Peptide self-assembly driven by oxo-ester mediated native chemical ligation

Rasale, Dnyaneshwar B.; Maity, Indrajit; Konda, Maruthi; Das, Apurba K.

doi:10.1039/c3cc41475b

Cited by 22 publications

(26 citation statements)

References 31 publications

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“…Over the past few years, we have explored various applications of low molecular weight linear peptides, which show remarkable selfassembled nano-structures under certain physical conditions. [64][65][66][67][68][69][70][71]…”

Section: Introductionmentioning

confidence: 99%

Modulating Hydrogen Bonded Self-assembled Patterns and Morphological Features by a Change in Side Chain of Third Amino Acid of Synthetic γ- Amino Acid Based Tripeptides

et al. 2016

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Self‐assembled structure and functions of peptides could be achieved by the design and synthesis of hybrid peptides. Here, we report structural and morphological studies of designed hybrid tripeptides Boc‐Gpn‐Aib‐Xaa‐OMe (where Xaa=Leu(L) for 1 and Phe(F) for 2), which show different conformations both in solid and solution states. The conformational modulations are achieved by the design and synthesis of reported peptides 1 and 2 by suitable choice of conventional and non‐conventional amino acid building blocks and slight change in side‐chain of third amino acids of tripeptides. The conformational modulations exhibited by peptides 1 and 2 are well probed and confirmed using Single crystal XRD, FT‐IR, CD and 2D NMR studies. The morphological studies of peptides 1 and 2 show different self‐assembled morphological preferences in THF – water (1:1) under similar experimental conditions.

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Section: Introductionmentioning

confidence: 99%

Modulating Hydrogen Bonded Self-assembled Patterns and Morphological Features by a Change in Side Chain of Third Amino Acid of Synthetic γ- Amino Acid Based Tripeptides

et al. 2016

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“…Inspired by nature, researchers have developed many biofunctional nanomaterials formed by the specific interactions between metal ions and peptides34567. Among them, supramolecular hydrogels89101112, especially those of peptides13141516171819202122232425, have attracted research interests due to their inherent biocompatibility, degradability, and fast responsiveness to external stimuli26272829303132. Successful examples of metal ion-induced supramolecular hydrogelations have been reported.…”

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confidence: 99%

Gd(III)-induced Supramolecular Hydrogelation with Enhanced Magnetic Resonance Performance for Enzyme Detection

Hua

et al. 2017

Sci Rep

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Here we report a supramolecular hydrogel based on Gd(III)-peptide complexes with dramatically enhanced magnetic resonance (MR) performance. The hydrogelations were formed by adding Gd(III) ion to the nanofiber dispersion of self-assembling peptides naphthalene-Gly-Phe-Phe-Tyr-Gly-Arg-Gly-Asp (Nap-GFFYGRGD) or naphthalene-Gly-Phe-Phe-Tyr-Gly-Arg-Gly-Glu (Nap-GFFYGRGE). We further showed that, by adjusting the molar ratio between Gd(III) and the corresponding peptide, the mechanical property of resulting gels could be fine-tuned. The longitudinal relaxivity (r1) of the Nap-GFFYGRGE-Gd(III) was 58.9 mM−1 S−1, which to our knowledge is the highest value for such peptide-Gd(III) complexes so far. Such an enhancement of r1 value could be applied for enzyme detection in aqueous solutions and cell lysates.

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“…Das et al. applied the oxo‐ester mediated native chemical ligation (NCL) reaction to generate peptide self‐assembly . The Nmoc‐protected amino acids/peptides were synthesized as precursors, which underwent self‐assembly via NCL, producing supramolecular nanofibers and self‐supporting hydrogels.…”

Section: Hydrogels and Nanofibersmentioning

confidence: 99%

Molecular Self‐Assembly Constructed in Physiological Conditions for Cancer Diagnosis and Therapy

Qiao

Wang

2018

Advanced Therapeutics

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For the purpose of cancer theranostics, the performance and potential biosafety of drug/imaging agents remain major challenges. Although passive and active targeting strategies have been reported for effectively enhanced bioimaging or drug delivery performance, researchers are still looking for emerging methods for better targeting, accumulation, and penetration of solid tumors. The strategy for constructing supramolecular self-assemblies in biologically relevant conditions may partially overcome these challenges. Regarding the biomedical applications, supramolecular entities with naturally dynamic and modular properties, are capable of constructing structurally and functionally diversified materials and meeting the requirements of biological complexity. Modules and integrated systems enable response to bio-environment by the modification of their constitution through component exchange or reorganization. In this review, the authors summarize the self-assembled nanosystems (nanoparticles, nanoaggregates, micelles, vesicles, nanofibers, hydrogels, etc.) in physiological/pathological environments and their applications in cancer theranostics. The authors focus on chemical structures, stimuli-responsive bonds, and self-assembly property of nanomaterials, which may offer a guide for the optimal design of self-assembled nanomaterials in clinical cancer treatment and imaging.

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Peptide self-assembly driven by oxo-ester mediated native chemical ligation

Abstract: We use the oxo-ester mediated native chemical ligation (NCL) reaction to generate a peptide self-assembly process to make supramolecular nanofibers and self-supporting gels.

Cited by 22 publications

References 31 publications

Modulating Hydrogen Bonded Self-assembled Patterns and Morphological Features by a Change in Side Chain of Third Amino Acid of Synthetic γ- Amino Acid Based Tripeptides

Modulating Hydrogen Bonded Self-assembled Patterns and Morphological Features by a Change in Side Chain of Third Amino Acid of Synthetic γ- Amino Acid Based Tripeptides

Gd(III)-induced Supramolecular Hydrogelation with Enhanced Magnetic Resonance Performance for Enzyme Detection

Molecular Self‐Assembly Constructed in Physiological Conditions for Cancer Diagnosis and Therapy

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