Directing an oligopeptide amphiphile into an aligned nanofiber matrix for elucidating molecular structures

Qin, Si‐Yong; Ding, Wenqiang; Jiang, Zhiwei; Lei, Xinxiang; Zhang, Aiqing

doi:10.1039/c8cc09548e

Cited by 20 publications

(20 citation statements)

References 35 publications

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“…Along with the increase in OPA concentration, both OPA2 and OPA3 displayed the similar blue‐shift with OPA1 in UV‐Vis absorption spectra (Figure A, C, E). Meanwhile, similar red‐shift in fluorescence spectra were also observed for OPA1‐3 (Figure B, D, F), suggesting that NR was incorporated into the hydrophobic domain . Meanwhile, the shift values of blue‐shift in UV‐Vis absorption spectra and red‐shift in fluorescence spectra were coincident with the CAC investigation, indicating the stronger hydrophobic interaction of OPA1 and OPA3 than that of OPA2 for the self‐assembly.…”

Section: Resultssupporting

confidence: 72%

“…Inspired by the robust self‐assembly tendency of peptides, peptide‐bearing derivatives have been well designed and exploited to build functional nanostructures. Over the past few decades, a variety of structural motifs such as rigid aromatic rings, active drugs, hydrophilic phosphate, and hydrophobic alkyl chains have been proposed to design various peptide derivatives. Among them, oligopeptide amphiphiles (OPAs) comprising of hydrophilic peptide headgroups and hydrophobic tails are widely employed as building blocks for the self‐assembly and form shape‐specific nanostructures.…”

Section: Introductionmentioning

confidence: 99%

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Unsaturation‐Dependent Nanostructures Self‐Assembled from Oligopeptide Amphiphiles Capable of Generating Singlet Oxygen

et al. 2019

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We report here on three oligopeptide amphiphiles (OPA1-3) with different unsaturated double bonds, which self-assemble into shape-specific nanostructures. It was found that OPA1 with saturated hydrophobic tail self-assembled into conventional cylindrical nanofibers, while the unsaturated OPA2-3 molecules self-organized into helical nanoarchitectures. Due to the different double bond numbers in hydrophobic tails of OPA2-3, the helical pitch and width of their self-assemblies varied. Specially, linoleic acid-bearing OPA3 could be oxidized by lipoxidase to create hydroperoxide-containing OPA4, which further generated singlet oxygen ( 1 O 2 ) in the presence of catalytic iron (II) ion. The established system may provide a self-deliverable nanoplatform for 1 O 2 -mediated cancer treatment. Results and DiscussionFirstly, three oligopeptide amphiphiles (OPA1-3) were synthesized manually by Fmoc-based solid phase synthesis. To obtain OPA4, OPA3 with linolic acid group was oxidized by lipoxidase. [20] The molecular weights of OPA1-4 were measured by matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS) ( Figure S1, Supporting [a] J.

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Section: Resultssupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

Unsaturation‐Dependent Nanostructures Self‐Assembled from Oligopeptide Amphiphiles Capable of Generating Singlet Oxygen

et al. 2019

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“…[1g, 23] Due to the different polarities of these analytes,R DC measurements of 1-4 were performed in the CD 3 OD-bearing medium, while 5-6 were aligned in the [D 6 ]DMSO-bearing phase.A dditionally,( À)proline (7)w as selected since it has been previously established as am odel system for RDC investigation in the D 2 Obearing medium (Table 1). [15,24] We included 1 Hand 13 CNMR assignments of all model compounds 1-7 in the Supporting Information (Table S1-S7).…”

Section: Methodsmentioning

confidence: 99%

“…[14] Relying on the intramolecular non-covalent interactions,this bottom-up approach evades the challenging synthesis for polymers.Inthis respect, oligopeptides have been considered as promising candidates because of their structural diversity and strong tendencytoform self-assemblies in solution. In our previous study,w ep roposed two types of oligopeptides as aligning media that are compatible with D 2 O [15] and CD 3 OD, [16] respectively.N otably,u sing AAKLVFF as alignment medium, the relative configuration of as eries of challenging novel natural products including spiroepicoccin A, [17] sarcomililate A, [18] xylarichalasin A, [19] herpotrichones Aa nd B, [20] polyoxygenated sesquiterpenoid, [21] and curtachalasins [22] have been elucidated based on the RDC and residual chemical-shift anisotropy (RCSA) analysis.D espite these encouraging results,s ome challenges still exist. First, until now,t here has been no DMSO-bearing medium based on molecular self-assembly.S econd, the formation of selfassembly in organic solvents usually takes several hours or even days to complete.Third, residual background signals and broad linewidths frequently hinder an accurate measurement of the dipolar couplings.F inally,d espite the feasible solidphase peptide-synthesis (SPPS) technique,t he time-consuming peptide-purification step quite often prohibits the largescale production of peptide-based media.…”

Section: Introductionmentioning

confidence: 99%

Measurement of Residual Dipolar Couplings of Organic Molecules in Multiple Solvent Systems Using a Liquid‐Crystalline‐Based Medium

et al. 2020

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Residual dipolar coupling (RDC), a robust anisotropic NMR parameter for structural elucidation of organic molecules, is only accessible in an anisotropic environment. Herein, we introduce a novel alignment medium based on the molecular self‐assembly of oligopeptide amphiphile (OPA). This medium is compatible with different intermediate and polar solvent systems, such as CD3OD, [D6]DMSO, and D2O. The preparation of the OPA‐based medium is simple and rapid, while only very weak background signals were observed from OPAs. Furthermore, we show that the purity of OPA has only a minor influence on the quality of the RDC data. These advantages allow RDC measurements of organic molecules with different polarities and solubilities with high efficiency and accuracy.

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“…[3] In recent years, natural polymer hydrogels have been demonstrated with the potential as wound dressings because they can afford a moist environment to promote the wound healing. [19] The appearance of amide absorption reveals the successful amidation. The successful amidation of HA was verified by Fourier transform infrared (FT-IR) and 1 H NMR.…”

mentioning

confidence: 99%

Mussel‐Inspired Adhesive Polydopamine‐Functionalized Hyaluronic Acid Hydrogel with Potential Bacterial Inhibition

Zhang

Jiang

et al. 2019

Global Challenges

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etc. Among them, hyaluronic acid (HA)derived hydrogel is one of the ideal candidates due to its inherent biological homology, feasible structure modification, as well as good degradability. [9,10] The high water retention capacity and high viscoelasticity of HA also allow it to be suitable for wound dressings.To construct desirable HA-based hydrogels, different strategies have been established. Relying on the intermolecular noncovalent interactions, the physical cross-linking HA hydrogels emerged. Rodell et al. developed a shearthinning and self-healing HA hydrogel due to the host-guest interaction between β-cyclodextrin (β-CD) and adamantine (AD) appended HA. [11] The hydrogel properties could be rationally tailored through the material concentration, degree of modification, and the ratio of β-CD to AD. Nevertheless, the physical hydrogels may exhibit undesirable mechanical properties and suffer from premature dissociation. Chemical crosslinking of pendant reactive groups by coordination chemistry or polymerization ignites an alternative route to fabricate HAbased hydrogels. In the meanwhile, transition metal ions or exogenous cross-linking agents usually involve, [12] which may impair the systemic biocompatibility due to their possible cytotoxicity. Recently, various compatible strategies have been proposed to develop biocompatible hydrogels, such as enzymemediated covalent linking, [13,14] disulfide cross-linking, [15,16] and Diels-Alder reaction. [17,18] Indeed, these chemical cross-linked hydrogels exhibit good mechanical property and are cytocompatible. However, their further applications are restricted by their limited functions. Thus, endowing HA hydrogels with multiple functions seems to be very promising, and fabricating HA-based functional hydrogels with good biocompatibility is still challengeable.In this study, a multifunctional hydrogel (PDA-HA) comprising of polydopamine (PDA) and thiolated hyaluronic acid (HA-SH) is developed (Scheme 1). PDA was introduced because of its good biocompatibility, strong tissue adhesion and effective free radical scavenging ability. Specially, it could act as the nanosized cross-linking agent that reacts with thiolated HA via Michael addition. The biocompatibility, gelling ability, tissue adhesion, free radical scavenging, and bacterial inhibition of the hybrid hydrogel were evaluated. The potential bacterial inhibition and good tissue adhesion endow the hydrogel with great potential for wound dressing.As shown in Figure 1A, thiolated hyaluronic acid (HA-SH) was obtained by two steps that referred to the amidation of Hyaluronic acid (HA)-based hydrogels have been receiving increasing attention for wound management. However, pure HA hydrogels usually exhibit weak mechanical strength and poor anti-infection. Herein, a hybrid HA-based hydrogel (PDA-HA) comprised of polydopamine (PDA) and thiolated hyaluronic acid (HA-SH) is developed based on the Michael addition reaction. The introduction of PDA into HA hydrogel can decrease the critical gel concentration, improve the c...

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Directing an oligopeptide amphiphile into an aligned nanofiber matrix for elucidating molecular structures

Abstract: An aligned nanofiber matrix is obtained from the self-assembly of an oligopeptide amphiphile, which can capture the residual dipolar couplings of biomolecules.

Cited by 20 publications

References 35 publications

Unsaturation‐Dependent Nanostructures Self‐Assembled from Oligopeptide Amphiphiles Capable of Generating Singlet Oxygen

Unsaturation‐Dependent Nanostructures Self‐Assembled from Oligopeptide Amphiphiles Capable of Generating Singlet Oxygen

Measurement of Residual Dipolar Couplings of Organic Molecules in Multiple Solvent Systems Using a Liquid‐Crystalline‐Based Medium

Mussel‐Inspired Adhesive Polydopamine‐Functionalized Hyaluronic Acid Hydrogel with Potential Bacterial Inhibition

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