Schiff-base based hydrogels as degradable platforms for hydrophobic drug delivery

Jalalvandi, Esmat; Hanton, Lyall R.; Moratti, Stephen C.

doi:10.1016/j.eurpolymj.2017.03.003

Cited by 45 publications

(39 citation statements)

References 43 publications

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“…3). The results are in agreement with previously reported spectra (Jalalvandi et al, 2016;Jalalvandi et al, 2017).…”

Section: Synthesis and Characterization Of Precursorssupporting

confidence: 93%

“…Synthesis of mono (6-amino-6-deoxy)-β-CD, CD functionalized alginate and methacrylated gelatin 2.3.1. Mono (6-amino-6-deoxy)-β-CD or EDA-β-CD EDA-β-CD was synthesized through a two-step reaction according to the reported procedure (Jalalvandi et al, 2016;Jalalvandi et al, 2017). First, a monotosyl derivative of β-CD was prepared by the reaction of ptoluene sulfonyl chloride with β-CD in water.…”

Section: Instrumentationmentioning

confidence: 99%

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Shear thinning/self-healing hydrogel based on natural polymers with secondary photocrosslinking for biomedical applications

Jalalvandi

Shavandi

2019

Journal of the Mechanical Behavior of Biomedical Materials

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“…3). The results are in agreement with previously reported spectra (Jalalvandi et al, 2016;Jalalvandi et al, 2017).…”

Section: Synthesis and Characterization Of Precursorssupporting

confidence: 93%

Section: Instrumentationmentioning

confidence: 99%

Shear thinning/self-healing hydrogel based on natural polymers with secondary photocrosslinking for biomedical applications

Jalalvandi

Shavandi

2019

Journal of the Mechanical Behavior of Biomedical Materials

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“…Combined strategies have been used to improve the compatibility of hydrogel materials with hydrophobic drugs, including the insertion of cyclodextrins, hydrophobic moieties, nanoparticles or micelles within the hydrogel structure (Concheiro and Alvarez-Lorenzo 2013;Gu, et al 2016;Jalalvandi, et al 2017;Machín, et al 2013;McKenzie, et al 2015). These systems provided controlled drug release over different periods of time, ranging from a few hours to several days (Gu, et al 2016).…”

Section: Discussionmentioning

confidence: 99%

Hydrogels based on poly(methyl vinyl ether-co-maleic acid) and Tween 85 for sustained delivery of hydrophobic drugs

Larrañeta

Barturen

Ervine

et al. 2018

International Journal of Pharmaceutics

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Hydrogels based on poly(methyl vinyl ether-co-maleic acid) and Tween 85 were prepared for hydrophobic drug delivery. The hydrogels were synthesized following a simple procedure carried out in solid state. The process did not require the use of any solvent and, as it is based on an esterification reaction, no toxic by-products were obtained. The resulting hydrogels contained Tween 85 inside the structure and due to the amphiphilic nature of this compound, hydrophobic domains within the hydrogel structure were formed. The obtained hydrogels showed good swelling capacities ranging from 100% to 600%. The esterification reaction that took place between poly(methyl vinyl ether-co-maleic acid) and Tween 85 was confirmed by infrared spectroscopy. Hydrogels were loaded with a hydrophobic drug model, Curcumin (CUR), showing that the hydrogels were able to retain up to 36 mg of CUR per g of hydrogel. Additionally, the synthesized hydrogels provided in vitro sustained CUR release over periods of up to 30 days. Finally, and due to the mucoadhesive nature of the prepared materials, one of the hydrogels was tested in vitro as an oral drug delivery system. For this purpose, the selected material was milled into microparticles (45-90 µm diameter). The release of CUR from the microparticles was evaluated under simulated gastric and intestinal conditions. The microparticles were able to release their cargos in 7 h. However, further work is required to optimize this system for oral drug delivery applications.

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“…This may be attributed by the lower cross-linking density of the DOX@Dex nanogel because -NH 2 groups on the Dex-CHO chains were partially consumed by the DOX conjugations, resulting in a hydrogel network with higher swelling ratio. As reported by previous publications, 23,45 cross-linking density is a key factor which can affect the swelling property of hydrogel, and the swelling ratio would increase as the cross-linking degree decrease. In addition, particle size of these hydrogel particles observed from SEM images are slightly smaller than that measured from DLS data, which is probably due to the shrink of hydrogel network during the drying process for SEM study.…”

Section: Synthesis Of Aldehyded Dextranmentioning

confidence: 60%

“…21 Schiff bases are promising candidate for the development of acid-sensitive linkages, since they are biodegradable via hydrolysis, and their stability decreases as the surrounding pH decreases. [22][23][24] Schiff bases are of the general formula R 1 R 2 C¼N-R 3 , where R 3 is an aryl or alkyl group that makes the Schiff base a stable imine. Compounds based on Schiff base are characterized by great biological activity which play an important role in biological systems.…”

Section: Introductionmentioning

confidence: 99%

Schiff base-containing dextran nanogel as pH-sensitive drug delivery system of doxorubicin: Synthesis and characterization

Zhang

et al. 2018

J Biomater Appl

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Stimuli-responsive hydrogels have been widely researched as carrier systems, due to their excellent biocompatibility and responsiveness to external physiologic environment factors. In this study, dextran-based nanogel with covalently conjugated doxorubicin (DOX) was developed via Schiff base formation using the inverse microemulsion technique. Since the Schiff base linkages are acid-sensitive, drug release profile of the DOX-loaded nanogel would be pH-dependent. In vitro drug release studies confirmed that DOX was released much faster under acidic condition (pH 2.0, 5.0) than that at pH 7.4. Approximately 66, 28, and 9% of drug was released in 72 h at pH 2.0, 5.0, and 7.4, respectively. Cell uptake by the human breast cancer cell (MCF-7) demonstrated that the DOX-loaded dextran nanogel could be internalized through endocytosis and distributed in endocytic compartments inside tumor cells. These results indicated that the Schiff base-containing nanogel can serve as a pH-sensitive drug delivery system. And the presence of multiple aldehyde groups on the nanogel are available for further conjugations of targeting ligands or imaging probes.

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Schiff-base based hydrogels as degradable platforms for hydrophobic drug delivery

Cited by 45 publications

References 43 publications

Shear thinning/self-healing hydrogel based on natural polymers with secondary photocrosslinking for biomedical applications

Shear thinning/self-healing hydrogel based on natural polymers with secondary photocrosslinking for biomedical applications

Hydrogels based on poly(methyl vinyl ether-co-maleic acid) and Tween 85 for sustained delivery of hydrophobic drugs

Schiff base-containing dextran nanogel as pH-sensitive drug delivery system of doxorubicin: Synthesis and characterization

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