last. Elisabeth Garanger (CNRS: Centre national de la recherche scientifique)H-Index: 18
view all 7 authors...
Abstract Medicine formulations at the nanoscale, referred to as nanomedicines, have managed to overcome key challenges encountered during the development of new medical treatments and entered clinical practice, but considerable improvement in terms of local efficacy and reduced toxicity still need to be achieved. Currently, the fourth-generation of nanomedicines is being developed, employing biocompatible nanocarriers that are targeted, multifunctional, and stimuli-responsive. Proteins and polyp...
4 CitationsSource
Polypeptides are used as building blocks that assemble into polymeric hierarchical architectures with various functionalities based on their amino acid sequences. Chemoenzymatic polymerization using a protease as a catalyst allows us to synthesize peptides with various primary structures in an environmentally benign way. In this work, we performed papain-catalyzed polymerization in the presence of terminal-modifying agents to synthesize peptides modified with a functional group at their N-termin...
1 CitationsSource
#1Isabel S. Aguirre-Díaz (UNAM: National Autonomous University of Mexico)H-Index: 1
#2Carmina Montiel (UNAM: National Autonomous University of Mexico)H-Index: 8
Last. Miquel Gimeno (UNAM: National Autonomous University of Mexico)H-Index: 18
view all 6 authors...
Chemoenzymatic polypeptide synthesis offers several advantages over chemical or other biological routes, however, the use of aqueous-based media suffers from reverse hydrolysis reactions that challenge peptide chain propagation. Herein, the protease from subtilisin Carlsberg biocatalyzed the synthesis of poly-L-PheOEt, poly-L-LeuOEt, and the copolymers poly-L-PheOEt-co-L-LeuOEt from their amino acid ethyl ester substrates in a neat liquid 1,1,1,2-tetrafluoroethane solvent. The products, achieved...
2 CitationsSource
#1Anna Puiggalí-Jou (UPC: Polytechnic University of Catalonia)H-Index: 7
#2Alberto Cejudo (UPC: Polytechnic University of Catalonia)H-Index: 1
Last. Carlos Alemán (UPC: Polytechnic University of Catalonia)H-Index: 56
view all 4 authors...
Electrospun poly(e-caprolactone) (PCL) microfibers loaded with poly(3,4-ethylenedioxythiophene) nanoparticles (PEDOT NPs) and curcumin with diameter of 3.9 ± 0.7 μm have been prepared and subsequently characterized using different spectroscopic techniques, scanning electron microscopy, and atomic force microscopy. PEDOT NPs, which are mainly located inside the PCL microfibers, exhibit a diameter of 99 ± 21 nm. PEDOT- and curcumin-containing PCL microfibers behave as extracellular cell matrices, ...
15 CitationsSource
#1Minee L. Choi (UCL Institute of Neurology)H-Index: 9
#2Sonia Gandhi (UCL Institute of Neurology)H-Index: 35
: Misfolding and aggregation of the proteins amyloid-β, tau and alpha-synuclein is the predominant pathology underlying the neurodegenerative disorders, Alzheimer's and Parkinson's disease. While end stage insoluble products of aggregation have been well characterised in human and animal models of disease, accumulating evidence from biophysical, cellular and in vivo studies has shown that soluble intermediates of aggregation, or oligomers, may be the key species that mediate toxicity and underli...
49 CitationsSource
#1Carlo Diaferia (University of Naples Federico II)H-Index: 12
#2Nicole BalascoH-Index: 8
Last. Antonella Accardo (University of Naples Federico II)H-Index: 21
view all 7 authors...
: Over the years, a large number of multidisciplinary investigations has unveiled that the self-assembly of short peptides and even of individual amino acids can generate a variety of different biomaterials. In this framework, we have recently reported that polyethylene glycol (PEG) conjugates of short homopeptides, containing aromatic amino acids such as phenylalanine (Phe, F) and naphthylalanine (Nal), are able to form elongated fibrillary aggregates having interesting chemical and physical pr...
12 CitationsSource
#1Justin G. Julander (USU: Utah State University)H-Index: 33
#2Venkatraman Siddharthan (USU: Utah State University)H-Index: 20
Last. John D. Morrey (USU: Utah State University)H-Index: 51
view all 11 authors...
Zika virus (ZIKV) can cause various diseases in offspring after congenital infection. The purpose of this study was to identify disease phenotypes in pups exposed to ZIKV in utero. Female interferon-α/β, -γ receptor knockout mice (AG129) were infected intraperitoneally with ZIKV 7.5 days’ post coitus (dpc). Viral RNA, antigen and infectious virus were detected in some, but not all, maternal and fetal tissues at various times during gestation. Fetuses of infected dams had significant intrauterine...
216 CitationsSource
#1Guobin Qi (Center for Excellence in Education)H-Index: 18
#2Yu-Juan Gao (Center for Excellence in Education)H-Index: 14
Last. Hao Wang (Center for Excellence in Education)H-Index: 108
view all 4 authors...
: Peptide-based materials are one of the most important biomaterials, with diverse structures and functionalities. Over the past few decades, a self-assembly strategy is introduced to construct peptide-based nanomaterials, which can form well-controlled superstructures with high stability and multivalent effect. More recently, peptide-based functional biomaterials are widely utilized in clinical applications. However, there is no comprehensive review article that summarizes this growing area, fr...
142 CitationsSource
Zika virus (ZIKV) has recently caused a pandemic disease, and many cases of ZIKV infection in pregnant women resulted in abortion, stillbirth, deaths and congenital defects including microcephaly, which now has been proposed as ZIKV congenital syndrome. This study aimed to investigate the in situ immune response profile and mechanisms of neuronal cell damage in fatal Zika microcephaly cases. Brain tissue samples were collected from 15 cases, including 10 microcephalic ZIKV-positive neonates with...
2,518 CitationsSource
Cited By0
Newest
#1Xun-Hui Xu (Hefei University of Technology)H-Index: 6
#2Wen-Bin Liu (Hefei University of Technology)H-Index: 1
Last. Zong-Quan Wu (Hefei University of Technology)H-Index: 22
view all 0 authors...
Source