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Self-assembling peptide

Alberto Fuertes, Marisa Juanes, Juan R Granja, Javier Montenegro
The fabrication of functional molecular devices constitutes one of the most important current challenges for chemical sciences. The complex processes accomplished by living systems continuously demand the assistance of non-covalent interactions between molecular building blocks. Additionally, these building blocks (proteins, membranes, nucleotides) are also constituted by self-assembled structures. Therefore, supramolecular chemistry is the discipline required to understand the properties of the minimal self-assembled building blocks of living systems and to develop new functional smart materials...
June 21, 2017: Chemical Communications: Chem Comm
Hitesh Kulhari, Srinivasa R Telukutla, Deep Pooja, Ravi Shukla, Ramakrishna Sistla, Vipul Bansal, David J Adams
AIM: To synthesize cRGDfK peptide conjugated poly(γ-glutamic acid)-phenylalanine nanoparticles to improve the therapeutic efficacy of camptothecin (CPT) against glioblastoma multiforme. METHODS: Peptide-conjugated, drug-loaded nanoparticles (cRGDfK-conjugated camptothecin-loaded PGA-PA nanoparticles [RCPN]) were prepared and physico-chemically characterized using different techniques. Nanoparticles were evaluated for in vitro anticancer activity, cellular uptake, induction of apoptosis and wound healing cell migration against U87MG human glioblastoma cells...
June 21, 2017: Nanomedicine
Xi-Rui Zhou, Yimeng Cao, Qiang Zhang, Xi-Bo Tian, He Dong, Long Chen, Shi-Zhong Luo
Peptides are considered as a new generation of drugs due to their high structural and functional diversity. However, the development of peptide drugs is always limited by their poor stability and short circulation time. Carriers are applied for peptide drug delivery, but there may be problems like poor loading efficiency and undesired xenobiotic toxicity. Peptide self-assembly is an effective approach to improve the stability and control the release of peptide drugs. In this study, two self-assembling anticancer peptides are designed by appending a pair of glutamic acid and asparagine to either the N-terminus or the C-terminus of a lytic peptide...
June 16, 2017: International Journal of Pharmaceutics
Run Chang, Keerthana Subramanian, Mian Wang, Thomas J Webster
The emergence of antibiotic resistance in bacteria has caused many healthcare problems and social burdens. Herein, we designed and studied self-assembled peptide amphiphiles (PAs) functionalized with a heparin-binding Cardin-motif peptide (sequence (AKKARK)2) to combat bacteria drug resistance. These amphiphilic Cardin antimicrobial peptides (ACA-PAs) self-assembled into nanorods (7-10 nm in diameter) with the cationic Cardin-motif peptide exposed on the surface. The ACA nanorods formed above the critical micelle concentration (CMC) of 45 µM into a β-sheet secondary structure...
June 19, 2017: ACS Applied Materials & Interfaces
Mark P Del Borgo, Ketav Kulkarni, Marie-Isabel Aguilar
β-Amino acids are being increasingly used in the design of bioactive ligands and more recently in the generation of novel biomaterials. Peptides containing either individual β-amino acid substitutions or peptides comprised entirely of β-amino acids, display unique properties in terms of their structural and/or chemical characteristics. β-Peptides form well-defined secondary structures that exhibit different geometries compared to the corresponding α-peptides. β-Peptides, including α-peptides containing only one or two β-amino acids, can be easily modified with different functional groups and are metabolically stable and, together with the predictable side chain topography, have led to the design of a growing number of bioactive β-peptides with a range of biological targets and therapeutic applications...
June 15, 2017: Current Pharmaceutical Design
O Morris, M A Elsawy, M Fairclough, K J Williams, A McMahon, J Grigg, D Forster, A F Miller, A Saiani, C Prenant
Positron emission tomography (PET) and fluorescence labelling have been used to assess the pharmacokinetics, biodistribution and eventual fate of a hydrogel-forming nonapeptide, FEFKFEFKK (F9) in healthy mice, using (18) F-labelled and fluoresceinisothiocyanate (FITC) - labelled F9 analogues. F9 was site-specifically radiolabelled with 2-[(18) F]fluoro-3-pyridinecarboxaldehyde ([(18) F]FPCA) via oxime bond formation. [(18) F]FPCA-F9 in vivo fate was evaluated both as a solution, following intravenous administration, and as a hydrogel when subcutaneously injected...
June 17, 2017: Journal of Labelled Compounds & Radiopharmaceuticals
John T M DiMaio, Danielle M Raymond, Bradley L Nilsson
The display of functional proteins on self-assembled peptide nanofibrils is challenging since the steric bulk of proteins attached to simple self-assembling peptides often impedes incorporation into nanofibrils. Herein is described a split-protein strategy to tether functional proteins to preassembled peptide nanofibrils. In this strategy, a short affinity motif peptide derived from a split protein system is appended to a self-assembly motif (the amphipathic Ac-(FKFE)2-NH2 peptide) to form an affinity-assembly fusion peptide...
June 16, 2017: Organic & Biomolecular Chemistry
Angelo Bella, Santanu Ray, Maxim G Ryadnov
Biomineralisation is essential for biology. Specialist proteins use peptide motifs that catalyse mineral deposition into nano-to-microscale inorganic materials. Unlike in native proteins, the motifs incorporated into self-assembled fibres can persistently propagate on the microscopic scale enabling empirically defined silica nanostructures. Herein we show that the two main modes of motif templating - linear and orthogonal - in self-assembling, fibre-forming peptide sequences effectively silicify protein fibres...
June 16, 2017: Organic & Biomolecular Chemistry
Yejiao Shi, Yang Hu, Guy Ochbaum, Ran Lin, Ronit Bitton, Honggang Cui, Helena S Azevedo
We report here a proof-of-concept design of a multi-domain cell-penetrating peptide amphiphile (CPPA) which can self-assemble into fibrous nanostructures and transform into spherical micelles upon enzymatic degradation by matrix metalloproteinase-2 (MMP-2) up-regulated in the tumour environment. Concomitant with this morphological transition, the cell-penetrating peptide (CPP), which was previously buried inside the CPPA fibers, could be presented on the surface of the CPPA micelles, enhancing their cell-penetrating ability...
June 14, 2017: Chemical Communications: Chem Comm
Sergii Afonin, Vladimir Kubyshkin, Pavel K Mykhailiuk, Igor V Komarov, Anne S Ulrich
The cell-penetrating peptide SAP, which was designed as an amphipathic poly-L-proline helix II (PPII), was suggested to self-assemble into regular fibrils that are relevant for its internalization. Herein we have analyzed the structure of SAP in the membrane-bound state by solid-state (19)F-NMR, which revealed other structural states, in addition to the expected surface-aligned PPII. (2S)-2-Amino-2-[3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl]ethanoic acid and two rigid isomers of trifluoromethyl-4,5-methanoprolines (CF3-MePro) were used as labels for (19)F-NMR analysis...
June 13, 2017: Journal of Physical Chemistry. B
L A Lima, R de Vries, L S Biswaro, I M Vasconcelos, O L Franco, S C Dias
One of the roadblocks towards the practical use of antimicrobial peptides for medical use is their relatively high cost when synthesized chemically. Effective recombinant production has only been successful in some cases, such as the previously reported production in Pichia pastoris of the antimicrobial plectasin derivative peptide NZ2114. The same production host has also been used extensively to produce so-called protein-polymers: sequences that consist of repetitions of simple amino acid motifs found in structural proteins such as collagen and elastin, and that can be designed to self-assemble in micelles, fibers and hydrogels...
June 12, 2017: Biopolymers
Tzu-Wei Wang, Chia-Wei Yeh, Chen-Hsiang Kuan, Li-Wen Wang, Liang-Hsin Chen, Hsi-Chin Wu, Jui-Shen Sun
Breast cancer has become the second leading cause of cancer-related mortality in female wherein more than 90% of breast cancer-related death results from cancer metastasis to distant organs at advanced stage. The purpose of this study is to develop biodegradable nanoparticles composed of natural polypeptides and calcium phosphate (CaP) with sequential pH-responsivity to tumor microenvironments for active targeted drug delivery. Two different amphiphilic copolymers, poly(ethylene glycol)3400-aconityl linkage-poly(l-glutamic acid)15-poly(l-histidine)10-poly(l-leucine)10 and LyP1-poly(ethylene glycol)1100-poly(l-glutamic acid)15-poly(l-histidine)10-poly(l-leucine)10, were exploited to self-assemble into micelles in aqueous phase...
June 9, 2017: Acta Biomaterialia
Na Li, Hyunbum Jang, Ming Yuan, Wanrong Li, Xiaolin Yun, Joon Lee, Qiqige Du, Ruth Nussinov, Jiahua Hou, Ratnesh Lal, Feng Zhang
Self-assembly of peptides is closely related to many diseases, including Alzheimer's, Parkinson's, and prion diseases. Understanding the basic mechanism of this assembly is essential for designing ultimate cure and preventive measures. Template-assisted self-assembly (TASA) of peptides on inorganic substrates can provide fundamental understanding of substrate-dependent peptides assemble, including the role of hydrophobic interface on the peptide fibrillization. Here, we have studied the self-assembly process of a potential pentapeptide inhibitor on the surface of highly oriented pyrolytic graphite (HOPG) using real time atomic force microscopy (RT-AFM) as well as molecular dynamics (MD) simulation...
June 12, 2017: Langmuir: the ACS Journal of Surfaces and Colloids
Jun Liang, Gang Liu, Jing Wang, Xiuzhi Susan Sun
Previously, it has been reported that a novel PepGel (h9e peptide) can be triggered into a solid physical hydrogel by the addition of selected ions and proteins for various biomedical applications. Moreover, PepGel displays shear-thinning and repeatedly reversible sol-gel transfer properties that enable it to be easily transferred via an injector. In this study, PepGel is proposed as a carrier for controlled releases of bovine serum albumin (BSA)-bound or -linked drugs. BSA-linked cisplatin (BSA-CP) is used as a model drug in this study and plays two roles: as a trigger of hydrogel and as a target drug for controlled release...
June 12, 2017: Amino Acids
C J Buettner, A J Wallace, S Ok, A A Manos, M J Nicholl, A Ghosh, M F Tweedle, J E Goldberger
While the influence of alkyl chain length and headgroup size on self-assembly behaviour has been well-established for simple surfactants, the rational control over the pH- and concentration-dependent self-assembly behaviour in stimuli responsive peptides remains an elusive goal. Here, we show that different amphiphilic peptides can have similar self-assembly phase diagrams, providing the relative strengths of the attractive and repulsive forces are balanced. Using palmitoyl-YYAAEEEEK(DO3A:Gd)-NH2 and palmitoyl-YAAEEEEK(DO3A:Gd)-NH2 as controls, we show that reducing hydrophobic attractive forces through fewer methylene groups in the alkyl chain will lead to a similar self-assembly phase diagram as increasing the electrostatic repulsive forces via the addition of a glutamic acid residue...
June 21, 2017: Organic & Biomolecular Chemistry
Biswadip Banerji, Moumita Chatterjee, Uttam Pal, Nakul Chandra Maiti
Both the hydrogen bonding and hydrophobic interactions play a significant role in molecular assembly including self assembly of proteins and peptides. In this investigation, we reported formation of annular protofibrillar structure (diameter ~500 nm) made of a newly synthesized s-benzyl-protected cysteine tripeptide which was primarily stabilized by hydrogen bonding and hydrophobic interactions. AFM and FESEM analyses found small oligomers (~ 60 nm in diameter) to bigger annular (~ 300 nm) with an inner diameter of 100 nm and protofibrillar structure after 1-2 days incubation...
June 8, 2017: Journal of Physical Chemistry. B
Anhe Wang, Lingyun Cui, Sisir Debnath, Qianqian Dong, Xuehai Yan, Xi Zhang, Rein V Ulijn, Shuo Bai
Solvent molecules significantly affect the supramolecular self-assembly, for example, in forming solvent-bridged hydrogen bonding networks. Even small changes in solvent composition can have dramatic impact on supramolecular assembly. Herein, we demonstrate the use of trace solvents (as low as 0.04%) to tune the morphology and consequent functions of supramolecular nanostructures based on an aromatic peptide bola-amphiphile. Specifically, perylene bisimide-(di)glycine-tyrosine (PBI-[GY]2) bola-amphiphile was shown to give rise to red-emitting nanofibers when assembled in water, while exposure to trace organic solvents such as tetrahydrofuran (THF) and others via solvent-evaporation followed by aqueous assembly gave rise to white-light-emitting nanospheres...
June 15, 2017: ACS Applied Materials & Interfaces
Sandip V Jadhav, Paolo Amabili, Hans-Georg Stammler, Norbert Sewald
Gabapentin, an anti-epileptic drug, is known to form stable helical structures in short peptides. Distinctly, we report on the newly synthesized gamma-analogue of gabapentin, i.e. gamma-gabapentin (gamma-Gpn), manifests beta-sheet character at molecular and nanofibrous hydrogel at supramolecular level. We have undertaken the study to investigate the influence of proximally immobilized cationic amino acids (lysine and arginine) on self-assembly of backbone expanded tripeptide motif. Interestingly, arginine was found to be superior, both physically and mechanically, over lysine in driving hydrogelation...
June 7, 2017: Chemistry: a European Journal
Chivukula Subbalakshmi, Pratyay Basak, Ramakrishnan Nagaraj
Short peptides composed of phenylalanine and sequences derived from amyloidogenic peptides have the ability to self-assemble to form nanostructures including hydrogels. The self-assembly of peptides composed of only hydrophobic amino acids and aliphatic protecting groups have not been investigated in detail. We have examined various aspects of nanostructures formed by N-terminal t-butyloxycarbonyl-protected aliphatic dipeptide methyl esters dissolved in various solvents. Scanning electron microscopic images indicate that depending on the sequence, position of the amino acid and solvent of dissolution, the peptides self-assemble into superstructures such as nanotubes and needles particularly from aqueous mixtures of organic solvents...
June 7, 2017: Biopolymers
Björne B Mollet, Iven L J Bogaerts, Geert C van Almen, Patricia Y W Dankers
Renal applications in healthcare, such as renal replacement therapies and nephrotoxicity tests, could potentially benefit from bioartificial kidney membranes with fully differentiated and functional human tubular epithelial cells. A replacement of the natural environment of these cells is required to maintain and study cell functionality cell differentiation in vitro. Our approach was based on synthetic supramolecular biomaterials to mimic the natural basement membrane (BM) on which these cells grow and a bioreactor to provide the desired organotypical culture parameters...
June 2017: Journal of Tissue Engineering and Regenerative Medicine
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