Electrostatic interactions regulate the release of small molecules from supramolecular hydrogels

Abraham, Brittany L.; Toriki, Ethan S.; Tucker, N’Dea J.; Nilsson, Bradley L.

doi:10.1039/d0tb01157f

Cited by 27 publications

(35 citation statements)

References 69 publications

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“…Drug delivery simulation studies were carried on gels of CNB-Phe-ΔPhe-OH ( 2 ), to determine if a short treatment with UV light could stimulate an increased rate of release of model drug compound from within a disrupted, or partially disrupted, gel matrix. Following an adaptation of a method described by Abraham et al [ 47 ], the dyes methylene blue and methyl orange were used as examples of negatively and positively charged model drug compounds, respectively, which after incorporation into hydrogels their release could be studied by measuring the absorbance at their respective λ max values of 666 nm and 486 nm. The antimicrobial compound, ciprofloxacin, was also used, as an example of an overall neutral compound, whose release could be studied by HPLC [ 54 ].…”

Section: Resultsmentioning

confidence: 99%

“…Hydrogels of 2 were prepared as described in Section 2.2 in UV cuvettes, to form 1 mL hydrogels containing 4.0 mg of 2 and the appropriate cargo—methylene blue (0.1 mM), methyl orange (0.2 mM) or ciprofloxacin (0.2 mM), in a slightly modified version of the procedure described by Abraham et al [ 47 ]. After allowing to stand overnight, 1.5 mL of water was carefully added to the surface of the hydrogels, and the cuvettes were sealed.…”

Section: Methodsmentioning

confidence: 99%

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Evaluation of a Model Photo-Caged Dehydropeptide as a Stimuli-Responsive Supramolecular Hydrogel

et al. 2021

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Short peptides capped on the N-terminus with aromatic groups are often able to form supramolecular hydrogels, via self-assembly, in aqueous media. The rheological properties of these readily tunable hydrogels resemble those of the extracellular matrix (ECM) and therefore have potential for various biological applications, such as tissue engineering, biosensors, 3D bioprinting, drug delivery systems and wound dressings. We herein report a new photo-responsive supramolecular hydrogel based on a “caged” dehydropeptide (CNB-Phe-ΔPhe-OH 2), containing a photo-cleavable carboxy-2-nitrobenzyl (CNB) group. We have characterized this hydrogel using a range of techniques. Irradiation with UV light cleaves the pendant aromatic capping group, to liberate the corresponding uncaged model dehydropeptide (H-Phe-ΔPhe-OH 3), a process which was investigated by 1H NMR and HPLC studies. Crucially, this cleavage of the capping group is accompanied by dissolution of the hydrogel (studied visually and by fluorescence spectroscopy), as the delicate balance of intramolecular interactions within the hydrogel structure is disrupted. Hydrogels which can be disassembled non-invasively with temporal and spatial control have great potential for specialized on-demand drug release systems, wound dressing materials and various topical treatments. Both 2 and 3 were found to be non-cytotoxic to the human keratinocyte cell line, HaCaT. The UV-responsive hydrogel system reported here is complementary to previously reported related UV-responsive systems, which are generally composed of peptides formed from canonical amino acids, which are susceptible to enzymatic proteolysis in vivo. This system is based on a dehydrodipeptide structure which is known to confer proteolytic resistance. We have investigated the ability of the photo-activated system to accelerate the release of the antibiotic, ciprofloxacin, as well as some other small model drug compounds. We have also conducted some initial studies towards skin-related applications. Moreover, this model system could potentially be adapted for on-demand “self-delivery”, through the uncaging of known biologically active dehydrodipeptides.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Evaluation of a Model Photo-Caged Dehydropeptide as a Stimuli-Responsive Supramolecular Hydrogel

et al. 2021

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“…GF adsorption on the defect site has to be steady and localized, and a GF–receptor interaction must occur to activate signaling cascades, inducing osteoblast proliferation, to effectively allow tissue regeneration [ 125 ]. Accordingly, an equilibrium between anchored adsorption on the substrate and protein activity protection must be attained [ 126 ]. The properties of the scaffold can be preserved using this method, and it does not shatter the bioactivity of GFs.…”

Section: Encapsulation Incorporation and Related Delivery Stratementioning

confidence: 99%

Advances in Growth Factor Delivery for Bone Tissue Engineering

Oliveira

Nie

Podstawczyk

et al. 2021

IJMS

116

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Shortcomings related to the treatment of bone diseases and consequent tissue regeneration such as transplants have been addressed to some extent by tissue engineering and regenerative medicine. Tissue engineering has promoted structures that can simulate the extracellular matrix and are capable of guiding natural bone repair using signaling molecules to promote osteoinduction and angiogenesis essential in the formation of new bone tissues. Although recent studies on developing novel growth factor delivery systems for bone repair have attracted great attention, taking into account the complexity of the extracellular matrix, scaffolding and growth factors should not be explored independently. Consequently, systems that combine both concepts have great potential to promote the effectiveness of bone regeneration methods. In this review, recent developments in bone regeneration that simultaneously consider scaffolding and growth factors are covered in detail. The main emphasis in this overview is on delivery strategies that employ polymer-based scaffolds for spatiotemporal-controlled delivery of both single and multiple growth factors in bone-regeneration approaches. From clinical applications to creating alternative structural materials, bone tissue engineering has been advancing constantly, and it is relevant to regularly update related topics.

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“…Hydrogels containing cationic, anionic or zwitter ionic model drugs were prepared using the same conditions described in Section 2.2, but with the water component (1 mL) being replaced by a methylene blue solution, methyl orange solution or ciprofloxacin solution. In a modified version of the method described by Abraham et al [1], water was carefully layered on top of hydrogel surface. The percentage release of model drug was then recorded versus time, through UV absorption measurements or by HPLC, and subsequent fitting to a standard calibration curve (Figures S10 in Supplementary Information).…”

Section: Drug Release Studiesmentioning

confidence: 99%

“…Supramolecular hydrogels have attracted considerable attention due to their potential applications as promising biomaterials for many biotechnological and biomedical applications, such as: drug delivery, [1,2] cell culture, [3] tissue engineering, [4] wound healing [5,6] and many others. Upon receiving an external trigger, short peptides capped with aromatic groups on the Nterminus can often self-assemble into three-dimensional (3D) networks, forming fibres which can trap water molecules, providing biocompatible and biodegradable supramolecular hydrogels [7].…”

Section: Introductionmentioning

confidence: 99%

Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

Amorim¹,

Veloso²,

Castanheira³

et al. 2021

Preprint

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

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Electrostatic interactions regulate the release of small molecules from supramolecular hydrogels

Abstract: Supramolecular hydrogels have great potential as biomaterials for sustained delivery of therapeutics.

Cited by 27 publications

References 69 publications

Evaluation of a Model Photo-Caged Dehydropeptide as a Stimuli-Responsive Supramolecular Hydrogel

Evaluation of a Model Photo-Caged Dehydropeptide as a Stimuli-Responsive Supramolecular Hydrogel

Advances in Growth Factor Delivery for Bone Tissue Engineering

Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

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