Permeation Enhancement via Thiolation: In Vitro and Ex Vivo Evaluation of Hyaluronic Acid-Cysteine Ethyl Ester

Laffleur, Flavia; Psenner, Julia; Suchaoin, Wongsakorn

doi:10.1002/jps.24456

Cited by 32 publications

(18 citation statements)

References 25 publications

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“…LDH release is an important indicator of the integrity of the cell membrane. LDH is located in the cytoplasm under normal conditions [ 28 ]. When cells are attacked by foreign materials, the structure of the cell membrane will be destructed and cytoplasmic enzymes, such as LDH, will be released into the cell culture media.…”

Section: Resultsmentioning

confidence: 99%

“…When cells are attacked by foreign materials, the structure of the cell membrane will be destructed and cytoplasmic enzymes, such as LDH, will be released into the cell culture media. Thus, cytotoxicity can be quantitatively analyzed by detecting the amount of LDH released into culture media to evaluate the integrity of the cell membrane [ 28 ].…”

Section: Resultsmentioning

confidence: 99%

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Structural Characterization and Repair Mechanism of Gracilaria lemaneiformis Sulfated Polysaccharides of Different Molecular Weights on Damaged Renal Epithelial Cells

Guo

Sun

et al. 2018

Oxidative Medicine and Cellular Longevity

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Natural Gracilaria lemaneiformis sulfated polysaccharide (GLP0, molecular weight = 622 kDa) was degraded by H2O2 to obtain seven degraded fragments, namely, GLP1, GLP2, GLP3, GLP4, GLP5, GLP6, and GLP7, with molecular weights of 106, 49.6, 10.5, 6.14, 5.06, 3.71, and 2.42 kDa, respectively. FT-IR and NMR results indicated that H2O2 degradation does not change the structure of GLP polysaccharides, whereas the content of the characteristic −OSO3H group (13.46% ± 0.10%) slightly increased than that of the natural polysaccharide (13.07%) after degradation. The repair effects of the polysaccharide fractions on oxalate-induced damaged human kidney proximal tubular epithelial cells (HK-2) were compared. When 60 μg/mL of each polysaccharide was used to repair the damaged HK-2 cells, cell viability increased and the cell morphology was restored, as determined by HE staining. The amount of lactate dehydrogenase released decreased from 16.64% in the injured group to 7.55%–13.87% in the repair groups. The SOD activity increased, and the amount of MDA released decreased. Moreover, the mitochondrial membrane potential evidently increased. All polysaccharide fractions inhibited S phase arrest through the decreased percentage of cells in the S phase and the increased percentage of cells in the G2/M phase. These results reveal that all GLP fractions exhibited repair effect on oxalate-induced damaged HK-2 cells. The repair ability is closely correlated with the molecular weight of the fractions. GLP2 with molecular weight of about 49.6 kDa exhibited the strongest repair effect, and GLP with higher or lower molecular weight than 49.6 kDa showed decreased repair ability. Our results can provide references for inhibiting the formation of kidney stones and developing original anti-stone polysaccharide drugs.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Structural Characterization and Repair Mechanism of Gracilaria lemaneiformis Sulfated Polysaccharides of Different Molecular Weights on Damaged Renal Epithelial Cells

Guo

Sun

et al. 2018

Oxidative Medicine and Cellular Longevity

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“…Previously, Laffleur et al proved by IR spectra the successfully modified HACYS and CMCCYS, displaying specific peaks proving the attachment via amide bond formation as 3161 cm À1 and 3159 cm À1 representing the C-H stretch as well as the N-H bend and -C ¼ C-at 1653-1619 cm À1 . The amide bond could be seen at 1735-1700 cm À1 for modified polymers but not for unmodified ones [21].…”

Section: Synthesis and Characterizationmentioning

confidence: 91%

Screening of anionic-modified polymers in terms of stability, disintegration, and swelling behavior

Laffleur

Ijaz

Menzel

2017

Drug Development and Industrial Pharmacy

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This study aimed to screen the stability, disintegration, and swelling behavior of chemically modified anionic polymers. Investigated polymers were well-known and widely used staples of the pharmaceutical and medical field, namely, alginate (AL), carboxymethyl cellulose (CMC), polycarbophil (PC), and hyaluronic acid (HA). On the basis of amide bond formation between the carboxylic acid moieties of anionic polymers and the primary amino group of the modification ligand cysteine (CYS), the modified polymers were obtained. Unmodified polymers served as controls throughout all studies. With the Ellman's assay, modification degrees were determined of synthesized polymeric excipients. Stability assay in terms of erosion study at physiological conditions were performed. Moreover, water uptake of compressed polymeric discs were evaluated and further disintegration studies according to the USP were carried out to define the potential ranking. Results ranking figured out PCCYS > CMCCYS > HACYS > ALCYS in terms of water uptake capacity compared to respective controls. Cell viability assays on Caco-2 cell line as well as on RPMI 2650 (ATTC CCL30) proved modification not being harmful to those. Due to the results of this study, an intense screening of prominent anionic polymer derivate was performed in order to help the pharmaceutical research for the best choice of polymeric excipients for developments of controlled drug release systems.

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“…The anionic polymer hyaluronic acid sodium salt (HA) was hydrated to obtain a 0.4% (w/v) solution with a pH of 5.5 . By the addition of 50 m M of carbodiimide (EDAC) and NHS, respectively, l ‐cysteine ethyl ester (SH) was anchored to hyaluronic acid via amide bond formation between carboxylic moieties of hyaluronic acid and primary amino groups of cysteine ethyl ester.…”

Section: Methodsmentioning

confidence: 99%

Comparative mucoadhesive study of hyaluronic acid‐based conjugates on different mucosae

Laffleur

2017

J of Applied Polymer Sci

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The incentive of this study was to provide a detailed mucoadhesive comparison on adhesive properties on diverse mucosal surfaces such as nasal, buccal, and vaginal mucosa, respectively. Mucoadhesive hyaluronic acid-cysteine ethyl ester (HA-SH) conjugate was synthesized by the anchorage of sulfhydryl groups (SH) on the polymeric backbone of HA via amide bond formation between the carboxylic acid moieties of hyaluronic acid and sulfhydryl groups of cysteine ethyl ester. Histology assay in terms of alcian blue staining was performed on mucosal tissue in order to evaluate the potential impact on viability. The proficiency of water uptake was studied in various simulated body fluid. Moreover, mucoadhesive assays based on rotating cylinder, total work of adhesion, and maximum detachment force were carried out on various mucosae. The findings revealed in presence of 2.7-, 2.6-, and 1.25-fold improvement in swelling behavior in comparison to unmodified HA on nasal, buccal, and vaginal mucosa. Furthermore, mucoadhesive studies showed a 3.2-, 2.6-, 2.6-fold more extended residence time on nasal, buccal, and vaginal in presence of HA-SH in comparison to unmodified HA, respectively. Taken together, the comprehensive mucoadhesive study serve as guidance in the development of mucoadhesive drug delivery systems for versatile application.

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Permeation Enhancement via Thiolation: In Vitro and Ex Vivo Evaluation of Hyaluronic Acid-Cysteine Ethyl Ester

Cited by 32 publications

References 25 publications

Structural Characterization and Repair Mechanism of Gracilaria lemaneiformis Sulfated Polysaccharides of Different Molecular Weights on Damaged Renal Epithelial Cells

Structural Characterization and Repair Mechanism of Gracilaria lemaneiformis Sulfated Polysaccharides of Different Molecular Weights on Damaged Renal Epithelial Cells

Screening of anionic-modified polymers in terms of stability, disintegration, and swelling behavior

Comparative mucoadhesive study of hyaluronic acid‐based conjugates on different mucosae

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