Phosphonium hydrogels for controlled release of ionic cargo

Harrison, Tristan D.; Ragogna, Paul J.; Gillies, Elizabeth R.

doi:10.1039/c8cc05083j

Cited by 9 publications

(11 citation statements)

References 24 publications

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“…One of the most promising pathways for application of ionic polymeric materials in the biomedical fields regroups drug, 119,188,189 gene, 190,191 nucleic acid 192 and protein 193 delivery. Incorporating a zwitterionic sequence within polypeptides, 194 adding phosphonium groups into PEG-based hydrogels, 195 or functionalizing chitosan-PEG nanoparticles 196 are among recent strategies to design drug delivery systems. Besides, polyethyleneimines and phosphonium-based ionomers depict non-viral vectors to target tumors or cancers as they show high cellular uptake efficiency and easy assembly with small interfering RNA through electrostatic interactions.…”

Section: Applications Of Ionic Polymeric Materialsmentioning

confidence: 99%

A comprehensive review of the structures and properties of ionic polymeric materials

et al. 2020

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Section: Applications Of Ionic Polymeric Materialsmentioning

confidence: 99%

A comprehensive review of the structures and properties of ionic polymeric materials

et al. 2020

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“…Monomers were synthesized by reacting triethylphosphine, triethylamine, tri( n -butyl)phosphine, tri- n -butylamine, and tris(hydroxypropyl)phosphine with 4-vinylbenzyl chloride to generate the corresponding salts ( Et-P , Et-N , Bu-P , Bu-N , and Hp-P ; Scheme ) as reported previously. − Tris(hydroxypropyl)amine also reacted with 4-vinylbenzyl chloride, but the reaction did not proceed to completion, and upon work-up the products swelled extensively and could not be purified. Polymerization of the remaining monomers was performed in water at 60 °C using the thermal initiator VA-044 for 16 h. Conventional free-radical polymerization was chosen as it could provide high molar mass polymers .…”

Section: Resultsmentioning

confidence: 99%

“…Triethyl(4-vinylbenzyl)phosphonium chloride ( Et-P ), triethyl(4-vinylbenzyl)ammonium chloride ( Et-N ), tri( n -butyl)(4-vinylbenzyl)phosphonium chloride ( Bu-P ), tri( n -butyl)(4-vinylbenzyl)ammonium chloride ( Bu-N ), and tris(hydroxypropyl)(4-vinylbenzyl)phosphonium chloride ( Hp-P ) were synthesized as previously reported. , Poly[triethyl(4-vinylbenzyl)phosphonium chloride] ( P-Et-P ), poly[tri( n -butyl)(4-vinylbenzyl)phosphonium chloride] ( P-Bu-P ), and poly[tris(hydroxypropyl)(4-vinylbenzyl)phosphonium chloride] ( P-Hp-P ) were also synthesized as previously reported . Triethylamine, tributylamine, 4-vinylbenzyl chloride, fluorescein sodium salt, and D 2 O were purchased from Sigma-Aldrich and used as received.…”

Section: Methodsmentioning

confidence: 99%

Phosphonium versus Ammonium Compact Polyelectrolyte Complex Networks with Alginate—Comparing Their Properties and Cargo Encapsulation

et al. 2020

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Phosphonium and ammonium polymers can be combined with polyanions to form polyelectrolyte complex (PEC) networks, with potential application in self-healing materials and drug delivery vehicles. While various structures and compositions have been explored, to the best of our knowledge, analogous ammonium and phosphonium networks have not been directly compared to evaluate the effects of phosphorus versus nitrogen cations on the network properties. In this study, we prepared PECs from sodium alginate and poly[triethyl(4-vinylbenzyl)phosphonium chloride], poly[triethyl(4-vinylbenzyl)ammonium chloride], poly[tri(n-butyl)(4-vinylbenzyl)phosphonium chloride], poly[tri(n-butyl)(4-vinylbenzyl)ammonium chloride], and poly[tris(hydroxypropyl)(4-vinylbenzyl)phosphonium chloride]. These networks were ultracentrifuged to form compact PECs (CoPECs), and their physical properties, chemical composition, and self-healing abilities were studied. In phosphate-buffered saline, the phosphonium polymer networks swelled to a higher degree than their ammonium salt-containing counterparts. However, the viscous and elastic moduli, along with their relaxation times, were quite similar for analogous phosphoniums and ammoniums. The CoPEC networks were loaded with anions including fluorescein, etodolac, and methotrexate, resulting in loading capacities ranging from 5 to 14 w/w % and encapsulation efficiencies from 29 to 93%. Anion release occurred over a period of several days to weeks, with the rate depending largely on the anion structure and polycation substituent groups. Whether the cation was an ammonium or a phosphonium had a smaller effect on the release rates. The cytotoxicities of the networks and polycations were investigated and found to depend on both the network and polycation structure.

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“…This trend also does not strictly follow the trends observed for hydrogel viscoelasticity or network morphology (ratio of tube structures to fibers/tapes), indicating that differences in the total amount of diclofenac released cannot be explained entirely by these emergent properties of the hydrogels. A recent study of release of diclofenac from positively charged phosphonium gels indicated that the diclofenac release profiles were unaffected by changes in pH, but diclofenac release was slower from hydrogels containing triphenylphosphine compared to hydrogels with nonaromatic phosphines . Presumably, aromatic diclofenac molecules participate in specific π–π interactions with aromatic triphenylphosphine that is not possible with nonaromatic phosphines.…”

Section: Drug Release Profiles From Cationic Fmoc-phenylalanine Deriv...mentioning

confidence: 99%

“…A recent study of release of diclofenac from positively charged phosphonium gels indicated that the diclofenac release profiles were unaffected by changes in pH, but diclofenac release was slower from hydrogels containing triphenylphosphine compared to hydrogels with nonaromatic phosphines. 68 Presumably, aromatic diclofenac molecules participate in specific π−π interactions with aromatic triphenylphosphine that is not possible with nonaromatic phosphines. This suggests that the molecular structure of the gelators in this study may play a role in the differences in the amount of diclofenac released at saturation.…”

Section: Acs Applied Bio Materialsmentioning

confidence: 99%

Low-Molecular-Weight Supramolecular Hydrogels for Sustained and Localized in Vivo Drug Delivery

Raymond

Abraham

Fujita

et al. 2019

ACS Appl. Bio Mater.

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Supramolecular hydrogels are emerging as next-generation alternatives to synthetic polymers for drug delivery applications. Self-assembling peptides are a promising class of supramolecular gelators for in vivo drug delivery that have been slow to be adopted despite advantages in biocompatibility due to the relatively high cost of producing synthetic peptide hydrogels compared to synthetic polymer gels. Herein, we describe the development and use of inexpensive low-molecular-weight cationic derivatives of phenylalanine (Phe) as injectable hydrogels for in vivo delivery of an anti-inflammatory drug, diclofenac, for pain mitigation in a mouse model. N-Fluorenylmethoxycarbonyl phenylalanine (Fmoc-Phe) derivatives were modified at the carboxylic acid with diaminopropane (DAP) to provide Fmoc-Phe-DAP molecules that spontaneously and rapidly self-assemble in aqueous solutions upon addition of physiologically relevant sodium chloride concentrations to give hydrogels. When self-assembly occurs in the presence of diclofenac, the drug molecule is efficiently encapsulated within the hydrogel network. These hydrogels exhibit robust shear-thinning behavior, mechanical stability, and drug release profiles to enable application as injectable hydrogels for in vivo drug delivery. Delivery of diclofenac in vivo was demonstrated by a localized injection of an Fmoc-F 5 -Phe-DAP/diclofenac hydrogel into the ankle joint of mice with induced ankle injury and associated inflammation-induced pain. Remediation of pain in the ankle joint was observed immediately after the initial injection and was sustained for a period of nearly 2 weeks, while diclofenac controls remediated pain for less than 1 day. These data demonstrate the promise of these supramolecular hydrogels as inexpensive next-generation materials for sustained and localized drug delivery in vivo.

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Phosphonium hydrogels for controlled release of ionic cargo

Cited by 9 publications

References 24 publications

A comprehensive review of the structures and properties of ionic polymeric materials

A comprehensive review of the structures and properties of ionic polymeric materials

Phosphonium versus Ammonium Compact Polyelectrolyte Complex Networks with Alginate—Comparing Their Properties and Cargo Encapsulation

Low-Molecular-Weight Supramolecular Hydrogels for Sustained and Localized in Vivo Drug Delivery

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