Low Molecular Weight Gelators Based on Functionalized l-Dopa Promote Organogels Formation

Giuri, Demetra; Zanna, Nicola; Tomasini, Claudia

doi:10.3390/gels5020027

Cited by 17 publications

(17 citation statements)

References 56 publications

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“…In a recent paper, we demonstrated the biocompatibility of other gelators derived from the Oxd moiety [36]. Molecules F0, F1 and F2 were dissolved in ethanol, then the solutions were diluted in Dulbecco's phosphate-buffered saline (DPBS), with final concentrations of 5 mg/mL and 0.5 mg /mL.…”

Section: Resultsmentioning

confidence: 99%

“…To carry on this study, we compared the gelation ability of three gelators: Boc-D-Phe-L-Oxd-OH, [36] Boc-D-F1Phe-L-Oxd-OH and Boc-D-F2Phe-L-Oxd-OH [27] (Phe= phenylalanine; F1Phe = 4-fluorophenylalanine; F2Phe = 3,4-difluorophenylalanine) (Figure 1). We report the preparation of gels starting from these three compounds and using several methodologies and triggers: solvent switch (from either ethanol or 2-propanol to water), pH change and calcium ions addition [37][38][39].…”

Section: Introductionmentioning

confidence: 99%

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Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Ravarino

Domenico

Barbalinardo

et al. 2022

Gels

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The three gelators presented in this work (Boc-D-Phe-L-Oxd-OH F0, Boc-D-F1Phe-L-Oxd-OH F1 and Boc-D-F2Phe-L-Oxd-OH F2) share the same scaffold and differ in the number of fluorine atoms linked to the aromatic ring of phenylalanine. They have been applied to the preparation of gels in 0.5% or 1.0% w/v concentration, using three methodologies: solvent switch, pH change and calcium ions addition. The general trend is an increased tendency to form structured materials from F0 to F1 and F2. This property ends up in the formation of stronger materials when fluorine atoms are present. Some samples, generally formed by F1 or F2 in 0.5% w/v concentration, show high transparency but low mechanical properties. Two gels, both containing fluorine atoms, show increased stiffness coupled with high transparency. The biocompatibility of the gelators was assessed exposing them to fibroblast cells and demonstrated that F1 and F2 are not toxic to cells even in high concentration, while F0 is not toxic to cells only in a low concentration. In conclusion, the presence of even only one fluorine atom improves all the gelators properties: the gelation ability of the compound, the rheological properties and the transparency of the final materials and the gelator biocompatibility.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Ravarino

Domenico

Barbalinardo

et al. 2022

Gels

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“…The three gelators have been obtained as derivatives of D-F 2 Phe. The introduction of the Oxd moiety was done, taking into consideration our previous work, where we prepared supramolecular materials containing the moiety L-Phe-D-Oxd [ 14 , 15 ], or, more recently, the L-Tyr-D-Oxd [ 16 , 17 ] and L-Dopa-D-Oxd [ 18 , 19 ]. In particular, F 2 -Phe is similar to the structure of Dopa, where the hydroxyl groups have been replaced with fluorine atoms.…”

Section: Resultsmentioning

confidence: 99%

Designing a Transparent and Fluorine Containing Hydrogel

Ravarino

Giuri

Faccio

et al. 2021

Gels

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Physical hydrogels are supramolecular materials obtained by self-assembly of small molecules called gelators. Aromatic amino acids and small peptides containing aromatic rings are good candidates as gelators due to their ability to form weak bonds as π-π interactions and hydrogen bonds between NH and CO of the peptide chain. In this paper we show our results in the preparation of a transparent hydrogel that was obtained by self-assembly of a fluorine-containing dipeptide that relies on the additional formation of halogen bonds due to the fluorine atoms contained in the dipeptide. We used Boc-D-F2Phe-L-Oxd-OH (F2Phe = 3,4-difluorophenylalainine; Oxd = 4-methyl-5-carboxy-oxazolidin-2-one) that formed a strong and transparent hydrogel in 0.5% w/w concentration at pH = 4.2. The formation of a hydrogel made of unnatural fluorinated amino acids may be of great interest in the evaluation of patients with parkinsonian syndromes and may be used for controlled release.

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“…The results from these studies are used to design carefully tailored gel materials for diverse applications from tissue engineering [4][5][6][7] to nanoscale electronics [8][9][10][11][12]. Generally, low-molecular-weight organogelators (LMOGs) are molecules that can form thermoreversible physical gels at concentrations less than 5% gelator/weight organic solvent [13][14][15][16][17][18]. Highly anisotropic 3D structures often form fibers during gelation, but they can also form ribbons, platelets, tubular structures, or cylinders [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

In Situ Supramolecular Gel Formed by Cyclohexane Diamine with Aldehyde Derivative

et al. 2022

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Low-molecular-weight gels have great potential for use in a variety of fields, including petrochemicals, healthcare, and tissue engineering. These supramolecular gels are frequently metastable, implying that their properties are kinetically controlled to some extent. Here, we report on the in situ supramolecular gel formation by mixing 1,3-cyclohexane diamine (1) and isocyanate derivative (2) without any catalysis at room temperature in various organic solvents. A mixture of building blocks 1 and 2 in various organic solvents, dichloromethane, tetrahydrofuran, chloroform, toluene, and 1,4-dioxane, resulted in the stable formation of supramolecular gel at room temperature within 60–100 s. This gel formation was caused by the generation of urea moieties, which allows for the formation of intermolecular hydrogen-bonding interactions via reactions 1 and 2. In situ supramolecular gels demonstrated a typical entangled fiber structure with a width of 600 nm and a length of several hundred μm. In addition, the supramolecular gels were thermally reversible by heating and cooling. The viscoelastic properties of supramolecular gels in strain and frequency sweets were enhanced by increasing the concentration of a mixed 1 and 2. Furthermore, the supramolecular gels displayed a thixotropic effect, indicating a thermally reversible gel.

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Low Molecular Weight Gelators Based on Functionalized l-Dopa Promote Organogels Formation

Cited by 17 publications

References 56 publications

Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Fluorine Effect in the Gelation Ability of Low Molecular Weight Gelators

Designing a Transparent and Fluorine Containing Hydrogel

In Situ Supramolecular Gel Formed by Cyclohexane Diamine with Aldehyde Derivative

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