Fmoc-diphenylalanine as a suitable building block for the preparation of hybrid materials and their potential applications

Diaferia, Carlo; Morelli, Giancarlo; Accardo, Antonella

doi:10.1039/c9tb01043b

Cited by 80 publications

(76 citation statements)

References 87 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To overcome these limitations, assembly of multiple peptidic components can result in a broader range of applications as compared to the self-assemblies of either component. This epitome expands the conformational space of peptide selfassemblies in terms of structural and functional complexities (Makam and Gazit, 2018;Diaferia et al, 2019). For example, mixed dipeptide gelators are assumed to co-assemble to form fibers containing both the gelators randomly.…”

Section: Applications Of Peptide Self-assembliesmentioning

confidence: 99%

“…The Fmoc-Phe-Phe-OH/HA hydrogel, composed of two components, could allow fine-tuning of the hydrogel parameters, adjusted for injection and malleable and facilitating its use in drug-delivery and tissue engineering applications (Aviv et al, 2018). A review by Diaferia et al describes the immense potential of the hydrogel specially in the field of drug delivery, tissue-engineering and catalytic behavior (Diaferia et al, 2019). Fmoc-Phe-Phe-OH based hydrogel nanoparticles have been explored as nano-carriers to encapsulate and deliver drugs/bioactive molecules.…”

Section: Dipeptides For Biologics Deliverymentioning

confidence: 99%

See 1 more Smart Citation

Ultrashort Peptide Self-Assembly: Front-Runners to Transport Drug and Gene Cargos

Gupta

Singh

Sharma

et al. 2020

Front. Bioeng. Biotechnol.

View full text Add to dashboard Cite

The translational therapies to promote interaction between cell and signal come with stringent eligibility criteria. The chemically defined, hierarchically organized, and simpler yet blessed with robust intermolecular association, the peptides, are privileged to make the cutoff for sensing the cell-signal for biologics delivery and tissue engineering. The signature service and insoluble network formation of the peptide self-assemblies as hydrogels have drawn a spell of research activity among the scientists all around the globe in the past decades. The therapeutic peptide market players are anticipating promising growth opportunities due to the ample technological advancements in this field. The presence of the other organic moieties, enzyme substrates and well-established protecting groups like Fmoc and Boc etc., bring the best of both worlds. Since the large sequences of peptides severely limit the purification and their isolation, this article reviews the account of last 5 years' efforts on novel approaches for formulation and development of single molecule amino acids, ultra-short peptide self-assemblies (di-and tri-peptides only) and their derivatives as drug/gene carriers and tissue-engineering systems.

show abstract

Section: Applications Of Peptide Self-assembliesmentioning

confidence: 99%

Section: Dipeptides For Biologics Deliverymentioning

confidence: 99%

Ultrashort Peptide Self-Assembly: Front-Runners to Transport Drug and Gene Cargos

Gupta

Singh

Sharma

et al. 2020

Front. Bioeng. Biotechnol.

View full text Add to dashboard Cite

show abstract

“…Additionally, their involvement in the regulation of the neuroimmuno-endocrine system cannot be neglected (Sá nchez & Vá zquez, 2017;Kraskovskaya et al, 2017;Zamorskii et al, 2017;Khavinson et al, 2017). In particular, modified AAs and ultra-short peptides have broad applications for either the biomedical industry or research, namely, anticancer therapy, immunology, tissue engineering, the design of modern drugs delivery systems, catalysis or biofunctional supramolecular materials (Zhou et al, 2017;Diaferia et al, 2019). AAs and dipeptides protected at the N-terminus with large aromatic groups, like fluorenylmethoxycarbonyl (Fmoc), are used as inter alia effective low-molecular-weight hydrogelators (especially Fmoc-tyrosine and Fmoc-phenylalanine).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, experimental andin silicostudies ofN-fluorenylmethoxycarbonyl-O-tert-butyl-N-methyltyrosine, coupled with CSD data: a survey of interactions in the crystal structures of Fmoc–amino acids

Bojarska

Remko²,

Madura

et al. 2020

Acta Crystallogr C Struct Chem

View full text Add to dashboard Cite

Recently, fluorenylmethoxycarbonyl (Fmoc) amino acids (e.g. Fmoc–tyrosine or Fmoc–phenylalanine) have attracted growing interest in biomedical research and industry, with special emphasis directed towards the design and development of novel effective hydrogelators, biomaterials or therapeutics. With this in mind, a systematic knowledge of the structural and supramolecular features in recognition of those properties is essential. This work is the first comprehensive summary of noncovalent interactions combined with a library of supramolecular synthon patterns in all crystal structures of amino acids with the Fmoc moiety reported so far. Moreover, a new Fmoc‐protected amino acid, namely, 2‐{[(9H‐fluoren‐9‐ylmethoxy)carbonyl](methyl)amino}‐3‐{4‐[(2‐hydroxypropan‐2‐yl)oxy]phenyl}propanoic acid or N‐fluorenylmethoxycarbonyl‐O‐tert‐butyl‐N‐methyltyrosine, Fmoc‐N‐Me‐Tyr(t‐Bu)‐OH, C29H31NO5, was successfully synthesized and the structure of its unsolvated form was determined by single‐crystal X‐ray diffraction. The structural, conformational and energy landscape was investigated in detail by combined experimental and in silico approaches, and further compared to N‐Fmoc‐phenylalanine [Draper et al. (2015). CrystEngComm, 42, 8047–8057]. Geometries were optimized by the density functional theory (DFT) method either in vacuo or in solutio. The polarizable conductor calculation model was exploited for the evaluation of the hydration effect. Hirshfeld surface analysis revealed that H…H, C…H/H…C and O…H/H…O interactions constitute the major contributions to the total Hirshfeld surface area in all the investigated systems. The molecular electrostatic potentials mapped over the surfaces identified the electrostatic complementarities in the crystal packing. The prediction of weak hydrogen‐bonded patterns via Full Interaction Maps was computed. Supramolecular motifs formed via C—H…O, C—H…π, (fluorenyl)C—H…Cl(I), C—Br…π(fluorenyl) and C—I…π(fluorenyl) interactions are observed. Basic synthons, in combination with the Long‐Range Synthon Aufbau Modules, further supported by energy‐framework calculations, are discussed. Furthermore, the relevance of Fmoc‐based supramolecular hydrogen‐bonding patterns in biocomplexes are emphasized, for the first time.

show abstract

“…Self-assembled molecular gels with nanofibrillar networks are receiving significant attention as soft materials with attractive properties arising from the nanomorphology and the noncovalent nature of the networks. [1][2][3][4][5][6] Their potential applications range from therapeutics, [7][8][9][10][11] sensing and detection, [3,12,13] and templates for nanomaterials [14] to optoelectronics. [12,15] To access new properties of gel, the discovery of novel gelator molecules would be the most straightforward idea but has been cellulose oligomers into network structures composed of nanoribbon-shaped crystalline fibers, followed by cooling for the formation of gelatin networks.…”

Section: Introductionmentioning

confidence: 99%

pH‐Triggered Self‐Assembly of Cellulose Oligomers with Gelatin into a Double‐Network Hydrogel

Hata

Kojima

Maeda

et al. 2020

Macromolecular Bioscience

View full text Add to dashboard Cite

Multicomponent systems for self‐assembled molecular gels provide huge opportunities to generate collective or new functions that are not inherent in individual single‐component gels. However, gelation tends to require careful and complicated procedures, because, among a myriad of kinetically trapped structures related to the degree of mixing of multiple components over a wide range of scales, from molecular level to macroscopic scale, a limited number of structures that exhibit the desired function need to be constructed. This study presents a simple method for the construction of double‐network (DN) hydrogels with improved stiffness composed of crystalline cellulose oligomers and gelatin. The pH‐triggered self‐assembly of cellulose oligomers leads to the formation of robust networks composed of crystalline nanofibers in the presence of dissolved gelatin, followed by cooling to allow for the formation of soft gelatin networks. The resultant DN hydrogels exhibit improved stiffness; the improvement in gel stiffness with double networking is comparable to that of previously reported DN hydrogels produced via a time‐consuming enzymatic reaction.

show abstract

Fmoc-diphenylalanine as a suitable building block for the preparation of hybrid materials and their potential applications

Abstract: Due to its capability to self-assemble in self-supporting hydrogels (HG) under physiological conditions, Fmoc-FF is one of the most studied ultra-short peptide. This feature pushed towards the development of novel Fmoc-FF multicomponent systems.

Cited by 80 publications

References 87 publications

Ultrashort Peptide Self-Assembly: Front-Runners to Transport Drug and Gene Cargos

Ultrashort Peptide Self-Assembly: Front-Runners to Transport Drug and Gene Cargos

Synthesis, experimental andin silicostudies ofN-fluorenylmethoxycarbonyl-O-tert-butyl-N-methyltyrosine, coupled with CSD data: a survey of interactions in the crystal structures of Fmoc–amino acids

pH‐Triggered Self‐Assembly of Cellulose Oligomers with Gelatin into a Double‐Network Hydrogel

Contact Info

Product

Resources

About