Supramolecular ultra-short carboxybenzyl-protected dehydropeptide-based hydrogels for drug delivery

Veloso, Sérgio Rafael Silva; Jervis, P. J.; Silva, Joana F G; Hilliou, L.; Moura, C.; Pereira, David M.; Coutinho, Paulo J. G.; Martins, José A.; Castanheira, Elisabete M. S.; Ferreira, Paula M. T.

doi:10.1016/j.msec.2021.111869

Cited by 27 publications

(35 citation statements)

References 72 publications

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“…The latter shows that nucleation and growth of peptide aggregates occurs on the same time scale for compound 1, whereas nucleation is much slower for compound 2. The values computed for the rate constants of compound 2 are consistent with the values reported recently from turbidity experiments of a hydrogel based on a dehydrodipeptide N-protected with a carboxybenzyl group [17]. After reaching the structural equilibrium established by the reading of constant shear moduli G and G" with time, a frequency-sweep from 100 down to 0.1 Hz was performed with a strain of 0.01% (Figure S6 in Supplementary Information).…”

Section: Rheologysupporting

confidence: 86%

“…The STEM measurements reported for the dehydrodipeptides phenylalanyldehydrophenylalanine and tyrosyldehydrophenylalanine N-capped with the carboxybenzyl group are similar to those described for bolaamphiphiles 1-3 (Figure S4 in Supplementary Information) [17]. The average width reported for the fibers of these hydrogels is 26.1 nm.…”

Section: Stem Studiessupporting

confidence: 73%

“…Finally, the CD spectrum of compound 3 shows two positive bands at 200 nm and 250 nm and a large negative peak around 290 nm (Figure 5, blue line), reflecting the importance that naphthalene interactions have in self-assembly. The STEM measurements reported for the dehydrodipeptides phenylalanyldehydrophenylalanine and tyrosyldehydrophenylalanine N-capped with the carboxybenzyl group are similar to those described for bolaamphiphiles 1-3 (Figure S4 in Supplementary Information) [17]. The average width reported for the fibers of these hydrogels is 26.1 nm.…”

Section: Circular Dichroism (Cd) Spectroscopysupporting

confidence: 73%

“…This is explained by the scatter in the data and by the fact that gelling is not fully completed after 10 h. However, the errors in the values computed for the rate constants (Table 2) are small enough to offer a quantitative comparison between the gelling kinetics of the two compounds. The gelation kinetics of compounds 1 and 2 (Figure S5 in Supplementary Information) show that G′ is significantly larger than G″ after 2 h, which indicates that the hydrogels formed relatively quickly, within the same time scale of gel formation for carboxybenzyl-protected dehydropeptides Cbz-L-Phe-Z-ΔPhe-OH and Cbz-L-Tyr-Z-ΔPhe-OH [17], but faster than some Fmoc-dipeptides [29]. Bolaamphiphile 1 shows an initial time lag of 2300 s before the significant rise in G′ and the final slower equilibration step, while for compound 2, this time is longer (4600 s).…”

Section: Rheologymentioning

confidence: 99%

“…These materials showed promise as controlled drug delivery systems, in release studies using anti-cancer compounds such as curcumin and doxorubicin [12,13]. More recently, we found that compounds containing a structurally simpler carboxybenzyl (Cbz) group attached to the N-terminus of dehydrodipeptides (i.e., Cbz-L-Phe-Z-∆Phe-OH and Cbz-L-Tyr-Z-∆Phe-OH) are capable of forming hydrogels with very low CGCs (0.1%) and therefore represent a new minimum gelator module for this class of gelator, at least under the gelation conditions tested (Figure 1A) [17].…”

Section: Introductionmentioning

confidence: 99%

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Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

Amorim

Veloso

Castanheira

et al. 2021

Gels

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The self-assembly of nanometric structures from molecular building blocks is an effective way to make new functional materials for biological and technological applications. In this work, four symmetrical bolaamphiphiles based on dehydrodipeptides (phenylalanyldehydrophenylalanine and tyrosyldehydrophenylalanine) linked through phenyl or naphthyl linkers (terephthalic acid and 2,6-naphthalenedicarboxylic acid) were prepared, and their self-assembly properties were studied. The results showed that all compounds, with the exception of the bolaamphiphile of tyrosyldehydrophenylalanine and 2,6-naphthalene dicarboxylic acid, gave self-standing hydrogels with critical gelation concentrations of 0.3 wt % and 0.4 wt %, using a pH trigger. The self-assembly of these hydrogelators was investigated using STEM microscopy, which revealed a network of entangled fibers. According to rheology, the dehydrodipeptide bolaamphiphilic hydrogelators are viscoelastic materials with an elastic modulus G′ that falls in the range of native tissue (0.37 kPa brain–4.5 kPa cartilage). In viability and proliferation studies, it was found that these compounds were non-toxic toward the human keratinocyte cell line, HaCaT. In sustained release assays, we studied the effects of the charge present on model drug compounds on the rate of cargo release from the hydrogel networks. Methylene blue (MB), methyl orange (MO), and ciprofloxacin were chosen as cationic, anionic, and overall neutral cargo, respectively. These studies have shown that the hydrogels provide a sustained release of methyl orange and ciprofloxacin, while methylene blue is retained by the hydrogel network.

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Section: Rheologysupporting

confidence: 86%

Section: Stem Studiessupporting

confidence: 73%

Section: Circular Dichroism (Cd) Spectroscopysupporting

confidence: 73%

Section: Rheologymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

Amorim

Veloso

Castanheira

et al. 2021

Gels

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An Injectable Composite Co‐Assembled Dehydropeptide‐Based Magnetic/Plasmonic Lipogel for Multimodal Cancer Therapy

Veloso,

Vázquez‐González,

Spuch

et al. 2024

Adv Funct Materials

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Advancing therapeutic effectiveness through the strategic co‐delivery of drugs in a sequential manner represents a compelling strategy. However, achieving precise and selective release of chemotherapeutic agents remains a formidable challenge. In this study, a co‐assembled Arginine‐Glycine‐Aspartate (RGD)‐functionalized dehydropeptide‐based gel loaded with magnetic liposomes and mesoporous silica‐coated gold nanorods is introduced. This composite system serves as a sophisticated tool to independently modulate the release of doxorubicin and methotrexate. The gel's properties are intricately tuned by the incorporation of liposomes or nanorods and/or the co‐assembly with an RGD‐functionalized peptide. Furthermore, the combined effects of sequential drug release, photothermia, and magnetic hyperthermia synergistically enhance therapeutic efficacy against 3D cancer cell cultures. Noteworthy attributes of the gel include its ability to orthogonally trigger loaded drugs, along with features such as injectability, rapid gelation, self‐healing, and mechanical properties suitable for drug delivery. Consequently, this versatile multimodal platform emerges as a promising option for therapeutic applications, particularly in the context of cancer therapy.

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π‐System Functionalization Transforms Amyloidogenic Peptide Fragment of Human Islet Amyloid Polypeptide into a Super Hydrogelator

Unnikrishnan

Sushana

Saveri

et al. 2023

Chemistry An Asian Journal

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While a considerable number of ultra-short/short amyloid peptides have been reported to form 3D supramolecular hydrogels, they all possess high minimum gelation concentration (MGC) (� 1 wt%), which preclude their applications. In this context, we demonstrate that functionalisation of a well-known amyloidogenic ultra-short peptide fragment NFGAIL (IAPf) of human Islet amyloid polypeptide with a π-system (Fluorenyl, Fm) at the N-terminus of the peptide (Fm-IAPf) yield not only highly thermostable hydrogel at physiological pH but also exhibited super gelator nature as the MGC (0.08 wt%) falls below 0.1 wt%. Various experimental results confirmed that aromatic π-π interactions from fluorenyl moieties and hydrogen bonding interactions between the IAPf drive the self-assembly/fibril formation. Fm-IAPf is the first super hydrogelator derived from amyloid-based ultra-short peptides, to the best of our knowledge. We strongly believe that this report, i. e., functionalization of an amyloid peptide with π-system, provides a lead to develop super hydrogelators from other amyloid-forming peptide fragments for their potential applications.

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Supramolecular ultra-short carboxybenzyl-protected dehydropeptide-based hydrogels for drug delivery

Cited by 27 publications

References 72 publications

Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

An Injectable Composite Co‐Assembled Dehydropeptide‐Based Magnetic/Plasmonic Lipogel for Multimodal Cancer Therapy

π‐System Functionalization Transforms Amyloidogenic Peptide Fragment of Human Islet Amyloid Polypeptide into a Super Hydrogelator

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